生物技术通报 ›› 2021, Vol. 37 ›› Issue (11): 14-31.doi: 10.13560/j.cnki.biotech.bull.1985.2021-1052
• 食用菌生物技术专题(专题主编: 黄晨阳) • 上一篇 下一篇
收稿日期:
2021-08-18
出版日期:
2021-11-26
发布日期:
2021-12-03
作者简介:
李晶,女,博士,助理研究员,研究方向:菌草栽培食药用菌、牛樟芝三萜合成及定向调控;E-mail: 基金资助:
LI Jing1(), FENG Na2, WANG Sheng-yang3, LIN Zhan-xi1()
Received:
2021-08-18
Published:
2021-11-26
Online:
2021-12-03
摘要:
近年来,牛樟芝以其稀有的资源和独特的功效逐渐被人们关注。越来越多的研究表明牛樟芝子实体、菌丝体和发酵液中均含有大量三萜、多糖等功效成分,也有公开报道其部分化合物具有抑制肿瘤、抗氧化、抗炎症等重要功效。本文对已公开报道的牛樟芝主要化合物、生物和化学合成及其药理功效等进行较全面的整理,对于牛樟芝产业的发展提出期望并指明方向,以期为牛樟芝在药物研究、开发、应用和提升牛樟芝商品化程度、市场价值等方面提供科学参考,促进牛樟芝在我国及世界的发展。
李晶, 冯娜, 王升陽, 林占熺. 牛樟芝化学成分及其药理作用研究进展[J]. 生物技术通报, 2021, 37(11): 14-31.
LI Jing, FENG Na, WANG Sheng-yang, LIN Zhan-xi. Research Progress in Chemical Constituents of Taiwanofungus camphoratum and Its Pharmacological Activities[J]. Biotechnology Bulletin, 2021, 37(11): 14-31.
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
1 | Methyl antcinate A[ | 23 | Antcamphin K[ | ||
2 | Methyl antcinate G[ | 24 | Antcamphin L[ | ||
3 | Methyl antcinate H[ | 25 | 15-acetyldehydrosulfurenic[ | ||
4 | Methyl antcinate L[ | 26 | 15α-acetyl-dehydrosulphurenic acid[ | ||
5 | Zhankuic acid B[ | 27 | Antcamphin E[ | ||
6 | Zhankuic acid D[ | 28 | Antcamphin F[ | ||
7 | Antcin A[ | 29 | Antcamphin G[ | ||
8 | Antcin B (Zhankuic acid A)[ | 30 | Methyl antcinateK[ | ||
9 | Antcin C[ | 31 | Antcamphin H[ | ||
10 | Antcin D (Zhankuic acid F)[ | 32 | Antcin K[ | ||
11 | Antcin E[ | 33 | Dehydrosulphurenic acid[ | ||
12 | Antcin F[ | 34 | Dehydroeburicoic acid[ | ||
13 | Antcin G[ | 35 | 15-O-acetylganolucidate A[ | ||
14 | Antcin H (Zhankuic acid C)[ | 36 | Ethyl lucidenate A[ | ||
15 | Antcin M[ | 37 | Ethyl lucidenate F[ | ||
16 | Zhankuic acid E[ | 38 | 3, 7, 11-trioxolanosta-8, 24-dien-26-al, 26-carboxylic acid, 11a-alcohol, me ester[ | ||
17 | Antcamphin A[ | 39 | 3, 7, 11-trioxolanosta-8, 24-dien-26-oic acid[ | ||
18 | Antcamphin B[ | 40 | 3, 7, 12-trihydroxy-11, 15, 23-trioxolanost-8-en-26-oic acid, 3, 7, 12-triketone, me ester[ | ||
19 | Antcamphin C[ | 41 | 3, 7, 12-trihydroxy-11, 15, 23-trioxolanost-8-en-26-oic acid, 3, 7, 12-triketone, et ester[ | ||
20 | Antcamphin D[ | 42 | Eburicol[ | ||
21 | Antcamphin I[ | 43 | Dehydroeburicoic acid monoucetate[ | ||
22 | Antcamphin J[ | 44 | Epi-friedelinol[ |
表1 三萜类化合物结构式
Table 1 Structures of triterpenoids
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
