Plants of
According to the research studies, the alkaloids are the main constituents with physiological activities in
Diterpenoid alkaloids are derived from the amination of tetracycline diterpenoids or pentacyclic diterpenoids to heterocyclic systems containing
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
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
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-
The skeleton structures of C-20 diterpene alkaloids.
At present, 155 alkaloids were isolated from
C-18 diterpenoid alkaloids isolated from
No. | Compound | Type | Source | Molecular formula | Reference |
---|---|---|---|---|---|
1 | Anthriscifolcine A | Ranaconitine | C26H38NO7 | [ | |
2 | Anthriscifolcine B | Ranaconitine | C24H37NO6 | [ | |
3 | Anthriscifolcine C | Ranaconitine | C25H37NO7 | [ | |
4 | Anthriscifolcine D | Ranaconitine | C26H39NO7 | [ | |
5 | Anthriscifolcine E | Ranaconitine | C24H37NO6 | [ | |
6 | Anthriscifolcine F | Ranaconitine | C25H37NO8 | [ | |
7 | Anthriscifolcine G | Ranaconitine | C25H37NO7 | [ | |
8 | Naviconine | Lappacinitine | C31H40N2O9 | [ | |
9 | Anthriscifolcone A | Ranaconitine | C27H39NO8 | [ | |
10 | Anthriscifolcone B | Ranaconitine | C23H33NO7 | [ | |
11 | Grandifline A | Ranaconitine | C22H33NO7 | [ | |
12 | Tuguaconitine | Ranaconitine | C23H35NO7 | [ | |
13 | Linearilin | Ranaconitine | C24H39NO8 | [ | |
14 | Anthriscifoltine A | Ranaconitine | C30H45NO9 | [ | |
15 | Anthriscifoltine B | Ranaconitine | C28H43NO8 | [ | |
16 | Anthriscifoltine C | Ranaconitine | C29H43NO9 | [ | |
17 | Anthriscifoltine D | Ranaconitine | C32H41NO9 | [ | |
18 | Anthriscifoltine E | Ranaconitine | C25H35NO8 | [ | |
19 | Anthriscifoltine F | Ranaconitine | C23H33NO7 | [ | |
20 | Anthriscifoltine G | Ranaconitine | C23H31NO7 | [ |
C-19 diterpenoid alkaloids isolated from
No. | Compound | Type | Source | Molecular formula | Reference |
---|---|---|---|---|---|
21 | Anthriscifoldine A | Lycoctonine | C25H37NO7 | [ | |
22 | Anthriscifoldine B | Lycoctonine | C25H39NO7 | [ | |
23 | Anthriscifoldine C | Lycoctonine | C27H41NO7 | [ | |
24 | Naviculine | Lycoctonine | C26H42NO7+ | [ | |
25 | Naviconitine | Aconitine | C34H46N2O9 | [ | |
26 | Grandifline B | Lycoctonine | C25H39NO8 | [ | |
27 | Grandifline C | Lycoctonine | C25H40NO7+ | [ | |
28 | Olivimine | Lycoctonine | C24H37NO7 | [ | |
29 | Hohenackeridine | Lycoctonine | C22H31NO7 | [ | |
30 | 14-O-Methyldelphinifoline | Lycoctonine | C24H39NO7 | [ | |
31 | N-Deethyldelphatine | Lycoctonine | C24H39NO7 | [ | |
32 | Browniine | Lycoctonine | C25H41NO7 | [ | |
33 | 14-Dehydrobrowniine | Lycoctonine | C25H39NO7 | [ | |
34 | Linearilobin | Aconitine | C37H46N2O9 | [ | |
35 | Melpheline | Lycoctonine | C24H37NO6 | [ | |
36 | 19-Oxoisodelpheline | Lycoctonine | C25H37NO7 | [ | |
