Journal of Chemistry
Volume 2020 (2020), Article ID 9375619, 23 pages
https://doi.org/10.1155/2020/9375619

Review Article

Review of Compounds and Pharmacological Effects of Delphinium

Sitan Chen,¹ Lijun Meng,¹ Fatma M. El-Demerdash,2,3 Li Zhou,1,2 Syed Arif Hussian Rizvi,2,4 Lili Cui,1,5 and Wenyi Kang1,2,5,6

¹National R & D Center for Edible Fungus Processing Technology, Henan University, Kaifeng 475004, China
²Joint International Research Laboratory of Food & Medicine Resource Function, Henan University, Kaifeng 475004, Henan Province, China
³Department of Environmental Studies Institute of Graduate Studies and Research Alexandria University Alexandria, Alexandria, Egypt
⁴Institute of Plant and Environmental Protection (IPEP), National Agriculture Research Center (NARC) Islamabad, Islamabad, Pakistan
⁵Functional Food Engineering Technology Research Center, Kaifeng 475004, Henan Province, China
⁶Kaifeng Key Laboratory of Functional Components in Health Food, Kaifeng 475004, Henan, China

Correspondence should be addressed to Lili Cui; cuill@vip.henu.edu.cn and Wenyi Kang; kangweny@hotmail.com

Received 15 June 2020; Revised 21 August 2020; Accepted 2 September 2020; Published 21 September 2020

Academic Editor: Pedro M. Mancini

Copyright © 2020 Sitan Chen 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.

Plants of Delphinium are herbal medicine used in the Tibet region with whole grass as a drug, which have the effects of analgesic, antibacterial, antipyretic, and anticancer. The main bioactive compounds are alkaloids, flavonoids, and sterols. This review summarized the compounds and pharmacological effects of Delphinium and provides a reference for further research on Delphinium.

1. Introduction

Delphinium of the Ranunculaceae family is widely distributed in the North temperate zone, with about 350 species worldwide. 173 species (150 endemic) of Delphinium are distributed in China [1]. Delphinium is composed of subgen. Delphinastrum, subgen. Delphinium, and subgen. Oligophyllon, in the world, of which subgen. Delphinastrum has the most species [2]. In China, there are 18 species of Delphinium used as folk medicine, which are used to treat bruises, rheumatism, toothache, and enteritis. In addition, four species of Delphinium can be used as soil pesticides for their effects of killing lice, mosquitoes, and fly larvae [3]. The main compounds of Delphinium are diterpenoid alkaloids, and most of them have physiological activities [4]. In addition, Delphinium also contains chemical constituents such as flavonoids and sterols. In recent years, with the development of analysis methods and increasing focus on Delphinium, more and more chemical constituents and pharmacological activities of Delphinium had been researched. In this paper, the chemical constituents and pharmacological effects of Delphinium were reviewed in order to improve the development and utilization of the Delphinium resources.

2. Chemical Constituents

According to the research studies, the alkaloids are the main constituents with physiological activities in Delphinium and diterpenoid alkaloids are the most characteristic constituents with toxicity [5]. In addition, flavonoids and sterols are also present [6].

2.1. Diterpenoid Alkaloids

Diterpenoid alkaloids are derived from the amination of tetracycline diterpenoids or pentacyclic diterpenoids to heterocyclic systems containing β-aminoethanol, methylamine, or ethylamine nitrogen atoms [7]. There are abundant diterpenoid alkaloids in Delphinium, which can be classified into C-18 diterpenoid alkaloids, C-19 diterpenoid alkaloids, and C-20 diterpenoid alkaloids according to the carbon skeleton configuration [5]. Characteristic quaternary carbon signal and substituent signal are important information to distinguish different diterpene alkaloids.

C-18 diterpenoid alkaloids are the diterpenoid alkaloids whose C-18 are mostly substituted by C(4)-H/OH or the ester group, and a few of them contain 3,4-epoxide. According to the oxygen-containing groups on C-7, they can be sorted into two types (Figure 1): lappacinitine-type and ranaconitine-type, and C-7 of the ranaconitine-type has an oxygen-substituent group. C₄ (δc 30–40, s), C₈ (δc 73–84, s), and C₁₁ (δc 47–55, s) are C-18’s characteristic signals [8]. Characteristic signal of the ranaconitine-type on C-7 is at δc 91–93 (s), and the characteristic signal of the lappacinitine-type on C-7 is at δc 45–48 (s).

Figure 1: The skeleton structures of C-18 diterpene alkaloids.

