curcumin and procurcumenol

Four new germacranes [heyneanones A-D (1-4)], three new guaianes [4,10-epizedoarondiol (5), 15-hydroxyprocurcumenol (6), 12-hydroxycurcumenol (7)], and two new spirolactones [curcumanolides C (8) and D (9)] were isolated from the rhizomes of Curcuma heyneana together with 13 known sesquiterpenes and two known labdane-type diterpenes. Among the isolated compounds, heyneanone A (1), heyneanone C (3), 4,10-epizedoarondiol (5), procurcumenol (16), aerugidiol (17), zerumin A (23), and (E)-15,16-bisnorlabda-8(17),11-dien-13-one (24) inhibited protein tyrosine phosphatase 1B (PTP1B) with IC(50) values of 42.5, 35.2, 35.1, 45.6, 35.7, 10.4, and 14.7 μM, respectively.

Topics: Curcuma; Inhibitory Concentration 50; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Protein Tyrosine Phosphatase, Non-Receptor Type 1; Rhizome; Sesquiterpenes

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

Neocurdione, isoprocurcumenol, and a new sesquiterpene, 9-oxo-neoprocurcumenol, were isolated from fresh rhizomes of Curcuma aromatica and Curcuma zedoaria (Zingiberaceae) as attachment inhibitors against the blue mussel, Mytilus edulis galloprovincialis. The structures of these compounds were elucidated on the basis of spectroscopic evidence.

Topics: Adhesiveness; Animals; Bivalvia; Curcuma; Rhizome; Sesquiterpenes

Tumor necrosis factor-alpha (TNF-alpha) is one of the major mediators produced in activated macrophages which contribute to the circulatory failure associated with septic shock. In the course of screening marketed oriental anti-inflammatory herbal drugs for TNF-alpha antagonistic activity, a crude methanolic extract of the rhizomes of Curcuma zedoaria exhibited significant activity. The activity-guided fractionation and repetitive chromatographic procedures with the EtOAc-soluble fraction resulted in the isolation of three active compounds. They were identified as 1,7-bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one (1), procurcumenol (2) and epiprocurcumenol (3) by spectral data analysis. They inhibited the production of TNF-alpha by lipopolysaccharide (LPS)-activated macrophages from the results of bioassay (IC(50) values of 1 and 2 are 12.3 and 310.5 microM, respectively) and Western blot assay. These results imply that the traditional use of C. zedoaria rhizome as anti-inflammatory drug may be explained at least in part, by the inhibition of TNF-alpha production.

Topics: Anti-Inflammatory Agents, Non-Steroidal; Biological Assay; Blotting, Western; Cell Line; Cell Survival; Curcumin; Inhibitory Concentration 50; Macrophages; Magnetic Resonance Spectroscopy; Phenols; Plant Extracts; Plant Structures; Plants, Medicinal; Sesquiterpenes; Tumor Necrosis Factor-alpha; Zingiberaceae