A Review on the Terpenes from Genus Vitex
Abstract
:1. Introduction
2. Chemical Constituents
2.1. Monoterpenoids and Sesquiterpenoids
2.1.1. Monoterpenoids
2.1.2. Sesquiterpenoids
2.2. Diterpenoids
2.3. Triterpenoids
3. Pharmacological Effects
3.1. Anti-Inflammatory Activity
3.2. Anti-Tumor Activity
3.3. Antibacterial and Antifungal Activities
3.4. Antioxidant Activity
3.5. Other Pharmacological Activities
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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No. | Compound Name | Source | Reference | |
---|---|---|---|---|
1 | Nishindaside | a, h | [7,8,9] | |
2 | Isonishindaside | h | [8] | |
3 | Agnuside | a–h | [9,10,11,12,13,14,15,16,17,18,19,20,21] | |
4 | 10-O-Vanilloyl aucubin | d, e, h | [9,14,15,16] | |
5 | Limoniside | g | [10] | |
6 | Aucubin | f | [11,18] | |
7 | Eurostoside | d | [12] | |
8 | Harpagide | f | [22] | |
9 | 8-O-Acetylharpagide | f | [22] | |
10 | Geniposide | h | [9] | |
11 | Mussaenosidic acid | f | [11] | |
12 | 6′-O-p-Hydroxybenzoylmussaenosidic acid | a, b, f | [11,21,23] | |
13 | Agnucastoside A | f | [11] | |
14 | Agnucastoside B | f | [11] | |
15 | Agnucastoside C | f | [11] | |
16 | 2′-O-trans-p-Coumaroylloganic acid | a | [23] | |
17 | 6′-O-trans-Feruloylnegundoside | c | [13] | |
18 | 6′-O-trans-Caffeoylnegundoside | c | [13] | |
19 | 2′-O-p-Hydroxybenzoyl-6′-O-trans-caffeoylgardoside | c | [13] | |
20 | 2′-O-p-Hydroxybenzoyl-6′-O-trans-caffeoyl-8-epiloganic acid | c | [13] | |
21 | 2′-O-p-Hydroxybenzoyl gardoside | c | [13] | |
22 | 2′-O-p-Hydroxybenzoyl-8-epiloganic acid | c | [13] | |
23 | Negundoside | a, c | [7,13,23,24,25,26,27] | |
24 | 6′-O-p-Hydroxybenzoyl-gardoside | a | [23] | |
25 | 1,4a,5,7a-Tetrahydro-1-β-d-glucosyl-7-(3′,4′-dihydroxybenzoyloxymethyl)-5-ketocyclopenta[c]pyran-4-carboxylic acid | a | [7] | |
26 | Iridolactone | d | [14] | |
27 | Viteoid II | d | [14] | |
28 | Viteoid I | d | [14] | |
29 | Pedicularis lactone | d | [14] | |
30 | Eucommiol | d | [14] | |
31 | 1-Oxoeucommiol | d | [14] | |
32 | (1S,2S,4R)-2-endo-Hydroxy-1,8-cineole-β-d-glucopyranoside | d | [5] | |
33 | (1R,2R,4S)-2-endo-Hydroxy-1,8-cineole-β-d-glucopyranoside | d | [5] | |
34 | Vitexoid | b | [6] |
No. | Compound Name | Source | Reference |
---|---|---|---|
35 | Negunfurol | a | [28] |
36 | 1,6-Dioxo-2(3),9(10)-dehydrofuranoeremophilane | a | [29] |
37 | 4,6-Dimethyl-11-formyl-1-oxo-4H,2,3-dihydronaphthofuran | a | [28,29] |
38 | 4,6-Dimethyl-11-dimethoxymethyl-1-oxo-4H,2,3-dihydronaphthofuran | a | [29] |
