curcumin and alpha-curcumene

Curcuma longa (Zingiberaceae) is a native plant of southern Asia and is cultivated extensively throughout the warmer parts of the world. Jianghuang and Yujin are rhizome and tuberous root of C. longa, respectively, which were traditionally used as two Chinese medicines. In this paper, pressurized liquid extraction (PLE) and gas chromatography-mass spectrometry (GC-MS) were developed for quantitative determination/estimation of eight characteristic compounds including beta-caryophyllene, ar-curcumene, zingiberene, beta-bisabolene, beta-sesquiphellandrenendrene, ar-turmerone, alpha-turmerone and beta-turmerone in Jianghuang and Yujin. A HP-5MS capillary column (30 m x 0.25 mm i.d.) coated with 0.25 microm film 5% phenyl methyl siloxane was used for separation and selected ion monitoring (SIM) method was used for quantitation. Hierarchical cluster analysis based on characteristics of eight identified peaks in GC-MS profiles showed that 10 samples were divided into two main clusters, Jianghuang and Yujin, respectively. Four components such as ar-curcumene, ar-turmerone, alpha-turmerone and beta-turmerone were optimized as markers for quality control of rhizome (Jianghuang) and tuberous root (Yujin), which are two traditional Chinese medicines, from Curcuma longa.

Topics: Chromatography, High Pressure Liquid; Cluster Analysis; Curcuma; Curcumin; Drugs, Chinese Herbal; Gas Chromatography-Mass Spectrometry; Ketones; Molecular Structure; Monocyclic Sesquiterpenes; Plant Tubers; Polycyclic Sesquiterpenes; Quality Control; Rhizome; Sesquiterpenes; Technology, Pharmaceutical; Toluene

Solvolysis reaction of methyl (4S,5S)-4-(4'-methoxyphenyl)-5-tosyloxy-2(E)-hexenoate 5 in water-saturated MeNO(2) gave the 1,2-migration product, (4S,5S)-5-hydroxy-4-(4'-methoxyphenyl)-2-(E)-hexenoate 6 (55% yield), which was converted to methyl (R)-(4'-methylphenyl)hexanoate 11 in 25% overall yield (5 steps). Treatment of (R)-11 with MeLi gave tertiary alcohol congener 12, which was subjected to dehydration to afford (R)-(-)-curcumene 1. An introduction of hydroxyl group at meta-position of the aromatic ring in (R)-11 was achieved based on consecutive treatment [1) selective iodination, 2) conversion of aryl iodide to aryl boronate, 3) conversion of aryl boronate to phenol]. Thus obtained phenol (R)-16 was treated with MeLi to give tertiary alcohol congener 17, which was subjected to dehydration to afford (R)-(-)-xanthorrizol 2.

Topics: Boronic Acids; Cations; Chromatography, Thin Layer; Curcumin; Indicators and Reagents; Iodides; Magnetic Resonance Spectroscopy; Phenols; Sesquiterpenes; Solvents

Rumput roman extract is used as a natural food preservative. Its antimicrobial activity and constituents were investigated as part of an ongoing study to evaluate its quality and safety as a food additive. The constituents were analyzed by GC/MS, and 5 major constituents were isolated and identified as capillin, capillene, caryophyllene oxide, alpha-curcumene and methyleugenol using NMR analysis. The antimicrobial activities against E. coli, S. cerevisiae and A. niger were measured by means of the halo test. Based on the results, we confirmed that capillin was the major active constituent. The concentrations of capillin and capillene were determined to 17.9 mg/mL and 36.1 mg/mL, respectively, from standard curves of authentic compounds on HPLC.

Topics: Anti-Infective Agents; Artemisia; Curcumin; Diynes; Eugenol; Food Preservatives; Gas Chromatography-Mass Spectrometry; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes

[reaction: see text] A three-step, two-pot procedure involving asymmetric hydrovinylation followed by Suzuki-Miyaura reaction represents by far the shortest synthesis of this popular bisabolane. Other applications for the synthesis of similar compounds with chiral benzyl centers can be easily envisioned.

Topics: Benzene Derivatives; Catalysis; Curcumin; Indicators and Reagents; Molecular Structure; Sesquiterpenes; Stereoisomerism

Composition of ginger oil prepared from fresh ginger rhizomes, Zingiber officinale Roscoe (Zingiberaceae) was determined by gas chromatography (GC) and GC-mass spectrometric techniques. The main sesquiterpene hydrocarbons identified were alpha-zingiberene (27-30%), alpha-curcumene (8-9%), beta-sesquiphellandrene (4.8%). and bisabolene (3.2%). The function of zingiberene and curcumene as insecticides, repellents, and insect feeding deterrents has been previously reported. Other plant species having similar constituents might be found. Leaves of six wild tomato accessions of Lycopersicon hirsutum f. glabratum (Mull); three accessions of L. hirsutum f. typicum (Humb & Bonpl.); two accessions of L. pennellii Corr. (D'Arcy); one accession of L. pimpinellifolium; and one commercial tomato L. esculentumm cv. Fabulous were analyzed. Analysis of L. hirsutum f. typicum (Solanaceae) accessions indicated the presence of zingiberene, curcumene, and other lipophilic secondary metabolites in the leaves of two accessions (PI-127826 and PI-127827). An average three month old wild tomato plant of accessions PI-127826 and PI-127827 provided 1.93 and 1.30 kg fresh leaves (averaging about 38,307 and 28,130 cm2 exposed leaf surface area, respectively) and produced 19.3 and 10.1 g of zingiberene and curcumene (PI-127826) and 17.2 and 1.8 g of zingiberene and curcumene (PI-127827), respectively. Leaf extracts of the wild tomato L. hirsutum f. typicum (accessions PI-127826 and PI-127827) can be used as a biorational source of zingiberene and curcumene.

Topics: Chromatography, Gas; Curcumin; Gas Chromatography-Mass Spectrometry; Monocyclic Sesquiterpenes; Plant Extracts; Plant Leaves; Sesquiterpenes; Solanum lycopersicum; Zingiber officinale

Male Wistar rats were fed a control diet or the control diet supplemented with 1% (by weight) turmeric for 10 wk. In rats injected with 30 mg Fe2+/kg body weight, lipid peroxidation was 29 and 35% lower in liver homogenates and microsomes, respectively, of turmeric-fed rats than in those of rats fed the control diet. The activities of superoxide dismutase, catalase and glutathione peroxidase were higher (by 19, 19 and 20%, respectively) in liver homogenates of rats fed the turmeric-containing diet in comparison with the controls. These studies indicate that dietary turmeric lowers lipid peroxidation by enhancing the activities of antioxidant enzymes.

Topics: Animals; Catalase; Curcuma; Curcumin; Diet; Ferrous Compounds; Glutathione Peroxidase; Lipid Peroxidation; Liver; Male; Microsomes, Liver; Plant Extracts; Rats; Rats, Wistar; Reactive Oxygen Species; Sesquiterpenes; Superoxide Dismutase