Most C-19 diterpene alkaloids are natural diterpenoid alkaloids and belong to pentacyclic diterpene alkaloids. According to the oxygen-containing groups on C-7 and the difference of skeleton, they can be classified into six types (Figure 2): lycoctonine-type, aconitine-type, 7,17-seco type (δc8 137–139, s; δc10 48–49, s; δc14 216–218, s), lactone-type, pyro-type (δc8,15 146–147, s), and rearranged-type (δc8 40–55, s; δc10 44–45, s; δc14 210–211, s) [8]. The majority of C-19 diterpenoid alkaloids are lycoctonine-type and aconitine-type. The differences between them are that C-7 (δc 87–93) of the lycoctonine-type has an oxygen-substituent group and others do not have [9]. And, C-19 diterpenoid alkaloids isolated from Delphinium are mostly lycoctonine-type [10]. C-19 diterpene alkaloids contain oxygen substituent (δH3.0–5.0; δc 70–90) and methoxy substituent (δH3.2–3.6, s; δc 55–59, q). C₄ (δc 37–41, s), C₈, and C₁₁ (δc 47–51, s) are C-19 characteristic signals [8].

Figure 2: The skeleton structures of C-19 diterpene alkaloids.

C-20 diterpenoid alkaloids are tetracyclic diterpenes with a carbon skeleton of 20 carbon atoms and have a trans-a-ring alkaloid that connects C-19 to C-20 in N-ethyl or N-β-hydroxyl ethyl [11]. Compared with C-18 and C-19, C-20 diterpene alkaloid skeletons are complex, and most of them have exocyclic double bond structures. At present, 22 types of C-20 diterpenoid alkaloids were found [12]. The C-20 diterpenoid alkaloids isolated from Delphinium mainly belong to atisine-type, veatchine-type, hetisine-type, hetidine-type, denudatine-type, delnudine-type [13], and vakognavine-type (Figure 3) [14, 15]. C₄ (δc 30–40, s), C₈ (δc 30–50, s), C₁₁ (δc 30–40, s), C₁₆ (δc-143, s), and C₁₇ (δH-5, brs; δc-110, t) are C-20’s characteristic signals. C₆ (δc 17–20, s), C₇ (δc 31–35, s), C₁₀ (δc 36–40, s), C₁₄ (δc 25–26, s), and C₂₀ (δc 50–54, s) are characteristic signals of atisine-type, and C₆ (δc −24, s), C₇ (δc −43, s), C₁₀ (δc 48–51, s), C₁₄ (δc 36–39, s), and C₂₀ (δc −69, s) are characteristic signals of hetidine-type [16].

Figure 3: The skeleton structures of C-20 diterpene alkaloids.

At present, 155 alkaloids were isolated from Delphinium, and the details are shown in Tables 1–3 and Figures 4–6. Based on the references listed in Tables 1–3, it can be summarized that D. anthriscifolium varietas and D. elatum and its varietas have been further studied in chemistry.

Table 1: C-18 diterpenoid alkaloids isolated from Delphinium.