39 | Spathulenol | b, f, i | [17,18,30,31] |
40 | ent-4α,10β-Dihydroxyaromadendrane | b | [17] |
41 | 4β,10β-Dihydroxyaromadendrane | f | [32] |
42 | 4α,10α-Dihydroxyaromadendrane | f | [33] |
Type | No. | Compound Name | Source | Reference |
---|---|---|---|---|
Labdane | 43 | Rotundifuran | b, d, f | [31,35,38,39,40,41,42] |
44 | Vitetrifolin B | b, f | [31,39] | |
45 | Dihydrosolidagenone | b | [39] | |
46 | (+)-Polyalthic acid | a | [43] | |
47 | Vitetrifolin C | b, f | [31,39] | |
48 | Vitetrifolin H | b | [6,38] | |
49 | Vitexilactone C | h | [44] | |
50 | Vitextrifolin C | b | [38] | |
51 | Vitextrifolin D | b | [38] | |
52 | Vitextrifolin E | b | [38] | |
53 | Vitexilactone | b, d, f | [6,31,33,35,36,40,45,46,47,48,49,50] | |
54 | (rel 5S,6R,8R,9R,10S)-6-Acetoxy-9-hydroxy-13(14)-labden-16,15-olide | b,d | [6,48,50] | |
55 | (rel 5S,6S,8R,9R,10S)-6-Acetoxy-9-hydroxy-13(14)-labden-16,15-olide | d | [50] | |
56 | (rel 5S,6R,8R,9R,10S)-6-Acetoxy-9-hydroxy-15-methoxy-13(14)-labden-16,15-olide | d | [46,50] | |
57 | Viteagnusin I | b, d, f | [38,45,51] | |
58 | Viteagnusin H (methoxy-vitexilactone) | f | [32,52] | |
59 | 9-Hydroxy-13(14)-labden-15,16-olide | b | [53] | |
60 | Deacetylvitexilactone | b | [38] | |
61 | Viterotulin A | d | [45] | |
62 | (rel 3S,5S,8R,9R,10S)-3,9-Dihydroxy-13(14)-labden-16,15-olide | d | [45] | |
63 | Viterotulin B | d | [45] | |
64 | Vitexilactone B | a, b | [38,54] | |
65 | Viteoside A | d | [34] | |
66 | Viteagnuside A | f | [33] | |
67 | Vitexolide E | j | [55] | |
68 | Vitexolide D | j | [55] | |
69 | Vitexolide A | j | [55] | |
70 | 12-Epivitexolide A | j | [55] | |
71 | Vitexolide B | j | [55] | |
72 | Vitexolide C | j | [55] | |
73 | Vitexlactam A | d,f | [18,36] | |
74 | Vitexlactam B | f | [18,35] | |
75 | Vitexlactam C | f | [18,35] | |
76 | 12S,16S/R-Dihydroxy-ent-labda-7,13-dien-15,16-olide | k | [56] | |
77 | Vitextrifolin G | b | [38] | |
78 | Prerotundifuran | d | [42] | |
79 | Previtexilactone | b, d | [6,38,47,48,49] | |
80 | 6-Acetoxy-9,13,15,16-diepoxy-15-methoxylabdane | b | [6] | |
81 | Viteagnusin E | f | [57] | |
82 | (rel 5S,6R,8R,9R,10S,13S)-6-Acetoxy-9,13-epoxy-15-methoxylabdan-16,15-olide | d, f | [33,50] | |
83 | Viteagnusin I | f | [33] | |
84 | (rel 5S,6R,8R,9R,10S,13S,16S)-6-Acetoxy-9,13-epoxy-16-methoxy-labdan-15,16-olide | d, f | [33,50] | |
85 | Vitextrifolin F | b | [38] | |
86 | Nishindanol | a | [19] | |
