Evidence-Based Complementary and Alternative Medicine
Volume 2016 (2016), Article ID 7584952, 36 pages
http://dx.doi.org/10.1155/2016/7584952

Review Article

The Genus Phyllanthus: An Ethnopharmacological, Phytochemical, and Pharmacological Review

Xin Mao,1,2 Ling-Fang Wu,¹ Hong-Ling Guo,³ Wen-Jing Chen,¹ Ya-Ping Cui,¹ Qi Qi,¹ Shi Li,¹ Wen-Yi Liang,¹ Guang-Hui Yang,¹ Yan-Yan Shao,¹ Dan Zhu,¹ Gai-Mei She,¹ Yun You,2,4 and Lan-Zhen Zhang¹

¹School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 100102, China
²Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China
³Institute of Zoology, Chinese Academy of Sciences, Beijing 100101, China
⁴Key laboratory of Chinese Internal Medicine, Beijing University of Chinese Medicine, Beijing 100700, China

Received 22 January 2016; Revised 23 March 2016; Accepted 30 March 2016

Academic Editor: Gloria Brusotti

Copyright © 2016 Xin Mao et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract.

The plants of the genus Phyllanthus (Euphorbiaceae) have been used as traditional medicinal materials for a long time in China, India, Brazil, and the Southeast Asian countries. They can be used for the treatment of digestive disease, jaundice, and renal calculus. This review discusses the ethnopharmacological, phytochemical, and pharmacological studies of Phyllanthus over the past few decades. More than 510 compounds have been isolated, the majority of which are lignins, triterpenoids, flavonoids, and tannins. The researches of their remarkable antiviral, antioxidant, antidiabetic, and anticancer activities have become hot topics. More pharmacological screenings and phytochemical investigations are required to support the traditional uses and develop leading compounds.

1. Introduction

Phyllanthus (Euphorbiaceae) is a large genus and widely distributed in tropical and subtropical zones like tropical Africa, tropical America, Asia, and Oceania. This genus, consisting of more than 700 species, can be classified into 11 subgenuses [1, 2]. The most popular 24 species are chiefly belonging to subgenus Kirganelia, Cicca, and Phyllanthus and they are traditionally used by different nationalities.

Genus Phyllanthus has been employed as herbal drugs for a long time in China, India, Brazil, and Southeast Asian countries. The most abundant species are used in India and have a beneficial role in Ayurveda for the treatment of digestive, genitourinary, respiratory, and skin diseases [3, 4]. In China, herbs and their prescriptions are used to treat hepatitis B, hypertension, dropsy, and sore throat [2]. These herbal drugs are employed by local inhabitants of Thailand, Latin America (especially Brazil), and Africa to cure jaundice, renal calculus, and malaria, respectively [5–7].

By virtue of the wide uses of Phyllanthus as anti-HIV, anticancer, and anti-HBV agents, there has been considerable interest in the investigations of this genus in recent years and the researches about pharmacology and chemistry had been finished in a deep going way. This report reviews the ethnopharmacological, phytochemical, and pharmacological investigations of Phyllanthus over the past few decades. More than three hundred articles were selected from the data taken from SciFinder Scholar database by searching the keyword “Phyllanthus”.

2. Ethnopharmacological Uses

The traditional application experiences of these herbs may have reference value for the treatment of recent diseases. Botanical data, folk name, and medicinal properties of twenty-four Phyllanthus species are depicted in Table 1. In Asia, seventeen plants are considered to have bitter and astringent taste. They are regarded as stomachic, diuretic, febrifuge, deobstruent, and antiseptic agents and effective remedies for hepatopathy, hypertensive, diabetes, and jaundice. In Africa, six herbs are widely employed by many tribes for the treatment of malaria wound and tetanus. Six species are used extensively in Latin America for the treatment of urination disorder and diabetes. The distribution and the main uses of Phyllanthus are pictured in Figure 1.

Table 1: The traditional use of Phyllanthus.

Species
Region
Local name
Plant part used
Traditional use
Reference

P. emblica
Bangladesh

Fruit
Constipation, urinary diseases
[8]

Burma

Juice/bark
Constipation, hemostasis, keratitis
[8]

Cambodia

Leaves
Muscle pain, fever
[8]

China
Yuganzi
Fruit
Digestive disease, hypertension, fever, respiratory inflammation
[8]

Fiji

Fruit
Tonic
[8]

India
Amla, Indian gooseberry
Fruit
Diabetes, chronic diarrhea, inflammation, fever, liver diseases, stomach ulcers, metabolic disorders, skin disorders, beauty care
[3, 4]

Indonesia

Leaves/fruit
Diarrhea, abdominal pain, stomach Disease, gallbladder disease, bleeding
[8]

Iran

Fruit
Parasitic
[8]

Iraq

Fruit
Bleeding, gastrointestinal system disorder
[8]

Nepal

Stem/fruit/seed
Urination disorder, constipation, bleeding, diarrhea, ophthalmopathy, asthma, bronchitis
[8]

Pakistan

Fruit
Diarrhea, preterm, skin diseases, gonorrhea, ophthalmopathy, anemia, hair care
[8, 9]

Sri Lanka

Fruit/whole plant
Constipation, indigestion, keratitis
[8]

Thailand
Makham pom
Juice/bark
Diarrhea, leukorrhagia, cough, parasitosis, gastrointestinal chronic diseases, hair treatment and nourishment, skin care
[8, 10, 11]

Turkey

Fruit
Diarrhea, dysentery, hemostasis, gastroenteritis
[8]

P. reticulatus
Bangladesh

Whole plant
Edema, constipation, helminthiasis, dysentery, diarrhea, pain
[12]

China
Huangguo yexiazhu

Inflammation, rheumatism
[13]

India
Pancoli, karineli
Leaves/bark
Urination disorder, fever, smallpox, colic, constipation, diabetes
[12, 14, 15]

Kenya

Malaria
[7]

Malaysia

Leaves
Smallpox, syphilis, asthma, diarrhea, bleeding from gums, diabetes, urination disorder, sores, burn, suppuration, chafe, venereal sores
[16, 17]

Sri Lanka

Bark/fruit
Enteritis, urination disorder
[15]

Sudan

Urination disorder, fever
[15]

Tanzania

Whole plant/leaves
Dysmenorrhea, gonorrhea, urination disorder, intestinal hemorrhage and anemia, muscle spasms, diarrhea with anal bleeding, promoting fertility, sores
[12, 15]

Thailand

Urination disorder, asthma, anemia, fever, thirst, astringent, inflammation
[16]

P. niruri
Brazil
Quebra-pedra
Whole plant
Kidney calculi
[18]

China
zhuzicao
Whole plant
Hepatitis, dysentery, enteritis, urinary infection
[19]

Congo

Whole plant
Malaria
[20]

India
Chanka piedra, bhuiamlki
Fruit/whole plant
Bronchitis, anaemia, leprosy, asthma, kidney calculi, ulcer, wound, sore, scabies, ring worm, jaundice, gonorrhea, menstruation, diabetes
[18, 21–23]

Indonesia

Whole plant
Viral infection, hepatitis
[22]

Latin America
Chanca piedra
Whole plant
Gallstone, kidney calculi, fever, excess uric acid
[6, 18, 24]

Malaysia
Dukong anak
Whole plant
Diarrhoea, kidney disorder, gonorrhea, cough
[22]

Thailand

Aerial parts
Anorexia, malaria
[18]

P. muellerianus
Africa

Malaria
[25]

Cameroon
Mbolongo
Stem bark
Wound, tetanus
[26]

Ghana

Wound
[27]

Ivory Coast

Leaves
Fever
[26]

Nigeria

Root
Fever
[26]

Zambia

leaves
Fever
[26]

P. amarus
Africa

Whole plant
Urinary concretions, dysentery, jaundice, diarrhoea
[28]

India
Bhuiamlki
Whole plant
Gastropathy, diarrhoea, dysentery, intermittent fevers, ophthalmopathy, scabies, ulcers, wound, malaria, jaundice, diabetes, asthma, hepatitis, tuberculosis, urinary diseases, bodyache, immunomodulatory
[29–34]

Nigeria

Leaves
Diabetes mellitus, obesity, hyperlipidemia, malaria
[35, 36]

Peru
Chanca piedra
Leaves
Diabetes, jaundice, kidney diseases, urination disorder, sedative, astringent, tonic
[37]

Thailand
Look tai bai

Gonorrhea, jaundice, diabetes, liver diseases
[5]

P. urinaria
China
Yexiazhu
Whole plant
Kidney calculi, painful disorder, jaundice, enteritis, diarrhea, dropsy, inflammation
[38–41]

India

Inflammation, diarrheal, kidney calculi, painful disorder
[38, 39]

Thailand
Look tai bai

Inflammation, diarrheal, gonorrhea, jaundice, diabetes
[5, 38]

P. acidus
India
Harfarauri
Fruit/leaves/roots
Jaundice, constipation, vomiting, biliousness, urinary concretions, piles, fever, smallpox, rheumatism, asthma, hepatic disease, diabetes, gonorrhea, ophthalmopathy, amnesia, psoriasis
[42, 43]

Thailand
Otaheiti gooseberry, star gooseberry, mayom
Leaves/bark/root
Constipation, alcoholic addicts, hypertension, fever, dermatitis, menstruation fever
[44–46]

P. debilis
India
Bhuiamlki

Swelling, intestinal worms, fever, wound, inflammation, rheumatism
[34]

Sri Lanka

Diabetes
[47]

P. simplex
India
Bhuiaveli, uchchiyusirika
Leaves/whole plant
Ophthalmopathy, gonorrhea, jaundice, mammary abscess, pruritus, diarrhea, hepatitis, urinary infection
[48, 49]

China
Huang zhuzicao

Ophthalmopathy, diarrhea, hepatitis, urinary infection
[49]

P. discoideus
Cameroon

Insomnia, epilepsy
[50]

P. fraternus
India
Bhuiamlki
Whole plant
Constipation, jaundice, hepatic disorder, kidney disorders, bacterial infection
[29, 51, 52]

P. hookeri
India

Diabetes, wound, fever, inflammation, snake bite, bacterial infection
[34]

P. kozhikodianus
India

Dysentery, jaundice, ulcer, itching, bacterial infection
[34]

P. maderaspatensis
India
Bhuiamlki
Whole plant
Headache, constipation, diarrhea, edematous, dysentery, fever, ulcer, burn, jaundice, bacterial infection, immunomodulatory
[34, 52]

P. nozeranii
India

Spasmodic, piles, headache, boils, indigestion, viral and bacterial infection
[34]

P. orbicularis
Cuba

Jaundice, diabetes, kidney calculi, ulcer, rheumatism, fever
[53, 54]

P. piscatorum
Venezuela

Aerial parts
Wound, fungal infection
[55]

P. polyanthus
Kenya

Root
Sexually transmitted diseases
[56]

P. polyphyllus
India
Sirunelli
Leaves
Liver disease
[57]

P. rheedii
India

Whole plant
Diabetes
[58]

P. sellowianus
South America
Sarandi blanco
Stems/leaves
Urination disorder, diabetes
[59]

P. taxodiifolius
Thailand

Leaves/twigs
Urination disorder
[60]

P. tenellus
Brazil
Erva pombinha, quebra-pedra
Leaves
Urination disorder, kidney calculi
[61]

P. virgatus
Thailand
Look tai bai

Gonorrhea, jaundice, diabetes, liver disease
[5]

Figure 1: Traditional use of genus Phyllanthus in different countries. Different color represents the number of plants traditionally used in different countries: red, orange, yellow, green, blue, and purple represent fifteen, eight, five, three, two, and one kinds of plants under use, respectively. In Asia, Phyllanthus are used to treat digestive system disease, in south America, Phyllanthus are used to treat urinary system disease, and in Africa, Phyllanthus are used to treat malaria and wound.