No.
Compound
Type
Source
Molecular formula
Reference

1
Anthriscifolcine A
Ranaconitine
D. anthriscifolium var. savatieri
C₂₆H₃₈NO₇
[17]

2
Anthriscifolcine B
Ranaconitine
D. anthriscifolium var. savatieri
C₂₄H₃₇NO₆
[17]

3
Anthriscifolcine C
Ranaconitine
D. anthriscifolium var. savatieri
C₂₅H₃₇NO₇
[17]

4
Anthriscifolcine D
Ranaconitine
D. anthriscifolium var. savatieri
C₂₆H₃₉NO₇
[17]

5
Anthriscifolcine E
Ranaconitine
D. anthriscifolium var. savatieri
C₂₄H₃₇NO₆
[17]

6
Anthriscifolcine F
Ranaconitine
D. anthriscifolium var. savatieri
C₂₅H₃₇NO₈
[18]

7
Anthriscifolcine G
Ranaconitine
D. anthriscifolium var. savatieri
C₂₅H₃₇NO₇
[18]

8
Naviconine
Lappacinitine
D. naviculare var. lasiocarpum W. T. Wang.
C₃₁H₄₀N₂O₉
[19]

9
Anthriscifolcone A
Ranaconitine
D. anthriscifolium var. majus
C₂₇H₃₉NO₈
[20]

10
Anthriscifolcone B
Ranaconitine
D. anthriscifolium var. majus
C₂₃H₃₃NO₇
[20]

11
Grandifline A
Ranaconitine
D. grandiflorum Linn
C₂₂H₃₃NO₇
[21]

12
Tuguaconitine
Ranaconitine
D. grandiflorum
C₂₃H₃₅NO₇
[22]

13
Linearilin
Ranaconitine
D. linearilobum (Trautv.) N. Busch
C₂₄H₃₉NO₈
[23]

14
Anthriscifoltine A
Ranaconitine
D. anthriscifolium var. majus
C₃₀H₄₅NO₉
[24]

15
Anthriscifoltine B
Ranaconitine
D. anthriscifolium var. majus
C₂₈H₄₃NO₈
[24]

16
Anthriscifoltine C
Ranaconitine
D. anthriscifolium var. majus
C₂₉H₄₃NO₉
[25]

17
Anthriscifoltine D
Ranaconitine
D. anthriscifolium var. majus
C₃₂H₄₁NO₉
[25]

18
Anthriscifoltine E
Ranaconitine
D. anthriscifolium var. majus
C₂₅H₃₅NO₈
[25]

19
Anthriscifoltine F
Ranaconitine
D. anthriscifolium var. majus
C₂₃H₃₃NO₇
[25]

20
Anthriscifoltine G
Ranaconitine
D. anthriscifolium var. majus
C₂₃H₃₁NO₇
[25]

Table 2: C-19 diterpenoid alkaloids isolated from Delphinium.

No.
Compound
Type
Source
Molecular formula
Reference

21
Anthriscifoldine A
Lycoctonine
D. anthriscifolium var. savatieri
C₂₅H₃₇NO₇
[17]

22
Anthriscifoldine B
Lycoctonine
D. anthriscifolium var. savatieri
C₂₅H₃₉NO₇
[17]

23
Anthriscifoldine C
Lycoctonine
D. anthriscifolium var. savatieri
C₂₇H₄₁NO₇
[17]

24
Naviculine
Lycoctonine
D. naviculare var. lasiocarpum W. T. Wang.
C₂₆H₄₂NO₇⁺
[19]

25
Naviconitine
Aconitine
D. naviculare var. lasiocarpum W. T. Wang.
C₃₄H₄₆N₂O₉
[19]

26
Grandifline B
Lycoctonine
D. grandiflorum Linn
C₂₅H₃₉NO₈
[21]

27
Grandifline C
Lycoctonine
D. grandiflorum Linn
C₂₅H₄₀NO₇⁺
[21]

28
Olivimine
Lycoctonine
D. grandiflorum
C₂₄H₃₇NO₇
[22]

29
Hohenackeridine
Lycoctonine
D. grandiflorum
C₂₂H₃₁NO₇
[22]

30
14-O-Methyldelphinifoline
Lycoctonine
D. grandiflorum
C₂₄H₃₉NO₇
[22]

31
N-Deethyldelphatine
Lycoctonine
D. grandiflorum
C₂₄H₃₉NO₇
[22]

32
Browniine
Lycoctonine
D. grandiflorum
C₂₅H₄₁NO₇
[22]

33
14-Dehydrobrowniine
Lycoctonine
D. grandiflorum
C₂₅H₃₉NO₇
[22]

34
Linearilobin
Aconitine
D. linearilobum (Trautv.) N. Busch
C₃₇H₄₆N₂O₉
[23]

35
Melpheline
Lycoctonine
D. elatum
C₂₄H₃₇NO₆
[26]

36
19-Oxoisodelpheline
Lycoctonine
D. elatum
C₂₅H₃₇NO₇
[26]

37
N-Deethyl-19-oxoisodelpheline
Lycoctonine
D. elatum
C₂₃H₃₃NO₇
[26]

38
N-Deethyl-19-oxodelpheline
Lycoctonine
D. elatum
C₂₃H₃₃NO₇
[26]

39
N-Formyl-4,19-secopacinine
Lycoctonine
D. elatum cv. Pacific Giant
C₂₅H₃₇NO₇
[27]

40
Iminoisodelpheline
Lycoctonine
D. elatum cv. Pacific Giant
C₂₃H₃₃NO₆
[27]

41
Iminodelpheline
Lycoctonine
D. elatum cv. Pacific Giant
C₂₃H₃₃NO₆
[27]

42
Iminopaciline
Lycoctonine
D. elatum cv. Pacific Giant
C₂₄H₃₅NO₆
[27]

43
6-Dehydroeladine
Lycoctonine
D. elatum cv. Pacific Giant
C₂₄H₃₅NO₆
[27]