37 | N-Deethyl-19-oxoisodelpheline | Lycoctonine | C23H33NO7 | [ | |
38 | N-Deethyl-19-oxodelpheline | Lycoctonine | C23H33NO7 | [ | |
39 | N-Formyl-4,19-secopacinine | Lycoctonine | C25H37NO7 | [ | |
40 | Iminoisodelpheline | Lycoctonine | C23H33NO6 | [ | |
41 | Iminodelpheline | Lycoctonine | C23H33NO6 | [ | |
42 | Iminopaciline | Lycoctonine | C24H35NO6 | [ | |
43 | 6-Dehydroeladine | Lycoctonine | C24H35NO6 | [ | |
44 | Elapacidine | Lycoctonine | C24H37NO6 | [ | |
45 | Yunnanensine A | Rearranged-type | C37H48N2O9 | [ | |
46 | Iliensine A | Lycoctonine | C40H55NO14 | [ | |
47 | Iliensine B | Lycoctonine | C26H41NO8 | [ | |
48 | Pseudophnine A | Lycoctonine | C25H40NO7+ | [ | |
49 | Pseudophnine B | Lycoctonine | C24H38NO7+ | [ | |
50 | Pseudophnine C | Lycoctonine | C27H42NO7+ | [ | |
51 | Pseudophnine D | Lycoctonine | C26H40NO7+ | [ | |
52 | Pseudorenines A | Lycoctonine | C39H53N2O11+ | [ | |
53 | Pseudorenines B | Lycoctonine | C39H53N2O11+ | [ | |
54 | Pseudonidine A | Lycoctonine | C24H35NO7 | [ | |
55 | Pseudonidine B | Lycoctonine | C29H45NO8 | [ | |
56 | Navicularine | Lycoctonine | C27H43NO8 | [ | |
57 | Shawurensine | Lycoctonine | C37H52N2O11 | [ | |
58 | Sharwuphinine B | Lycoctonine | C26H40NO7+ | [ | |
59 | Ajacisine A | Lycoctonine | C31H44N2O9 | [ | |
60 | Ajacisine B | Lycoctonine | C32H46N2O9 | [ | |
61 | Ajacisine C | Lycoctonine | C31H42N2O8 | [ | |
62 | Ajacisine D | Lycoctonine | C30H42N2O8 | [ | |
63 | Ajacisine E | Lycoctonine | C30H42N2O8 | [ | |
64 | Caerudelphinine A | Lycoctonine | C25H39NO8 | [ | |
65 | Grandiflodine B | Lycoctonine | C33H48N2O10 | [ | |
66 | Majusine A | Lycoctonine | C32H44N2O9 | [ | |
67 | Majusine B | Lycoctonine | C24H37NO6 | [ | |
68 | Majusine C | Lycoctonine | C26H37NO8 | [ | |
69 | Davidisine A | Lycoctonine | C23H37NO7 | [ | |
70 | Davidisine B | Lycoctonine | C24H37NO8 | [ | |
71 | Laxicymine 1 | Lycoctonine | C24H35NO7 | [ | |
72 | Laxicymisine 2 | Lycoctonine | C24H37NO7 | [ | |
73 | Laxicyminine 3 | Lycoctonine | C24H35NO6 | [ | |
74 | Tiantaishansine | Lycoctonine | C22H33NO7 | [ | |
75 | Tiantaishannine | Lycoctonine | C26H39NO7 | [ | |
76 | Tiantaishanmine | Lycoctonine | C25H35NO7 | [ | |
77 | Trifoliolasine A | Lycoctonine | C35H50N2O9 | [ | |
78 | Trifoliolasine B | Lycoctonine | C36H52N2O9 | [ | |
79 | Trifoliolasine C | Lycoctonine | C40H57N3O11 | [ | |
80 | 14-Demethyl-14-isobutyrylanhweidelphinine | Lycoctonine | C38H48N2O11 | [ | |
81 | 14-Demethyl-14-acetylanhweidelphinine | Lycoctonine | C36H44N2O11 | [ | |
82 | Giraldine G | Lycoctonine | C40H57N3O11 | [ | |
83 | Giraldine H | Lycoctonine | C41H59N3O11 | [ | |
84 | Giraldine I | Aconitine | C22H35NO3 | [ | |
85 | Giraldine D | Lycoctonine | C24H37NO6 | [ | |
86 | Giraldine E | Lycoctonine | C25H39NO7 | [ | |
87 | Giraldine F | Lycoctonine | C23H33NO6 | [ | |