1 | Methyl antcinate A[ | 23 | Antcamphin K[ | ||
2 | Methyl antcinate G[ | 24 | Antcamphin L[ | ||
3 | Methyl antcinate H[ | 25 | 15-acetyldehydrosulfurenic[ | ||
4 | Methyl antcinate L[ | 26 | 15α-acetyl-dehydrosulphurenic acid[ | ||
5 | Zhankuic acid B[ | 27 | Antcamphin E[ | ||
6 | Zhankuic acid D[ | 28 | Antcamphin F[ | ||
7 | Antcin A[ | 29 | Antcamphin G[ | ||
8 | Antcin B (Zhankuic acid A)[ | 30 | Methyl antcinateK[ | ||
9 | Antcin C[ | 31 | Antcamphin H[ | ||
10 | Antcin D (Zhankuic acid F)[ | 32 | Antcin K[ | ||
11 | Antcin E[ | 33 | Dehydrosulphurenic acid[ | ||
12 | Antcin F[ | 34 | Dehydroeburicoic acid[ | ||
13 | Antcin G[ | 35 | 15-O-acetylganolucidate A[ | ||
14 | Antcin H (Zhankuic acid C)[ | 36 | Ethyl lucidenate A[ | ||
15 | Antcin M[ | 37 | Ethyl lucidenate F[ | ||
16 | Zhankuic acid E[ | 38 | 3, 7, 11-trioxolanosta-8, 24-dien-26-al, 26-carboxylic acid, 11a-alcohol, me ester[ | ||
17 | Antcamphin A[ | 39 | 3, 7, 11-trioxolanosta-8, 24-dien-26-oic acid[ | ||
18 | Antcamphin B[ | 40 | 3, 7, 12-trihydroxy-11, 15, 23-trioxolanost-8-en-26-oic acid, 3, 7, 12-triketone, me ester[ | ||
19 | Antcamphin C[ | 41 | 3, 7, 12-trihydroxy-11, 15, 23-trioxolanost-8-en-26-oic acid, 3, 7, 12-triketone, et ester[ | ||
20 | Antcamphin D[ | 42 | Eburicol[ | ||
21 | Antcamphin I[ | 43 | Dehydroeburicoic acid monoucetate[ | ||
22 | Antcamphin J[ | 44 | Epi-friedelinol[ |
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
45 | 1, 6-cyclo-1, 10-secoergosta-5, 7, 9, 22-tetraen-3-ol[ | 50 | Stigmasterol[ | ||
46 | Ergostatrien-3β-ol[ | 51 | β-sitostenone[ | ||
47 | Ergosta-4, 6, 8(14), 22-tetraen-3-one[ | 52 | β-sitosterol[ | ||
48 | Ergosterol peroxide[ | 53 | (14α, 22E)-14-hydroxyergosta-7, 22-diene-3, 6-dione[ |
表2 甾醇类化合物结构式
Table 2 Structures of steroids
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
45 | 1, 6-cyclo-1, 10-secoergosta-5, 7, 9, 22-tetraen-3-ol[ | 50 | Stigmasterol[ | ||
46 | Ergostatrien-3β-ol[ | 51 | β-sitostenone[ | ||
47 | Ergosta-4, 6, 8(14), 22-tetraen-3-one[ | 52 | β-sitosterol[ | ||
48 | Ergosterol peroxide[ | 53 | (14α, 22E)-14-hydroxyergosta-7, 22-diene-3, 6-dione[ |
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
54 | 14-dexyandrographolide[ | 73 | 19-hydroxy-8(17)-labden-16, 15-olide[ | ||
55 | 3, 19-dihydroxy-8(17), 11-labdadien-16, 15-olide[ | 74 | Pinusolidic acid[ | ||
56 | 3, 19-dihydroxy-8(17), 11-labdadien-16, 15-olide, 13-epimer[ | 75 | 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone[ | ||