44
Elapacidine
Lycoctonine
D. elatum cv. Pacific Giant
C₂₄H₃₇NO₆
[27]

45
Yunnanensine A
Rearranged-type
D. yunnanense
C₃₇H₄₈N₂O₉
[28]

46
Iliensine A
Lycoctonine
D. iliense
C₄₀H₅₅NO₁₄
[29]

47
Iliensine B
Lycoctonine
D. iliense
C₂₆H₄₁NO₈
[29]

48
Pseudophnine A
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₂₅H₄₀NO₇⁺
[30]

49
Pseudophnine B
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₂₄H₃₈NO₇⁺
[30]

50
Pseudophnine C
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₂₇H₄₂NO₇⁺
[30]

51
Pseudophnine D
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₂₆H₄₀NO₇⁺
[30]

52
Pseudorenines A
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₃₉H₅₃N₂O₁₁⁺
[30]

53
Pseudorenines B
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₃₉H₅₃N₂O₁₁⁺
[30]

54
Pseudonidine A
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₂₄H₃₅NO₇
[30]

55
Pseudonidine B
Lycoctonine
D. pseudoaemulans C. Y. Yang et B. Wang
C₂₉H₄₅NO₈
[30]

56
Navicularine
Lycoctonine
D. naviculare var. lasiocarpum
C₂₇H₄₃NO₈
[31]

57
Shawurensine
Lycoctonine
D. shawurense W. T. Wang
C₃₇H₅₂N₂O₁₁
[32]

58
Sharwuphinine B
Lycoctonine
D. shawurense W. T. Wang
C₂₆H₄₀NO₇⁺
[33]

59
Ajacisine A
Lycoctonine
D. ajacis L.
C₃₁H₄₄N₂O₉
[34]

60
Ajacisine B
Lycoctonine
D. ajacis L.
C₃₂H₄₆N₂O₉
[34]

61
Ajacisine C
Lycoctonine
D. ajacis L.
C₃₁H₄₂N₂O₈
[34]

62
Ajacisine D
Lycoctonine
D. ajacis L.
C₃₀H₄₂N₂O₈
[34]

63
Ajacisine E
Lycoctonine
D. ajacis L.
C₃₀H₄₂N₂O₈
[34]

64
Caerudelphinine A
Lycoctonine
D. caeruleum Jacq.ex Camb
C₂₅H₃₉NO₈
[35]

65
Grandiflodine B
Lycoctonine
D. grandiflorum
C₃₃H₄₈N₂O₁₀
[36]

66
Majusine A
Lycoctonine
D. majus W. T. Wang
C₃₂H₄₄N₂O₉
[37]

67
Majusine B
Lycoctonine
D. majus W. T. Wang
C₂₄H₃₇NO₆
[37]

68
Majusine C
Lycoctonine
D. majus W. T. Wang
C₂₆H₃₇NO₈
[37]

69
Davidisine A
Lycoctonine
D. davidii Franch.
C₂₃H₃₇NO₇
[38]

70
Davidisine B
Lycoctonine
D. davidii Franch.
C₂₄H₃₇NO₈
[38]

71
Laxicymine 1
Lycoctonine
D. laxicymosum var. pilostachyum W. T. Wang
C₂₄H₃₅NO₇
[39]

72
Laxicymisine 2
Lycoctonine
D. laxicymosum var. pilostachyum W. T. Wang
C₂₄H₃₇NO₇
[39]

73
Laxicyminine 3
Lycoctonine
D. laxicymosum var. pilostachyum W. T. Wang
C₂₄H₃₅NO₆
[39]

74
Tiantaishansine
Lycoctonine
D. tiantaishanense W. J. Zhang et G. H. Chen
C₂₂H₃₃NO₇
[40]

75
Tiantaishannine
Lycoctonine
D. tiantaishanense W. J. Zhang et G. H. Chen
C₂₆H₃₉NO₇
[40]

76
Tiantaishanmine
Lycoctonine
D. tiantaishanense W. J. Zhang et G. H. Chen
C₂₅H₃₅NO₇
[40]

77
Trifoliolasine A
Lycoctonine
D. trifoliolatum Finet et Gagnep
C₃₅H₅₀N₂O₉
[41]

78
Trifoliolasine B
Lycoctonine
D. trifoliolatum Finet et Gagnep
C₃₆H₅₂N₂O₉
[41]

79
Trifoliolasine C
Lycoctonine
D. trifoliolatum Finet et Gagnep
C₄₀H₅₇N₃O₁₁
[41]

80
14-Demethyl-14-isobutyrylanhweidelphinine
Lycoctonine
D. pentagynum Lam.
C₃₈H₄₈N₂O₁₁
[42]

81
14-Demethyl-14-acetylanhweidelphinine
Lycoctonine
D. pentagynum Lam.
C₃₆H₄₄N₂O₁₁
[42]

