海绵Haliclona baeri中两个新的哌嗪二酮类化合物

doi:10.6023/cjoc202201024

有机化学 ›› 2022, Vol. 42 ›› Issue (6): 1839-1842.DOI: 10.6023/cjoc202201024 上一篇下一篇

研究简报

海绵Haliclona baeri中两个新的哌嗪二酮类化合物

王灿彬, 雷玉, 廖小建, 徐石海^*(), 赵冰心^*()

暨南大学化学与材料学院广州 510632

收稿日期:2022-01-17 修回日期:2022-02-24 发布日期:2022-03-21
通讯作者: 徐石海, 赵冰心
基金资助:
国家重点研发计划(2019YFD0901905); 国家重点研发计划(2018YFC0310900); 国家自然科学基金(41876145); 国家自然科学基金(81874292); 国家自然科学基金(21672084); 广州市科技计划(202102010066); 广州市科技计划(201704030042)

Two New 2,5-Dioxopiperazines from the Marine Sponge Haliclona baeri

Canbin Wang, Yu Lei, Xiaojian Liao, Shihai Xu(), Bingxin Zhao()

College of Chemistry and Materials Science, Jinan University, Guangzhou 510632

Received:2022-01-17 Revised:2022-02-24 Published:2022-03-21
Contact: Shihai Xu, Bingxin Zhao
Supported by:
National Key Research and Development Plan of China(2019YFD0901905); National Key Research and Development Plan of China(2018YFC0310900); National Natural Science Foundation of China(41876145); National Natural Science Foundation of China(81874292); National Natural Science Foundation of China(21672084); Science and Technology Planning Project of Guangzhou(202102010066); Science and Technology Planning Project of Guangzhou(201704030042)

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摘要/Abstract

迄今为止, 研究者们已从Haliclona海绵中分离得到了一系列次生代谢产物, 它们大多表现出抗菌、细胞毒和酶活性等. 然而, 对海绵H. baeri的化学成分及其生物活性的研究非常少, 为了进一步挖掘该种海绵的化学成分, 本课题组对海绵H. baeri进行了系统的化学成分研究, 从中分离得到两个新的哌嗪二酮类化合物, 分别是Haliclines A (1)和B (2), 以及五个已知化合物(3~7). 通过光谱分析阐明了这些化合物的结构, 并通过计算电子圆二色谱(ECD)的方法确定了新化合物1和2的绝对构型. 化合物1是首次发现的具有L-氮杂环丁烷-2-羧酸结构片段的天然哌嗪二酮类化合物. 此外, 还对化合物1和2的抗菌活性进行了测试.

关键词: 海绵, Haliclona baeri, 哌嗪二酮

A series of secondary metabolites had been isolated from the sponge of genus Haliclona, most of which indicated antibacterial, cytotoxic and enzyme activities. However, few literatures about H. baeri had been reported before. In order to search more new bioactive marine natural products from this sponge, H. baeri had been studied systematically. Two new 2,5-dioxopiperazines, haliclines A (1) and B (2), together with five known ones (3~7), were isolated from the marine sponge Haliclona baeri. The structures of these compounds were elucidated by spectroscopic analysis. The absolute configurations of 1 and 2 were established by the method of electronic circular dichroism (ECD) calculation. Compound 1 represented the first example of natural 2,5-dioxopiperazine bearing an L-azetidine-2-carboxylic acid moiety. The antibacterial activities of 1 and 2 were also evaluated.

Key words: sponge, Haliclona baeri, 2,5-dioxopiperazines

引用此文

王灿彬, 雷玉, 廖小建, 徐石海, 赵冰心. 海绵Haliclona baeri中两个新的哌嗪二酮类化合物[J]. 有机化学, 2022, 42(6): 1839-1842.

Canbin Wang, Yu Lei, Xiaojian Liao, Shihai Xu, Bingxin Zhao. Two New 2,5-Dioxopiperazines from the Marine Sponge Haliclona baeri[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1839-1842.

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图/表 4

Figure 1. Chemical structures of 1~7

Figure 2. Key 1H-1H COSY, HMBC and NOE correlations of 1 and 2

Figure 3. Experimental ECD spectrum of 1 and calculated ECD spectra of (3R,6R)-1 and (3S,6S)-1 (UV correction 10 nm, band width σ 0.3 eV)

Figure 4. Experimental ECD spectrum of 2 and calculated ECD spectra of (3R, 6R)-2 and (3S, 6S)-2 (UV correction=0 nm, band width σ=0.3 eV)

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海绵Haliclona baeri中两个新的哌嗪二酮类化合物

Two New 2,5-Dioxopiperazines from the Marine Sponge Haliclona baeri

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