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源自昆虫病原真菌聚壳菌素 BCC53152 的色满酮和芳基葡萄糖苷类似物。

Chromanones and aryl glucoside analogs from the entomopathogenic fungus Aschersonia confluens BCC53152.

机构信息

Integrated Applied Chemistry Research Unit, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Chalongkrung Road, Ladkrabang, Bangkok 10520, Thailand; Department of Chemistry, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Chalongkrung Road, Ladkrabang, Bangkok 10520, Thailand.

National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand Science Park, Phaholyothin Road, Klong Luang, Pathum Thani 12120, Thailand.

出版信息

Fitoterapia. 2020 Jul;144:104606. doi: 10.1016/j.fitote.2020.104606. Epub 2020 May 3.

DOI:10.1016/j.fitote.2020.104606
PMID:32376482
Abstract

Six new compounds [ascherlactones A (1) and B (2), ascherchromanone A (3), phenethyl 4'-O-methylglucoside (8), 4'-O-methylpleoside (10), and 4'-O-methyltorachrysone 8-O-glucoside (11)] and one naturally new compound [4'-O-methyl-β-d-benzylglucoside (9)] together with fourteen known compounds, including paecilodepsipeptides A (5), B (7), and D (4), conoideocrellide A (6), eugenin (12), 5-hydroxy-2,3-dimethyl-7-methoxychromone (13), (S)-1-phenyl-1,2-ethanediol (14), (2S)-l-3-phenyllactic acid (15), papuline [or (2S)-l-3-phenyllactic acid methyl ester, 16], 2'-epi terpendole A (17), terpendoles C (18) and D (19), cholic acid, and zeorin were isolated from the entomopathogenic fungus Aschersonia confluens BCC53152. Their chemical structures were elucidated on the basis of NMR spectroscopic and mass spectrometric analyses. The absolute configurations were determined by using the evidence from NOESY correlations, chemical means, optical rotation values together with comparison of ECD spectroscopic data with the calculated ECD spectra. The plausible biosynthetic pathway of compounds 1-3 was also proposed. Moreover, antimicrobial activity such as antimalarial, antitubercular, antifungal, and antibacterial activities and cytotoxicity against cancerous (MCF-7, KB, and NCI-H187) and non-cancerous (Vero) cells of the isolated compounds were evaluated.

摘要

从昆虫病原真菌 Aschersonia confluens BCC53152 中分离得到了六个新化合物[阿舍尔内酯 A(1)和 B(2)、阿舍尔色酮 A(3)、苯乙基 4'-O-甲基葡萄糖苷(8)、4'-O-甲基比莱苷(10)和 4'-O-甲基 torachrysone 8-O-葡萄糖苷(11)]和一个天然新化合物[4'-O-甲基-β-d-苄基葡萄糖苷(9)],以及 14 种已知化合物,包括 paecilodepsipeptides A(5)、B(7)和 D(4)、conoideocrellide A(6)、eugenin(12)、5-羟基-2,3-二甲基-7-甲氧基色酮(13)、(S)-1-苯基-1,2-乙二醇(14)、(2S)-l-3-苯乳酸(15)、papuline[或(2S)-l-3-苯乳酸甲酯,16]、2'-epi terpendole A(17)、terpendoles C(18)和 D(19)、胆酸和 zeorin。这些化合物的化学结构是基于 NMR 光谱和质谱分析确定的。通过使用来自 NOESY 相关、化学方法、旋光值以及与计算 ECD 光谱数据的比较的证据,确定了绝对构型。还提出了化合物 1-3 的可能生物合成途径。此外,还评估了分离化合物的抗疟疾、抗结核、抗真菌和抗菌活性以及对癌细胞(MCF-7、KB 和 NCI-H187)和非癌细胞(Vero)的细胞毒性。

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