82
Giraldine G
Lycoctonine
D. giraldii
C₄₀H₅₇N₃O₁₁
[43]

83
Giraldine H
Lycoctonine
D. giraldii
C₄₁H₅₉N₃O₁₁
[43]

84
Giraldine I
Aconitine
D. giraldii
C₂₂H₃₅NO₃
[43]

85
Giraldine D
Lycoctonine
D. giraldii
C₂₄H₃₇NO₆
[44]

86
Giraldine E
Lycoctonine
D. giraldii
C₂₅H₃₉NO₇
[44]

87
Giraldine F
Lycoctonine
D. giraldii
C₂₃H₃₃NO₆
[44]

88
Campylocine
Lycoctonine
D. campylocentrum Maxim.
C₂₅H₃₇NO₇
[45]

89
Campylotine
Lycoctonine
D. campylocentrum Maxim.
C₂₄H₃₇NO₇
[45]

90
Davidiisine A
Lycoctonine
D. davidii Franch
C₂₃H₃₇NO₇
[46]

91
Davidiisine B
Lycoctonine
D. davidii Franch
C₂₄H₃₇NO₈
[46]

92
Ajadelphine
Lycoctonine
D. honanense var. piliteram W. T. Wang
C₂₅H₃₉NO₇
[47]

93
Aconine
Aconitine
D. honanense var. piliteram W. T. Wang
C₂₅H₄₁NO₉
[47]

94
Siwanine E
Lycoctonine
D. honanense var. piliteram W. T. Wang
C₂₈H₃₉NO₉
[47]

95
Grandiflorine III
Aconitine
D. grandiflorum L.
C₂₆H₃₉NO₉
[48]

96
Isotalatizidine
Aconitine
D. grandiflorum L.
C₂₃H₃₇NO₅
[48]

97
14-O-Methyl isotalatizidine
Aconitine
D. grandiflorum L.
C₂₄H₃₉NO₅
[48]

98
Anthranoyllycoctonine
Lycoctonine
D. grandiflorum L.
C₃₂H₄₆N₂O₈
[48]

99
Deoxylycoctonine
Lycoctonine
D. grandiflorum L.
C₂₆H₄₃NO₆
[48]

100
Umbrosine
Lycoctonine
D. grandiflorum L.
C₂₄H₃₉NO₆
[48]

101
Anthriscifolrine A
Lycoctonine
D. anthriscifolium var. majus
C₂₅H₃₇NO₆
[49]

102
Anthriscifolrine B
Lycoctonine
D. anthriscifolium var. majus
C₂₇H₄₁NO₈
[49]

103
Anthriscifolrine C
Lycoctonine
D. anthriscifolium var. majus
C₂₇H₄₁NO₉
[49]

104
Anthriscifolrine D
Lycoctonine
D. anthriscifolium var. majus
C₂₇H₃₉NO₉
[49]

105
Anthriscifolrine E
Lycoctonine
D. anthriscifolium var. majus
C₂₆H₃₉NO₈
[49]

106
Anthriscifolrine F
Lycoctonine
D. anthriscifolium var. majus
C₂₅H₃₉NO₇
[49]

107
Tianshanisine A
Lycoctonine
D. tianshanicum W. T. Wang
C₃₀H₄₁NO₆
[50]

108
Tianshanisine B
Lycoctonine
D. tianshanicum W. T. Wang
C₂₃H₃₇NO₅
[50]

109
Tianshanisine C
Lycoctonine
D. tianshanicum W. T. Wang
C₂₅H₃₉NO₆
[50]

110
Tianshanisine D
Lycoctonine
D. tianshanicum W. T. Wang
C₂₃H₃₅NO₅
[50]

111
Tianshanisine E
Lycoctonine
D. tianshanicum W. T. Wang
C₂₃H₃₅NO₇
[50]

112
Elapacigine
Lycoctonine
Delphinium elatum cv. Pacific Giant
C₂₃H₃₁NO₆
[51]

113
N-Deethyl-N-formylpaciline
Lycoctonine
Delphinium elatum cv. Pacific Giant
C₂₅H₃₇NO₇
[51]

114
N-Deethyl-N-formylpacinine
Lycoctonine
Delphinium elatum cv. Pacific Giant
C₂₄H₃₃NO₇
[51]

115
N-Formyl-4,19-secoyunnadelphinine
Lycoctonine
Delphinium elatum cv. Pacific Giant
C₂₄H₃₅NO₇
[51]

Table 3: C-20 diterpenoid alkaloids isolated from Delphinium.

No.
Compound
Type
Source
Molecular formula
Reference

116
Yunnanensine B
Hetisine
D. yunnanense
C₂₈H₃₇NO₇
[28]

117
Yunnanensine C
Hetisine
D. yunnanense
C₂₆H₃₅NO₆
[28]

118
Grandiflodine A
Hetisine
D. grandiflorum
C₂₂H₂₈N₂O₃
[36]

119
Majusimine A
Vakognavine
D. majus W. T. Wang
C₄₅H₄₇NO₁₅
[37]

120
Majusimine B
Vakognavine
D. majus W. T. Wang
C₄₃H₄₅NO₁₄
[37]

121
Majusimine C
Vakognavine
D. majus W. T. Wang
C₄₁H₄₃NO₁₃
[37]

122
Majusimine D
Vakognavine
D. majus W. T. Wang
C₃₄H₃₇NO₁₂
[37]

123
Majusidine A
Hetisine
D. majus W. T. Wang
C₂₂H₂₉NO₅
[37]

124
Majusidine B
Hetisine
D. majus W. T. Wang
C₂₅H₃₃NO₄
[37]

125
Tiantaishandine
Hetisine
D. tiantaishanense W. J. Zhang et G. H. Chen
C₂₉H₃₃NO₅
[40]

126
2-Dehydrodeacetylhetero phylloidine
Hetidine
D. pentagynum Lam.
C₂₁H₂₅NO₃
[42]