2.1. Asia

In Asia, the clinical use of genus Phyllanthus is very prevalent. The fruit of P. emblica has a long history of use in India and is called “amla” or “Indian gooseberry.” As a tonic in Indian Ayurveda, it is often used for liver diseases [3, 4]. This fruit is known as “yuganzi” in China. It has sweet and slightly astringent taste and is used for clearing heat from throat and moistening lung for arresting cough in Traditional Chinese Medicine (TCM). In Tibetan medicine this herb is used to treat blood and bile disease, and its preparations are clinically applicable to hypertension and anuria [2]. In Thailand, it is named “makham pom” and is employed to treat gastrointestinal chronic diseases. P. emblica is commonly used together with Terminalia chebula and T. belerica and called “Triphala.” “Triphala” is used as a clinical treatment protocol of gastropathy in India and as a remedy for pestilence and fatigue in China [62].

In India, fifteen species of genus Phyllanthus are widely used by indigenous medicine. These plants have bitter and astringent taste and are considered as stomachic, diuretic, febrifuge, deobstruent, antiseptic, and effective remedies for hepatopathy. Some herbs such as P. niruri, P. amarus, P. fraternus, P. debilis, and P. maderaspatensis share the same name “bhuiamlki” [29]. The fruits of “bhuiamlki” are employed by Ayurveda to cure jaundice. P. simplex, P. reticulatus, and P. acidus are therapy of urinary disease and have the names of “bhuiaveli,” “pancoli,” and “harfarauri,” respectively. The leaves of P. polyphyllus, called “sirunelli,” are used for liver disease. Additionally, the rest of these herbs can be employed as remedies for diabetes, jaundice, wound, fever, and inflammation.

In China, five herbs are commonly used by TCM, Tibetan medicine, Dai People, and Yi People [2]. They have bitter and sweet taste and are usually used as prescriptions. The whole plant of P. urinaria, known as “yexiazhu,” can clear heat-toxin and remove dampness and is employed to treat jaundice, enteritis, diarrhea, and dropsy. Besides, the TCM prescription, named “yexiazhu capsule,” performs a beneficial role in curing hepatitis B. Other herbs such as P. reticulatus, P. niruri, and P. simplex are beneficial to the treatment of ophthalmopathy, urinary infection, inflammation, and rheumatism.

In Thailand, eight herbs of this genus are widely used by residents. P. amarus, P. urinaria, and P. virgatus share the name “look tai bai,” all of which are used for treating gonorrhea, jaundice, diabetic, and liver disease. P. acidus has three names: “otaheiti gooseberry,” “star gooseberry,” and “mayom,” and it can be used as remedy for hypertensive, constipation, skin disease, and fever. The rest of herbal drugs including P. taxodiifolius, P. niruri, and P. reticulatus are employed for the treatment of urination disorder and malaria.

2.2. Africa

Many African tribes employ six plants of genus Phyllanthus to treat malaria, fever, and wound. P. muellerianus is the most popular herbal drugs of this genus in Africa. It is named “mbolongo” in Cameroon. In Ghana and Cameroon, the stem bark is used for the therapy of wound and tetanus. In Nigeria, Zambia, and Ivory Coast the leaves and root are applied as a fever remedy. In Kenya, the root of P. polyanthus is used to cure sexually transmitted diseases. What is more, the whole plants of P. muellerianus and P. reticulatus can be used for the treatment of malaria.

2.3. Latin America

About six herb species of this genus are used in many countries in Latin America. In Brazil, P. tenellus is popularly known as “quebra-pedras” whose leaves can be used as diuretic. P. amarus is named “chanca piedra” in Peru and the leaves are employed for diabetic and jaundice therapy or as sedative and astringent. P. sellowianus is called “sarandi blanco” in South America and used widely in folk for the treatment of urination disorder and diabetes.

In summary, P. emblica, P. reticulatus, and P. niruri are the top three species widely used around the world. P. niruri is probably the most widespread herb of Phyllanthus, which is named “chanka piedra,” “bhuiamlki,” “zhuzicao,” “dukung anak,” “quebra-pedra,” and “chanca piedra.” Its whole plant can treat inflammation, lithiasis, fever, malaria, hepatitis, and gonorrhea [7, 18, 19, 21, 22].

3. Chemical Constituents

More than 510 compounds have been isolated from Phyllanthus, the majority of which are lignins, triterpenoids, flavonoids, and tannins. The compositions isolated from each species and their biological activities are partially summarized in Table 2. Lignins and tannins exhibit various activities and are considered to be the biological active compounds of this genus. Corilagin, geraniin, and gallic acid are three most prevalent compounds in this genus, and the pharmacological researches mainly focus on phyllanthin, niranthin, and geraniin.

Table 2: The compounds isolated from the genus Phyllanthus and part of pharmacological effects.

Number
Compounds
Species
Pharmacological effects
References

1
(20S)-3α-Acetoxy-24-methylenedammaran-20-ol
P. polyanthus

[56]

2
(20S)-3β-Acetoxy-24-methylenedammaran-20-ol
P. polyanthus

[56]

3
Ocotillol-II
P. flexuosus

[63]

4
Phyllanthenol
P. niruri

[64]

5
Phyllanthenone
P. niruri

[64]

6
Phyllantheol
P. niruri

[64]

7
(+)-Songbodichapetalin
P. songboiensis

[65]

8
Acutissimatriterpene A
P. acutissima

[66]

9
Acutissimatriterpene B
P. acutissima

[66]

10
Acutissimatriterpene C
P. acutissima

[66]

11
Acutissimatriterpene D
P. acutissima

[66]

12
Acutissimatriterpene E
P. acutissima

[66]

13
Flexuosoids A
P. flexuosus

[67]

14
Flexuosoids B
P. flexuosus

[67]

15
δ-Amyrin acetate
P. polyanthus

[56]

16
12(13)-Dehydro-3α-acetoxyolean-28-oic acid
P. pulcher

[68]

17
3′-O-Acetyl-3-O-α-L-arabinosyl-23-hydroxyolean-12-en-28-oic acid
P. polyphyllus

[69]

18
3α-Acetoxyl-25-hydroxyolean-12-en-28-oic acid
P. pulcher
Antitumor
[68]

19
4′-O-Acetyl-3-O-α-L-arabinosyl-23-hydroxyolean-12-en-28-oic acid
P. polyphyllus

[69]

20
Olean-12-en-3β,15α,24-triol
P. flexuosus
Antitumor
[70, 71]

21
Olean-12-en-3β,15α-diol
P. flexuosus
Antitumor
[70, 71]

22
Olean-12-en-3β,24-diol
P. flexuosus

[70]

23
Olean-18-en-3α-ol
P. fraternus

[72]

24
Oleana-11:13(18)-dien-3β-ol
P. flexuosus

[70]

25
Oleana-11:13(18)-dien-3β,24-diol
P. flexuosus

[70]

26
Oleana-9(11):12-dien-3β-ol
P. flexuosus

[70]

27
Oleanolic acid
P. urinaria

[73]

28
Phyllanoside
P. amarus

[74]

29
Phyllenolide A
P. myrtifolius

[75]

30
Phyllenolide B
P. myrtifolius

[75]

31
Phyllenolide C
P. myrtifolius

[75]

32
Taraxerol
P. columnaris

[76]

33
Taraxerone
P. reticulatus

[77]

33
Taraxerone
P. columnaris

[76]

34
Taraxeryl acetate
P. reticulatus

[77]

35
α-Amyrin
P. singampattiana

[78]

36
β-Amyrin
P. urinaria

[79]

36
β-Amyrin
P. flexuosus

[80]

36
β-Amyrin
P. acidus

[81]

37
11β-Hydroxy-D:A-friedoolean-1-en-3-one
P. flexuosus

[82]

38
1β,22β-Dihydroxyfriedelin
P. muellerianus

[83]

39
21α-Hydroxyfriedel-4(23)-en-3-one
P. reticulatus

[84]

40
21α-Hydroxyfriedelan-3-one
P. reticulatus

[84]

41
22β-Hydroxyfriedel-1-ene
P. muellerianus

[83]

42
26-Nor-D:A-friedoolean-14-en-3-one
P. watsonii

[85]

43
26-Nor-D:A-friedoolean-14-en-3β-ol
P. watsonii

[85]

43
Friedelin
P. columnaris

[86]

44
3,20-Dioxo-dinorfriedelane
P. emblica

[87]

45
Epifriedelinol
P. reticulatus

[77]

45
Epifriedelinol
P. singampattiana

[78]

46
Friedelan-3β-ol
P. reticulatus

[84]

47
Friedelin
P. niruri

[88]

47
Friedelin
P. reticulatus

[84]

47
Friedelin
P. flexuosus

[80]

47
Friedelin
P. watsonii

[85]

47
Friedelin
P. wightianus

[89]

47
Friedelin
P. singampattiana

[78]

48
Polpunonic acid
P. oxyphyllus

[90]

49
Trichadenic acid B
P. flexuosus

[91]

50
3-Friedelanone
P. muellerianus

[92]

51
Betulin
P. reticulatus

[77]

51
Betulin
P. flexuosus
Antitumor
[70, 71]

52
Betulinic acid
P. reticulatus

[84]

53
Glochidiol
P. urinaria

[73]

53
Glochidiol
P. sellowianus

[93]

54
Glochidone
P. virgatus

[94]

54
Glochidone
P. sellowianus

[95]

54
Glochidone
P. watsonii

[85]

54
Glochidone
P. taxodiifolius
Antitumor
[60, 96]

54
Glochidone
P. pulcher
Antitumor
[68]

54
Glochidone
P. flexuosus

[80]

55
Glochidonol
P. reticulatus

[84]

55
Glochidonol
P. sellowianus

[93]

55
Glochidonol
P. watsonii

[85]

55
Glochidonol
P. pulcher
Antitumor
[68]

56
Lup-20(29)-en-3β,15α-diol
P. flexuosus
Antitumor
[63, 71]

57
Lup-20(29)-en-3β,24-diol
P. flexuosus
Antitumor
[70, 71]

58
Lup-20(29)-en-3β-ol
P. urinaria

[97]

59
Lup-20(29)-ene-3β,24-diol
P. flexuosus

[98]

60
Lup-20(29)-ene-1β,3β-diol
P. sellowianus

[93]

60
Lup-20(29)-ene-1β,3β-diol
P. watsonii

[85]

61
Lupanyl acetate
P. urinaria

[99]

61
Lupanyl acetate
P. watsonii

[85]

61
Lupanyl acetate
P. columnaris

[86]

61
Lupanyl acetate
P. pulcher

[68]

62
Lupenone
P. polyanthus

[56]

63
Lupenyl palmitate
P. watsonii

[85]

64
Lupeol
P. emblica

[100]

64
Lupeol
P. urinaria

[79]

64
Lupeol
P. reticulatus

[17]

