Isolation, characterization, and biological activities of halogenated sesquiterpenes and C15 acetogenins from the Okinawan sea hare, Aplysia argus

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2025-06-01 Epub Date: 2025-03-10 DOI:10.1016/j.tet.2025.134588

Ryunosuke Nakamura , Koushi Matsuyama , Naomichi Arima , Fumito Tani , Satoaki Onitsuka , Hiroaki Okamura , Tetsuo Iwagawa , Masayuki Sudoh , Toshiyuki Hamada

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Abstract

The sea hare, scientifically known as Aplysia argus, is the focus of considerable research interest owing to its unique halogenated metabolites that may have vast potential in the fields of medicine and pharmaceuticals. This paper reports the isolation of a new laurane-type sesquiterpene, 10-bromoisolaurinsiol (1), and a new halogenated C₁₅ acetogenin (2), along with several known halogenated secondary metabolites from the sea hare Aplysia argus. Their structures and relative stereochemistries were established through comprehensive 1D and 2D NMR analyses. Fourteen compounds, some of which were novel, were evaluated for their cytotoxic effects against S1T cells (a cancer cell line derived from adult T-cell leukemia patients) and their potential as SARS-CoV-2 main protease inhibitors.

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冲绳海兔中卤代倍半萜和C15乙酰素的分离、鉴定及生物活性研究

海兔，科学上称为海兔，由于其独特的卤化代谢物在医学和制药领域可能具有巨大的潜力，因此成为相当大的研究兴趣的焦点。本文报道了一种新的月桂烷型倍半萜，10-溴异aurinol(1)和一种新的卤化C15 acetogenin(2)，以及几种已知的卤化次生代谢物。通过全面的一维和二维核磁共振分析，确定了它们的结构和相对立体化学性质。研究人员评估了14种化合物（其中一些是新的）对S1T细胞（一种来自成人t细胞白血病患者的癌细胞系）的细胞毒性作用，以及它们作为SARS-CoV-2主要蛋白酶抑制剂的潜力。

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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.