Cytotoxic components of Zingiber zerumbet, Curcuma zedoaria and C. domestica

Matthes, Hans W. D.; Luu, Bang; Ourisson, Guy

doi:10.1016/s0031-9422(00)83937-0

Cited by 152 publications

(83 citation statements)

References 21 publications

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“…As shown in Scheme 1, dehydrozingerone (6−13) and chalcone (14−17) analogs with various substitution patterns on the benzylidene ring were easily obtained from substituted benzaldehydes (5) reacted with the appropriate ketone (acetone for 6−13, acetophenone for 14 −17) using an aldol condensation. 12 Alkylation/allylation of the phenol of 1 or 3 was achieved by a standard procedure 25 using an alkyl/allyl halide to give the corresponding phenoxy analogs 18−26 and 27−35, respectively, as shown in Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents

et al. 2006

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Twenty-eight compounds related to dehydrozingerone (1), isoeugenol (3), and 2-hydroxychalcone (4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogs 27−35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR (a multi-drug resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC 50 value of 0.6 μg/mL. Furthermore, dehydrozingerone analog 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC 50 values of 2.0, 1.0, and 2.0 μg/mL, respectively) and KB-VCR (IC 50 values of 1.9, 1.0, and 2.0 μg/mL, respectively) cells, suggesting that they are not substrates for the p-glycoprotein drug efflux pump.Dehydrozingerone (1), isolated from ginger (Zingiber officinale), 1,2 is a well known phenolic natural product with anti-inflammatory, antioxidant, and antitumor promoting activities. 3 It is the structural half analog, as well as biosynthetic intermediate, 4 of curcumin (2), which possesses various remarkable bioactivities such as cytotoxic effects on cancer cell lines 5-8 and induction of apoptotic cell death in human promyelocytic leukemia HL-60 and human oral squamous carcinoma HSC-4 cells. 9 Dehydrozingerone (1), isoeugenol (3) and 2-hydroxychalcone (4) (Figure 1) have similar structures (acetyl, methyl and benzoyl, respectively, attached to a styrene skeleton). Both 3 and 4 are also prominent bioactive compounds. 10,11 Thus, we expected that 1-analogs should show a wide range of pharmacological activities. In spite of the interesting and simple structure of 1, we found only a few literature reports on analog syntheses and structure-activity relationships (SAR), 12,13 although we recently reported the cytotoxic effects of curcumin analogs. 7,14,15 It is known that the presence of a prenyl or geranyl group on flavonoids, including chalcones, can lead to a remarkable increase in bioactivity. 16,17 As dehydrozingerone (1) is structurally related to chalcones, the introduction of a prenyl or geranyl group on any position of 1 might also increase activity. In fact, most prenylflavonoids and geranylflavonoids as well as related compounds are known to have potent cytotoxic effects. 18-21 Furthermore, with respect to cancer research, a prenyl moiety has been demonstrated to be essential for chemopreventive

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Section: Resultsmentioning

confidence: 99%

Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents

et al. 2006

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“…6) During our isolation work, we found some isomerization of 7 to 6. Wethought 6 which was the same compoundas that isolated by Matthes et al,6) might have been an artifact produced from 7 in the extraction and/or purification steps.…”

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confidence: 76%

“…The structures of the isolated compounds were determined to be kaempferol-3,4' -O-dimethylether (3), kaempferol-3-O-methylether (4), kaempferol-3-O-(3,4-Odiacetyl-a-L-rhamnopyranoside) (6) and kaempferol-3-0-(2,4-O-diacetyl-<z-L-rhamnopyranoside) (7). The stability of the two flavonoid glycosides (6 and 7) and their occurrence in the fresh rhizome are also discussed.…”

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confidence: 99%

Flavonoid constituents of Zingiber zerumbet Smith.

Nakatani

Jitoe

Masuda

et al. 1991

Agricultural and Biological Chemistry

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“…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.…”

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Anti-inflammatory sesquiterpenes fromCurcuma zedoaria

Makabe

Maru

Kuwabara

et al. 2006

Natural Product Research

165

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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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Cytotoxic components of Zingiber zerumbet, Curcuma zedoaria and C. domestica

Cited by 152 publications

References 21 publications

Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents

Dehydrozingerone, Chalcone, and Isoeugenol Analogues as in Vitro Anticancer Agents

Flavonoid constituents of Zingiber zerumbet Smith.

Anti-inflammatory sesquiterpenes fromCurcuma zedoaria

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