Curcumenone, curcumanolide A and curcumanolide B, three sesquiterpenoids from curcuma zedoaria

Shiobara, Yoshinori; Asakawa, Yoshinori; Kodama, Masashi; Yasuda, Koji; Takemoto, Tsunematsu

doi:10.1016/s0031-9422(00)80683-4

Cited by 74 publications

(40 citation statements)

References 12 publications

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“…All isolated compounds were identified by comparison of [a] D , NMR and mass spectral data with those reported. [10][11][12][13][14][15] All chemicals were of analytical grade, and chromatographic solvents were of HPLC grade.…”

Section: Methodsmentioning

confidence: 99%

Prediction of Cyclooxygenase Inhibitory Activity of Curcuma Rhizome from Chromatograms by Multivariate Analysis

Tanaka

Kuba

Ina

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Methodsmentioning

confidence: 99%

Prediction of Cyclooxygenase Inhibitory Activity of Curcuma Rhizome from Chromatograms by Multivariate Analysis

Tanaka

Kuba

Ina

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…10) From 30% EtOAc in hexane eluate gave dehydrocurdione (9), 11) 40% EtOAc in hexane eluate gave zederone (4), 12) and curcumenone (10), 13) and 50% EtOAc in hexane eluate afforded 13-hydroxygermacrone (8). 9) The EtOAc soluble part afforded zedoaronediol (11).…”

mentioning

confidence: 99%

Anti-inflammatory sesquiterpenes fromCurcuma zedoaria

Makabe

Maru

Kuwabara

et al. 2006

Natural Product Research

161

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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

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“…zedoaria rhizome is widely used as stimulant, stomachic, carminative, diuretic, antidiarrhoeal, antiemetic, antipyretic and depurative [13]. Sesquiterpenes, aerugidiol, curdione, curcumin, curcumanolide, curcumenone, curcumenol, furanodiene, germacrone, isocurcumenol, neocurdione, zedoarol and zedoarondiol have been isolated from this plant and some of them showed an inhibitory effect on Dgalactosamine and lipopolysacharide-induced acute liver injury in mice [9,11,18,19]. The rhizome extract of this plant displayed moderate antibabesial activity with IC 50 41.7 µg/ml.…”

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confidence: 99%

Effects of Central Kalimantan Plant Extracts on Intraerythrocytic Babesia gibsoni in Culture

subeki

Matsuura

Yamasaki

et al. 2004

The Journal of Veterinary Medical Science

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ABSTRACT. The inhibitory effects of 45 plant extracts selected from Central Kalimantan, Indonesia on Babesia gibsoni in vitro and their acute toxicity to mice were evaluated. Of these plant extracts studied, Arcangelisia flava, Curcuma zedoaria, Garcinia benthamiana, Lansium domesticum and Peronema canescens were found to have appreciable antibabesial activity with IC 50 values from 5.3 to 49.3 µg/ml without acute toxicity in mice at the intraperitoneal dose of 0.7 g/kg of body weight.KEY WORDS: antibabesial activity, Babesia gibsoni, Central Kalimantan plant, toxicity.J. Vet. Med. Sci. 66(7): 871-874, 2004 Canine babesiosis is a tick-borne disease of wild and domestic dogs caused by intraerythrocytic parasites, Babesia gibsoni and Babesia canis. The parasites are widely distributed in tropical and subtropical areas worldwide and cause hemolytic anemia of the affected dogs [2,5,22]. Diminazene aceturate (Ganazeg) is an aromatic diamidine used extensively for the treatment of B. gibsoni infection in affected areas of the world [5]. Although the medicine can reduce the severity of clinical signs and the mortality associated with the disease, it sometimes induces severe side effects such as weakness, irritability, paralysis, non-responsiveness to stimuli and fatal central nervous system haemorrhage [3]. Dogs that have recovered from the babesiosis also commonly become chronic carriers, thereby posing a source of infection for other dogs and ticks. Notably, production of this drug was recently stopped. Therefore, for the treatment of B. gibsoni infected dogs, an alternative chemotherapeutic agent having few side effects is urgently needed. One possible source of such affordable treatment lies in the use of plant extracts.Central Kalimantan, Indonesia is well known for its green tropical vegetation and peat swamp forests. Its diverse nature and uses are claimed to have medicinal properties. No data are available to assess the extent to which these plant extracts can be used for the treatment of B. gibsoni infected dogs. The aims of the present study were to evaluate the inhibitory effects of the Central Kalimantan plant extracts on the B. gibsoni in vitro and their acute toxicity to mice.Forty-five plants were collected from Central Kalimantan, Indonesia based on ethnopharmacological characteristics. These plants were identified at the Herbarium Bogoriense, Indonesia. Voucher specimens were deposited at the Department of Research and Development for Biology, Indonesian Institute of Sciences, Bogor. Each plant sample (10 g) was boiled for 30 min in 200 ml of water twice. The boiling water was freeze-dried and then ground into powder.To evaluate the antibabesial activity, the powder of plant extracts was dissolved in dimethyl sulfoxide (DMSO) and further diluted with RPMI 1640 medium supplemented with sodium pyruvate (0.1 mg/ml), glutamine (0.3 mg/ml), sodium bicarbonate (2 mg/ml), penicillin (100 units/ml) and streptomycin (100 µg/ml). The final DMSO concentration was not more than 0.1%. B. gibsoni used in this stu...

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Curcumenone, curcumanolide A and curcumanolide B, three sesquiterpenoids from curcuma zedoaria

Cited by 74 publications

References 12 publications

Prediction of Cyclooxygenase Inhibitory Activity of Curcuma Rhizome from Chromatograms by Multivariate Analysis

Prediction of Cyclooxygenase Inhibitory Activity of Curcuma Rhizome from Chromatograms by Multivariate Analysis

Anti-inflammatory sesquiterpenes fromCurcuma zedoaria

Effects of Central Kalimantan Plant Extracts on Intraerythrocytic Babesia gibsoni in Culture

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