海洋来源真菌 KFD28 中具有蛋白酪氨酸磷酸酶抑制活性的吲哚二萜类化合物

Indole-Diterpenoids with Protein Tyrosine Phosphatase Inhibitory Activities from the Marine-Derived Fungus sp. KFD28.

机构信息

College of Life Science, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education , Hebei University , Baoding 071002 , People's Republic of China.

Hainan Key Laboratory for Research and Development of Natural Product from Li Folk Medicine , Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agriculture Sciences , Haikou 571101 , People's Republic of China.

出版信息

J Nat Prod. 2019 Sep 27;82(9):2638-2644. doi: 10.1021/acs.jnatprod.9b00620. Epub 2019 Aug 30.

DOI:10.1021/acs.jnatprod.9b00620

PMID:31469560

Abstract

Five new indole-terpenoids named penerpenes E-I (-), along with seven known ones (-), were isolated from the marine-derived fungus sp. KFD28 from a bivalve mollusk, . The structures of the new compounds were elucidated from spectroscopic data and ECD spectroscopic analyses. Compound was assigned as an indole-diterpenoid with a unique 6/5/5/6/6/5/5 heptacyclic ring system. Compound represents an indole-diterpenoid with a new carbon skeleton derived from paxilline by the loss of three carbons (C-23/24/25). Compound contains an additional oxygen atom between C-21 and C-22 compared to paxilline to form an unusual 6/5/5/6/6/7 hexacyclic ring system bearing a 1,3-dioxepane ring, which is rarely encountered in natural products. Compounds , , , and showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC values of 14, 27, 23, and 13 μM, respectively.

摘要

从双壳贝类软体动物中分离到的海洋来源真菌 sp. KFD28 中，分离得到了 5 种新的吲哚萜烯命名为 penerpenes E-I（-），以及 7 种已知的化合物（-）。新化合物的结构通过光谱数据和 ECD 光谱分析确定。化合物被分配为具有独特的 6/5/5/6/6/5/5 个七元环系统的吲哚二萜烯。化合物代表一种吲哚二萜烯，其骨架来源于 paxilline，通过失去三个碳原子（C-23/24/25）而形成。化合物与 paxilline 相比，在 C-21 和 C-22 之间额外含有一个氧原子，形成一个不寻常的 6/5/5/6/6/7 六元环系统，带有 1,3-二氧戊环，这在天然产物中很少见。化合物、、、和对蛋白酪氨酸磷酸酶 1B（PTP1B）显示出抑制活性，IC 值分别为 14、27、23 和 13 μM。