64
Lupeol
P. flexuosus
Antitumor
[71, 80]

64
Lupeol
P. oxyphyllus

[90]

64
Lupeol
P. watsonii

[85]

64
Lupeol
P. taxodiifolius
Antitumor
[60, 96]

64
Lupeol
P. wightianus

[89]

64
Lupeol
P. columnaris

[86]

65
Lupeol acetate
P. reticulatus

[17]

66
29-Nor-3,4-seco-friedelan-4(23),20(30)-dien-3-oic acid
P. oxyphyllus

[90]

67
3,7,11,15,19,23-Hexamethyl-2Z,6Z,10Z,14E,18E,22E-tetracosahexen-1-ol
P. niruri

[101]

68
Phyllanthol
P. sellowianus

[102]

68
Phyllanthol
P. polyanthus

[56]

68
Phyllanthol
P. acidus

[81]

69
Phyllanthone
P. polyanthus

[56]

70
4′-Hydroxyphyllaemblicin B
P. emblica

[103]

71
5-Hydroxy-6,9-epoxyguaiane
P. oxyphyllus

[90]

72
5-O-Acetyl-6,9-epoxyguaiane
P. oxyphyllus

[90]

73
Cloven-2β,9α-diol
P. urinaria

[73]

74
Descinnamoylphyllanthocindiol
P. acuminatus

[104]

75
Didesacetylphyllanthostatin 3
P. acuminatus

[104]

76
Dihydrophaseic acid-4′-O-β-D-glucopyranoside
P. reticulatus

[105]

77
Englerins A
P. engleri
Antitumor
[106]

78
Englerins B
P. engleri

[106]

79
Glochicoccin D
P. emblica

[107]

80
Jaslanceoside B
P. cochinchinensis

[108]

81
Jasminoside
P. cochinchinensis

[108]

82
Phyllaemblic acid
P. emblica

[109]

83
Phyllaemblic acid B
P. emblica

[110]

84
Phyllaemblic acid C
P. emblica

[110]

85
Phyllaemblicin A
P. emblica

[109]

86
Phyllaemblicin B
P. emblica
Antiviral and antitumor
[109, 111, 112]

87
Phyllaemblicin C
P. emblica
Antitumor and antiviral
[109, 111, 113]

88
Phyllaemblicin D
P. emblica

[110]

89
Phyllaemblicin E
P. emblica

[103]

90
Phyllaemblicin F
P. emblica

[103]

91
Phyllaemblicin G1
P. emblica

[107]

92
Phyllaemblicin G2
P. emblica

[107]

93
Phyllaemblicin G3
P. emblica

[107]

94
Phyllaemblicin G4
P. emblica

[107]

95
Phyllaemblicin G5
P. emblica

[107]

96
Phyllaemblicin G6
P. emblica
Antiviral
[107]

97
Phyllaemblicin G7
P. emblica

[107]

98
Phyllaemblicin G8
P. emblica

[107]

99
Phyllaemblinol
P. emblica

[114]

100
Phyllanthocin
P. brasiliensis

[115]

101
Phyllanthoside
P. acuminatus
Antitumor
[116]

101
Phyllanthoside
P. veuminatus
Antitumor
[117]

101
Phyllanthoside
P. brasiliensis
Antitumor
[115]

102
Phyllanthostatin 1
P. acuminatus
Antitumor
[116]

102
Phyllanthostatin 1
P. veuminatus
Antitumor
[117]

103
Phyllanthostatin 2
P. acuminatus
Antitumor
[117]

103
Phyllanthostatin 2
P. veuminatus
Antitumor
[117]

104
Phyllanthostatin 3
P. acuminatus
Antitumor
[117]

104
Phyllanthostatin 3
P. veuminatus
Antitumor
[117]

105
Phyllanthostatin 6
P. acuminatus
Antitumor
[104]

106
Phyllanthusol A
P. acidus
Antitumor
[46]

107
Phyllanthusol B
P. acidus
Antitumor
[46]

108
β-Caryophyllene
P. emblica

[113]

109
β-Bourbonene
P. emblica

[113]

110
19-Hydroxyspruceanol 19-O-β-D-glucopyranoside
P. reticulatus

[118]

111
Cleistanthol
P. urinaria

[73]

111
Cleistanthol
P. reticulatus

[13]

111
Cleistanthol
P. flexuosus
Antitumor
[119]

111
Cleistanthol
P. oxyphyllus

[90]

112
Ent-3β-Hydroxykaur-l6-ene
P. flexuosus

[80]

113
Orthosiphol G
P. niruri

[120]

114
Orthosiphol I
P. niruri

[120]

115
Phyllanflexoid A
P. flexuosus
Antitumor
[119]

116
Phyllanflexoid B
P. flexuosus
Antitumor
[119]

117
Phyllanflexoid C
P. flexuosus

[119]

118
Phyllanterpenyl ester
P. fraternus

[121]

119
Spruceanol
P. urinaria

[73]

119
Spruceanol
P. reticulatus

[13]

119
Spruceanol
P. oxyphyllus

[90]

119
Spruceanol
P. songboiensis

[65]

120
trans-Phytol
P. niruri

[122]

121
(3S,5R,6S,9R)-Megastigmane-3,9-diol 3-O-α-L-arabinofuranosyl-(1 → 6)-β-D-glucopyranoside
P. reticulatus

[13]

122
(6R)-Menthiafolic acid
P. urinaria

[73]

123
7-Megastigmen-3-ol-9-one 3-O-α-L-arabinofuranosyl-(1 → 6)-β-D-glucopyranoside
P. reticulatus

[13]

124
Turpenionoside A
P. reticulatus

[118]

125
Turpenionoside B
P. reticulatus

[118]

126
7-O-[(2,3,4-Tri-O-acetyl)-α-L-arabinopyranosyl]diphyllin
P. poilanei
Antitumor
[123]

127
Arabelline
P. flexuosus

[67]

128
Acutissimalignans A
P. songboiensis

[65]

128
Acutissimalignans A
P. acutissima

[66]

129
Cleistanthin A
P. taxodiifolius
Antitumor
[96, 124]

130
Cleistanthin A acetate
P. taxodiifolius
Antitumor
[96, 124]

131
Cleistanthin A Me ether
P. taxodiifolius
Antitumor
[96, 124]

132
Cleistanthin B
P. poilanei

[123]

133
Cleistanthoside A
P. taxodiifolius

[96]

134
Cleistanthoside A tetraacetate
P. taxodiifolius
Antitumor
[96, 124]

135
Dextrobursehernin
P. urinaria

[125]

136
Diphyllin
P. poilanei

[123]

136
Diphyllin
P. polyphyllus
Anti-inflammatory
[126]

137
Hypophyllanthin
P. niruri
Hepatoprotection and hypotensive
[127–129]

137
Hypophyllanthin
P. urinaria
Hypotensive
[125, 130]

137
Hypophyllanthin
P. virgatus

[131]

137
Hypophyllanthin
P. amarus
Antitumor and anti-CYP3A4
[132–134]

137
Hypophyllanthin
P. debilis

[135]

138
Isolariciresinol
P. emblica

[114]

139
Isolintetralin
P. niruri

[136]

139
Isolintetralin
P. urinaria

[125]

139
Isolintetralin
P. virgatus

[131]

140
Justicidin A
P. myrtifolius

[131]

141
Iusticidin B
P. myrtifolius

[137]

141
Iusticidin B
P. polyphyllus
Anti-inflammatory
[126]

141
Iusticidin B
P. anisolobus

[138]

141
Iusticidin B
P. piscatorum
Antifungal, antitumor, and antiparasitic
[139]

142
Lintetralin
P. niruri

[128]

142
Lintetralin
P. urinaria

[125]

143
(+)-Lyoniresinol
P. reticulatus

[13]

144
(+)-Lyoniresiol
P. urinaria

[73]

145
Mananthoside I
P. reticulatus

[118]

146
Neonirtetralin
P. niruri

[140]

146
Neonirtetralin
P. urinaria

[141]

147
Nirtetralin
P. niruri
Antiviral and hypotensive
[127, 128, 142]

147
Nirtetralin
P. urinaria

[125]

147
Nirtetralin
P. virgatus
Antiviral
[131, 143]

147
Nirtetralin
P. amarus
Anti-inflammatory and antitumor
[132, 144, 145]

148
Nirtetralin A
P. niruri
Antiviral
[142]

149
Nirtetralin B
P. niruri
Antiviral
[142, 146]

150
Phyllamyricin A
P. myrtifolius

[137]

151
Phyllamyricin B
P. myrtifolius

[137]

152
Phyllamyricin C
P. myrtifolius

[137]

152
Phyllamyricin C
P. polyphyllus
Anti-inflammatory
[126]

153
Phyllamyricin D
P. myrtifolius

[147]

154
Phyllamyricin E
P. myrtifolius

[147]

155
Phyllamyricin F
P. myrtifolius

[147]

156
Phyllamyricoside A
P. myrtifolius
Anti-HIV
[147]

157
Phyllamyricoside B
P. myrtifolius

[147]

158
Phyllamyricoside C
P. myrtifolius

[147]

159
Phyllanthostatin A
P. acuminatus

[148]

159
Phyllanthostatin A
P. anisolobus

[138]

160
Phyllanthuoside C
P. cochinchinensis

[149]

161
Phyllanthusmin A
P. poilanei

[123]

161
Phyllanthusmin A
P. oligospermus
Antitumor
[150]

162
Phyllanthusmin B
P. reticulatus

[13]

162
Phyllanthusmin B
P. poilanei

[123]

162
Phyllanthusmin B
P. oligospermus

[150]

163
Phyllanthusmin C
P. reticulatus

[13]

163
Phyllanthusmin C
P. flexuosus

[67]

163
Phyllanthusmin C
P. poilanei
Antitumor
[123]

163
Phyllanthusmin C
P. oligospermus

[150]

164
Phyllanthusmin D
P. poilanei

[123]

165
Phyllanthusmin E
P. poilanei

[123]

166
Phyllanthusmin D′
P. flexuosus

[67]

167
Phyllanthusmin E′
P. flexuosus

[67]

168
Phyllanthusmin F
P. flexuosus

[67]

169
Phyltetralin
P. niruri

[128]

169
Phyltetralin
P. urinaria
Anti-inflammatory
[125, 151]

169
Phyltetralin
P. virgatus

[131]

169
Phyltetralin
P. amarus
Anti-inflammatory
[145]

170
Piscatorin
P. piscatorum
Antitumor
[139]

171
Reticulatuside A
P. reticulatus

[13]

172
Reticulatuside B
P. reticulatus

[13]

173
Retrojusticidin B
P. myrtifolius
Anti-HIV
[137, 152]

174
Seco-4-hydroxylintetralin
P. niruri

[153]

175
Taxodiifoloside
P. taxodiifolius
Antitumor
[124]

176
Urinatetralin
P. niruri

[154]

176
Urinatetralin
P. urinaria

[125]

177
2,3-Desmethoxy seco-isolintetralin
P. niruri

[155]

178
2,3-Desmethoxy seco-isolintetralin diacetate
P. niruri

[155]

179
4-(3,4-Dimethoxy-phenyl)-1-(7-methoxy-benzo1,3dioxol-5-yl)-2,3-bis-methoxymethyl-butan-1-ol
P. amarus

[132]

