来源于红树林内生真菌 sp. ZJ-68 的海蛇孢菌素型倍半萜。

Ophiobolin-Type Sesterterpenoids from the Mangrove Endophytic Fungus sp. ZJ-68.

机构信息

School of Chemistry , Sun Yat-sen University , Guangzhou 510275 , People's Republic of China.

School of Chemistry and Environment , South China Normal University , Guangzhou 510006 , People's Republic of China.

出版信息

J Nat Prod. 2019 Aug 23;82(8):2268-2278. doi: 10.1021/acs.jnatprod.9b00462. Epub 2019 Jul 31.

DOI:10.1021/acs.jnatprod.9b00462

PMID:31365251

Abstract

Eleven new ophiobolin-type sesterterpenoids, asperophiobolins A-K (-), along with 12 known analogues (-) were isolated from the cultures of the mangrove endophytic fungus sp. ZJ-68. The structures of the new compounds were elucidated through spectroscopic analyses, and their absolute configurations were assigned by a combination of Mo(AcO)-induced electronic circular dichroism spectra and quantum chemical calculations. Asperophiobolins A-D (-) represent the first examples possessing a five-membered lactam unit between C-5 and C-21 in ophiobolin derivatives. In the bioactivity assays, compounds - and - exhibited inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophage cells with IC values ranging from 9.6 to 25 μM, and compound was found to show comparable inhibition of protein tyrosine phosphatase B with an IC value of 19 μM.

摘要

从红树林内生真菌 sp. ZJ-68 的培养物中分离得到 11 种新型蛇孢菌素型倍半萜，分别命名为asperophiobolins A-K (-)，同时还分离得到了 12 种已知类似物 (-)。通过光谱分析阐明了新化合物的结构，并通过 Mo(AcO)-诱导的电子圆二色谱和量子化学计算的组合确定了它们的绝对构型。Asperophiobolins A-D (-)代表了在蛇孢菌素衍生物中具有 C-5 和 C-21 之间五元内酰胺单元的第一个例子。在生物活性测定中，化合物 - 和 - 对 LPS 诱导的 RAW 264.7 巨噬细胞中一氧化氮产生具有抑制作用，IC 值范围为 9.6-25 μM，并且发现化合物对蛋白酪氨酸磷酸酶 B 的抑制作用相当，IC 值为 19 μM。