127
Davidiisine C
Hetidine
D. davidii Franch
C₂₁H₃₃NO₄
[46]

128
12-Epinapelline
Veatchine
D. honanense var. piliteram W. T. Wang
C₂₂H₃₃NO₃
[47]

129
Anthriscifolsine B
Hetisine
D. anthriscifolium var. majus
C₂₄H₃₁NO₇
[49]

130
Anthriscifolsine C
Hetisine
D. anthriscifolium var. majus
C₃₀H₄₃NO₇
[49]

131
Anthriscifolmine A
Denudatine
D. anthriscifolium var. savatieri
C₂₅H₃₇NO₅
[52]

132
Anthriscifolmine B
Denudatine
D. anthriscifolium var. savatieri
C₂₅H₃₇NO₆
[52]

133
Anthriscifolmine C
Hetisine
D. anthriscifolium var. savatieri
C₂₉H₃₁NO₇
[52]

134
Trichodelphinines A
Hetisine
D. tichophorum Franch
C₂₆H₃₅NO₅
[53]

135
Trichodelphinines B
Hetisine
D. tichophorum Franch
C₂₄H₃₃NO₄
[53]

136
Trichodelphinines C
Hetisine
D. tichophorum Franch
C₂₇H₃₇NO₅
[53]

137
Trichodelphinines D
Hetisine
D. tichophorum Franch
C₂₄H₃₁NO₅
[53]

138
Trichodelphinines E
Hetisine
D. tichophorum Franch
C₂₆H₃₃NO₅
[53]

139
Trichodelphinines F
Delnudine
D. tichophorum Franch
C₂₈H₃₃NO₄
[53]

140
Flexiosine
Hetisine
D. flexuosum M. Bieb.
C₃₆H₄₃NO₉
[54]

141
Tatsienenseine A
Vakognavine
D. tatsienense Franch
C₄₃H₄₅NO₁₃
[55]

142
Tatsienenseine B
Hetisine
D. tatsienense Franch
C₂₄H₃₁NO₄
[55]

143
Tatsienenseine C
Hetisine
D. tatsienense Franch
C₂₄H₃₁NO₃
[55]

144
13-(2-Methyl butyryl) azitine
Atisine
D. scabriflorum
C₂₅H₃₇NO₃
[56]

145
Tatsienensine
Hetisine
D. tatsienense
C₁₉H₂₅NO₂
[57]

Figure 4: C-18 diterpenoid alkaloids isolated from Delphinium.

Figure 5: C-19 diterpenoid alkaloids isolated from Delphinium.

Figure 6: C-20 diterpenoid alkaloids isolated from Delphinium.

2.2. Amide Alkaloids

The typical groups of amide alkaloids are acyl groups. 9 amide alkaloids were isolated from Delphinium, and the details are shown in Table 4 and Figure 7.

Table 4: Amide alkaloids isolated from Delphinium.

No.
Compound
Type
Source
Molecular formula
Reference

146
Benzoic acid 2-[(4-methoxy-2-methyl-1,4-dioxobutyl) amino]-methyl ester
Amide
D. grandiflorum Linn
C₁₄H₁₇NO₅
[21]

147
N-Cinnamoyl-2-phenylethylamine
Amide
D. grandiflorum L.
C₁₇H₁₇NO
[48]

148
Delamide A
Amide
D. brunonianum
C₁₃H₁₃NO₄
[58]

149
Delamide B
Amide
D. brunonianum
C₁₄H₁₇NO₆
[58]

150
Delamide C
Amide
D. brunonianum
C₁₃H₁₅NO₅
[58]

151
Delamide D
Amide
D. brunonianum
C₁₃H₁₅NO₅
[58]

152
Delamide E
Amide
D. brunonianum
C₁₃H₁₅NO₅
[58]

153
Benzoic,4-[(3,4-dimethoxybenzoyl) amino]-3-hydroxy-methyl ester
Amide
D. brunonianum Royle
C₁₇H₁₇NO₆
[59]

154
Benzoic acid 2-[(4-methoxy-3-methyl-1,4-dioxobutyl) amino]-methyl ester
Amide
D. brunonianum Royle
C₁₄H₁₇NO₅
[59]

Figure 7: Amide alkaloids isolated from Delphinium.

2.3. Other Alkaloids

Except diterpene alkaloids and amide alkaloids, one other alkaloid (No.155, anthriscifolsine A, C₂₉H₃₁NO₇, [49]) was isolated from D. anthriscifolium var. majus. The structure is shown in Figure 8.

Figure 8: Other alkaloids isolated from Delphinium.