180
5-Demethoxy niranthin
P. urinaria

[125]

180
5-Demethoxy niranthin
P. amarus

[132]

181
7′-Hydroxy-3′,4′,5,9,9′-pentamethoxy-3,4-methylene dioxy lignan
P. urinaria
Antitumor
[156]

182
Demethylenedioxyniranthin
P. niruri

[155]

183
Dihydrocubebin
P. niruri

[155]

183
Dihydrocubebin
P. urinaria

[73]

184
Hydroxyniranthin
P. niruri

[153]

185
Linnanthin
P. niruri

[155]

186
Niranthin
P. niruri

[157]

186
Niranthin
P. urinaria

[125]

186
Niranthin
P. virgatus
Antiviral
[131, 143]

186
Niranthin
P. amarus
Anti-inflammatory, antiparasitic, antihyperalgesic, and antitumor
[132, 144, 158, 159]

187
Nirphyllin
P. niruri

[160]

188
Phyllanthin
P. niruri
Hepatoprotection, hypotensive, and antihyperuricemic
[127, 157, 161, 162]

188
Phyllanthin
P. urinaria
Immunomodulatory and hypotensive
[125, 130, 163]

188
Phyllanthin
P. amarus
Cell-protection, hepatoprotection, antitumor, and anti-CYP3A4
[134, 144, 164, 165]

188
Phyllanthin
P. fraternus

[72]

188
Phyllanthin
P. debilis

[135]

189
Seco-isolariciresinol
P. oxyphyllus

[90]

190
Seco-isolariciresinol trimethyl ether
P. niruri

[153]

191
(+)-8-(3,4-(Methylenedioxy)benzyl)-8′-(3′,4′-dimethoxybenzyl)-butyrolactone
P. virgatus

[131]

192
(+)-Secoisolariciresinol
P. songboiensis

[65]

193
(+)-Songbosin
P. songboiensis

[65]

194
2S,3S-Bursehernin
P. urinaria

[166]

195
3-(3,4-Dimethoxy-benzyl)-4-(7-methoxy-benzo1,3dioxol-5-yl-methyl)-dihydrofuran-2-one
P. amarus

[132]

196
Acutissimalignans B
P. acutissima

[66]

197
Bursehernin
P. amarus

[132]

198
Cubebin dimethyl ether
P. niruri

[154]

199
Dibenzylbutyrolactone
P. niruri

[153]

200
Heliobuphthalmin lactone
P. urinaria

[125]

200
Heliobuphthalmin lactone
P. amarus

[132]

201
Hinokinin
P. niruri

[136]

201
Hinokinin
P. virgatus
Antiviral
[131, 143]

202
(7 R,7′R,8S,8′S)-Icariol A2
P. urinaria

[73]

203
Phyllnirurin
P. niruri

[160]

204
Urinaligran
P. urinaria

[125]

205
Virgatusin
P. urinaria

[125]

205
Virgatusin
P. virgatus

[131]

205
Virgatusin
P. amarus

[132]

206
(+)-Diasyringaresinol
P. flexuosus

[67]

207
(−)-Episyringaresinol
P. urinaria

[73]

207
(−)-Episyringaresinol
P. songboiensis

[65]

208
(−)-Lirioresinol-B
P. virgatus

[94]

209
4-Ketopinoresinol
P. emblica

[114]

210
4-Oxopinoresinol
P. urinaria

[73]

211
Lirioresinol A
P. emblica

[114]

212
Medioresinol
P. emblica

[114]

213
Pinoresinol
P. oxyphyllus

[90]

213
Pinoresinol
P. songboiensis

[65]

214
Syringaresinol
P. emblica

[114]

214
Syringaresinol
P. urinaria

[73]

214
Syringaresinol
P. reticulatus

[13]

215
Virgatyne
P. virgatus

[94]

216
4,9,9′-Trihydroxy-3,4′-dimethoxy-8-O-3′-neolignan
P. emblica

[114]

217
Caffeic acid
P. urinaria

[167]

217
Caffeic acid
P. sellowianus

[168]

217
Caffeic acid
P. muellerianus

[169]

217
Caffeic acid
P. simplex

[170]

218
Cinnamic acid
P. emblica
Antioxidant
[171]

219
Coniferyl aldehyde
P. emblica

[114]

220
Evofolin B
P. urinaria

[73]

221
Ferulic acid
P. urinaria

[172]

221
Ferulic acid
P. simplex

[170]

222
Methyl caffeate
P. emblica

[114]

223
Phyllanthuoside A
P. cochinchinensis
Antitumor
[149]

224
Phyllanthuoside B
P. cochinchinensis

[149]

225
Debelalactone
P. debilis
Hepatoprotection
[173]

226
Isofraxidin
P. sellowianus

[174]

227
Scopoletin
P. sellowianus

[174]

228
1,2,4,6-Tetra-O-galloyl-β-D-glucose
P. emblica
Antiviral
[175]

228
1,2,4,6-Tetra-O-galloyl-β-D-glucose
P. niruri
Antiviral
[176, 177]

229
1,3,4,6-Tetra-O-galloyl-β-D-glucose
P. virgatus

[94]

230
1,4,6-Tri-O-galloyl-β-D-glucose
P. virgatus

[94]

231
1,6-Di-O-galloyl-β-D-glucose
P. virgatus

[94]

232
1,2-Di-O-galloyl-3,6-(R)-hexa-hydroxydiphenoyl-β-D-glucose
P. niruri

[176]

233
Amariin
P. amarus
Hepatoprotection, radioprotective, and antioxidant
[178–181]

234
Amariinic acid
P. amarus

[182]

235
Amarulone
P. amarus

[183]

236
Carpinusnin
P. emblica

[184]

237
Chebulagic acid
P. emblica
Antioxidant and antitumor
[111, 184, 185]

237
Chebulagic acid
P. myrtifolius

[186]

238
Chebulanin
P. emblica
Antioxidant
[184, 185]

239
Corilagin
P. emblica
Antioxidant and antitumor
[111, 184, 187]

239
Corilagin
P. niruri
Antihyperalgesic and anti-inflammatory
[6, 176, 188]

239
Corilagin
P. urinaria
Antiviral and antiplatelet
[189–191]

239
Corilagin
P. reticulatus

[192]

239
Corilagin
P. virgatus

[94]

239
Corilagin
P. amarus
Antidiabetic, radioprotective, and anti-HIV
[179, 181, 193, 194]

239
Corilagin
P. myrtifolius

[186]

239
Corilagin
P. muellerianus

[169]

239
Corilagin
P. debilis
Antioxidant
[195]

239
Corilagin
P. matsumurae

[196]

239
Corilagin
P. wightianus

[89]

239
Corilagin
P. ussuriensis
Antioxidant
[197, 198]

240
Excoecarianin
P. urinaria
Antiviral
[199]

241
Furosin
P. emblica
Antioxidant
[184, 187]

241
Furosin
P. virgatus

[94]

241
Furosin
P. sellowianus
Antihyperalgesic
[200]

241
Furosin
P. muellerianus
Wound healing
[169]

241
Furosin
P. debilis
Antioxidant
[195]

242
Geraniin
P. emblica
Antioxidant and antitumor
[111, 185, 201]

242
Geraniin
P. niruri
Antiviral
[177]

242
Geraniin
P. urinaria
Immunomodulatory, antioxidant, and hypotensive
[41, 163]

242
Geraniin
P. virgatus
Antiviral
[94, 143]

242
Geraniin
P. amarus
Hepatoprotection, radioprotective, and anti-HIV
[179–181, 194]

242
Geraniin
P. myrtifolius

[186]

242
Geraniin
P. sellowianus
Antihyperalgesic
[200]

242
Geraniin
P. muellerianus
Wound healing and antimalarial
[169, 202]

242
Geraniin
P. debilis
Antioxidant
[195]

242
Geraniin
P. matsumurae

[196]

242
Geraniin
P. wightianus

[89]

242
Geraniin
P. ussuriensis

[197]

242
Geraniin
P. caroliniensis

[203]

243
Geraniinic acid B
P. amarus

[182]

244
Hippomanin A
P. urinaria
Antiviral
[204]

245
Isocorilagin
P. emblica
Antioxidant and antitumor
[185, 201, 205]

245
Isocorilagin
P. niruri
Cholinesterase inhibition
[206, 207]

246
Isomallotusinin
P. emblica
Antioxidant
[185]

247
Isostrictinin
P. emblica

[208]

247
Isostrictinin
P. urinaria

[209]

248
Mallonin
P. emblica

[184]

249
Mallotusinin
P. emblica
Antioxidant
[210]

249
Mallotusinin
P. myrtifolius

[186]

250
Neochebulagic acid
P. emblica

[184]

251
Phyllanemblinin A
P. emblica

[184]

251
Phyllanemblinin A
P. flexuosus

[211]

252
Phyllanemblinin B
P. emblica

[184]

252
Phyllanemblinin B
P. flexuosus

[211]

253
Phyllanemblinin C
P. emblica

[184]

253
Phyllanemblinin C
P. flexuosus

[211]

254
Phyllanemblinin D
P. emblica

[184]

254
Phyllanemblinin D
P. flexuosus

[211]

255
Phyllanemblinin E
P. emblica

[184]

255
Phyllanemblinin E
P. flexuosus

[211]

256
Phyllanemblinin F
P. emblica

[184]

257
Phyllanthunin
P. emblica

[212]

258
PhyllanthusiinC
P. myrtifolius

[186]

259
PhyllanthusiinD
P. niruri

[176]

259
PhyllanthusiinD
P. amarus
Radioprotective and antioxidant
[178, 181]

260
Phyllanthusiin G
P. urinaria

[213]

261
Phyllanthusiin U
P. urinaria

[167]

262
Pinocembrin-7-O-[3′′-O-galloyl-4′′,6′′-(S)-hexahydroxydiphenoyl-β-D-glucose
P. tenellus

[214]

263
Pinocembrin-7-O-[4′′,6′′-(S)-hexahydroxydiphenoyl-β-D-glucose
P. tenellus

[214]

264
Punicafolin
P. emblica

[184]

265
Putranjivain A
P. emblica

[184]

266
Putranjivain B
P. emblica

[185]

267
Repandusinic acid
P. amarus
Antioxidant
[178, 182]

268
Terchebin
P. niruri

[176]

269
Tercatain
P. emblica

[184]

270
Virganin
P. virgatus

[94]

271
Dimeric procyanidins mono-gallates
P. orbicularis
Antiviral
[53]

272
Dimeric procyanidins-3,3′-di-O-gallates
P. orbicularis
Antiviral
[53]

273
Epicatechin-(4β → 8)-epigallocatechin
P. emblica

[184]

274
Oligomeric procyanidins
P. orbicularis
Antiviral
[53]

275
Oligomeric procyanidins mono-gallates
P. orbicularis
Antiviral
[53]

276
Phyllemtannin
P. emblica
Antitumor
[111]

277
Prodelphinidin B1
P. emblica

[184]

277
Prodelphinidin B1
P. niruri

[215]

277
Prodelphinidin B1
P. sellowianus

[216]

277
Prodelphinidin B1
P. orbicularis

[215]

277
Prodelphinidin B1
P. matsumurae

[217]

278
Prodelphinidin B2
P. emblica

[184]

278
Prodelphinidin B2
P. orbicularis
Antioxidant
[53, 54]

278
Prodelphinidin B2
P. simplex

[170]