57 | 14-deoxy-11, 12-didehyd-roandrographolide[ | 76 | 2, 3, 6-trimethoxy-4-methylphenol[ | ||
58 | Antrocin[ | 77 | 2, 3, 6-trimethoxy-5-methylphenol[ | ||
59 | Antrocamphin A[ | 78 | 6-methoxy-4-methyl-7-(1-methylethenyl)-1, 3-benzodioxol-5-ol[ | ||
60 | Antrocamphin B[ | 79 | 2-hydroxy-4, 4’-dimethoxy-3, 5'-dimethyl-2’, 3':5, 6-bis(methylenedioxy)biphenyl[ | ||
61 | Antrocamphin C[ | 80 | 4, 4’-dihydroxy-5, 5'-dimethoxy-6, 6’-dimethyl-2, 3:2’, 3'-bis(methylenedioxy)biphenyl[ | ||
62 | Antrocamphin O[ | 81 | 2-hydroxybenzeneethanol[ | ||
63 | Antrodioxolanone[ | 82 | 4, 5-dimethoxy-2, 3-(methylenedioxy)benzoic acid[ | ||
64 | 2-(4-hydroxyphenyl)-3-(2-methylpropyl)-2-butenedioic acid, di-me ester[ | 83 | 4-isobutylphenol[ | ||
65 | 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone[ | 84 | 5-methyl-1, 3-benzodioxole-4, 7-dione[ | ||
66 | 2, 3, 4, 5-tetrahydroxybenzoic acid[ | 85 | 5-methoxy-7-methyl-1, 3-benzodioxol-4-ol[ | ||
67 | 2, 3-dimethoxy-5-methyl-1, 4-benzenediol[ | 86 | 5-methyl-1, 3-benzodioxole-4, 7-diol[ | ||
68 | 4, 7-dimethoxy-5-methyl-1, 3-benzodioxole[ | 87 | 7-methoxy-6-methyl-1, 3-benzodioxol-4-ol[ | ||
69 | 2, 4-dimethoxy-6-methyl-1, 3-benzenediol[ | 88 | 2-methoxy-6-methyl-1, 4-benzoquinone[ | ||
70 | 4, 4’, 7, 7’-tetramethoxy-6, 6’-dimethyl-5, 5'-bi-1, 3-benzodioxole[ | 89 | 4-hydroxysesamin[ | ||
71 | (-)-sesamin[ | 90 | 2-(2-hydroxyethyl)phenol[ | ||
72 | (+)-sesamin[ | 91 | 3, 19-dihydroxy-8(17), 11-labdadien-16, 15-olide, 13-Epimer[ |
表3 二萜、倍半萜及苯环衍生物化合物结构式
Table 3 Structures of diterpenes,sesquiterpenes and benzene derivatives
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
54 | 14-dexyandrographolide[ | 73 | 19-hydroxy-8(17)-labden-16, 15-olide[ | ||
55 | 3, 19-dihydroxy-8(17), 11-labdadien-16, 15-olide[ | 74 | Pinusolidic acid[ | ||
56 | 3, 19-dihydroxy-8(17), 11-labdadien-16, 15-olide, 13-epimer[ | 75 | 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone[ | ||
57 | 14-deoxy-11, 12-didehyd-roandrographolide[ | 76 | 2, 3, 6-trimethoxy-4-methylphenol[ | ||
58 | Antrocin[ | 77 | 2, 3, 6-trimethoxy-5-methylphenol[ | ||
59 | Antrocamphin A[ | 78 | 6-methoxy-4-methyl-7-(1-methylethenyl)-1, 3-benzodioxol-5-ol[ | ||
60 | Antrocamphin B[ | 79 | 2-hydroxy-4, 4’-dimethoxy-3, 5'-dimethyl-2’, 3':5, 6-bis(methylenedioxy)biphenyl[ | ||
