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天然产物

从自然界存在的生物体内分离、提取得到的有机化合物被称为天然产物,它们在动、植物体内通过生化作用和光合作用形成。例如,淀粉来源于植物的种子、茎及根块;蛋白质则主要来自肉类、乳品、蛋类以及谷物和豆类;许多药物如麻黄碱、薄荷脑、蛇胆等都源自相应生物体;而蓝色染料靛蓝与红色染料茜素分别从天然靛叶和茜草中提取;天然香料如麝香、茉莉、玫瑰等亦来自特定动、植物。

在大多数情况下,这些天然产物对产生它们的植物、昆虫或微生物而言似乎是不必需的,这与糖类、氨基酸、核酸及其多聚体等其他有机化合物显著不同。例如吗啡仅存在于少数几种植物中,如罂粟属的刚毛罂粟和虞美人以及头花千金藤;尽管人类使用它作为镇痛药,但其在这些植物中的功能仍不清楚。青霉素是由少数真菌产生的,而不会被其他生物产生。尽管它们作为抗菌药物用于治疗各种感染性疾病,在产生它们的微生物中却无明显用途。

海洋天然产物指的是从海洋生物中提取的一系列有机物质,包括脂肪族、芳香族、萜类、甾醇以及含氮、含硫等各种类型的化合物。海洋是一个蕴藏丰富药理活性天然产物的宝库,其中生活着地球上约80%的动植物和大约1500种细菌。例如,海藻在中国已有悠久的历史被用作食品和药物,《神农本草经》中就有记载“海藻疗瘿”、“牡蛎强骨节,杀邪气”。海藻富含各种独特结构的有机化合物,其代谢产物具有多种多样的生理活性,特别是以卤素为特征的萜类、脂肪族化合物、含硫和含氮类化合物以及甾醇类化合物等都表现出显著的抗菌及抗心血管疾病的作用。高分子多糖,如醇脂、褐藻胶和卡拉胶,也是由海藻中制得,在工业及医药上具有重要应用价值。

从海洋数千种有毒生物中提取出的强效生理活性成分(如河豚毒素)是大自然赐予人类的宝贵财富。研究发现,在海洋动物的提取物中约10%有抗P388淋巴细胞白血病和KB细胞的作用;而约3.5%的海洋植物提取物具有抗肿瘤或细胞毒性作用。美国研究人员在400多种海洋天然产物中,发现了100种具有生物、药理活性的化合物。