87 | (rel 5S,6R,8R,9R,10S,13S,15S)-6-Acetoxy-9,13,15,16-diepoxy-15-methoxylabdane | d, f | [32,58] | |
88 | (rel 5S,6R,8R,9R,10S,13S,15R)-6-Acetoxy-9,13;15,16-diepoxy-15-methoxylabdane | d, f | [32,58] | |
89 | (rel 5S,6R,8R,9R,10S,13S,15S,16R)-6-Acetoxy-9,13,15,16-diepoxy-15,16-dimethoxylabdane | d | [58] | |
90 | (rel 5S,6R,8R,9R,10S,13S,15R,16S)-6-Acetoxy-9,13,15,16-diepoxy-15,16-dimethoxylabdane | d | [58] | |
91 | (rel 5S,6R,8R,9R,10S,13S,15R,16R)-6-Acetoxy-9,13,15,16-diepoxy-15,16-dimethoxylabdane | d | [58] | |
92 | (rel 5S,6R,8R,9R,10S,13S,15S,16S)-6-Acetoxy-9,13,15,16-diepoxy-15,16-dimethoxylabdane | d | [58] | |
93 | (rel 5S,8R,9R,10S,13S,15S,16R)-9,13;15,16-Diepoxy-15,16-dimethoxylabdane | d | [50] | |
94 | (rel 5S,8R,9R,10S,13S,15R,16S)-9,13;15,16-Diepoxy-15,16-dimethoxylabdane | d | [50] | |
95 | (rel 5S,8R,9R,10S,13S,15R,16R)-9,13;15,16-Diepoxy-15,16-dimethoxylabdane | d | [50] | |
96 | Negundol | a, b | [38,59] | |
97 | Negundoin D | a | [37] | |
98 | Negundoin E | a | [37] | |
99 | Vitextrifolin A | b | [38] | |
100 | Vitextrifolin B | b | [38] | |
101 | (rel 5S,6R,8R,9R,10S,13R)-6-Acetoxy-9,13-epoxy-15-methoxylabdan-16,15-olide | d,f | [33,50,57] | |
102 | (rel 5S,6R,8R,9R,10S,13R,16S)-6-Acetoxy-9,13-epoxy-16-methoxylabdan-15,16-olide | d,f | [33,50] | |
103 | Viteagnusin J | f | [33] | |
104 | (rel 5S,6R,8R,9R,10S,13R,15R)-6-Acetoxy-9,13,15,16-diepoxy-15-methoxylabdane | d, f | [32,58] | |
105 | (rel 5S,6R,8R,9R,10S,13R,15S)-6-Acetoxy-9,13,15,16-diepoxy-15-methoxylabdane | d, f | [32,58] | |
106 | Viteagnusin F | d, f | [32,45] | |
107 | Viteagnusin G | d, f | [32,45] | |
108 | Limonidilactone | g | [60] | |
109 | Acuminolide | j | [55] | |
110 | Vitexolin A | j | [55] | |
111 | Vitexolin B | j | [55] | |
112 | 6α,7α-Diacetoxy-13-hydroxy-8(9),14-labdadiene | b | [53] | |
113 | 6β,7β-Diacetoxy-13-hydroxylabda-8,14-diene | f | [40,41] | |
114 | Viteagnusin D | f | [57] | |
115 | Vitexifolin A | d | [61] | |
116 | Viteagnusin C | a, f | [33,54,57] | |
117 | 8,13-Dihydroxy-14-labdene | f | [41] | |
118 | 8-epi-Sclareol | a, f | [19,33,54,57] | |
119 | Vitrifolin B | d | [36] | |
120 | 8-Epimanoyl oxide | f | [18,35,51] | |
Norlabdane | 121 | Vitrifolin A | l | [62] |
122 | Negundoal | a | [28] | |
123 | Negundoin A | a | [37] | |
124 | Negundoin B | a | [37] | |
125 | Negundoin C | a | [37] | |
126 | 9,13-Epoxy-16-norlabda-13E-en-15-al (norditerpene aldehyde 1) | b, d | [45,48] | |
127 | Norditerpene aldehyde 2 | b | [48] | |
128 | Vitexifolin D | d | [61] | |
129 | Trisnor-γ-lactone | d | [61] | |