61 | Antrocamphin C[ | 80 | 4, 4’-dihydroxy-5, 5'-dimethoxy-6, 6’-dimethyl-2, 3:2’, 3'-bis(methylenedioxy)biphenyl[ | ||
62 | Antrocamphin O[ | 81 | 2-hydroxybenzeneethanol[ | ||
63 | Antrodioxolanone[ | 82 | 4, 5-dimethoxy-2, 3-(methylenedioxy)benzoic acid[ | ||
64 | 2-(4-hydroxyphenyl)-3-(2-methylpropyl)-2-butenedioic acid, di-me ester[ | 83 | 4-isobutylphenol[ | ||
65 | 2, 3-dimethoxy-5-methyl-1, 4-benzoquinone[ | 84 | 5-methyl-1, 3-benzodioxole-4, 7-dione[ | ||
66 | 2, 3, 4, 5-tetrahydroxybenzoic acid[ | 85 | 5-methoxy-7-methyl-1, 3-benzodioxol-4-ol[ | ||
67 | 2, 3-dimethoxy-5-methyl-1, 4-benzenediol[ | 86 | 5-methyl-1, 3-benzodioxole-4, 7-diol[ | ||
68 | 4, 7-dimethoxy-5-methyl-1, 3-benzodioxole[ | 87 | 7-methoxy-6-methyl-1, 3-benzodioxol-4-ol[ | ||
69 | 2, 4-dimethoxy-6-methyl-1, 3-benzenediol[ | 88 | 2-methoxy-6-methyl-1, 4-benzoquinone[ | ||
70 | 4, 4’, 7, 7’-tetramethoxy-6, 6’-dimethyl-5, 5'-bi-1, 3-benzodioxole[ | 89 | 4-hydroxysesamin[ | ||
71 | (-)-sesamin[ | 90 | 2-(2-hydroxyethyl)phenol[ | ||
72 | (+)-sesamin[ | 91 | 3, 19-dihydroxy-8(17), 11-labdadien-16, 15-olide, 13-Epimer[ |
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
92 | 4-acetyl-antroquinonol B[ | 98 | Antrocamol LT2[ | ||
93 | Antroquinonol A[ | 99 | Antroquinonol B[ | ||
94 | AC0009[ | 100 | Antroquinonol D[ | ||
95 | Antrocamol LT1[ | 101 | 4-acetylantrocamol LT3[ | ||
96 | Antrocamol LT3[ | 102 | 4-acetylantroquinonol B[ |
表4 泛醌及衍生物结构式
Table 4 Structures of antroquinonol and its derivatives
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
92 | 4-acetyl-antroquinonol B[ | 98 | Antrocamol LT2[ | ||
93 | Antroquinonol A[ | 99 | Antroquinonol B[ | ||
94 | AC0009[ | 100 | Antroquinonol D[ | ||
95 | Antrocamol LT1[ | 101 | 4-acetylantrocamol LT3[ | ||
96 | Antrocamol LT3[ | 102 | 4-acetylantroquinonol B[ |
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
103 | 2-(4-hydroxyphenyl)-3-isobutylmaleimide, 3R, 4S-dihydro, O-(3-methyl-2-butenyl)[ | 118 | Antrocinnamomin H[ | ||
104 | 2-(4-hydroxyphenyl)-3-isobutylmaleimide, 3R*, 4S*-dihydro, N-hydroxy[ | 119 | Antrodin C (Camphorataimide C)[ | ||
105 | 3, 4-dihydro-3-(4-hydroxyphenyl)-4-(2-methylpropyl)-2, 5-furandione[ | 120 | Antrodin D (Camphorataimide E)[ | ||
106 | Antrodin B (Camphorataimide B)[ | 121 | Antrodin E (Camphorataimide D)[ | ||
107 | Antrocinnamomin A[ | 122 | Antrodin A[ | ||
108 | Antrocinnamomin B[ | 123 | Himanimide C[ | ||
109 | Antrocinnamomin C[ | 124 | Himanimide A[ | ||
