Zerumbone

Zingiber zerumbet Smith Qiu Jiang (Ginger) (rhizome)55-60 3".4"-0-diacetylafzelin, zerumbone, zerumbone epoxide, curcuminoids diferuloylmethane, feruloyl-p-coumaroylmethane, di-p-coumaroylmethane, essential oils, alpha-humulene.192-193-195 These compounds are cytotoxic. A tonic, stimulant, depurative, to treat asthma, stomachache, antimicrobial properties. This plant plays an important role in masculine rituals and it makes women sterile. 

Formic acid catalyzed transannulation of the 8,9-epoxide (163), derived from natural zerumbone, has been shown to lead to a mixture of the bicyclo[6.3.0]undecane (164) and the hydroazulene (165 equation 72). 

Direct methods of converting humulene (332) into its 8,9-monoepoxide (337)t and into zerumbone (338) have proved to be very inefficient. Shirahama et al. have now brought about these conversions by indirect means. Thus, for the epoxide (337),169 humulene is first transformed to the acetate (339) by treatment with boron trifluoride etherate in glacial acetic acid followed by mono-epoxidation. Reduction of this acetate with LiAlH, followed by elimination with mesyl chloride in pyridine gives the epoxide (337). In the case of zerumbone (338),170 the readily... 

Further research on terpenoid plant growth regulators has shown that cross-conjugated dienones such as zerumbone (288), epoxyzerumbone (289), and santonin (290) display root-promoting activity whereas related compounds (291)—(293) devoid of this structural feature do not. Molecular mechanics... 

Zerumbone, from Zingiber zerumbet, was shown to effectively suppress free radical generation, pro-inflammatory protein production, and cancer cell proliferation while additionally inducing the apoptosis of these same cells. An analysis of the relationship between the compound s structure and its activity indicated that the a, (5-unsaturated carbonyl group in the sesquiterpene structure is a requisite for the compound s... 

Several monoterpenes [320,321], humulene (364) [320] and zerumbone (365) [322] have been reported from the essential oil from the rhizomes of Zingiber zerumbet. The characterization and elucidation of structure 365 of zerumbone was reported later [323]. The crystal structure of zerumbone isolated from the rhizomes of Z. zerumbet was determined by single-crystal X-ray diffraction [324]. The stereochemistry of the double bonds of humulene was established by crystallographic study of its silver nitrate adduct [325, 326]. The essential oil from the rhizomes of Z. 

Murakami, A. et al.. Identification of zerumbone in Zingiber zerumbet Smith as a potent inhibitor of 12-0-tetradecanoylphorbol-l3-acetate-induced Epstein-Barr virus activation, Biosci. Biotechnol. Biochem., 63, 1811, 1999. 

Murakami, A. et al., Zerumbone, a Southeast Asian ginger sesquiterpene, markedly suppresses free radical generation, proinflammatory protein production, and cancer cell proliferation accompanied by apoptosis the alpha,beta-unsaturated carbonyl group is a prerequisite. 

Kirana, C. et al., Antitumor activity of extract of Zingiber aromaticum and its bioactive sesquiterpenoid zerumbone, Nutr. Cancer, 45,218,2003. 

Tanaka, T. et al., Chemoprevention of azoxymethane-induced rat aberrant crypt foci by dietary zerumbone isolated fiom Zingiber zerumbet, Life Set, 69, 1935, 2001. 

Fig. 8.13 Pathways employed for the pioduetion of noot-katone, 8-hydroxy-a-humulene, 8-hydroxyeadinene, and artemisinic aeid in microbial hosts. Further downstream metabolites like zerumbone, gossypol, and artemisinin are also shown. In studies using E. coli, an engineered mevalonate (MVA) pathway as well as the endogenous methyleiythritol phosphate (MEP) pathway and fame-syl diphosphate FTP) synthase support FPP production. When using S. cerevisiae as host, either the native (for...

A more complex example is the production of 8-hydroxy-a-humulene. This is the direct precursor of zerumbone, which is contained in Zingiber zerumbet ( shampoo ginger ). 8-Hydroxy-a-... 

The same substrate was incubated in A. niger, Aspergillus oryzae, Candida rugosa, Candida tropicalis, Mucor mucedo, Bacillus subtilis, and Schizosaccharomyces pombei however, any metabolites have been obtained. All microbes except for the last organism, zerumbone epoxide (409), prepared by mCPBA, bioconverted into two diastereoisomers, 27 ,65,75-dihydro- (411) and 2/ ,6/ ,7/ -derivative (412), whose ratio was determined by GC, and their enantio-excess was over 99% (Nishida and Kawai, 2007) (Figure 20.119). 

Nishida, E. and Y. Kawai, 2007. Bioconversion of zerumbone and its derivatives. Proceedings of 51st TEAC, pp. 387-389. 

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