130 | Isoambreinolide | b, d | [53,61] | |
131 | Vitedoin B | a, d | [37,45,63] | |
132 | Vitexifolin E | d | [61] | |
Halimane | 133 | Vitetrifolin G | b | [64] |
134 | 13-Hydroxy-5(10),14-halimadien-6-one | b | [53] | |
135 | Viteagnusin A | f | [57] | |
136 | Viteagnusin B | f | [57] | |
137 | Vitetrifolin I | b | [6] | |
138 | Vitetrifolin D | a, b, d, f | [6,19,33,35,45,46,52,54,61,64] | |
139 | Vitetrifolin E | b, d | [6,45,46,64] | |
140 | Vitetrifolin F | b, d | [6,45,46,64] | |
141 | Vitetrifolin H | d | [45] | |
Abietane | 142 | Ferruginol | d | [58] |
143 | Abietatrien-3β-ol | b, d | [39,58] | |
144 | 5β-Hydro-8,11,13-abietatrien-6α-ol | a | [65] | |
145 | 3β-Hydroxyabieta-8,11,13-trien-7-one | a | [37] | |
146 | Isolophanthin A | d | [45] | |
147 | Abieta-9(11),12-diene | d | [66] | |
148 | Vitetrifolin A | b | [39] | |
149 | Abietane 9(11):12(13)-di-α-epoxide | d | [66] | |
150 | Vitexifolin C | d | [61] | |
151 | Negundoin F | a | [37] | |
Clerodane | 152 | Vitexifolin B | d | [61] |
153 | Cleroda-7,14-dien-13-ol | f | [41] | |
154 | Cleroda-1,3,14-trien-13-ol | f | [41] | |
155 | 13-epi-2-Oxokolavelool | d | [45] | |
Isopimarane | 156 | Negundoin G | a | [37] |
Type | No. | Compound Name | Source | Reference |
---|---|---|---|---|
Oleanane | 157 | Oleanolic acid | a, b | [54,68,70,71] |
158 | Maslinic acid | a, c, f | [33,54,72,73] | |
159 | 3-Epimaslinic acid | a, c, f, h | [33,51,69,71,73] | |
160 | 2α,3α,24-Trihydroxyolean-12-en-28-oic acid | a, b, h | [69,72,74] | |
161 | 2α,3β,24-Trihydroxyolean-12-en-28-oic acid | b | [74] | |
162 | Vulgarsaponin A | a | [67] | |
163 | Cannabifolin F | h | [69] | |
164 | Oleanolic acid acetate | a | [75] | |
165 | Hederagenin | b | [68] | |
166 | 2α,3α,23-Trihydroxyolean-12-en-28-oic acid methyl ester | a | [71] | |
167 | 2α,3α,23-Trihydroxyolean-12-en-28-oic acid | a | [71] | |
168 | 2α,3β,19α,23-Tetrahydroxyolean-12-en-28-oic acid | a | [72] | |
169 | 2α,3β,23-Trihydroxyolean-12-en-28-oic acid | a | [72] | |
170 | 3β-Hydroxyolean-5,12-dien-28-oic acid | a | [76] | |
171 | 2α,3α-Dihydroxyoleana-5,12-dien-28-oic acid | a | [77] | |
172 | 2β,3α-Diacetoxyoleana-5,12-dien-28-oic acid | a | [77] | |
173 | 2α,3β-Diacetoxy-18-hydroxyoleana-5,12-dien-28-oic acid | a | [77] | |
174 | Taraxerol | b | [78] | |
175 | Taraxerone | l | [79] | |
176 | 3-Oxotaraxer-14-en-30-al | l | [79] | |
177 | β-Amyrin | a, b | [68,71] | |
178 | β-Amyrin-3-O-β-d-glucopyranoside | b | [68] | |
