Anti-inflammatory sesquiterpenes fromCurcuma zedoaria

Abstract

From the methanolic extract of the rhizome of Curcuma zedoaria, we isolated anti-inflammatory sesquiterpene furanodiene (1) and furanodienone (2) along with new sesquiterpene compound 3 and known eight sesquiterpenes, zederone (4), curzerenone (5), curzeone (6), germacrone (7), 13-hydroxygermacrone (8), dehydrocurdione (9), curcumenone (10), and zedoaronediol (11). Their structures were elucidated on the basis of spectroscopic data. The anti-inflammatory effect of isolated components on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation of mouse ears were examined. Compounds 1 and 2 suppressed TPA-induced inflammation of mouse ears by 75% and 53%, respectively, at a dose of 1.0 µmol. Their activities are comparable to that of indomethacin, the normally used anti-inflammatory agent.Keywords: anti-inflammatory; Curcuma zadoaria; 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced edema Zedoary (Curcuma zedoaria Roscoe, Zingiberaceae) is cultivated as a vegetable, spice, and perfumery material in Southeast Asian countries. The rhizome of this plant has been used as a stimulant, stomachic, carminative, diuretic, anti-diarrheal, anti-emetic, anti-pyretic, and depurator, and also as an ointment for ulcers, wounds, and other skin disorders. 1) Recently, Yoshikawa et al have revealed that chemical constituent of C. zedoaria showed vasorelaxant, heptatoprotective, and inhibitory activity of NO production. 2)-4) The zedoary is used to the treatment of the skin disease, however the study of the anti-inflammatory effect of chemical constituents from C. zedoaria has not been studied so far except that of dehydrocurdione (9) by Yoshioka et al. 5) Therefore, we tried to isolate sesquiterpens from zedoary and subject on anti-inflammatory test. For isolating sesquiterpens like dehydrocurudione, we used the reddish spot on thin layer chromatography with spraying of anisaldehyde/sulfuric acid as index.In the present paper, we describe the structure of isolated eleven sesquiterpenes from C. zedoaria and their anti-inflammatory effect on the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced edema of mouse ears.The zedoary rhizome (cultivated in Okinawa, Japan) was soaked in methanol, and the resulting methanol extract was concentrated in vacuo.The concentrate was successively partitioned between benzene and water, and then ethyl acetate and water.The benzene-soluble part showed anti-inflammatory activity (IE of 34% at a dose of 2 mg). The benzene-soluble part was chromatographed on silica gel to give 20% ethyl

Nutritional value, phytochemical composition, and biological activities of edibleCurcumaspecies: A review

“…[18,[81][82][83][84] Likewise, germacron has been identified as the main constituent present in the rhizome extracts of C. pierreana that showed inhibitory effect on the growth of microorganisms including Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus faecalis, and the fungus Candida albicans. [85] Germacrone has also been identified as the active principle responsible for the anti-inflammatory and analgesic activities Furanodiene, furanodienone, zederone, curzerenone, curzeone, germacrone, 13-hydroxygermacrone, dehydrocurdione, curcumenone, zedoaronediol, 13-hydroxycurzerenone, 1-oxocurzerenone, curcolone, procurcumenol, ermanin, curcumin, mixture of stigmast-4-en-3,6-dione and stigmasta-4,22-dien-3,6-dione, and mixture of 6ß-hydroxystigmast-4-en-3-one and 6ß-hydroxystigmasta-4,22-dien-3-one [150,151] of C. xanthorrhiza by Ozaki. [86] C. xanthorrhiza has also been shown to contain xanthorrhizol, a natural sesquiterpenoid, which possess antimetastatic effect and antimicrobial activities, as well as other curcumin analogues including 1-(4-hydroxyl-3,5-dimethoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-(1E, 6E)-1 and 6-heptadiene-3,4-dione responsible for the potent antioxidant activity of the plant extracts against auto-oxidation of linoleic acid.…”

Furanodiene induces G2/M cell cycle arrest and apoptosis through MAPK signaling and mitochondria-caspase pathway in human hepatocellular carcinoma cells

“…4,5 Furanodiene, a sesquiterpene compound, has been isolated from essential oil of Curcuma wenyujin. 6,7 Furanodiene hás been identified to have anti-inflammatory effects 8 and hepatoprotective effects. 9,10 Many sesquiterpenes are identified to possess protective effects against carcinogenesis or tumour growth.…”

Prasaplai: An essential Thai traditional formulation for primary dysmenorrhea treatment

“…Curcuma zedoaria, the anti-inflammatory activity of sesquiterpene furanodiene and furanodienone (Fig. 7) could suppress the 12-O-tetradecanoylphobol-13-acetate (TPA) -induced inflammation of mouse ears by 75% and 53%, respectively, at dose of 1.0 µmol (Makabe et al, 2006). Oh et al (2007) used bioassay-guided fractionation which led to an isolation of curdione from the rhizome of C. zedoaria with the inhibitory effect on the production of PGE2 in LPS-stimulated mouse macrophage RAW 264.7 cells in a concentrationdependent manner (IC 50 = 1.1 µM).…”