Curcumenol fromCurcuma zedoaria: a second monoclinic modification

Abstract

Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.003 Å; R factor = 0.037; wR factor = 0.090; data-to-parameter ratio = 10.2.The title compound, systematic name 9-isopropylidene-2,6-dimethyl-11-oxatricyclo[6.2.1.0 1,5 ]undec-6-en-8-ol, C 15 H 22 O 2 , which crystallizes with two molecules of similar conformation in the asymmetric unit, features three fused rings, two of which are five-membered and the third six-membered. Of the two five-membered rings, the one with an O atom has a distinct envelope shape (with the O atom representing the flap). The six-membered ring is also envelope-shaped as it shares a common O atom with the five-membered ring. In the crystal, the two independent molecules are linked by a pair of O-HÁ Á ÁO hydrogen bonds, generating a dimer. Related literatureFor the C2 modification isolated from Globba malaccensis Ridl, see: Muangsin et al. (2004). ExperimentalCrystal data Data collectionBruker SMART APEX diffractometer 13257 measured reflections 3298 independent reflections 2882 reflections with I > 2(I) R int = 0.046

Curcumenol isolated from Curcuma zedoaria suppresses Akt-mediated NF-κB activation and p38 MAPK signaling pathway in LPS-stimulated BV-2 microglial cells

“…26 Curcumenol was prepared and dissolved in DMSO(<0.5%) while LPS was dissolved at a concentration of 0.4 μg mL −1 in 10% DMEM medium before being added to the cells. Extraction and isolation was performed according to a previous report.…”

Antifungal activity, main active components and mechanism of Curcuma longa extract against Fusarium graminearum

“…The following chemical components of C . longa have been reported: curcumenol, curdione, curcumin, isocurcumenol, curcumol, stigmasterol, zingiberene and curcumene [ 26 – 31 ]. Nevertheless, the antifungal mechanisms and active components of natural products derived from C .…”

Cytotoxic Constituents from the Rhizomes ofCurcuma zedoaria

“…Fraction 10 was chromatographed and further purified by HPTLC to afford a second monoclinic modification of curcumenol as a crystallized dimer elucidated by single crystal X-ray diffraction analysis. This dimer is 9-isopropylidene-2, 6-dimethyl-11-oxatricyclo [6.2.1.0 1,5 ] undec-6-en-8-ol ( 10 , 5.4 mg) as previously described [ 20 ], whilst curcuzedoalide ( 18 , 13.4 mg) was isolated from fraction 10 using HPLC. Curcumenone ( 3 , 16.4 mg) was purified from fractions 12 and 13.…”

“…It is therefore important to identify the components which are responsible for the chemotherapeutic effects and the molecular pathway by which these compounds affect cancer cell death. Up to date, there are numerous reported articles on the cytotoxic components of Curcuma zedoaria and the mechanism of cell death exerted by some of these compounds [ 5 – 8 , 12 – 20 ]. In our continuous effort to study the bioactive and their mode of actions from medicinal plants of Curcuma species, this communication reports the isolation of 19 compounds and among these, two bioactive compounds (curcumenone and curcumenol) were identified as cytotoxic components and were able to induce apoptosis.…”