110 | Antrocinnamomin D[ | 125 | 3-(4-hydroxyphenyl)-4- isobutylfuran-2, 5-dione[ | ||
111 | Antrocinnamomin E[ | 126 | dimethyl 2-(4-hydroxyphenyl)-3-isobutylmaleate[ | ||
112 | Antrocinnamomin F[ | 127 | 3R*, 4R*-1-hydroxy-3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolidine-2, 5-dione[ | ||
113 | Antrocinnamomin G[ |
表5 琥珀酸和马来酸衍生物结构式
Table 5 Structures of succinic acid and maleic acid derivatives
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
103 | 2-(4-hydroxyphenyl)-3-isobutylmaleimide, 3R, 4S-dihydro, O-(3-methyl-2-butenyl)[ | 118 | Antrocinnamomin H[ | ||
104 | 2-(4-hydroxyphenyl)-3-isobutylmaleimide, 3R*, 4S*-dihydro, N-hydroxy[ | 119 | Antrodin C (Camphorataimide C)[ | ||
105 | 3, 4-dihydro-3-(4-hydroxyphenyl)-4-(2-methylpropyl)-2, 5-furandione[ | 120 | Antrodin D (Camphorataimide E)[ | ||
106 | Antrodin B (Camphorataimide B)[ | 121 | Antrodin E (Camphorataimide D)[ | ||
107 | Antrocinnamomin A[ | 122 | Antrodin A[ | ||
108 | Antrocinnamomin B[ | 123 | Himanimide C[ | ||
109 | Antrocinnamomin C[ | 124 | Himanimide A[ | ||
110 | Antrocinnamomin D[ | 125 | 3-(4-hydroxyphenyl)-4- isobutylfuran-2, 5-dione[ | ||
111 | Antrocinnamomin E[ | 126 | dimethyl 2-(4-hydroxyphenyl)-3-isobutylmaleate[ | ||
112 | Antrocinnamomin F[ | 127 | 3R*, 4R*-1-hydroxy-3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolidine-2, 5-dione[ | ||
113 | Antrocinnamomin G[ |
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
128 | 4-methoxy-2-oxo-2H-pyran-6-propanoic acid[ | 133 | 5-hydroxy-5-(methoxymethyl)-4-methyl-2(5H)-furanone[ | ||
129 | 11-hydroxy-4-dodecanolide[ | 134 | Dihydro-5-octyl-2(3H)-furanone[ | ||
130 | Dihydro-5-(6-hydroxyoctyl)-2(3H)-furanone[ | 135 | Camphosterol A[ | ||
131 | α-tocospiro B[ | 136 | 10-hydroxy-γ-dodecalactone[ | ||
132 | 12-hydroxydodecanoic acid methyl ester[ |
表6 其他杂环化合物结构式
Table 6 Structures of meroterpenoids
序号No. | 名称Name | 结构图Structure chart | 序号No. | 名称Name | 结构图Structure chart |
---|---|---|---|---|---|
128 | 4-methoxy-2-oxo-2H-pyran-6-propanoic acid[ | 133 | 5-hydroxy-5-(methoxymethyl)-4-methyl-2(5H)-furanone[ | ||
129 | 11-hydroxy-4-dodecanolide[ | 134 | Dihydro-5-octyl-2(3H)-furanone[ | ||
130 | Dihydro-5-(6-hydroxyoctyl)-2(3H)-furanone[ | 135 | Camphosterol A[ | ||
131 | α-tocospiro B[ | 136 | 10-hydroxy-γ-dodecalactone[ | ||
132 | 12-hydroxydodecanoic acid methyl ester[ |
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