Acanthopanax henryi: Review of Botany, Phytochemistry and Pharmacology
Abstract
:1. Introduction
2. Botany
3. Chemical Constituents
3.1. Monoterpenoids
3.2. Diterpenoids
3.3. Triterpenoid Saponins
3.4. Phenylpropanoids
3.5. Caffeoyl Quinic Acids
3.6. Flavonoids
3.7. Lignans
3.8. Steroids
3.9. Fatty Acids
3.10. Other Compounds
4. Pharmacology Research
4.1. Anti-Neuroinflammatory Activity
4.2. Anti-Adipogenic Effects
4.3. Anti-Inflammatory Activity
4.4. Antimicrobial Activity
4.5. Anticancer/Antitumor Activities
4.6. Anti-Oxidant, Anti-AChE, and Anti-BuChE Activities
4.7. Anti-Hyaluronidase Activity
5. Discussion
6. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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Classification | NO. | Chemical Component | Chemical Formula | Part of Plant | Ref. |
---|---|---|---|---|---|
Monoterpenoids | 1 | Eleuhenryiside A (new) | C18H30O8 | Fruit | [11] |
2 | Eleuhenryiside B (new) | C18H30O8 | Fruit | [11] | |
3 | Eleuhenryiside C (new) | C16H28O7 | Fruit | [11] | |
4 | 3,4-dihydroxy-p-menth-1-ene | C10H18O2 | Fruit | [12] | |
5 | (4R)-p-Menth-1-en-4,7-diol | C10H18O2 | Fruit | [12] | |
6 | (2E,6S)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-d-glucopyranoside | C16H28O7 | Fruit | [13] | |
7 | (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-d-glucopyranoside | C16H28O7 | Fruit | [13] | |
8 | (2Z,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-d-glucopyranoside | C16H28O7 | Fruit | [13] | |
9 | (2E,6R)-2,6-dimethyl-2,7-octadiene-1,6-diol | C10H18O2 | Fruit | [12] | |
10 | (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-d-glucopyranoside | C16H28O7 | Fruit | [13] | |
11 | (2E,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-d-glucopyranoside | C16H28O7 | Fruit | [13] | |
12 | (+)-(3S,4S,6R)-3,6-dihydroxy-1-menthene | C10H18O2 | Fruit | [12] | |
13 | (−)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 6-O-β-d-glucopyranoside | C16H28O7 | Fruit | [13] | |
14 | (−)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-β-d-glucopyranoside | C16H28O7 | Fruit | [13] | |
Diterpenoids | 15 | Acanthoic acid | C20H30O2 | Root | [14] |
16 | Kaurenoic acid | C20H30O2 | Root | [14] | |
17 | Pimaric acid | C20H30O2 | Root | [15] | |
Triterpenoid saponins | 18 | Ursolic acid 3-O-α-L-arabinopyranoside | C35H56O7 | Leaf | [16,17,18] |
19 | Echinocystic acid 3-O-α-L-arabinopyranoside | C35H56O8 | Leaf | [16,17,18] | |
20 | Eleutheroside K | C41H66O11 | Leaf | [16,17,18] | |
21 | Prosapogenin CP2b | C40H64O11 | Leaf | [16,17,18] | |
22 | Tauroside D | C41H66O12 | Leaf | [16,17,18] | |
23 | Guaianin N (Glycoside St-C1) | C41H66O12 | Leaf | [16,17,18] | |
24 | Matesaponin J2 | C41H66O12 | Leaf | [16,17,18] | |
25 | Echinocystic acid 3-O-β-d-glucopyranosyl-(1→3) -O-α-L-arabinopyranoside | C41H66O13 | Leaf | [16,17,18] | |
26 | Hemslonin A | C42H68O13 | Leaf | [16,17,18] | |
27 | Cussonoside B | C48H78O17 | Leaf | [16,17,18] | |
28 | Oleanolic acid 3-O-[β-d-glucopyranosyl-(1→3)]-β-d-galactopyranosyl -(1→2)-O-α-L-arabinopyranoside (Glycoside St-E2) | C47H76O17 | Leaf | [16,17,18] | |
29 | Ciwujianoside C3 | C53H86O21 | Leaf | [16,17,18] | |
30 | Ursolic acid 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4)-O-β-d -glucopyranosyl-(1→6)-O-β-d-glucopyranoside | C53H86O21 | Leaf | [16,17,18] | |
