Three new sesquiterpenes including a new elemane-type sesquiterpene, 5βH-elem-1,3,7,8-tetraen-8,12-olide (1), and two new carabrane-type sesquiterpenes, 7α,11-epoxy-6α-methoxy-carabrane-4,8-dione (2) and 8,11-epidioxy-8-hydroxy-4-oxo-6-carabren (3), together with eight known sesquiterpenes (4-11) were isolated from Curcuma wenyujin Y. H. Chen et C. Ling. Their structures were elucidated based on extensive spectroscopic analyses. A possible biogenetic scheme for the related compounds was postulated. All of the isolated compounds were tested for inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages. Meanwhile, preliminary structure-activity relationships for these compounds are discussed.
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Curcumaones A-N, sesquiterpenes from the secondary rhizomes of Curcuma wenyujin.
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School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, PR China; Shanghai Seventh People's Hospital, Shanghai University of Traditional Chinese Medicine, Shanghai, 200137, PR China. Electronic address:
Fourteen undescribed sesquiterpenes, named curcumaones A-N (1-14), as well as forty-four (15-58) known ones, were isolated from the secondary rhizomes of Curcuma wenyujin. The structures and absolute configurations of 1-14 were elucidated based on NMR spectroscopic analyses, high resolution electrospray ionization mass spectroscopy (HRESIMS) data and electronic circular dichroism (ECD) spectral analysis. Among these, five sesquiterpenes with the peroxide linkage (1-5) were obtained and the change of chemical shift between the α-C connecting the peroxide linkage and the oxygen atom has been discussed.
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School of Pharmacy, Hangzhou Normal University, Hangzhou, Zhejiang 311121, PR China; Key Laboratory of Elemene Class Anti-Cancer Chinese Medicines, Engineering Laboratory of Development and Application of Traditional Chinese Medicines, Collaborative Innovation Center of Traditional Chinese Medicines of Zhejiang Province, Hangzhou Normal University, Hangzhou, Zhejiang, 311121, PR China. Electronic address:
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(-)-β-Elemene is a primary bioactive compound derived from Curcuma wenyujin and has been widely utilized as an anti-tumor agent for various types of cancer. Due to the inefficiency of plant extraction methods for β-elemene, significant efforts have been directed toward the heterogeneous biosynthesis of β-elemene using microbial cell factories. However, there has been less emphasis on the stereochemical configuration of germacrene A and its rearranged product, β-elemene.
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