179 | 3β-Acetoxyolean-12-en-27-oic acid | a | [76,77] | |
180 | Cannabifolin E | h | [69] | |
181 | 23-Hydroxy-3α-[O-α-l-rhamnopyranosyl-(1′′′→4″)-O-[β-d-(E-6″-O-caffeoyl)-glucopyranosyl]-oxy]-olean-12-en-28-oic acid | b | [68] | |
182 | 23-hydroxy-3α-(O-sulfonyloxy)-olean-12-en-28-oic acid-28-O-[α-l-rhamnopyranosyl-(1′′′→4″)-O-β-d-glucopyranosyl-(1″→6′)-O-β-d-glucopyranosyl] ester | b | [68] | |
183 | Cannabifolin B | h | [69] | |
Ursane | 184 | Cannabifolin A | h | [69] |
185 | Ursolic acid | a–c, e, h | [49,53,54,69,72,73,78,80,81] | |
186 | 3-Epiursolic acid | b, l | [74,79] | |
187 | Corosolic acid | a–c, e, f, h, l | [33,53,67,69,73,79,80] | |
188 | 3-Epicorosolic acid | a–c, f, h | [28,33,51,69,73,78] | |
189 | 3β-Acetoxyurs-12-en-28-oic acid | b | [49,82] | |
190 | α-Amyrin | b | [53] | |
191 | Uvaol | b | [74] | |
192 | Tormentic acid | a, b, e, h | [69,72,78,83] | |
193 | 2α,3α,24-Trihydroxyurs-12-en-28-oic acid | b, c | [73,74] | |
194 | Euscaphic acid | c, h | [69,73] | |
195 | 2α,3α,24-Trihydroxyurs-12-en-28-oic acid-28-O-β-d-glucopyranosyl ester | a | [67] | |
196 | 2α,3α,24-Trihydroxyurs-12,20(30)-dien-28-oic acid-28-O-β-d-glucopyranosyl ester | a | [67] | |
197 | 2α,3α,24-Trihydroxyurs-12,20(30)-dien-28-oic acid | c | [73] | |
198 | 2α,3α-Dihydroxyurs-12,20(30)-dien-28-oic acid | h | [69] | |
199 | Cannabifolin C | h | [69] | |
200 | Cannabifolin D | h | [69] | |
201 | Ilelatifol D | f | [51] | |
Norursane | 202 | Negundonorin A | a | [28] |
203 | Negundonorin B | a | [28] | |
Lupane | 204 | Lupeol | l | [79] |
205 | Betulinic acid | a, b, l | [49,54,78,79,81] | |
206 | Lup-20(29)-en-3β,30-diol | a | [54] | |
207 | Obtusalin | a | [54] | |
208 | Platanic acid | b | [82] | |
Friedelane | 209 | Epifriedelinol | e | [84] |
9-epi-Cucurbitane | 210 | (24R/S)-24-Hydroxy-3α,10α-epoxy-9-epi-cucurbita-25-ene | a | [43] |
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Yao, J.-L.; Fang, S.-M.; Liu, R.; Oppong, M.B.; Liu, E.-W.; Fan, G.-W.; Zhang, H. A Review on the Terpenes from Genus Vitex. Molecules 2016, 21, 1179. https://doi.org/10.3390/molecules21091179
Yao J-L, Fang S-M, Liu R, Oppong MB, Liu E-W, Fan G-W, Zhang H. A Review on the Terpenes from Genus Vitex. Molecules. 2016; 21(9):1179. https://doi.org/10.3390/molecules21091179
Chicago/Turabian StyleYao, Jin-Long, Shi-Ming Fang, Rui Liu, Mahmood Brobbey Oppong, Er-Wei Liu, Guan-Wei Fan, and Han Zhang. 2016. "A Review on the Terpenes from Genus Vitex" Molecules 21, no. 9: 1179. https://doi.org/10.3390/molecules21091179