31 | Oleanolic acid 3-O-β-d-glucuronopyranoside | C36H56O9 | Leaf, fruit | [11,16,17,18] | |
32 | Araliasaponin II | C53H86O22 | Leaf | [16,17,18] | |
33 | Begoniifolide A | C59H96O26 | Leaf | [16,17,18] | |
Phenylpropanoids | 34 | Rosin | C15H20O6 | Fruit | [12] |
35 | Ferulic acid | C10H10O4 | Root | [19] | |
36 | Caffeic acid | C9H8O4 | Root, stem | [19,20] | |
37 | Syringin | C17H24O9 | Root | [19] | |
38 | Trans-coniferin | C16H22O8 | Root | [19] | |
39 | Trans-p-hydroxycinnamic acid | C9H8O3 | Stem | [20] | |
40 | (E)-caffeic acid methyl ester | C10H10O4 | Stem | [20] | |
41 | Trans-coniferyl aldehyde | C10H10O3 | Stem | [20] | |
42 | Trans-sinapaldehyde | C11H12O4 | Stem | [20] | |
43 | Eugenol glucoside | C16H22O7 | Flower | [21] | |
Caffeoyl quinic acids | 44 | 1,3-di-O-caffeoyl quinic acid | C25H24O12 | Fruit, root, stem, flower | [13,19,20,21] |
45 | 1,4-di-O-caffeoyl quinic acid | C25H24O12 | Fruit, root, stem, flower | [13,19,20,21] | |
46 | 1,5-di-O-caffeoyl quinic acid | C25H24O12 | Fruit, root, stem, flower, leaf | [13,19,20,21,22] | |
47 | 3,4-di-O-caffeoyl quinic acid | C25H24O12 | Fruit, flower, leaf | [13,21,22] | |
48 | 3,5-di-O-caffeoyl quinic acid | C25H24O12 | Fruit, flower, leaf | [13,21,22] | |
49 | 4,5-di-O-caffeoyl quinic acid | C25H24O12 | Fruit, flower, leaf | [13,21,22] | |
50 | Methyl chlorogenate | C17H20O9 | Fruit | [13] | |
51 | 3-O-caffeoyl quinic acid | C16H18O9 | Root, stem | [19,20] | |
52 | 4-O-caffeoyl quinic acid | C16H18O9 | Leaf | [22] | |
53 | 5-O-caffeoyl quinic acid | C16H18O9 | Root, stem, leaf | [19,20,22] | |
54 | 3,5-dicaffeoylquinic acid methyl ester | C26H26O12 | Flower | [21] | |
55 | 3,4-dicaffeoylquinic acid methyl ester | C26H26O12 | Flower | [21] | |
56 | 1,3-dicaffeoylquinic acid methyl ester | C26H26O12 | Flower | [21] | |
Flavonoids | 57 | Quercetin-3-O-β-d-glucopyranoside | C21H20O12 | Fruit, flower, leaf | [13,21,22,23] |
58 | Quercetin-3-O-β-d-galactopyranoside | C21H20O12 | Fruit | [13] | |
59 | Rutin | C27H30O16 | Fruit, flower, leaf | [13,21,22,23] | |
60 | Kaempferol-3-O-β-d-glucoside | C21H20O11 | Fruit, flower | [12,21] | |
61 | Kaempferol-3-rutinoside | C27H30O15 | Fruit, flower, leaf | [12,21,22] | |
62 | Kaempferol-3-O-α-L-rhamnoside | C21H20O10 | Flower | [21] | |
63 | Kaempferol | C15H10O6 | Flower, leaf | [21,23] | |
64 | Quercetin | C15H10O7 | Leaf | [22,23] | |
65 | Quercetin-3,7-di-β-O-glucopyranoside | C28H34O17 | Leaf | [22] | |
Lignans | 66 | (−)-Pinoresinol 4-O-β-d-glucopyranoside | C26H32O11 | Fruit | [12] |
67 | (+)-Simplexoside | C26H30O11 | Fruit | [12] | |
68 | (−)-Sesamin | C20H18O6 | Fruit, root, stem | [12,19,20] | |
69 | (−)-Kobusin | C21H22O6 | Fruit | [11] | |
70 | Styraxlignolide E | C26H32O11 | Fruit | [12] | |
71 | Styraxlignolide D | C26H32O11 | Fruit | [12] | |
72 | Helioxanthin | C20H12O6 | Root | [19] | |
73 | Savinin | C20H16O6 | Root | [19] | |
74 | Taiwanin C | C20H12O6 | Root | [19] | |
75 | (+)-threo-(7R,8R)-guaiacylglycerol-β-coniferyl aldehyde ether | C20H22O7 | Root | [19] | |
76 | (+)-erythro-(7S,8R)-guaiacylglycerol-β-coniferyl aldehyde ether | C20H22O7 | Root | [19] | |
77 | Dihydrosesamin-9-O-β-d-glucopyranoside | C26H30O11 | Flower | [21] | |
78 | Syringaresinol diglucoside (Eleutheroside E) | C34H46O18 | Root | [15,24,25] | |
79 | Syringaresinol | C22H26O8 | Root | [24] | |