278
Prodelphinidin B2
P. matsumurae

[218]

279
Prodelphinidin B-2,3′-O-gallate
P. emblica

[184]

280
5,7-Dihydroxy-4′-methoxyflavonol
P. virgatus

[94]

281
5,3′-Dihydroxy-6,7,4′-trimethoxyflavone
P. niruri

[207]

282
Astragalin
P. urinaria

[141]

282
Astragalin
P. virgatus

[94]

282
Astragalin
P. muellerianus

[169]

283
Avicularin
P. emblica

[219]

284
Galangin 3-O-β-D-glucoside 8-sulfonate
P. virgatus

[94]

285
Isoquercitrin
P. emblica

[201]

285
Isoquercitrin
P. urinaria

[220]

285
Isoquercitrin
P. reticulatus

[192]

285
Isoquercitrin
P. virgatus

[94]

285
Isoquercitrin
P. muellerianus

[169]

286
Kaempferol
P. emblica
Antioxidant
[201]

286
Kaempferol
P. niruri

[79]

286
Kaempferol
P. virgatus

[94]

286
Kaempferol
P. cochinchinensis

[149]

287
Kaempferol-3-O-α-L-(6′′-ethyl)-rhamnopyranoside
P. emblica

[221]

288
Kaempferol-3-O-α-L-(6′′-methyl)-rhamnopyranoside
P. emblica

[221]

289
Kaempferol-3-O-β-D-glucopyranoside
P. emblica
Antioxidant
[201]

290
Kaempferol 8-sulfonate
P. virgatus

[94]

291
Myricitrin
P. virgatus

[94]

292
Quercetin
P. emblica
Antioxidant
[171]

292
Quercetin
P. urinaria

[215]

292
Quercetin
P. virgatus

[94]

292
Quercetin
P. caroliniensis
Anti-inflammatory
[203]

293
Quercetin 3-O-α-L-(2,4-di-O-acetyl) rhamnopyranoside-7-O-α-L-rhamnopyranoside
P. urinaria

[222]

294
Quercetin 3-O-α-L-(3,4-di-O-acetyl) rhamnopyranoside-7-O-α-L-rhamnopyranoside
P. urinaria

[222]

295
Quercetin 3-O-α-L-rhamnopyranoside
P. urinaria

[222]

296
Quercetin-3-O-β-D-glucopyranoside
P. emblica
Antioxidant
[201]

297
Quercetin-3-O-β-D-glucopyranosyl(1 → 4)-α-rhamnopyranoside
P. niruri

[79]

298
Quercetin-3-O-β-D-glucosyl-(1 → 6)-β-D-glucoside
P. virgatus

[94]

299
Quercetin 3-O-β-D-glucopyranosyl-(2 → 1)-O-β-D-xylopyranoside
P. niruri

[223]

300
Quercetin pentaacetate
P. orbicularis

[54]

301
Quercitrin
P. niruri
Antinociceptive
[215, 224]

301
Quercitrin
P. urinaria
Anti-inflammatory
[151, 215]

301
Quercitrin
P. virgatus

[94]

301
Quercitrin
P. sellowianus

[95]

301
Quercitrin
P. muellerianus

[169]

301
Quercitrin
P. orbicularis

[54]

301
Quercitrin
P. ussuriensis

[225]

302
Rhamnocitrin
P. urinaria
Anti-inflammatory
[151]

302
Rhamnocitrin
P. amarus

[179]

302
Rhamnocitrin
P. cochinchinensis

[149]

302
Rhamnocitrin
P. simplex

[170]

303
Rutin
P. niruri
Anti-inflammatory
[224]

303
Rutin
P. urinaria
Anti-inflammatory
[151, 215]

303
Rutin
P. reticulatus

[192]

303
Rutin
P. virgatus

[94]

303
Rutin
P. amarus
Radioprotective and antioxidant
[178, 181]

303
Rutin
P. debilis
Antioxidant
[195]

304
Rutin decaacetate
P. orbicularis

[54]

305
Schaftoside
P. cochinchinensis

[149]

306
Sodium galangin-8-sulfonate
P. virgatus

[94]

307
Sodium galangin-3-O-β-glucoside-8-sulfonate
P. virgatus

[94]

308
Sodium kaempferol-8-sulfonate
P. virgatus

[94]

309
Vicenin-2
P. cochinchinensis

[149]

310
4′-Methoxyscutellarein
P. urinaria

[226]

311
Apigenin
P. amarus

[74]

311
Apigenin
P. orbicularis
Antioxidant
[54]

312
Apigenin-7-O-(6′′-butyryl-β-glucopyranoside)
P. emblica

[227]

312
Apigenin-7-O-(6′′-butyryl-β-glucopyranoside)
P. niruri

[215]

312
Apigenin-7-O-(6′′-butyryl-β-glucopyranoside)
P. urinaria

[215]

313
Demethoxysudachitin (4′,5,7-trihydroxy-6,8-dimethoxyflavone)
P. atropurpureus

[228]

314
Galangin 8-sulfonate
P. virgatus

[94]

315
Luteolin
P. amarus

[74]

315
Luteolin
P. singampattiana

[78]

316
Niruriflavone
P. niruri
Antioxidant
[206]

317
Urinariaflavone
P. urinaria

[141]

318
2-(4-Hydroxyphenyl)-8-(3-methylbut-2-enyl)-chroman-4-one
P. niruri

[23]

319
7-Hydroxyflavanone
P. sellowianus

[168]

320
8-(3-Methyl-but-2-enyl)-2-phenyl chroman-4-one
P. niruri
Antiparasitic
[23]

321
Nirurin
P. niruri

[229]

322
Nirurinetin
P. niruri

[229]

323
(S)-Eriodictyol 7-O-(6′′-O-(E)-β-coumaroyl)-β-D-glucopyranoside
P. emblica

[230]

324
(S)-Eriodictyol 7-O-(6′′-O-galloyl)-β-D-glucopyranoside
P. emblica

[230]

325
(+)-Catechin
P. niruri

[176]

325
(+)-Catechin
P. orbicularis

[53]

326
(−)-Epiafzelechin
P. emblica

[184]

327
(−)-Epicatechin
P. emblica

[184]

327
(−)-Epicatechin
P. niruri

[176]

327
(−)-Epicatechin
P. cochinchinensis

[149]

327
(−)-Epicatechin
P. orbicularis

[53]

328
(−)-Epigallocatechin
P. emblica

[184]

328
(−)-Epigallocatechin
P. niruri

[176]

328
(−)-Epigallocatechin
P. reticulatus

[118]

329
(+)-Gallocatechin
P. emblica

[184]

329
(+)-Gallocatechin
P. niruri

[176]

330
8-(2-Pyrrolidinone-5-yl)-(−)-epicatechin
P. cochinchinensis

[149]

331
5,7-Dimethoxy-3,4′-dihydroxy-3′,8-di-C-prenylflavanone
P. niruri

[231]

332
5,6,8,4′-Tetrahydroxy isoflavone
P. atropurpureus

[228]

333
6-Hydroxy-7,8,2′,3′,4′-pentamethoxyisoflavone
P. niruri

[207]

334
(−)-β-Sitosterol-3-O-β-D-(6-O-palmitoyl) glucopyranoside
P. songboiensis

[65]

335
(3β,22E)-Stigmasta-5,22-diene-3,25-diol
P. urinaria

[73]

336
24-Isopropylcholesterol
P. niruri

[157]

337
5α,6β-Dihydroxysitosterol
P. emblica

[232]

338
5α,6β,7α-Trihydroxysitosterol
P. emblica

[232]

339
6′-(Stigmast-5-en-3-O-β-D-glucopyranosidyl) hexadecanoate
P. emblica

[232]

340
6′-(Stigmast-5-en-7-one-3-O-β-D-glucopyranosidyl) hexadecanoate
P. emblica

[232]

341
7-Ketositosterol
P. emblica

[232]

342
7α-Hydroxysitosterol
P. emblica

[232]

343
7α-Acetoxysitosterol
P. emblica

[232]

344
7β-Ethoxysiterol
P. emblica

[232]

345
Amarosterol A
P. amarus

[233]

346
Amarosterol B
P. amarus

[233]

347
Campesterol
P. sellowianus

[216]

348
Daucosterol
P. emblica

[232]

348
Daucosterol
P. urinaria

[220]

348
Daucosterol
P. amarus

[74]

349
Fraternusterol
P. fraternus

[234]

350
Phyllanthosecosteryl ester
P. fraternus

[234]

351
Phyllanthosterol
P. fraternus

[234]

352
Phyllanthostigmasterol
P. fraternus

[234]

353
Stigmast-4-en-3-one
P. emblica

[232]

354
Stigmast-4-en-3,6-dione
P. emblica

[232]

355
Stigmast-4-en-6β-ol-3-one
P. emblica

[232]

356
Stigmast-4-ene-3β,6α-diol
P. emblica

[232]

357
Stigmast-4,5-en-3-one
P. oxyphyllus

[90]

358
Stigmast-5-en-3-ol, oleate
P. amarus

[74]

359
Stigmasterol
P. urinaria

[97]

359
Stigmasterol
P. sellowianus

[216]

359
Stigmasterol
P. columnaris

[76]

360
Stigmasterol 3-O-β-D-glucoside
P. urinaria

[97]

361
β-Daucosterol
P. emblica
Antioxidant
[171, 212]

362
β-Sitosterol
P. emblica

[100]

362
β-Sitosterol
P. niruri

[157]

362
β-Sitosterol
P. urinaria

[220]

362
β-Sitosterol
P. reticulatus

[77]

362
β-Sitosterol
P. sellowianus

[216]

362
β-Sitosterol
P. muellerianus

[92]

362
β-Sitosterol
P. oxyphyllus

[90]

362
β-Sitosterol
P. fraternus

[72]

362
β-Sitosterol
P. debilis

[135]

362
β-Sitosterol
P. singampattiana

[78]

363
β-Sitosterol-3-O-β-D-glucopyranoside
P. urinaria

[151]

364
14,15-Dihydroallosecurinin-15β-ol
P. discoideus

[148]

365
4-Hydroxysecurinine
P. niruri

[235]

366
4-Methoxydihydronorsecurinine
P. niruri

[235]

367
β-Sitosterol-3-β-D-glucopyranoside
P. singampattiana

[78]

368
4-Methoxynorsecurinine
P. niruri

[236]

369
4-Methoxytetrahydrosecurinine
P. niruri

[235]

370
Allosecurinine
P. niruri

[235]

370
Allosecurinine
P. glaucus

[237]

371
Dihydrosecurinine
P. niruri

[235]

372
Ent-norsecurinine
P. niruri

[238]

373
Epibubbialine
P. niruri

[239]

373
Epibubbialine
P. amarus

[240]

374
Isobubbialine
P. niruri

[215]

374
Isobubbialine
P. urinaria

[215]

374
Isobubbialine
P. amarus

[240]

375
Methyl (2S)-1-[2-(furan-2-yl)-2-oxoethyl-5-oxopyrrolidine-2-carboxylate
P. emblica

[114]

376
Nirurine
P. niruri

[241]

377
Niruroidine
P. niruroides

[242]

378
Nitidine
P. sellowianus

[243]

379
Norsecurinine
P. niruri

[235]

