Enshuol epoxide, an unusual squalene-derived bromotriterpene from Laurencia omaezakiana and its biological evaluation

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-04-29 DOI:10.1016/j.tet.2025.134686

Tatsuhide Miwa , Tomoki Tsuruta , Chikato Nozue , Ryoma Nakagawa , Ryosuke Fukada , Keisuke Nishikawa , Yoshiki Morimoto , Momochika Kumagai , Ryunosuke Nakamura , Toshiyuki Hamada , Yukimasa Yamagishi , Takashi Kamada

{"title":"Enshuol epoxide, an unusual squalene-derived bromotriterpene from Laurencia omaezakiana and its biological evaluation","authors":"Tatsuhide Miwa , Tomoki Tsuruta , Chikato Nozue , Ryoma Nakagawa , Ryosuke Fukada , Keisuke Nishikawa , Yoshiki Morimoto , Momochika Kumagai , Ryunosuke Nakamura , Toshiyuki Hamada , Yukimasa Yamagishi , Takashi Kamada","doi":"10.1016/j.tet.2025.134686","DOIUrl":null,"url":null,"abstract":"<div><div>The red seaweed, Laurencia omaezakiana, is a rich source of secondary metabolites derived from squalene. A new brominated polyether, enshuol epoxide (1), together with two known compounds, enshuol (2) and 15,16-anhydrothyrsiferol (3), were isolated and characterized from this alga. Interestingly, we also found cis-chondrin (4), a non-terpenoid C15 acetogenin, which has not been previously reported in this species. The gross structure and absolute configuration of 1 were elucidated by using spectroscopic methods, comparison with existing data, and chemical derivatization. Compounds 1–3, which exhibited significant cytotoxic activities against a panel of adult T-cell leukemia (ATL) cell lines, can potentially be used to develop novel drugs for leukemia.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"181 ","pages":"Article 134686"},"PeriodicalIF":2.1000,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S004040202500242X","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

Abstract

The red seaweed, Laurencia omaezakiana, is a rich source of secondary metabolites derived from squalene. A new brominated polyether, enshuol epoxide (1), together with two known compounds, enshuol (2) and 15,16-anhydrothyrsiferol (3), were isolated and characterized from this alga. Interestingly, we also found cis-chondrin (4), a non-terpenoid C₁₅ acetogenin, which has not been previously reported in this species. The gross structure and absolute configuration of 1 were elucidated by using spectroscopic methods, comparison with existing data, and chemical derivatization. Compounds 1–3, which exhibited significant cytotoxic activities against a panel of adult T-cell leukemia (ATL) cell lines, can potentially be used to develop novel drugs for leukemia.

Abstract Image

查看原文本刊更多论文

一种罕见的角鲨烯衍生溴三萜环氧化恩舒酚及其生物学评价

红海藻Laurencia omaezakiana是角鲨烯衍生的次生代谢物的丰富来源。从该藻中分离得到一种新的溴化聚醚，环氧化恩朔醇(1)，以及两种已知化合物恩朔醇(2)和15,16-无氢thyrsiferol(3)。有趣的是，我们还发现了顺式chondrin(4)，这是一种非萜类C15醋酸原蛋白，以前没有在该物种中报道过。利用光谱学方法、与现有资料的比较、化学衍生等方法对1的总结构和绝对构型进行了分析。化合物1-3对一组成人t细胞白血病（ATL）细胞系显示出显著的细胞毒活性，可用于开发治疗白血病的新药。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.