来自印度尼西亚海洋海绵Haliclona sp.的抗分枝杆菌生物碱——环状3-烷基吡啶二聚体

Anti-mycobacterial alkaloids, cyclic 3-alkyl pyridinium dimers, from the Indonesian marine sponge Haliclona sp.

作者信息

Maarisit Wilmar, Abdjul Delfly B, Yamazaki Hiroyuki, Kato Hajime, Rotinsulu Henki, Wewengkang Defny S, Sumilat Deiske A, Kapojos Magie M, Ukai Kazuyo, Namikoshi Michio

机构信息

Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, Sendai 981-8558, Japan; Faculty of Fisheries and Marine Science, Sam Ratulangi University, Kampus Bahu, Manado 95115, Indonesia; North Sulawesi Research and Development Agency, 17 Agustus Street, Manado 95117, Indonesia.

出版信息

Bioorg Med Chem Lett. 2017 Aug 1;27(15):3503-3506. doi: 10.1016/j.bmcl.2017.05.067. Epub 2017 May 23.

DOI:10.1016/j.bmcl.2017.05.067

PMID:28601525

Abstract

Three new dimeric 3-alkyl pyridinium alkaloids, named haliclocyclamines A-C (1-3), were isolated together with five known congeners, cyclostellettamines A (4), B (5), C (6), E (7), and F (8), from the Indonesian marine sponge Haliclona sp. The structures of 1-3 were assigned based on their spectroscopic data (1D and 2D NMR, HRFABMS, ESIMS/MS, UV, and IR). Compounds 1-8 exhibited antimicrobial activities against Mycobacterium smegmatis with inhibition zones of 17, 10, 13, 14, 8, 8, 12, and 12mm, respectively, at 10μg/disc. Compounds 3 and 8 also modestly inhibited the activity of vaccinia H-1-related phosphatase (VHR), a dual-specificity phosphatase, at 17-18μM.

摘要

从印度尼西亚海洋海绵Haliclona sp.中分离出三种新的二聚体3-烷基吡啶生物碱，命名为卤环胺A-C（1-3），同时还分离出了五种已知的同系物，环星胺A（4）、B（5）、C（6）、E（7）和F（8）。根据它们的光谱数据（一维和二维核磁共振、高分辨快原子轰击质谱、电喷雾离子化串联质谱、紫外和红外光谱）确定了1-3的结构。化合物1-8对耻垢分枝杆菌均表现出抗菌活性，在10μg/圆盘时，其抑菌圈直径分别为17、10、13、14、8、8、12和12mm。化合物3和8在17-18μM时也适度抑制了牛痘H-1相关磷酸酶（VHR，一种双特异性磷酸酶）的活性。