2.4. Other Compounds

Delphinium also contains compounds such as flavonoids and sterols. In recent years, other compounds isolated from Delphinium had also been reported, and a total of 13 nonalkaloids (Table 5 and Figure 9) were isolated from Delphinium.

Table 5: Other compounds isolated from Delphinium.

No.
Compound
Type
Source
Molecular formula
Reference

156
β-Carotene

D. grandiflorum Linn
C₃₄H₅₆NO₄
[21]

157
3,5-Dihydroxy-4′-methoxyflavon-7-yl-O-β-D-glucopyranosyl-(1⟶4)-α-L-rhamnopyranoside
Flavonoid
D. grandiflorum Linn
C₂₁H₁₈NO₈
[21]

158
β-D-Galactopyranoside,4-hydroxyphenyl

D. grandiflorum Linn
C₁₁H₁₂NO₅
[21]

159
β-Sitosterol
Sterol
D. honanense var. piliteram W. T. Wang
C₂₉H₅₀O
[47]

160
4′,7-Dimethoxy-5-hydroxyflavone
Flavonoid
D. grandiflorum L.
C₁₇H₁₄O₅
[48]

161
Kaempferol-7-O-α-L-pyranorhamnoside
Flavonoid
D. grandiflorum L.
C₂₁H₂₀O₁₀
[60]

162
5,7,3′,4′-Tetrahydroxy-8-methoxyflavone
Flavonoid
D. grandiflorum L.
C₁₆H₁₂O₇
[60]

163
Tachioside
Phenolics
D. grandiflorum L.
C₁₃H₁₈O₈
[60]

164
6-Methoxycoumarin
Coumarin
D. grandiflorum L.
C₁₀H₈O₃
[60]

165
para-Hydroxybenzoic acid

D. brunonianum Royle
C₇H₆O₃
[59]

166
Benzoic acid

D. brunonianum Royle
C₇H₆O₂
[59]

167
Cinnamic acid

D. brunonianum Royle
C₉H₈O₂
[59]

168
Dibutyl phthalate

D. brunonianum Royle
C₁₆H₂₂O₄
[59]

Figure 9: Other compounds isolated from Delphinium.

3. Biological Activities

Plants of Delphinium are used with whole grass as medicine. According to the ancient Tibetan medicine Jingzhubencao, plants of Delphinium had analgesic, anti-inflammatory, and insecticidal effects [9]. Literature studies showed that plants of Delphinium have many pharmacological effects including antibacterial, antiepileptic, detoxification, and Alzheimer’s disease treatment. In this section, this paper reviews the research studies on the antibacterial, analgesic, anti-inflammatory, antidepressant, and anticancer effects of Delphinium.

3.1. Antibacterial Activity

Hari et al. found that anthriscifoldine C (5.0 mg/mL) from D. brunonianum had a good inhibiting effect on Bacillus subtilis, Escherichia coli, and Salmonella flexnari, and its MIC were 24.0 µM, 23.4 µM, and 24.2 µM, respectively, in vitro [61]. Ren et al. carried out the bacteriostatic test on the total alkaloids extracted from the roots of Delphinium and found that the MIC of the total alkaloids extracted on S. aureus and Aspergillus niger was 50 mg/mL in vitro [62].

3.2. Analgesic Activity

Zaheer et al. used the eddy current hot plate method and the tail flick reaction method to evaluate the analgesic activity of D. denudatum on Wistar albino rats. The experimental results showed that the response time of rats given D. denudatum ethanol extract and methanol fraction was longer than that of the propylene glycol group, and the effects of the high doses of the ethanol extract (600 mg/kg) and methanol fraction (400 mg/kg) were equal to that of the positive control group, indicating that D. denudatum had a good analgesic activity [63]. Nesterova et al. investigated chronic immune inflammation which was induced by injecting 0.1 mL of complete Freund’s in outbred male rats, and the results showed that the 40% alcohol extract (0.12 mL/kg) and total alkaloids (0.05 mg/kg) of Delphinium could significantly reduce the frequency of joint swelling in outbred male rats. On the 14th day, the rats in the total alkaloids (0.05 mg/kg) treatment group of Delphinium had no pain when their joints were bended, which indicated a good analgesic effect of Delphinium [64]. Through the hot-plate method and the acetic acid writhing method, Suslov et al. found that the water extract (0.5 g/kg) and the alcohol extract (0.25 g/kg) of D. grandiflorum L. var. leiocarpum could prolong the pain threshold of mice, which was similar to the effect of acetaminophen (0.2 g/kg), and performed a good analgesic effect [65].

