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

doi:10.6023/cjoc202201024

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1839-1842.DOI: 10.6023/cjoc202201024 Previous Articles Next Articles

NOTES

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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Abstract

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

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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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Fig. & Tab. 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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