379
Norsecurinine
P. amarus
Antifungal
[240, 244]

379
Norsecurinine
P. simplex

[245]

379
Norsecurinine
P. discoides

[246]

380
Phyllanthine
P. niruri

[236]

380
Phyllanthine
P. amarus

[240]

381
Securinine
P. niruri

[235]

381
Securinine
P. amarus

[240]

381
Securinine
P. glaucus

[237]

382
Securinol A
P. niruri

[235]

383
Securinol B
P. niruri

[235]

384
Simplexine
P. simplex

[245]

385
Tetrahydrosecurinine
P. niruri

[235]

386
Virosecurinine
P. discoides

[247]

387
1,12-Diazacyclodocosane-2,11-dione
P. niruri

[248]

388
3-(3-Methylbut-2-en-1-yl) isoguanine
P. reticulatus

[118]

389
5-Hydroxy-isoquinoline
P. emblica

[249]

390
E,E-2,4-Octadienamide
P. fraternus
Antimalarial
[250]

391
E,Z-2,4-Decadienamide
P. fraternus
Antimalarial
[250]

392
Indole-3-carboxaldehyde
P. virgatus

[94]

393
Indole-3-carboxylic acid
P. virgatus

[131]

394
Phyllanthimide
P. sellowianus

[251]

395
Phyllurine
P. urinaria

[252]

396
(−)-Epicatechin 3-O-gallate
P. niruri

[176]

396
(−)-Epicatechin 3-O-gallate
P. orbicularis
Antiviral
[53]

397
(−)-Epigallocatechin 3-O-gallate
P. emblica

[111]

397
(−)-Epigallocatechin 3-O-gallate
P. niruri

[176]

398
(5RR)-4,6-Dimethoxycarbonyl-5-[2′,3′,4′-trihydroxy-6′-(methoxycarbonyl) phenyl-5,6-dihydro-2H-pyran-2-one
P. reticulatus

[16]

399
1-O-Galloyl-6-O-luteoyl-α-D-glucose
P. niruri
Antimalarial
[223]

400
1-O-Galloyl-β-D-glucose
P. emblica
Antidiabetic and antitumor
[111, 253, 254]

400
1-O-Galloyl-β-D-glucose
P. virgatus

[94]

401
2-(2-Methylbutyryl)phloroglucinol 1-O-(6′′-O-β-D-apiofuranosyl)-β-D-glucopyranoside
P. emblica

[230]

402
2,3,4,5,6-Pentahydroxybenzoic acid
P. urinaria

[255]

403
2,3,5,6-Tetrahydroxybenzyl acetate
P. niruri

[256]

404
2,6-Dimethoxy-4-(2-hydroxyethyl)phenol 1-O-β-D-glucopyranoside
P. emblica

[110]

405
2-Carboxylmethylphenol 1-O-β-D-glucopyranoside
P. emblica

[110]

406
3′′-Hydroxy robustaside A (6′-(3′′,4′′-dihydroxy cinnamoyl) arbutin)
P. atropurpureus

[228]

407
3,3′-Di-O-methylellagic acid
P. reticulatus

[105]

408
3,4,3′-Tri-O-methylellagic acid
P. urinaria

[172]

408
3,4,3′-Tri-O-methylellagic acid
P. reticulatus

[16]

409
3,4,8,9,10-Pentahydroxy-dibenzob,d pyran-6-one
P. emblica

[114]

410
3,4-di-O-Methylellagic acid
P. reticulatus

[105]

411
3,5-Dicaffeoylquinic acid
P. muellerianus

[169]

412
3,5-Dihydroxy-4-methoxybenzoic acid
P. urinaria

[73]

413
3-Ethylgallic acid
P. emblica

[208]

414
3-O-Methylellagic acid 4′-O-α-L-rhamnopyranoside
P. reticulatus

[105]

415
4,4′-Di-O-methylellagic acid
P. reticulatus

[105]

416
4-Hydroxy-3-methoxybenzaldehyde
P. emblica

[114]

417
4-Hydroxy-3-methoxy-benzoic acid
P. amarus

[74]

418
4-O-Caffeoylquinic acid
P. niruri

[257]

419
4-O-Methylellagic acid-3′-α-rhamnoside
P. emblica

[87]

420
4-O-Methylgallic acid
P. polyphyllus
Anti-inflammatory
[126]

421
8,9-Epoxy brevifolin
P. simplex
Hepatoprotective
[258]

422
Bergenin
P. flexuosus

[80]

422
Bergenin
P. wightianus

[89]

423
Brevifolin
P. urinaria

[259]

423
Brevifolin
P. virgatus

[94]

423
Brevifolin
P. simplex
Hepatoprotective
[260]

424
Brevifolin carboxylic acid
P. niruri

[261]

424
Brevifolin carboxylic acid
P. urinaria

[209]

424
Brevifolin carboxylic acid
P. amarus
Antidiabetic
[193]

424
Brevifolin carboxylic acid
P. matsumurae

[196]

425
Caffeoylmalic acid
P. muellerianus

[169]

426
Chebulic acid
P. emblica

[253]

427
Chlorogenic acid
P. sellowianus

[168]

427
Chlorogenic acid
P. muellerianus

[169]

428
Dehydrochebulic acid trimethyl ester
P. urinaria

[73]

429
Di 3,4,5-trihydroxy-phenyl ether
P. atropurpureus

[228]

430
Ellagic acid
P. emblica
Antioxidant
[100, 210]

430
Ellagic acid
P. niruri
Antidiabetic
[202, 261]

430
Ellagic acid
P. urinaria
Antitumor
[220, 262]

430
Ellagic acid
P. reticulatus

[192]

430
Ellagic acid
P. matsumurae

[196]

430
Ellagic acid
P. wightianus

[89]

431
Ethyl brevifolin carboxylate
P. niruri

[261]

431
Ethyl brevifolin carboxylate
P. urinaria

[189]

432
Ethyl gallate
P. emblica
Antitussive
[212, 263]

432
Ethyl gallate
P. myrtifolius

[186]

433
Flavogallonic acid bislactone
P. emblica

[184]

434
Gallic acid
P. emblica
Antiulcer and antioxidant
[210, 264]

434
Gallic acid
P. niruri
Anti-inflammatory
[202, 224]

434
Gallic acid
P. urinaria

[220]

434
Gallic acid
P. virgatus

[94]

434
Gallic acid
P. amarus
Antijaundice
[265]

434
Gallic acid
P. myrtifolius

[186]

434
Gallic acid
P. muellerianus

[169]

434
Gallic acid
P. debilis
Antioxidant
[195]

434
Gallic acid
P. simplex

[170]

434
Gallic acid
P. matsumurae

[196]

434
Gallic acid
P. wightianus

[89]

434
Gallic acid
P. ussuriensis

[225]

435
Gallic acid 3-O-(6′-O-galloyl)-β-D-glucoside
P. emblica

[184]

436
Gallic acid 3-O-β-D-glucoside
P. emblica

[184]

437
Gallic acid 4-methyl ether
P. cochinchinensis

[149]

438
Gallic acid ethyl ester
P. urinaria
Antihyperalgesic
[266]

438
Gallic acid ethyl ester
P. sellowianus

[95]

438
Gallic acid ethyl ester
P. caroliniensis
Anti-inflammatory
[203]

439
Koaburaside
P. cochinchinensis

[149]

440
L-Malic acid 2-O-gallate
P. emblica
Antitumor
[111, 253]

441
Methyl-4-hydroxybenzoate
P. emblica

[114]

442
Methyl brevifolin carboxylate
P. niruri
Hypotensive and antiplatelet
[206, 267, 268]

442
Methyl brevifolin carboxylate
P. urinaria
Antioxidant and anti-inflammatory
[151, 269]

442
Methyl brevifolin carboxylate
P. reticulatus

[192]

442
Methyl brevifolin carboxylate
P. virgatus

[94]

443
Methyl ester dehydrochebulic acid
P. urinaria

[269]

444
Methyl gallate
P. emblica
Antioxidant and antitussive
[187, 263]

444
Methyl gallate
P. urinaria
Antioxidant and anti-inflammatory
[151]

444
Methyl gallate
P. reticulatus

[192]

444
Methyl gallate
P. virgatus

[94]

444
Methyl gallate
P. myrtifolius

[186]

444
Methyl gallate
P. muellerianus

[169]

444
Methyl gallate
P. ussuriensis

[197]

445
Mucic acid 1,4-lactone 2-O-gallate
P. emblica

[253]

446
Mucic acid 1,4-lactone 3,5-di-O-gallate
P. emblica

[253]

447
Mucic acid 1,4-lactone 3-O-gallate
P. emblica
Antioxidant
[185, 253]

448
Mucic acid 1,4-lactone 5-O-gallate
P. emblica

[253]

449
Mucic acid 1,4-lactone 6-methyl ester 2-O-gallate
P. emblica

[253]

450
Mucic acid 1,4-lactone 6-methyl ester 5-O-gallate
P. emblica

[253]

451
Mucic acid 1-methyl ester 2-O-gallate
P. emblica

[253]

452
Mucic acid 2-O-gallate
P. emblica
Antitumor
[111, 253]

453
Mucic acid 3-O-gallate
P. emblica

[270]

454
Mucic acid 6-methyl ester 2-O-gallate
P. emblica

[253]

455
Mucic acid di-methyl ester 2-O-gallate
P. emblica

[253]

456
p-Hydroxybenzaldehyde
P. urinaria

[73]

457
Phloroglucinol
P. ussuriensis

[225]

458
Phyllangin
P. niruri

[256]

459
Phyllanthusin F
P. urinaria

[271]

460
Potassium brevifolin carboxylate
P. virgatus

[94]

461
Protocatechuic acid
P. urinaria

[189]

461
Protocatechuic acid
P. matsumurae

[196]

462
Pyrogallol
P. emblica
Antitumor and anti-inflammatory
[249, 272]

462
Pyrogallol
P. urinaria

[167]

463
Robustaside A
P. atropurpureus
Antitumor
[228]

464
Shikimic acid
P. myrtifolius

[186]

465
Syringaldehyde
P. emblica

[114]

466
Tri-Me dehydrochebulic acid
P. urinaria

[220]

467
Trimethyl-3,4-dehydrochebulate
P. urinaria
Antioxidant and anti-inflammatory
[151]

468
Vanillic acid
P. emblica

[114]

469
(−)-7′-Hydroxydivanillyltetrahydrofuran
P. songboiensis

[65]

470
(+)-Cucurbic acid
P. urinaria

[73]

471
(+)-Methyl cucurbate
P. urinaria

[73]

472
(E)-3-(5′-Hydroperoxy-2,2′-dihydroxy1,1′-biphenyl-4-yl)-2-propenoic acid
P. urinaria

[255]

473
1′S-11-Dehydroxy penicillide
P. emblica

[114]

474
2R-Diethyl malate
P. emblica

[114]

475
3,6′-Di-O-benzoyl-2′-O-acetylsucrose
P. cochinchinensis

[108]

476
3,6′-Di-O-benzoyl-3′-O-acetylsucrose
P. cochinchinensis

[108]

477
3,6′-Di-O-benzoyl-4′-O-acetylsucrose
P. cochinchinensis

[108]

478
3,6′-Di-O-benzoylsucrose
P. cochinchinensis

[108]

479
3,4-Dimethoxyphenyl-β-D-glucopyranoside
P. cochinchinensis

[149]