Steroids | 80 | Stigmasterol | C29H48O | Root, stem, leaf | [15,19,20,23] |
81 | β-sitosterol | C29H50O | Root, stem | [15,19,20,24] | |
82 | Daucosterol | C35H60O6 | Root, leaf | [14,23] | |
83 | Stigmasterol-3-O-β-d-glucopyranoside | C35H58O6 | Leaf | [26] | |
Fatty acids | 84 | Behenic acid | C22H44O2 | Root | [19] |
85 | Undecanedioic acid, monomethyl ester | C14H26O4 | Stem | [20] | |
86 | Octacosanic acid | C28H56O2 | Root | [24] | |
87 | Fumaric acid | C4H4O4 | Leaf | [16] | |
88 | Melissic acid | C30H60O2 | Leaf | [23] | |
89 | Lacceroic acid | C32H64O2 | Leaf | [23] | |
90 | Palmitic acid | C16H32O2 | Leaf | [23] | |
91 | Gheddic acid | C34H68O2 | Leaf | [23] | |
Other compounds | 92 | 5-hydroxymethyl-2-furaldehyde | C6H6O3 | Fruit | [12] |
93 | 5-hydroxymaltol | C6H6O4 | Fruit | [12] | |
94 | Protocatechuic acid | C7H6O4 | Fruit | [12] | |
95 | 6-methoxy-7-hydroxycoumarin | C10H8O4 | Fruit, root, stem | [12,19,20] | |
96 | Phenylmethyl-β-d-glucopyranoside-6′-O-acetate | C15H20O7 | Fruit | [12] | |
97 | Adenosine | C10H13N5O4 | Root | [19] | |
98 | p-hydroxybenzoic acid | C7H6O3 | Stem | [20] | |
99 | Syringaldehyde | C9H10O4 | Stem | [20] | |
100 | Vanillin | C8H8O3 | Stem | [20] | |
101 | 1-O-β-d-glucopyranosyl-(2S,3S,4R,8E/Z)-2-(2′-hydrooxypalmitoyla mino)-8-octadecene-1,3,4-triol | C40H77NO10 | Leaf | [16] | |
102 | Glyceroyl-1,6,8-trihydroxy-3-methyl-9,10-dioxo-2-anthracene carboxylate | C19H16O9 | Leaf | [16] |
Biological Activity | In Vitro Studies | Ref. | |
---|---|---|---|
Cell/Bacteria Model | Effects | ||
Anti-neuroinflammatory | LPS-stimulated BV2 microglia | ↓ NO, PGE2, IL-1β, TNF-α production; ↓ iNOS, COX-2 expression, ↓ p38 MAPK phosphorylation | [11,12,19,20,21] |
Anti-adipogenic | 3T3-L1 cells | ↑ AMPK-↓ PPARγ-↓ C/EBPα mechanism | [30] |
Anti-inflammatory | LPS-stimulated RAW264.7 macrophages | ↓ NO, PGE2, IL-6, IL-1β, TNF-α production; ↓ iNOS, COX-2 expression, ↓ TLR4-NF-κB, MAPKs phosphorylation; ↓ NF-κB/p65 translocation | [11,20,21,31,32,33] |
Antimicrobial | MRSA | MIC, time-kill growth curves, OD600, damage to the cell wall, broken cell membranes and cell lysis, ↓ PBP2a expression | [34,35] |
Anticancer | HL-60, HT-29, A549 cells | ↓ Cell viability | [14,36] |
Anti-oxidant | - | ↑ DPPH, O2(−), ABTS scavenging activity | [22,36,37,38] |
Anti-AChE | - | ↑ AChE inhibitory activity | [22,36,37] |
Anti-BuChE | - | ↑ BuChE inhibitory activity | [37] |
Anti-hyaluronidase | - | ↑ hyaluronidase inhibitory activity | [36,38] |
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Li, X.-J.; Tang, S.-Q.; Huang, H.; Luo, J.; Zhang, X.-D.; Yook, C.-S.; Whang, W.-K.; Kim, Y.-C.; Liu, X.-Q. Acanthopanax henryi: Review of Botany, Phytochemistry and Pharmacology. Molecules 2021, 26, 2215. https://doi.org/10.3390/molecules26082215
Li X-J, Tang S-Q, Huang H, Luo J, Zhang X-D, Yook C-S, Whang W-K, Kim Y-C, Liu X-Q. Acanthopanax henryi: Review of Botany, Phytochemistry and Pharmacology. Molecules. 2021; 26(8):2215. https://doi.org/10.3390/molecules26082215
Chicago/Turabian StyleLi, Xiao-Jun, Si-Qi Tang, Hao Huang, Jiao Luo, Xiao-Dan Zhang, Chang-Soo Yook, Wan-Kyunn Whang, Youn-Chul Kim, and Xiang-Qian Liu. 2021. "Acanthopanax henryi: Review of Botany, Phytochemistry and Pharmacology" Molecules 26, no. 8: 2215. https://doi.org/10.3390/molecules26082215