Discovery of New Bohemamines and Synthesis of Methylene-Bridged Chimeric Derivatives through Natural Product Chimera Strategy

被引：5

作者：

Zhang, Rongxin ^{[1
]}

Yan, Xiaotang ^{[1
]}

Yin, Shupeng ^{[1
]}

Wang, Weihong ^{[1
]}

Zhu, Weiming ^{[1
,2
]}

Fu, Peng ^{[1
,2
]}

机构：

[1] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ China, Qingdao 266003, Shandong, Peoples R China

[2] Pilot Natl Lab Marine Sci & Technol Qingdao, Lab Marine Drugs & Bioprod, Qingdao 266237, Shandong, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2022年 / 40卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Natural products; Structure elucidation; Dimerization; Pyrrolizidine alkaloids; Biological activity; PYRROLIZIDINE ALKALOIDS; STREPTOMYCES SP; JENAMIDINE-A; PHENYLACETALDEHYDE; ACTIVATION; ASSAY;

D O I：

10.1002/cjoc.202200034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Comprehensive Summary Five new pyrrolizidine alkaloids, bohemamines J-N (1-5), were isolated from Streptomyces sp. CPCC 200497. Their structures were assigned based on detailed spectroscopic analysis and semisynthesis. Bohemamine J (1) possesses a new chimeric skeleton derived from bohemamine A (6) and phenylacetaldehyde. Inspired by the nonenzymatic formation mechanism of the methylene-bridged dimers isolated from this strain, we synthesized a series of chimeric derivatives (8, 9, and 12-23) through natural product chimera strategy. Compounds 13, 15, 19, and 21 showed significant antioxidant activity.

引用

页码：1413 / 1421

页数：9

共 35 条

[31] An Improved Synthesis of Natural Product Inspired Chromenopyrrolizines and Chromenoindolizines Scaffolds: Rapid Access to the Diverse Pyrrolizine Analogs of Aza-Medicarpin and Tetracyclic Isolamellarin Core through a General Base and Metal Free Strategy
Khan, Tabrez
Kumar, Virendra
Das, Oindreela
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2016, 89 (11) : 1331 - 1340
[32] Discovery, Synthesis, and Functional Characterization of a Novel Neuroprotective Natural Product from the Fruit of Alpinia oxyphylla for use in Parkinson's Disease Through LC/MS-Based Multivariate Data Analysis-Guided Fractionation
Li, Guohui
Zhang, Zaijun
Quan, Quan
Jiang, Renwang
Szeto, Samuel S. W.
Yuan, Shuai
Wong, Wing-tak
Lam, Herman H. C.
Lee, Simon Ming-Yuen
Chu, Ivan K.
JOURNAL OF PROTEOME RESEARCH, 2016, 15 (08) : 2595 - 2606
[33] Discovery of new 1,3-diphenylurea appended aryl pyridine derivatives as apoptosis inducers through c-MET and VEGFR-2 inhibition: design, synthesis, in vivo and in silico studies
Elsebaie, Heba A.
Nafie, Mohamed S.
Tawfik, Haytham O.
Belal, Amany
Ghoneim, Mohammed M.
Obaidullah, Ahmad J.
Shaaban, Salwa
Ayed, Abdelmoneim A.
El-Naggar, Mohamed
Mehany, Ahmed B. M.
Shaldam, Moataz A.
RSC MEDICINAL CHEMISTRY, 2024, 15 (07): : 2553 - 2569
[34] Discovery of N-methylbenzo[d]oxazol-2-amine as new anthelmintic agent through scalable protocol for the synthesis of N-alkylbenzo[d] oxazol-2-amine and N-alkylbenzo[d]thiazol-2-amine derivatives
Laohapaisan, Pavitra
Reamtong, Onrapak
Tummatorn, Jumreang
Thongsornkleeb, Charnsak
Thaenkham, Urusa
Adisakwattana, Poom
Ruchirawat, Somsak
BIOORGANIC CHEMISTRY, 2023, 131
[35] Expeditious synthesis of 2,3-dihydro-2-alkoxy-3-methylenebenzofurans from N-benzofuran-3-ylmethyl N,N,N-trialkylammonium bromides: a new approach to access the natural product, 2-hydroxy-3-methylene-6-methyl-2, 3-dihydrobenzofuran
Wang, Yuanxiang
Zhang, Ao
TETRAHEDRON, 2009, 65 (34) : 6986 - 6990

← 1 2 3 4 →