Novel synthesis of zerumbone-pendant derivatives and their biological activity

Kitayama, Takashi; Nakahira, Maki; Yamasaki, Kae; Inoue, Hiromi; Imada, Chika; Yonekura, Yuji; Awata, Masataka; Takaya, Hikaru; Kawai, Yasushi; Ohnishi, Kohta; Murakami, Akira

doi:10.1016/j.tet.2013.09.026

Cited by 14 publications

(12 citation statements)

References 29 publications

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“…The stem of S. pinnatifolia is one of the best-known traditional herbal medicines frequently used to treat cardiovascular symptoms in Mongolian medicine (Yan et al 2010). In our phytochemical studies, several sesquiterpenes Wang et al 2013) and lignans Wang et al 2012;Ao et al 2013) were isolated, of which sesquiterpenes exhibited various biological properties such as anti-tumour, anti-cancer and anti-HIV Kitayama et al 2013;Santosh Kumar et al 2013).…”

Section: Introductionmentioning

confidence: 78%

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

Bao

Wang

Han

et al. 2015

Natural Product Research

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We report the isolation of a new sesquiterpene, named as syripinol (1), and two known compounds from the volatile oil of the stems of Syringa pinnatifolia, for the first time. The structures of the isolated compounds were elucidated on the basis of spectroscopic methods including UV, IR, ESI-MS, 1D and 2D NMR techniques. The antibacterial activities of the compounds were also evaluated against various bacteria which showed good results.

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Section: Introductionmentioning

confidence: 78%

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

Bao

Wang

Han

et al. 2015

Natural Product Research

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“…47 As 14 contains three isolated olefins, it can be expected to have a high reactivity and to be converted into various other skeletons. As 1 was known to be converted into 7-bromozerumbone 15 by N-bromosuccinimide (NBS) through the radical reaction, 48 we conducted this reaction with NBS to see if 14 would also be transformed to 7-bromozerumbol or not. As a result, we found that the reaction for only 1 min in CH 3 CN aq produced mainly 16 and 17 (Scheme 4 and Table S4).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Remarkable Potential of Zerumbone to Generate a Library with Six Natural Product-like Skeletons by Natural Material-Related Diversity-Oriented Synthesis

et al. 2020

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Diversity-oriented synthesis (DOS) is an effective strategy for the quick creation of diverse and high three-dimensional compounds from simple starting materials. The selection of a starting material is the key to constructing useful, chemically diverse compound libraries for the development of new drugs. Here, we report a novel, general, and facile strategy for the creation of diverse compounds with high structural diversity from readily available natural products, such as zerumbone, as the synthetic starting material. Zerumbone is the major component of the essential oil from wild ginger, Zingiber zerumbet Smith. It is noteworthy that zerumbone has a powerful latent reactivity, partly because of its three double bonds, two conjugated and one isolated, and a double conjugated carbonyl group in an 11-membered ring structure. In fact, zerumbone has been shown to be a successful example of natural material-related DOS (NMRDOS). We will report that zerumbone can be converted in one chemical step from four zerumbone derivatives into rare and markedly different scaffolds by transannulation.

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“…To explore the functional group tolerance of compound 1 , a photoirradiation attempt was made on a functionalized C13 (OAc) of zerumbone epoxide 1 , prepared by a known method . It led to photoisomerization products 6 Z ,9 Z and 6 E ,9 Z , but no transannular cyclization was observed (Scheme S2).…”

mentioning

confidence: 86%

“…To explore the functional group tolerance of compound 1, a photoirradiation attempt was made on a functionalized C13 (OAc) of zerumbone epoxide 1, prepared by a known method. 15 It led to photoisomerization products 6Z,9Z and 6E,9Z, but no transannular cyclization was observed (Scheme S2). This result was akin to an attempt made on the photochemical transformation of asteriscunolide D, bearing C13 carbonyl functionality, that afforded a mixture of doublebond isomers, asteriscunolides A−C instead of the envisaged transannular cyclized aquatolide.…”

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confidence: 99%

Tandem Photoisomerization and Transannular Cyclizations of Zerumbone Epoxide: A Model for Diversity-Oriented Synthesis Using Abundant Natural Products

2021

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Photoirradiation of (6E,9E)-zerumbone-2,3-epoxide afforded a diverse range of transannular cyclized products in the presence of a catalytic amount of Sc(OTf) 3 . At the behest of the geometrical isomers produced by photoirradiation, the diversity encompasses an unprecedented eudesmane core and oxo-bridged hydroxy-olefin skeletons. Structure elucidation and the stereochemical outcome of the products are described via extensive NMR analysis. The present study serves as a model for tandem photoisomerization and transannular cyclization of natural products with enone/dienone functionality.Letter pubs.acs.org/OrgLett

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Novel synthesis of zerumbone-pendant derivatives and their biological activity

Cited by 14 publications

References 29 publications

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

The isolation and antimicrobial activities of three monocylic sesquiterpenes fromSyringa pinnatifolia

Remarkable Potential of Zerumbone to Generate a Library with Six Natural Product-like Skeletons by Natural Material-Related Diversity-Oriented Synthesis

Tandem Photoisomerization and Transannular Cyclizations of Zerumbone Epoxide: A Model for Diversity-Oriented Synthesis Using Abundant Natural Products

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