来自寄生假地心蕨的内生Nodulisporium真菌中的Seco-pimarane双萜类和androstane类类固醇。
Seco-pimarane diterpenoids and androstane steroids from an endophytic Nodulisporium fungus derived from Cyclosorus parasiticus.
发表日期:2023 Apr 12
作者:
Xiaoli Yang, Ping Wu, Jinghua Xue, Hanxiang Li, Xiaoyi Wei
来源:
PHYTOCHEMISTRY
摘要:
五种先前未描述过的特殊代谢产物,包括三种9,11-sec-pimarane二萜类化合物nodulisporenones A-C 和两种雄甾烷类化合物nodulisporisterones A和B,连同先前描述过的麦角固醇衍生物dankasterone A和demethylincisterol A3,从内生真菌Nodulisporium sp.SC-J597的固体培养物中分离出来。通过广泛的光谱分析和电子圆二色谱光谱的理论计算,确定了它们的结构,包括绝对构型。其中,nodulisporenones A和B是第一个环化形成前所未有的二萜内酯支架的9,11-sec-pimarane二萜类化合物。nodulisporisterones A和B代表了真菌起源的第一个正常C19雄甾烷类化合物。nodulisporisterone B对LPS刺激的RAW264.7巨噬细胞中NO的产生具有很强的抑制作用(IC50 = 2.95μM)。这种化合物与两个已知的麦角固醇衍生物一起,还显示出对A549、HeLa、HepG2和MCF-7肿瘤细胞系的细胞毒性,IC50值为5.2-16.9μM。Copyright © 2023. Elsevier Ltd. 发布。
Five previously undescribed specialized metabolites, including three 9,11-seco-pimarane diterpenoids, nodulisporenones A-C, and two androstane steroids, nodulisporisterones A and B, together with previously described ergosterol derivatives, dankasterone A and demethylincisterol A3, were isolated from solid cultures of the endophytic fungus Nodulisporium sp. SC-J597. Their structures including absolute configurations were elucidated by extensive spectroscopic analysis and theoretical calculations of electronic circular dichroism spectra. Among them, nodulisporenones A and B are the first examples of seco-pimarane diterpenoids that is cyclized to form an unprecedented diterpenoid lactone scaffold and nodulisporisterones A and B represent the first normal C19 androstane steroids of fungal origin. Nodulisporisterone B exhibited potent inhibitory effect on the production of NO in LPS-stimulated RAW264.7 macrophages (IC50 = 2.95 μM). This compound, together with the two known ergosterol derivatives, also displayed cytotoxicity against A549, HeLa, HepG2 and MCF-7 cancer cell lines with IC50 values of 5.2-16.9 μM.Copyright © 2023. Published by Elsevier Ltd.