3.3. Anti-Inflammatory Activity

Nesterova et al. found that the alkaloids and flavonoids in Delphinium had a good inhibitory effect on the inflammatory response through the experiment of the mice peritonitis model in the inflammatory exudation phase in vivo. Aqueous fraction of flavonoids (25.0 mg/kg) had a good therapeutic effect on the edema reaction caused by histamine (0.1%), and alkaloids (0.05 mg/kg) showed a good anti-inflammatory effect on the inflammatory reaction caused by 5-hydroxytryptamine (0.5 mg/kg) [66]. Andreeva and Liu established an acute inflammation model with increased capillary permeability induced by acetic acid in ICR male mice, and the results showed that the high- (1.5 g/kg), medium- (1.0 g/kg), and low-dose groups (0.5 g/kg) of the total flavonoids extracted from D. grandiflorum with ethanol had good anti-inflammatory activity [67].

3.4. Spiritual Influence

3.4.1. Antidepressant Activity

Ebrahimzadeh et al. demonstrated that the extract (250 mg/kg, 500 mg/kg, and 1000 mg/kg) of D. elbursense had good antidepressant activity by using the forced swimming experiment and the tail suspension experiment in mice. The results revealed that the extract at 1000 mg/kg had the same inhibitory activity as imipramine at 15 mg/kg in the control group [68].

3.4.2. Antianxiety Activity

Mohammad et al. found that the D. denudatum extract (200 and 400 mg/kg) had a certain therapeutic effect on anxiety in Wistar albino rats and a better synergistic effect toward the Amaranthus spinosus extract (100 mg/kg) [69].

3.5. Anticancer Activity

Zheng et al. used the MTT method to determine the antihepatoma activity of the ethyl acetate extract from D. caeruleum in vitro. After giving 25, 50, 100, and 200 μg/mL of HepG2 cells for 12, 24, and 48 hours, they found that the ethyl acetate extract from D. caeruleum had good antiliver cancer activity and had a good dose-effect and time-effect relationship on HepG2 cells and had less toxicity to L-02 cells. IC₅₀ of the ethyl acetate extract from D. caeruleum on HepG2 cells was 28.8 μg/mL [70].

3.6. Antipulmonary Fibrosis Activity

In the study on pulmonary fibrosis induced by bleomycin in SD rats, Lin et al. found that after 14 days of gavage with 4 g/kg, 2 g/kg, and 1 g/kg extracts of D. trichophorum, the expression of collagen in the tissues during the pathological process of pulmonary fibrosis could be inhibited and the symptoms of pulmonary fibrosis in rats could be improved [71].

3.7. Antifeedant Activity

Shan et al. determined the antifood activity of 12 alkaloids isolated from D. naviculare var. lasiocarpum on Spodoptera exigua, and the results showed that the chemical shawurensine had a strong antifeedant activity with an EC₅₀ of 0.45 mg/cm² [31]. González and Guadaño extracted 5 alkaloids from Delphinium for activity determination against Spodoptera littoralis and Leptinotarsa decemlineata by choice feeding assays, and the results showed that cardiopetamine had the strongest activity against S. littoralis with the EC₅₀ of 5.48 nmol/cm² and 15-acetylcardiopetamine had the strongest activity against L. decemlineata with the EC₅₀ of 12.86 nmol/cm² [72].

3.8. Antiparasite Activity

Reina et al. found that delphigraciline extracted from D. gracile had antileishmanicidal activity in vitro, and its IC₅₀ was 7.3 μg/mL [73].

4. Summary and Analysis

Delphinium is rich in germplasm resources and has a wide range of pharmacological effects. In recent years, 168 compounds were isolated from plants of Delphinium, including 155 alkaloids and 13 nonalkaloids. The alkaloids in the genus Delphinium are mainly diterpene alkaloids, including 20 C-18 diterpenoid alkaloids, 95 C-19 diterpenoid alkaloids, and 30 C-20 diterpenoid alkaloids. The study of chemical composition for Delphinium mainly focuses on D. anthriscifolium varietas, D. elatum, D. grandiflorum, D. brunonianum, D. tiantaishanense, and D. pseudoaemulans. Although there are many research studies, the pharmacological effects on the antibacterial, analgesic, anti-inflammatory, antidepressant, anticancer, antipulmonary fibrosis, antifeedant, and antiparasite effects of Delphinium are mainly on the crude extracts and few on compounds.

5. Future Prospects

The genus Delphinium is rich in new and novel compounds, but the current research is only focused on several species. In the future, more new compounds should be investigated from other species in depth. The pharmacological effects of Delphinium are extensive, but the current research is limited to extracts, so it is necessary to focus on the effects of the compounds from Delphinium and the structure-activity relationship in the future.

Data Availability

The data supporting this article are from previously reported studies, which have been cited. The data are available from the corresponding author upon request.

Conflicts of Interest

All authors declare that they have no conflicts of interest.

Authors’ Contributions

Sitan Chen and Lijun Meng contributed equally to this work.

Acknowledgments

This work was supported by the Basic Project in Science and Technology Agency of Kaifeng City (1908007).

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