Elsevier

Tetrahedron

Volume 24, Issue 11, 1968, Pages 4113-4122
Tetrahedron

Studies in sesquiterpenes—XXXVII: Sesquiterpenoids from the essential oil of zingiber zerumbet smith,☆☆

https://doi.org/10.1016/0040-4020(68)88174-8Get rights and content

Abstract

A complete analysis of the essential oil from the rhizomes of Zingiber zerumbet Smith, is given and the isolation of several new humulene-based sesquiterpenoids is described.

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  • Cited by (105)

    • Zingiber zerumbet (L.) Roscoe ex Sm. from northern India: Potential source of zerumbone rich essential oil for antiproliferative and antibacterial applications

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      The maximal content (88.5%) was reported from Z. zerumbet grown in northeastern India (Manipur) > southern India (74.8–84.8%); and minimal (12.6%) from eastern India (Baby et al., 2009; Rana et al., 2008, Srivastava et al., 2000). However, in few other reports, the content of zerumbone was found to vary with different studies carried out by different authors, which includes 74.8% of zerumbone in Z. zerumbet from Manipur, and 74.8% from Meghalaya of northeastern India; and 21.2–49.8% from Calicut and Kerala of south Indian origin (Damodaran and Dev, 1968; Madegowda et al., 2016; Rana et al., 2016; Singh et al., 2014). Besides these, variable content of zerumbone was reported in Z. zerumbet grown worldwide, viz. Malaysia (68.9–73.1%), Vietnam (72.3%), French Polynesia (63.0–65.3%), Fiji (59.0%), Japan (48.0–71.0%), China (48.13%), Thailand (41.7%–56.5%), Bangladesh (46.8%), Reunion Island (37.2%), France (37.0%), Philippines (35.5%), Indonesia (11.0%), and Vietnam (1.2%) (Batubara et al., 2013; Bhuiyan et al., 2009; Chane-Ming et al., 2003; Dai et al., 2013; Dung et al., 1993; Duve, 1980; Madegowda et al., 2016; Malek et al., 2005; Vahirua et al., 1993; Yu et al., 2008).

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      The aromatic bisabolanes are a further group of odorous sesquiterpenes subjected to different synthetic studies. More particularly, (S)-(+)-α-curcumene 48 and (S)-(+)-ar-turmerone 49 (Fig. 7.10) are constituents of many essential oils and have been recognized as flavor components of the Zingiber [56] and Curcuma [57] species. The structurally related compound (S)-dehydrocurcumene 50 possesses the same absolute configuration and was isolated from vetiver oil [58].

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    Communication No. 1132, National Chemical Laboratory, Poona 8.

    ☆☆

    Abstracted from the Ph.D. thesis of N.P. Damodarahn, Poona University (1965).

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