Isozedoarondiol

Bioactive chemical constituents from Curcuma caesia Roxb. rhizomes and inhibitory effect of curcuzederone on the migration of triple-negative breast cancer cell line MDA-MB-231.[Pubmed:31726856]

Nat Prod Res. 2019 Nov 15:1-5.

Rhizomes of Curcuma caesia are traditionally used to treat cancer in India. The aim is to isolate chemical constituents from C. caesia rhizomes through bioassay-guided fractionation. The extract, hexanes and chloroform fractions showed effect on MCF-7 and MDA-MB-231cells in cell viability assay. The chromatographic separation afforded germacrone (1), zerumbone (2), furanodienone (3), curzerenone (4), curcumenol (5), zederone (6), curcumenone (7), dehydrocurdione (8) from hexanes fraction and curcuminol G (9), curcuzederone (10), (1S, 10S), (4S,5S)-germacrone-1 (10), 4-diepoxide (11), wenyujinin B (12), alismoxide (13), aerugidiol (14), zedoarolide B (15), zedoalactone B (16), zedoarondiol (17), Isozedoarondiol (18) from chloroform fraction. This is first report of compounds 2, 9-13, 15-18 from C. caesia. The study demonstrated compounds 1-4 and 10 are the bioactive compounds. The effect of curcuzederone (10) on MDA-MB-231 cell migration showed significant inhibition in scratch and Transwell migration assays. The results revealed that curcuzederone could be a promising drug to treat cancer.

Simultaneous determination of multiple sesquiterpenes in Curcuma wenyujin herbal medicines and related products with one single reference standard.[Pubmed:23389255]

Molecules. 2013 Feb 6;18(2):2110-21.

Some Curcuma species are widely used as herbal medicines. Sesquiterpenes are their important bioactive compounds and their quantitative analysis is generally accomplished by gas chromatography (GC) or high performance liquid chromatography (HPLC), but the instability and high cost of some sesquiterpene reference standards have limited their application. It is necessary to find a practicable means to control the quality of herbal medicines. Using one stable component contained in Curcuma species to determine multiple analogues should be a practical option. In this study, a simple HPLC method for determination of sesquiterpenes using relative response factors (RRFs) has been developed. The easily available and stable active component curdione was selected as the reference compound for calculating the RRFs of the other eight sesquiterpenes, including zedoarondiol (Zedo), Isozedoarondiol (Isoz), aerugidiol (Aeru), (4S,5S)-(+)-germacrone-4,5-epoxide (Epox), curcumenone (Curc), neocurdione (Neoc), germacrone (Germ) and furanodiene (Fura). Their RRFs against curdione were between 0.131-1.301, with a good reproducibility. By using the RRFs, the quantification of sesquiterpenes in Curcuma wenyujin herbal medicines and related products was carried out. The method is especially useful for the determination of (4S,5S)-(+)-germacrone-4,5-epoxide, curcumenone, germacrone and furanodiene, which often are regarded as the principle components in Curcuma species, but unstable when were purified. It is an ideal means to analyze the components for which reference standards are not readily available.

Sesquiterpenes from Curcuma comosa.[Pubmed:18663560]

J Nat Med. 2009 Jan;63(1):102-4.

From the dried rhizomes of Curcuma comosa cultivating in Thailand, 26 known sesquiterpenes were isolated: zederone, zederone epoxide, furanodienone, isofuranodienone, 1(10)Z,4Z-furanodiene-6-one, glechomanolide, dehydrocurdione, neocurdione, curdione, 7 alpha-hydroxyneocurdione, 7 beta-hydroxycurdione, germacrone-1(10),4-diepoxide, germacrone, 13-hydroxygermacrone, curzerenone, curcolonol, alismol, alismoxide, zedoarondiol, Isozedoarondiol, procurcumenol, isoprocurcumenol, aerugidiol, zedoalactone B, curcumenone, and curcumadione. Their structures were elucidated on the basis of physicochemical evidence. Among them, glechomanolide, curzerenone, curcolonol, alismol, alismoxide, and zedoarondiol showed no significant optical activities, so they may be artifact products during the isolation or drying process.

A new eudesmane sesquiterpene lactone from Curcuma wenyujin.[Pubmed:18229613]

Yao Xue Xue Bao. 2007 Oct;42(10):1062-5.

The aim of the study was to investigate the sesquiterpene constituents from the rhizomes of Curcuma wenyujin Y. H. Chen et C. Ling. The isolation and purification of the constituents from the 50% EtOH extracts of the rhizomes were performed with repeated column chromatography over sillica gel and macroporous resin. Eight sesquiterpenes were obtained and identified as wenyujinlactone A (1), neolitamone A (2), zedoarondiol (3), Isozedoarondiol (4), aerugidiol (5), curcumol (6), curdione (7) and (1R, 10R)-epoxy-(-)-1, 10-dihydrocurdine (8) by means of spectral analysis. Among them, compound 1 was found to be a new eudesmane sesquiterpene lactone, whilst compounds 2-5 were obtained from this plant for the first time.

Structural determination of two new sesquiterpenes biotransformed from germacrone by Mucor alternata.[Pubmed:18098168]

Magn Reson Chem. 2008 Feb;46(2):178-81.

Eight transformed sesquiterpenes of germacrone by Mucor alternata were obtained. Their structures were characterized on the basis of spectral methods including 2D NMR. Among them, (1S, 4S, 5S, 10R)-Isozedoarondiol (2) and (1R, 4S, 5S, 10R)-diepoxy-12-hydroxygermacrone (3) are new compounds.