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从真菌 Botrysphaeria laricina 的培养物中分离得到的新萜类化合物和三酮类化合物。

New terpenoids and triketides from culture of the fungus Botrysphaeria laricina.

机构信息

Department of Natural Product Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Wenhua Road, Jinan 250012, PR China.

Department of Natural Product Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, 44 West Wenhua Road, Jinan 250012, PR China.

出版信息

Fitoterapia. 2020 Nov;147:104758. doi: 10.1016/j.fitote.2020.104758. Epub 2020 Oct 15.

DOI:10.1016/j.fitote.2020.104758
PMID:33069833
Abstract

Three new isopimarane-type diterpenoids, botrysphins G-I (1-3), a new muurolane-type sesquiterpenoid, 11,12-dihydroxylentideusether (4), and two new triketides, 4-dechlorobotrysphone C (5) and 4,5-dihydroxy-3-methoxy-6-undecanoyloxy-2-cyclohexen-1-one (6), together with one known diterpenoid, sphaeropsidin A (7), one sesquiterpenoid, lentideusether (8), and one triketide sphaeropsidone (9), were isolated from culture of the fungus Botrysphaeria laricina associated with the moss Rhodobryum umgiganteum. The structures of the new compounds were established on the basis of extensive spectroscopic techniques including HRMS and 1D and 2D NMR data. Compounds 1 and 2 exhibited NO inhibitory activity with IC values of 13.9 μM and 41.9 μM, respectively. At the same time, these two compounds showed quinone reductase inducing activity with 2.7-fold of induction for 1 at 12.5 μM and 1.6-fold for 2 at 25.0 μM.

摘要

三种新的异贝壳杉烷型二萜类化合物,即 botrysphins G-I(1-3),一种新的木烷型倍半萜类化合物 11,12-二羟基-10-表松烯醚(4),以及两种新的三酮类化合物 4-去氯 botrysphone C(5)和 4,5-二羟基-3-甲氧基-6-十一烷酰氧基-2-环己烯-1-酮(6),连同一种已知的二萜类化合物 sphaeropsidin A(7)、一种倍半萜类化合物 lentideusether(8)和一种三酮类化合物 sphaeropsidone(9),从与 Rhodobryum umgiganteum 共生的真菌 Botrysphaeria laricina 的培养物中分离得到。新化合物的结构是基于广泛的光谱技术,包括高分辨率质谱和 1D 和 2D NMR 数据建立的。化合物 1 和 2 表现出对 NO 的抑制活性,IC 值分别为 13.9 μM 和 41.9 μM。同时,这两种化合物表现出醌还原酶诱导活性,在 12.5 μM 时,1 的诱导倍数为 2.7 倍,在 25.0 μM 时,2 的诱导倍数为 1.6 倍。

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