Cephalotane diterpenoids: structural diversity, biological activity, biosynthetic proposal, and chemical synthesis†

IF 10.2 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Natural Product Reports Pub Date : 2024-07-17 DOI:10.1039/d3np00067b

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Abstract

Covering: up to the end of 2023

Cephalotane diterpenoids are a unique class of natural products exclusive to the genus Cephalotaxus, featuring a rigid 7,6,5,6-fused tetracyclic architecture. The study of cephalotanes dates back to the 1970s, when harringtonolide (1), a Cephalotaxus troponoid with a peculiar norditerpenoid carbon skeleton, was first discovered. In recent years, prototype C₂₀ diterpenoids proposed as cephalotane were disclosed, which triggered intense studies on this diterpenoid family. To date, a cumulative total of 105 cephalotane diterpenoids with great structural diversity and biological importance have been isolated. In addition, significant advances have been made in the field of total synthesis and biosynthesis of cephalotanes in recent years. This review provides a complete overview of the chemical structures, bioactivities, biosynthetic aspects, and completed total synthesis of all the isolated cephalotane diterpenoids, which will help guide future research on this class of compounds.

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头状二萜：结构多样性、生物活性、生物合成建议和化学合成。

覆盖范围：截至 2023 年底头孢烷二萜是头孢属独有的一类天然产物，具有刚性的 7,6,5,6 融合四环结构。头孢烷类化合物的研究可追溯到 20 世纪 70 年代，当时首次发现了一种头孢烷类滋养素内酯（Harringtonolide）(1)，它具有奇特的北端萜类碳骨架。近年来，C20 二萜类化合物的原型被认为是头陀烷，这引发了对该二萜类化合物家族的深入研究。迄今为止，已累计分离出 105 种结构多样、具有重要生物学意义的头萜类二萜化合物。此外，近年来头孢烷类化合物的全合成和生物合成领域也取得了重大进展。本综述全面概述了所有分离出的头烷类二萜化合物的化学结构、生物活性、生物合成方面以及已完成的全合成，这将有助于指导今后对这类化合物的研究。

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来源期刊

Natural Product Reports 化学-生化与分子生物学

CiteScore

21.20

自引率

3.40%

发文量

127

审稿时长

1.7 months

期刊介绍： Natural Product Reports (NPR) serves as a pivotal critical review journal propelling advancements in all facets of natural products research, encompassing isolation, structural and stereochemical determination, biosynthesis, biological activity, and synthesis. With a broad scope, NPR extends its influence into the wider bioinorganic, bioorganic, and chemical biology communities. Covering areas such as enzymology, nucleic acids, genetics, chemical ecology, carbohydrates, primary and secondary metabolism, and analytical techniques, the journal provides insightful articles focusing on key developments shaping the field, rather than offering exhaustive overviews of all results. NPR encourages authors to infuse their perspectives on developments, trends, and future directions, fostering a dynamic exchange of ideas within the natural products research community.