480
3,4-Dihydroxyphenylpropanol 3-O-β-D-glucopyranoside
P. reticulatus

[118]

481
3,4,5-Trimethoxy-phenyl-β-D-glucopyranoside
P. cochinchinensis

[149]

482
3-O-Benzoyl-6′-O-(E)-cinnamoylsucrose
P. cochinchinensis

[108]

483
4,4,8-Trimethoxy chroman
P. amarus

[273]

484
5-Hydroxymethyl-2-furaldehyde
P. urinaria

[73]

485
4-Hydroxysesamin
P. niruri

[274]

486
5-Hydroxymethylfurfural
P. emblica
Antioxidant
[171]

487
Aquilegiolide
P. anisolobus

[138]

487
Aquilegiolide
P. klotzschianus

[275]

488
Bis(2-ethylicosyl)phthalate
P. muellerianus

[92]

489
Bis(2-ethyloctyl)phthalate
P. muellerianus

[92]

490
Di-O-methylcrenatin
P. cochinchinensis

[149]

491
Byzantionoside B
P. multiflorus

[276]

492
Carthamoside B5
P. reticulatus

[118]

493
Dendranthemoside B
P. urinaria

[141]

494
Hovetrichoside A
P. reticulatus

[118]

495
Isotachioside
P. reticulatus

[118]

496
Menisdaurilide
P. anisolobus

[138]

496
Menisdaurilide
P. klotzschianus

[275]

497
Methyl (1 R,2R,2′Z)-2-(5′-hydroxy-pent-2′-enyl)-3-oxocyclopentaneacetate
P. urinaria

[73]

498
Mucic acid
P. emblica

[277]

499
Mucic acid 1-methyl ester-6-ethyl ester
P. emblica

[114]

500
Penicillide
P. emblica

[114]

501
Phthalic acid bis(2,5-dimethylhexyl) ester
P. urinaria

[99]

502
Phyllanthoid A
P. cochinchinensis
Antitumor
[278]

503
Phyllanthoid B
P. cochinchinensis

[278]

504
Phyllanthurinolactone
P. urinaria

[279]

505
Phyllanthusone
P. fraternus

[121]

506
Phyllester
P. niruri

[157]

507
Purpactin A
P. emblica

[114]

508
Roseoside
P. multiflorus

[276]

509
Succinic acid
P. niruri

[280]

510
Terephthalic acid mono-[2-(4-carboxy-phenoxycarbonyl)-vinyl ester
P. urinaria

[255]

511
Vanilloloside
P. cochinchinensis

[149]

512
Xanthoxyline
P. sellowianus

[281]

3.1. Terpenoids

Terpenoids are the most prevalent chemical class of the genus. About 125 compounds including 69 triterpenoids (1–69), 40 sesquiterpenes (70–109), 11 diterpenoids (110–120), and 5 monoterpenes (121–125) are mainly identified from P. flexuosus, P. reticulatus, P. watsonii, P. emblica, P. acuminatus, and P. veuminatus. Compounds 1–14 are tetracyclic triterpenoids, and compounds 15–69 are pentacyclic triterpenoids. In pentacyclic triterpenoids, compounds 15–36, compounds 37–49, and compounds 50–65 are oleanane type, friedelane type, and lupine type, respectively. Glochidone and lupeol are representatives of lupine type triterpenoids, which were suggested to have antitumor activities and mainly isolated from Phyllanthus species [68, 80, 96].

3.2. Phenylpropanoids

Phenylpropanoids (126–227) have typical C6–C3 constituents, which chiefly involve three groups including lignins, simple phenylpropanoids, and coumarins. 90 lignins (126–215) have been isolated from genus Phyllanthus since 1944. Compounds 126–176 are arylnaphthalene type lignins with a ring caused by the link of C-6 and C-7′. Compounds 177–190 are dibenzylbutane type lignins with two simple phenylpropanoids bounded by C-8 and C-8′. Phyllanthin, which had been studied to the most extent, was considered to be correlated with anti-inflammatory, immunomodulatory, antitumor, and hypotensive activities [127, 144, 163]. Pharmacokinetic studies of retrojusticidin B, a potential anti-HIV compound, had been done. The oral bioavailabilities dissolved in Tween 80 and in corn oil were found to be 22.1 and 33.1%, respectively [152].

3.3. Tannins

Tannins were progressively reported from the genus Phyllanthus since 1992. Hydrolyzable tannins (228–270) are characterized by the presence of one or more galloyl, hexahydroxydiphenoyl (HHDP), and HHDP metabolites attached to a glucopyranose core, which are mainly isolated from P. emblica, P. amarus, P. niruri, and P. urinaria. Compounds 271–279 are condensed tannins, which are the condensation of flavan-3-ols and linked by C-C. A great many condensed tannins were proved to have antiviral activity [53]. Ellagitannins (232–270) are the largest group of hydrolyzable tannins. Corilagin and geraniin are most extensively obtained from this genus and are characteristic compounds of ellagitannins, which exhibited multiple activities such as antioxidant, anti-HIV, antitumor, and antihyperalgesic activities [6, 111, 188, 195, 196, 199, 201, 202].

3.4. Flavonoids

Compounds 281–334 are flavonoids, which mainly contain flavonols (280–309), flavones (310–317), flavonones (318–324), flavan-3-ols (325–330), flavanonols (331), and isoflavone (332-333). Flavan-3-ols are the basic constitution of condensed tannins. Flavonols such as quercetin, quercitrin, and rutin demonstrated anti-inflammatory and antioxidant activities [151, 171, 178, 195, 203, 224].

3.5. Sterols

Until now, thirty sterols (334–363) from Phyllanthus have been reported. All the sterols are phytosterols with a side chain (C8–C10) substitution at C-17, and half of which were isolated from P. emblica.

3.6. Alkaloids

Thirty-two alkaloids (364–395) have been found in genus Phyllanthus, most of which are securinine and securinine-related compounds and mainly distributed in P. niruri. Compounds 390-391 isolated from P. fraternus are amide type alkaloids and exhibited antimalarial potential [250].

3.7. Phenols and Others

Compounds 396–468 belong to phenols, which have one and several phenolic hydroxyl groups. Thirty other constitutions (469–512) have been isolated. Mucic acid (compounds 445–455) and its derivatives (compounds 498-499) can only be found in P. emblica among this genus.

4. Biological Activity

The remarkable traditional uses of genus Phyllanthus lead to the various researches of biological activities, such as antiviral, antioxidant, antidiabetic, anticancer, and immunomodulatory activities. In this section, biological activity researches of the extracts of the plants are highlighted.

4.1. Antiviral Activity

Various Phyllanthus plants were reported to have strong antiviral potential such as anti-HIV, anti-HCV, anti-HSV, and anti-HCMV. The aqueous extract of P. emblica reduced viral load of HIV significantly at the dose of 400 μg/mL [282]. DNA-polymerase and ribonuclease H (RNase H) activities of HIV-1 reverse transcriptase were inhibited by aqueous extract of P. sellowianus with IC₅₀ values of  μg/mL and  μg/mL, respectively [283]. Moreover, methanol extract of P. reticulatus strongly inhibited the activity of RNase H by 99% at the dose of 50 μg/mL [284].

HCV-infected HuH7 cells were used to test the anti-HCV activities of methanolic fraction of P. amarus. The fraction was proved to suppress the replication of HCV monocistronic replicon RNA and HCV H77S viral RNA without toxic effect in host cells. Inhibiting HCV-NS3 protease enzyme and NS5B enzyme may be the main mechanism [285]. Aqueous extract of P. orbicularis revealed inhibition activity against the replication of HCMV, HSV-1, and HSV-2 as well as BHV-1 with EC₅₀ values of 57.7, 28.8, 25.7, and 21.27 μg/mL, respectively. The selectivity indexes (SI) were ranged from 8.7 to 37.6 [286, 287].

Friend murine leukemia virus (FMuLv) induced erythroleukemia in BALB/c mice was relieved by metabolic extract of P. amarus. The extract inhibited leukemic cells from infiltrating into the sinusoidal space, decreased the morbidity of anemia, and improved survival rate of leukemia animals. Besides, the extract induced the upregulation of p53 and p45NFE2 and downregulation of Bcl-2 in the spleen [288].

4.2. Antioxidant Activity

Methanolic and aqueous parts of this genus have remarkable antioxidant activity, which may be correlated with the hydroxyl rich compositions. P. acidus, P. polyphyllus, and P. fraternus showed remarkable hepatoprotective activity against liver toxicity which was induced by acetaminophen, carbon tetrachloride, bromobenzene, and thioacetamide [42, 289–291]. The biochemical parameters as well as antioxidants levels were restored by these parts at the dose of 300 mg/kg. What is more, mitochondrial dysfunction in liver, induced by bromobenzene, was relieved by prior oral administration of aqueous part of P. fraternus at the dose of 100 mg/kg [51, 291].

Antimycin A governed mitochondrial protein degeneration, lipid peroxidation and mitochondrial DNA damage, and H₂O₂ induced membrane damage of Hep3B cells were considerably mitigated by aqueous fraction of P. amarus [164]. Mutagenesis induced by PhIP and 4-ABP and DNA damage induced by γ-ray and UVB were protected by aqueous fraction of P. orbicularis [292–294].

Methanol extract of P. debilis showed strong antioxidant activity when tested by various antioxidant assays including total antioxidant, free radical scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging, and nitric oxide scavenging assays. Besides, further study demonstrated that total phenolic was correlated with antioxidant activity [52]. In addition, hydromethanolic extract of P. virgatus exhibited substantially antioxidant capacity in both DPPH scavenging (IC₅₀ = 30.4 μg/mL) and linoleic acid oxidation inhibiting (84%) method [5].

4.3. Antidiabetic Activity

Twelve herb drugs such as P. emblica, P. reticulatus, P. niruri, P. amarus, P. urinaria, P. acidus, P. debilis, P. virgatus, P. sellowianus, P. rheedii, P. orbicularis, and P. hookeri are traditionally employed for diabetes in many countries. Recent researches about the hypoglycemic effect of Phyllanthus plants were abundant. Streptozotocin- and alloxan-induced diabetic rats were employed for the evaluation of antidiabetic potential of P. emblica, P. niruri, P. reticulatus, P. sellowianus, P. virgatus, and P. simplex [4, 295–299]. After oral administration of these (aqueous, methanol, and ethanol) extracts for 21–45 days, the concentration of blood glucose was significantly reduced, and the effects of P. sellowianus and P. simplex were similar to the glibenclamide group (10 mg/kg). In addition, methanol fraction of P. virgatus considerably inhibited the activity of α-amylase in the noncompetitive pattern with IC₅₀ of  μg/mL [300].

After oral aqueous extract of P. niruri for 28 days, the levels of LPO and MDA were decreased while the concentrations of SOD, CAT, and GPx were increased. After being pretreated with the aqueous fraction of P. sellowianus, hemorheological parameters were ameliorated and red blood cells (RBCs) showed large globular aggregates and agglutination [301].