88 | Campylocine | Lycoctonine | C25H37NO7 | [ | |
89 | Campylotine | Lycoctonine | C24H37NO7 | [ | |
90 | Davidiisine A | Lycoctonine | C23H37NO7 | [ | |
91 | Davidiisine B | Lycoctonine | C24H37NO8 | [ | |
92 | Ajadelphine | Lycoctonine | C25H39NO7 | [ | |
93 | Aconine | Aconitine | C25H41NO9 | [ | |
94 | Siwanine E | Lycoctonine | C28H39NO9 | [ | |
95 | Grandiflorine III | Aconitine | C26H39NO9 | [ | |
96 | Isotalatizidine | Aconitine | C23H37NO5 | [ | |
97 | 14-O-Methyl isotalatizidine | Aconitine | C24H39NO5 | [ | |
98 | Anthranoyllycoctonine | Lycoctonine | C32H46N2O8 | [ | |
99 | Deoxylycoctonine | Lycoctonine | C26H43NO6 | [ | |
100 | Umbrosine | Lycoctonine | C24H39NO6 | [ | |
101 | Anthriscifolrine A | Lycoctonine | C25H37NO6 | [ | |
102 | Anthriscifolrine B | Lycoctonine | C27H41NO8 | [ | |
103 | Anthriscifolrine C | Lycoctonine | C27H41NO9 | [ | |
104 | Anthriscifolrine D | Lycoctonine | C27H39NO9 | [ | |
105 | Anthriscifolrine E | Lycoctonine | C26H39NO8 | [ | |
106 | Anthriscifolrine F | Lycoctonine | C25H39NO7 | [ | |
107 | Tianshanisine A | Lycoctonine | C30H41NO6 | [ | |
108 | Tianshanisine B | Lycoctonine | C23H37NO5 | [ | |
109 | Tianshanisine C | Lycoctonine | C25H39NO6 | [ | |
110 | Tianshanisine D | Lycoctonine | C23H35NO5 | [ | |
111 | Tianshanisine E | Lycoctonine | C23H35NO7 | [ | |
112 | Elapacigine | Lycoctonine | C23H31NO6 | [ | |
113 | N-Deethyl-N-formylpaciline | Lycoctonine | C25H37NO7 | [ | |
114 | N-Deethyl-N-formylpacinine | Lycoctonine | C24H33NO7 | [ | |
115 | N-Formyl-4,19-secoyunnadelphinine | Lycoctonine | C24H35NO7 | [ |
C-20 diterpenoid alkaloids isolated from
No. | Compound | Type | Source | Molecular formula | Reference |
---|---|---|---|---|---|
116 | Yunnanensine B | Hetisine | C28H37NO7 | [ | |
117 | Yunnanensine C | Hetisine | C26H35NO6 | [ | |
118 | Grandiflodine A | Hetisine | C22H28N2O3 | [ | |
119 | Majusimine A | Vakognavine | C45H47NO15 | [ | |
120 | Majusimine B | Vakognavine | C43H45NO14 | [ | |
121 | Majusimine C | Vakognavine | C41H43NO13 | [ | |
122 | Majusimine D | Vakognavine | C34H37NO12 | [ | |
123 | Majusidine A | Hetisine | C22H29NO5 | [ | |
124 | Majusidine B | Hetisine | C25H33NO4 | [ | |
125 | Tiantaishandine | Hetisine | C29H33NO5 | [ | |
126 | 2-Dehydrodeacetylhetero phylloidine | Hetidine | C21H25NO3 | [ | |
127 | Davidiisine C | Hetidine | C21H33NO4 | [ | |
128 | 12-Epinapelline | Veatchine | C22H33NO3 | [ | |
129 | Anthriscifolsine B | Hetisine | C24H31NO7 | [ | |
130 | Anthriscifolsine C | Hetisine | C30H43NO7 | [ | |
131 | Anthriscifolmine A | Denudatine | C25H37NO5 | [ | |
132 | Anthriscifolmine B | Denudatine | C25H37NO6 | [ | |
133 | Anthriscifolmine C | Hetisine | C29H31NO7 | [ | |
134 | Trichodelphinines A | Hetisine | C26H35NO5 | [ | |
135 | Trichodelphinines B | Hetisine | C24H33NO4 | [ | |
136 | Trichodelphinines C | Hetisine | C27H37NO5 | [ | |
