germacrone and dehydrocurdione

Simple gas chromatography-mass spectrometry (GC-MS) and high-performance liquid chromatography (HPLC) methods were developed for quantifying eight volatile compounds and 10 sesquiterpenoids, respectively. GC-MS analysis was performed on an HP-5MS capillary column (30 m×0.25 mm i.d.) coated with 0.25 μm film 5% phenyl-95% methylpolysiloxane and selected ion monitoring was used for quantification. Four volatile and previously unquantified monoterpenoids were determined. HPLC analysis was performed on a C18 column with water and acetonitrile as mobile phase. The proposed method, determined 10 non-polar and polar sesquiterpenoids simultaneously, which covered a wider polar range of analytes and had a more perfect resolution. Among them, five sesquiterpenoids were not determined before and some specific components, (4S,5S)-germacrone-4,5-epoxide, curcumenone and dehydrocurdione were completely separated for the first time. Both methods were validated for linearity, limit of detection and quantification, precision, accuracy, recovery and system suitability. The methods were simple, effective, reliable and successfully applied to global detection and analysis of volatile and non-volatile components of steamed and non-steamed rhizomes of Curcuma wenyujin (Wen-E-Zhu (WEZ) and Pian-Jiang-Huang (PJH)). Multivariate statistical analysis was employed to distinguish PJH and WEZ and seven chemical components, including (4S,5S)-germacrone-4,5-epoxide, curcumenone, β-elemene, curzerene, borneol, isoborneol and camphor, were screened as chemical markers. The present study provided a promising method for accurate discrimination of the herbal medicines with the same origin.

Topics: Chromatography, High Pressure Liquid; Curcuma; Drugs, Chinese Herbal; Gas Chromatography-Mass Spectrometry; Multivariate Analysis; Plant Extracts; Principal Component Analysis; Quality Control; Reproducibility of Results; Rhizome; Sesquiterpenes; Sesquiterpenes, Germacrane; Steam

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.

Topics: Curcuma; Furans; Heterocyclic Compounds, 2-Ring; Plant Extracts; Sesquiterpenes; Sesquiterpenes, Germacrane