4.4. Anticancer Activity

Different extracts of the plants have been assessed for anticancer effects and the related mechanisms. Cancer cell lines such as NCI-H1703, MDA-MB-231, HeLa, 143B, PC-3, MCF-7, HepG2, A549, SKOV3, and HT-29 were considerably inhibited by P. emblica, P. urinaria, P. polyphyllus, P. watsonii, and P. pulcher [57, 68, 302–309]. In addition, P. emblica showed no toxicity to normal cells (MRC5). The extracts inhibited growth of cells through fragmentation of DNA and dysfunction of mitochondrial including upregulated mitochondrial fission 1 protein and downregulated optic atrophy type 1 and mitofusin 1 [304]. Moreover, the extracts suppressed the ability of cell invasion, migration, and adhesion. Further researches demonstrated that the fractions induced apoptosis, invasion, and migration through increasing the expression of caspase-3, caspase-7, caspase-8, and p-JNK and decreasing the expression of ERK, p-ERK1/2, JNK, MMP-2, MMP-9, Wnt, NF-κB, Myc/Max, and hypoxia [302, 303, 307].

Ehrlich ascites carcinoma tumor model was used to evaluate the antitumor activity of P. polyphyllus. Oral administration of methanol fraction at the dose of 200 mg/kg could significantly reduce the solid tumor volume. Hematological parameters, protein, packed cellular volume (PCV), and antioxidant enzymes such as LPO, GPx, GST, SOD, and CAT were greatly regulated [57].

4.5. Immunomodulatory Activity

Ethanol extracts of P. urinaria and P. amarus were demonstrated to have inhibitory effects on the chemotaxis of neutrophils and monocytes with IC₅₀ lower than 2.92 μg/mL. In addition, phagocytic activity and CD18 expression of neutrophils and monocytes were downregulated [163].

Oral administration of P. reticulatus extract at the dose of 100 mg/kg demonstrated a significant increase in phagocytic activity, the percentage of neutrophil adhesion, and white blood cell in albino mice [310].

4.6. Analgesic Activity

The extracts of P. corcovadensis, P. niruri, and P. tenellus showed significant reduction in writhing response induced by acetic acid, with ID₅₀ values of 30, 19, and >30 mg/kg, respectively. The late phase of formalin-induced pain could be relieved by P. tenellus with ID₅₀ of 100 mg/kg and both phases of formalin-induced pain could be reduced by P. corcovadensis and P. niruri with ID₅₀ values of 100 and 52 mg/kg, respectively. The analgesic effects could not be antagonized by naloxone [311]. In addition, intraperitoneally given hydroalcoholic extracts of P. amarus, P. orbicularis, and P. fraternus produced a marked analgesic activity by inhibiting acetic acid-induced abdominal constriction, capsaicin-induced neurogenic pain, and late phase of formalin-induced paw licking [312]. The ethanol and aqueous extracts of P. emblica succeeded in inhibiting acetic acid-induced writhing response but failed in the tail-immersion test [313].

4.7. Anti-Inflammatory Activity

In recent years, different inflammatory models such as Freund’s complete adjuvant induced arthritis, carrageenin induced paw edema, and cotton pellet induced granuloma were employed to evaluate the anti-inflammatory effect of Phyllanthus. After receiving the aqueous extract of P. amarus, indexes of arthritis, joint diameter, and paw volume were decreased and thresholds of mechanical hyperalgesia and nociceptive were increased [314]. The ethanol fraction of P. simplex ameliorated the parameters of paw edema and granuloma and substantially inhibited nitric oxide (NO) production [315].

4.8. Antispasmodic Activity

Isolated rabbit jejunum and guinea-pig ileum were employed for the in vitro tests for the antispasmodic effects of P. emblica. Carbachol and K⁺ induced contractions of rabbit jejunum were released by the extract with IC₅₀ values of 0.09 mg/mL and 1.38 mg/mL. The pretreatment of guinea-pig ileum with the extract at 0.3 mg/mL caused a rightward parallel shift in the concentration-response curves of acetylcholine without suppression of the maximum contractile response. Dual blockade of muscarinic receptors and Ca²⁺ channels can explain its antispasmodic activity [316].

4.9. Hypotensive and Hypolipidemic Activity

Aqueous extract of the leaves of P. amarus was found to restrain both force and rate of myocardial contraction and to inhibit the intrinsic myogenic contraction of isolated rat portal vein [317]. Aqueous part of P. reticulatus was effective in releasing total cholesterol, lipid profile, and oxidative stress in hypercholesterolemic albino rats after oral administrated for 45 days at 250 mg/kg [14].

4.10. Wound Healing

Extracts of P. emblica and P. niruri were demonstrated to have wound healing effect. Topical application with P. emblica could promote the proliferation of cells and cross-link of collagen in the full thickness excision wound [318]. Oral administration of P. emblica at the dose of 60 mg/kg showed healing effect against NSAID-induced gastric ulcer through upregulating the concentration of IL-10 and downregulating the levels of TNF-α and IL-1β [319]. After treatment with P. niruri at the dose of 200 mg/kg, 98.8% of wound could be recovered in the excision and incision wound models on the 16th day [320].

4.11. Antimalarial Activity

Malaria is a prevalent disease in many tropical and subtropical countries and folks of these places especially African people employed Phyllanthus as antimalarial agency. Plasmodium falciparum was suppressed by ethyl acetate fraction of P. acidus with IC₅₀ of 9.37 μg/mL, and the SI equals 4.88 for HEp-2 cells and 11.75 for Vero cells [321]. What is more, chloroquine-resistant P. falciparum could be exhibited by P. amarus and P. muellerianus with IC₅₀ values of 11.7 and 9.4 μg/mL, respectively. P. amarus presented protection effect on human RBCs damage caused by the virus [322]. The SI of P. muellerianus was higher than 5.3 for L-6 and MRC-5 cell lines [25, 202].

4.12. Antidepressant Activity

The aqueous extract of P. emblica (200 mg/kg) significantly decreased immobility period in both tail suspension test and forced swim test by decreasing the levels of MAO-A and GABA [323]. In the plus-maze, Hebb-Williams maze, and passive avoidance apparatus test, preparation of P. emblica produced a dose-dependent upgrade in scores. The preparation was also proved to reverse the amnesia induced by diazepam and scopolamine and to reduce the cholinesterase activity and total cholesterol level in brain [324, 325].

4.13. Others

The essential oil fraction of P. muellerianus exhibited strong antibacterial activity against Clostridium sporogenes, Streptococcus mutans, and S. pyogenes with MIC values ranging from 13.5 to 126 μg/mL [326]. Methanol extract of P. acuminatus (100 mg/mL) showed stronger antifungal than Dithane M-45 (10 000-ppm solution) against Pythium ultimum [327].

Aqueous extract of P. acidus was proved to regulate electrolyte transport in cystic fibrosis airways by increasing the intracellular levels of cAMP and Ca²⁺, stimulating basolateral K⁺ channels, and activating and redistributing cellular localization of cystic fibrosis transmembrane conductance regulator [328].

Eight hours after being treated with the aqueous extract of P. sellowianus at a dose of 400 mg/kg, urine output of test animals was decreased from 2.59 to 3.69 mL/100 g [329].

5. Clinical Studies

The extracts of P. niruri were proved to have immunomodulatory effect and played a crucial role in treating pulmonary tuberculosis and vaginal candidiasis as well as varicella. In patients with pulmonary tuberculosis, after oral administration of P. niruri 50 mg/mL for 2–6 months, the level of IL-10 was decreased and the levels of plasma IFN-γ and TNF-α were significantly increased. After 1-month treatment, the increase of the ratio of CD4⁺/CD8⁺ was observed. In the vaginal candidiasis patients, after receiving P. niruri 100 mg/mL for 1–3 months, the levels of IFN-γ and IL-12 were elevated. As for varicella patients, the number of papules and the number crusts were decreased after treatment with the extract at the dose of 5 mg/mL [330].

Clinical studies of P. niruri in Brazil had been finished, from which the P. niruri showed beneficial effects on the treatment of urolithiasis. After 3-month treatment, calculi elimination was increased. Furthermore, urinary calcium excretion and residual stone fragments after lithotripsy were decreased. Toxic effects on kidney, cardiovascular, and nervous systems were not found [331].

In China, the clinical study of P. urinaria in treating chronic hepatitis B with 140 patients was well established. The results indicated that, after treatment with P. urinaria capsule for 3 months or 2 years, especially in the long term, the recovery rate in the index of HBV-DNA and HBeAg was 88.2% and 52.5%, respectively. Once the treatment stopped, the recurrence rate was 10.4% to 13.4% [332].

6. Toxicity Studies

After given aqueous leaf extract of P. niruri at the dose of 2000 mg/mL, no acute toxicity was observed at the levels of bilirubin, ALT, AST, total protein, albumin, globulin, ALP, GGT, urea, creatinine, full blood count, and hemoglobin [333]. After being treated with ethanol extract of P. niruri over a period of 90 days at doses of 30 and 300 mg/kg, the rats showed no genotoxic effect at the test of PCE/NCE ratio [334]. Reproductive toxicity of P. niruri was tested using estrogen values, progesterone values, and testosterone levels. The estrogen and progesterone levels increased more than 1.5-fold above the control group after receiving 50 and 500 mg/kg aqueous leaf extract for 90 days, which reminded us of the cytotoxic of male antifertility properties [335].

Nephrotoxicity including interstitial oedema and tubular necrosis were detected after receiving 400 and 800 mg/kg of aqueous extract from P. amarus for 30 days [336]. The test animals were given 800 and 1600 mg/kg of the aqueous extract of P. amarus for 10 days, and significant pathological changes were found in the liver, kidney, and testis. The frequency of MNPCE, sperm abnormalities, total white blood cell, and lymphocyte counts were significantly increased, which suggested the genetic and systemic toxicity of P. amarus [337]. In addition, aqueous, methanolic, and hydromethanolic extracts of P. amarus (400 mg/kg) reduced locomotor activity and showed CNS depressant effect [338].

The LD₅₀ of ethanolic extract from P. fraternus was 1125 mg/kg in the toxicity test. When the rats received the extract at doses of 400 mg/kg for 7 days, no toxicity was detected in liver and kidney [339]. Hydroethanolic extract P. fraternus showed the quick onset and long duration of reduction of locomotor activity at the dose of 400 mg/kg [338].

7. Conclusion

514 compounds have been isolated from different species of Phyllanthus, including 126 terpenoids, 102 phenylpropanoids, 73 phenols, 54 flavonoids, 53 tannins, 33 sterols, 31 alkaloids, and a number of other compositions. Their wide range of biological activities such as antiviral, antioxidant, antidiabetic, anticancer, anti-inflammatory, hypolipidemic, immunomodulatory, and antidepressant activities are tested using polar solvents (water, methanol, and ethanol) extracts. These extracts are considered rich in phenols, flavonoids, and tannins, which may exhibit antioxidant activity in different degree due to their hydroxyl [340]. Consequently, most bioactivities of Phyllanthus may be correlated with the hydroxyl rich compounds.

In recent years, the traditional uses of Phyllanthus had been partly confirmed, and more evidences such as pharmacological researches and clinical studies are urgently needed to be taken. Further studies of phytochemical discovery and subsequent screenings are necessary to be taken to extend the use of Phyllanthus and to develop leading compound.

Competing Interests

The authors declare that they have no competing interests.

Acknowledgments

This project was supported by the National Natural Science Foundation of China (81274187 and 81274006) and Transformation and industrialization of Science and Technology Achievements, “New Drug AIKEXIN Development Research for the Treatment of AIDS.”

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