137 | Trichodelphinines D | Hetisine | C24H31NO5 | [ | |
138 | Trichodelphinines E | Hetisine | C26H33NO5 | [ | |
139 | Trichodelphinines F | Delnudine | C28H33NO4 | [ | |
140 | Flexiosine | Hetisine | C36H43NO9 | [ | |
141 | Tatsienenseine A | Vakognavine | C43H45NO13 | [ | |
142 | Tatsienenseine B | Hetisine | C24H31NO4 | [ | |
143 | Tatsienenseine C | Hetisine | C24H31NO3 | [ | |
144 | 13-(2-Methyl butyryl) azitine | Atisine | C25H37NO3 | [ | |
145 | Tatsienensine | Hetisine | C19H25NO2 | [ |
C-18 diterpenoid alkaloids isolated from
C-19 diterpenoid alkaloids isolated from
C-20 diterpenoid alkaloids isolated from
The typical groups of amide alkaloids are acyl groups. 9 amide alkaloids were isolated from
Amide alkaloids isolated from
No. | Compound | Type | Source | Molecular formula | Reference |
---|---|---|---|---|---|
146 | Benzoic acid 2-[(4-methoxy-2-methyl-1,4-dioxobutyl) amino]-methyl ester | Amide | C14H17NO5 | [ | |
147 | N-Cinnamoyl-2-phenylethylamine | Amide | C17H17NO | [ | |
148 | Delamide A | Amide | C13H13NO4 | [ | |
149 | Delamide B | Amide | C14H17NO6 | [ | |
150 | Delamide C | Amide | C13H15NO5 | [ | |
151 | Delamide D | Amide | C13H15NO5 | [ | |
152 | Delamide E | Amide | C13H15NO5 | [ | |
153 | Benzoic,4-[(3,4-dimethoxybenzoyl) amino]-3-hydroxy-methyl ester | Amide | C17H17NO6 | [ | |
154 | Benzoic acid 2-[(4-methoxy-3-methyl-1,4-dioxobutyl) amino]-methyl ester | Amide | C14H17NO5 | [ |
Amide alkaloids isolated from
Except diterpene alkaloids and amide alkaloids, one other alkaloid (No.155, anthriscifolsine A, C29H31NO7, [
Other alkaloids isolated from
Other compounds isolated from
No. | Compound | Type | Source | Molecular formula | Reference |
---|---|---|---|---|---|
156 | C34H56NO4 | [ | |||
157 | 3,5-Dihydroxy-4′-methoxyflavon-7-yl-O- | Flavonoid | C21H18NO8 | [ | |
158 | C11H12NO5 | [ | |||
159 | Sterol | C29H50O | [ | ||
160 | 4′,7-Dimethoxy-5-hydroxyflavone | Flavonoid | C17H14O5 | [ | |
161 | Kaempferol-7-O- | Flavonoid | C21H20O10 | [ | |
162 | 5,7,3′,4′-Tetrahydroxy-8-methoxyflavone | Flavonoid | C16H12O7 | [ | |
163 | Tachioside | Phenolics | C13H18O8 | [ | |
164 | 6-Methoxycoumarin | Coumarin | C10H8O3 | [ | |
165 | para-Hydroxybenzoic acid | C7H6O3 | [ | ||
166 | Benzoic acid | C7H6O2 | [ | ||
167 | Cinnamic acid | C9H8O2 | [ | ||
168 | Dibutyl phthalate | C16H22O4 | [ |
Other compounds isolated from
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The data supporting this article are from previously reported studies, which have been cited. The data are available from the corresponding author upon request.
All authors declare that they have no conflicts of interest.
Sitan Chen and Lijun Meng contributed equally to this work.
This work was supported by the Basic Project in Science and Technology Agency of Kaifeng City (1908007).