中文名称 英文名称 CAS号 化学式 结构式图片
—— (-)-lupinine 486-70-4 C10H19NO
(-)-lupinine
—— Lupinin 486-70-4 C10H19NO
Lupinin
—— methyl (1S,9R,10S,12S,13E,15S)-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8-aza-15-azoniapentacyclo[10.5.1.01,9.02,7.09,15]octadeca-2,4,6-triene-18-carboxylate 6871-44-9 C22H29N2O4+
methyl (1S,9R,10S,12S,13E,15S)-13-ethylidene-10-hydroxy-18-(hydroxymethyl)-15-methyl-8-aza-15-azoniapentacyclo[10.5.1.01,9.02,7.09,15]octadeca-2,4,6-triene-18-carboxylate
—— Berberine sulfate hydrate 316-41-6 C40H38N2O13S
Berberine sulfate hydrate
—— (-)Scopolamine methyl nitrate 6106-46-3 C18H24N2O7
(-)Scopolamine methyl nitrate
—— Nicotine hydrogen tartrate 65-31-6 C10H16N2(C4H5O6)2
Nicotine hydrogen tartrate
—— Pericyclivine 975-77-9 C20H22N2O2
Pericyclivine
—— [(4R,7S,9R,10S,12S)-4,12-diacetyloxy-1,9,15-trihydroxy-10-(hydroxymethyl)-14,17,17-trimethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 78432-78-7 C31H38O12
[(4R,7S,9R,10S,12S)-4,12-diacetyloxy-1,9,15-trihydroxy-10-(hydroxymethyl)-14,17,17-trimethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
—— (1S,2R,4R,7E)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one 20554-84-1 C15H20O3
(1S,2R,4R,7E)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
—— cis-khellactone 3'-O-β-D-glucopyranoside 86940-46-7 C20H24O10
cis-khellactone 3'-O-β-D-glucopyranoside
—— N-nornuciferine 4846-19-9 C18H19NO2
N-nornuciferine
—— gelsenicine 82354-38-9 C19H22N2O3
gelsenicine
—— gardenoside 24512-62-7 C17H24O11
gardenoside
—— jolkinolide E 54494-34-7 C20H28O2
jolkinolide E
—— (4a<i>S</i>,7<i>R</i>)-1<i>c</i>-β-D-glucopyranosyloxy-4'-((<i>S</i>)-1-hydroxy-ethyl)-5'-oxo-(4a<i>r</i>,7a<i>c</i>)-4a,7a-dihydro-1<i>H</i>,5'<i>H</i>-spiro[cyclopenta[<i>c</i>]pyran-7,2'-furan]-4-carboxylic acid 132586-69-7 C20H24O12
(4a<i>S</i>,7<i>R</i>)-1<i>c</i>-β-D-glucopyranosyloxy-4'-((<i>S</i>)-1-hydroxy-ethyl)-5'-oxo-(4a<i>r</i>,7a<i>c</i>)-4a,7a-dihydro-1<i>H</i>,5'<i>H</i>-spiro[cyclopenta[<i>c</i>]pyran-7,2'-furan]-4-carboxylic acid
—— Umbelliferon-7β-glucosid 93-39-0 C15H16O8
Umbelliferon-7β-glucosid
—— cyclosiversigenin 78574-94-4 C30H50O5
cyclosiversigenin
—— 6-methoxyspiro[1,2-dihydroindene-3,4'-cyclohexane]-1',4-diol 64052-90-0 C15H20O3
6-methoxyspiro[1,2-dihydroindene-3,4'-cyclohexane]-1',4-diol
—— cyclo(L)-Pro-(D)-Phe 26488-24-4 C14H16N2O2
cyclo(L)-Pro-(D)-Phe
—— Isopimarinsaeure 514-08-9 C20H30O2
Isopimarinsaeure
—— (1R,7S)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid 514-08-9 C20H30O2
(1R,7S)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
—— isopimaric acid 514-08-9 C20H30O2
isopimaric acid
—— euphorbia factor L<sub>1</sub> 76376-43-7 C32H40O8
euphorbia factor L<sub>1</sub>
—— (3-acetyloxy-7,7a-dimethyl-4'-methylidene-2'-oxospiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-4-yl) (E)-3-methylsulfanylprop-2-enoate 18456-03-6 C21H28O6S
(3-acetyloxy-7,7a-dimethyl-4'-methylidene-2'-oxospiro[3,3a,4,5,6,7-hexahydro-1H-indene-2,3'-oxolane]-4-yl) (E)-3-methylsulfanylprop-2-enoate
—— (10R)-1,8-Dihydroxy-3-(hydroxymethyl)-10-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one 8015-61-0 C21H22O9
(10R)-1,8-Dihydroxy-3-(hydroxymethyl)-10-[(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
—— (5Z)-5-Methyl-9-methylidene-2-propan-2-ylcyclodec-5-en-1-one 25645-19-6 C15H24O
(5Z)-5-Methyl-9-methylidene-2-propan-2-ylcyclodec-5-en-1-one
—— (1S,4S,5R,9R,13S)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadec-10-ene-5-carboxylic acid 22338-67-6 C20H28O2
(1S,4S,5R,9R,13S)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadec-10-ene-5-carboxylic acid
—— sandaracopimaradiene-3β,18-diol 59219-64-6 C20H32O2
sandaracopimaradiene-3β,18-diol
—— Sarpagin 482-68-8 C19H22N2O2
Sarpagin
—— Eichlerianic acid 56421-13-7 C30H50O4
Eichlerianic acid
—— (E)-16-epi-normacusine B 126640-98-0 C19H22N2O
(E)-16-epi-normacusine B
—— 4-hydroxy-19-nor-dehydroabietane 18530-08-0 C19H28O
4-hydroxy-19-nor-dehydroabietane
—— 18-norabieta-8,11,13-trien-4-ol 22478-65-5 C19H28O
18-norabieta-8,11,13-trien-4-ol
—— Tyromycic acid 104759-35-5 C30H44O3
Tyromycic acid
—— Tabersonin 4429-63-4 C21H24N2O2
Tabersonin
—— vomifoliol 23526-45-6 C13H20O3
vomifoliol
—— 4-epihederagenin 3-O-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside (CP3a) 27013-91-8 C41H66O12
4-epihederagenin 3-O-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside (CP3a)
—— α-Hederin 27013-91-8 C41H66O12
α-Hederin
—— α-Hederin 27013-91-8 C41H65O12*Na
α-Hederin
—— kalopanaxsaponin A 27013-91-8 C41H66O12
kalopanaxsaponin A
—— 5,5′-dimethoxysecoisolariciresinol 9-O-β-xylopyranoside 126882-53-9 C27H38O12
5,5′-dimethoxysecoisolariciresinol 9-O-β-xylopyranoside
—— saringosterol 6901-60-6 C29H48O2
saringosterol
—— hirsutanonol 41137-86-4 C19H22O6
hirsutanonol
—— hederagenin-3-O-α-L-arabinopyranoside 17184-21-3 C35H56O8
hederagenin-3-O-α-L-arabinopyranoside
—— Alphitolinsaeure 19533-92-7 C30H48O4
Alphitolinsaeure
—— (+)-(6a<i>r</i>,11b<i>c</i>)-7,11b-dihydro-indeno[2,1-<i>c</i>]chromene-3,6a,9,10-tetraol 474-07-7 C16H14O5
(+)-(6a<i>r</i>,11b<i>c</i>)-7,11b-dihydro-indeno[2,1-<i>c</i>]chromene-3,6a,9,10-tetraol
—— Sativan 41743-86-6 C17H18O4
Sativan
—— lupanine 486-87-3 C15H24N2O
lupanine
—— (+)-lupanine (6R,7S,9S,11S) 486-87-3 C15H24N2O
(+)-lupanine (6R,7S,9S,11S)
—— 5-hydroxy-3-(4-methoxyphenyl)-7-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one 5928-26-7 C22H22O10
5-hydroxy-3-(4-methoxyphenyl)-7-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one