Attractive Reactivity of a Natural Product, Zerumbone

Abstract

Zerumbone is a cyclic seaquiterpene and, a potential resource for natural materials-related diversityoriented synthesis (NMRDOS). Zerumbone, the main component of the essential oil of a wild ginger, Zingiber zerumbet Smith, showed strong reactivity with good chemo-, regio-, and stereoselectivity. To build the foundations for the industrial use of zerumbone, we examined conjugate addition, transannular reactions, ring cleavage, ring expansion, and asymmetric induction. The biological activity of zerumbone derivatives was also studied.

Zerumbone, a ginger sesquiterpene, induces apoptosis and autophagy in human hormone-refractory prostate cancers through tubulin binding and crosstalk between endoplasmic reticulum stress and mitochondrial insult

“…Accordingly, development of multitarget drugs has been proposed recently Csermely et al 2005). Zerumbone is a naturally occurring dietary compound and has been reported to (Sobhan et al 2013;Prasannan et al 2012;Abdelwahab et al 2012;Kitayama 2011;Yob et al 2011;Eguchi et al 2007). Although numerous studies have discovered the signaling pathways of zerumbone in several types of cancers, the primary targets and the crosstalk between key death programs have not been fully identified.…”

“…Zerumbone, a cyclic sesquiterpene, is the main component of Zingiber zerumbet Smith which has attracted extensive attention in the recent decade for anticancer activities (Prasannan et al 2012;Kitayama 2011;Yob et al 2011). Existing studies suggest that zerumbone can regulate numerous signaling pathways.…”

Zerumbone-loaded nanostructured lipid carrier induces G2/M cell cycle arrest and apoptosis via mitochondrial pathway in a human lymphoblastic leukemia cell line

“…7 Zerumbone is a natural compound isolated from essential volatile oil of rhizomes from the edible wild ginger, Zingiber zerumbet (L.) Smith. 9 Although zerumbone was recently shown to have several favorable pharmacologic properties, poor water solubility has limited its therapeutic use. The solubility of zerumbone can be improved by incorporation into an NLC.…”

Engineering Methylobacterium extorquens for de novo synthesis of the sesquiterpenoid α-humulene from methanol

“…In the last years, the monocyclic sesquiterpenoid α-humulene (also called α-caryophyllene) has received increased attention due to its anti-inflammatory and potential anti-cancerogenic properties Passos et al, 2007). In addition, it is a precursor in the biosynthetic route to zerumbone which itself shows striking anti-inflammatory and anti-cancerogenic effects (Kitayama, 2011;Prasannan et al, 2012). α-Humulene is a natural constituent of Humulus lupulus (Katsiotis et al, 1989) and the shampoo ginger plant Zingiber zerumbet (Yu et al, 2008).…”