Indole-Diterpenoids with Anti-H1N1 Activity from the Aciduric Fungus Penicillium camemberti OUCMDZ-1492
Indole-Diterpenoids with Anti-H1N1 Activity from the Aciduric Fungus Penicillium camemberti OUCMDZ-1492
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来自耐酸真菌卡门贝尔青霉 OUCMDZ-1492 的具有抗 H1N1 活性的吲哚二萜类化合物
DOI：
10.1021/np400304q
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发表时间：
2013-07-01
影响因子：
5.1
通讯作者：
Zhu, Weiming
中科院分区：
文献类型：
--
作者：
Fan, Yaqin;Wang, Yi;Zhu, Weiming
从红树林根周围的酸性海洋生态位--红树林土壤和淤泥中分离到一株耐酸真菌，命名为Penicilliumcamemberti OUCMDZ-1492。从pH5.0的卡门贝毕赤酵母OUCMDZ-1492发酵液中分离得到6个新的吲哚二萜类化合物（1-6），沿着5个已知的类似物，emindole SB（7），21-异戊烯基paxilline（8），paspaline（9），paxilline（10）和dehydroxypaxilline（11）。根据光谱分析、圆二色性光谱、量子化学计算和化学方法，确定了新化合物1-6为3-deoxo-4 b-deoxypaxilline，4a-demethylpaspaline-4a-carboxylic acid，4a-demethylpaspaline-3，4，4a-triol，2 ′-hydroxypaxilline，9，10-diisopentenylpaxilline，和（6S，7 R，10 E，14 E）-16-（1H-吲哚-3-基）-2，6，10，14-四甲基十六碳-2，10，14-三烯-6，7-二醇。化合物1-3和5-10表现出显著的抗H1N1病毒活性，IC 50值分别为28.3、38.9、32.2、73.3、34.1、26.2、6.6、77.9和17.7 μ M。结果表明，3-氧代，4 b-羟基，和9-异戊烯基取代倾向于增加六环吲哚-二萜类化合物的抗H1N1活性。
An aciduric fungal strain, Penicillium camemberti OUCMDZ-1492, was isolated from an acidic marine niche, mangrove soil and mud, around the roots of Rhizophora apiculata. Six new indole-diterpenoids (1-6), along with five known analogues, emindole SB (7), 21-isopentenylpaxilline (8), paspaline (9), paxilline (10), and dehydroxypaxilline (11), were isolated from the fermentation broth of P. camemberti OUCMDZ-1492 grown at pH 5.0. On the basis of spectroscopic analyses, CD spectra, quantum ECD calculations, and chemical methods, new structures 1-6 were established as 3-deoxo-4b-deoxypaxilline, 4a-demethylpaspaline-4a-carboxylic acid, 4a-demethylpaspaline-3,4,4a-triol, 2'-hydroxypaxilline, 9,10-diisopentenylpaxilline, and (6S,7R,10E,14E)-16-(1H-indol-3-yl)-2,6,10,14-tetramethylhexadeca-2,10,14-triene-6,7-diol, respectively. Compounds 1-3 and 5-10 exhibited significant activity against the H1N1 virus with IC50 values of 28.3, 38.9, 32.2, 73.3, 34.1, 26.2, 6.6, 77.9, and 17.7 mu M, respectively. The results showed that 3-oxo, 4b-hydroxy, and 9-isopentenyl substitutions tend to increase the anti-H1N1 activity of hexacyclic indole-diterpenoids.