79067-88-2

Upstream product

• 98885-93-9 curcumin 
• 458-37-7 curcumin 
• 36062-05-2 hexahydrocurcumin 
• 1135-23-5 3-(4-hydroxy-3-methoxyphenyl)propionic acid 
• 56024-44-3 methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate 
• 122-48-5 4-(4-hydroxy-3-methoxyphenyl)-2-butanone 
• 80638-48-8 3-(3'-methoxy-4'-hydroxyphenyl)propionaldehyde 
• 36062-04-1 1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione 

Downstream Products

• 685530-97-6 1,7-bis(4-hydroxy-3-methoxy-phenyl)heptan-3-one 
• 685530-96-5 1,7-bis(4-hydroxy-3-methoxyphenyl)-4,6-heptadien-3-one 
• 470466-02-5 C₂₁H₂₀O₅ 
• 1221590-24-4 C₂₁H₂₆O₅ 
• 39886-88-9 C₂₅H₂₈O₇ 
• 41137-87-5 hirsutenone 

Relevant academic research and scientific papers

First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry

Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls - a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.

Use of curcumin derivative

The invention provides the use of a curcumin derivative. The use of the curcumin derivative shown in a formula I (please see the specification for the formula), or salts of the curcumin derivative inthe preparation of drugs of anti-inflammatory diseases and/or a COX inhibitor is particularly provided. The curcumin derivative has good COX inhibitory activity and anti-inflammatory activity and canbe used for preparing the COX inhibitor and anti-inflammatory drugs. Compound 6 and compound 7 have the best effects on COX-2 inhibitory activity and anti-inflammatory activity and can be used for preparing a COX-2 inhibitor and the anti-inflammatory drugs.

FOOD COMPOSITION FOR PREVENTING OBESITY, PHARMACEUTICAL COMPOSITION FOR TREATING OBESITY, AND ANIMAL MEDICINE FOR TREATING OBESITY, CONTAINING GINGERNONE A

Disclosed is a composition comprising gingerenone A as an active ingredient. The composition includes a food composition for preventing obesity, a pharmaceutical composition for treating obesity and a medicine for treating animal obesity. Since the composition includes gingerenone A, which inhibits expression of the important transcriptional factors C/EBPα and PPARγ, expressed upon adipocyte differentiation, as well as FAS protein expression, the composition has superior potential for obesity prevention or treatment.

Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species

The natural curcuminoids curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) have been chemically modified to give 46 analogs and 8 pairs of 1:1 mixture of curcuminoid analogs and these parent curcuminoids and their analogs were assessed against protozoa of the Trypanosoma and Leishmania species. The parent curcuminoids exhibited low antitrypanosomal activity (EC50 for our drug-sensitive Trypanosoma brucei brucei line (WT) of compounds 1, 2 and 3 are 2.5, 4.6 and 7.7 μM, respectively). Among 43 curcuminoid analogs and 8 pairs of 1:1 mixture of curcuminoid analogs tested, 8 pure analogs and 5 isomeric mixtures of analogs exhibited high antitrypanosomal activity in submicromolar order of magnitude. Among these highly active analogs, 1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one (40) was the most active compound, with an EC50 value of 0.053 ± 0.007 μM; it was about 2-fold more active than the standard veterinary drug diminazene aceturate (EC50 0.12 ± 0.01 μM). Using a previously characterized diminazene-resistant T. b. brucei (TbAT1-KO) and a derived multi-drug resistant line (B48), no cross-resistance of curcuminoids was observed to the diamidine and melaminophenyl arsenical drugs that are the current treatments. Indeed, curcuminoids carrying a conjugated keto (enone) motif, including 40, were significantly more active against T. b. brucei B48. This enone motif was found to contribute to particularly high trypanocidal activity against all Trypanosoma species and strains tested. The parent curcuminoids showed low antileishmanial activity (EC50 values of compounds 1 and 2 for Leishmania mexicana amastigotes are 16 ± 3 and 37 ± 6 μM, respectively) while the control drug, pentamidine, displayed an EC50 of 16 ± 2 μM. Among the active curcuminoid analogs, four compounds exhibited EC50 values of less than 5 μM against Leishmania major promastigotes and four against L. mexicana amastigotes. No significant difference in sensitivity to curcuminoids between L. major promastigotes and L. mexicana amastigotes was observed. The parent curcuminoids and most of their analogs were also tested for their toxicity against human embryonic kidney (HEK) cells. All the curcuminoids exhibited lower toxicity to HEK cells than to T. b. brucei bloodstream forms and only one of the tested compounds showed significantly higher activity against HEK cells than curcumin (1). The selectivity index for T. b. brucei ranged from 3-fold to 1500-fold. The selectivity index for the most active analog, the enone 40, was 453-fold.

Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity

Curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was 1131-fold more active than curcumin (1), the parent compound, and was approximately 18 and 2-fold more active than the standard drugs kanamycin and isoniazid, respectively. Compound 53 also exhibited high activity against the multidrug-resistant M. tuberculosis clinical isolates, with the MICs of 0.195-3.125 μg/mL. The structural requirements for a curcuminoid analog to exhibit antimycobacterial activity are the presence of an isoxazole ring and two unsaturated bonds on the heptyl chain. The presence of a suitable para-alkoxyl group on the aromatic ring which is attached in close proximity to the nitrogen function of the isoxazole ring and a free para-hydroxyl group on another aromatic ring enhances the biological activity.

Pharmacognostic studies on ginger and related drugs - Part 1: Five sulfonated compounds from Zingiberis rhizome (Shokyo)

Five sulfonated compounds, namely 4-gingesulfonic acid and shogasulfonic acids A, B, C and D, were isolated together with seven known compounds including 6-gingesulfonic acid from Zingiberis rhizome (Japanese name: Shokyo) made out of ginger. Their struct

Synthesis of gingerenone-A and hirsutenone

Gingerenone-A 5, a diarylheptenone from Zingiber officinale, has been synthesized from vanillin 1 in four steps with an overall yield of 15%. Demethylation of 5 with AlCl3 gives hirsutenone 6, a metabolite of Alnus hirsute, in 36% yield. The spectral data of 5 and 6 are in agreement with those of natural metabolites 5 and 6 and both the compounds exhibited weak antibacterial activity.

STRUCTURES OF ANTIFUNGAL DIARYLHEPTENONES, GINGERENONES A, B, C AND ISOGINGERENONE B, ISOLATED FROM THE RHIZOMES OF ZINGIBER OFFICINALE

Four new diarylheptenones, 1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one (gingerenone A), 7-(3,5-dimethoxy-4-hydroxyphenyl)-1-(4-hydroxy-3-methoxyphenyl) hept-4-en-3-one (gingerenone B), 1- gingerol -> shogaol) of zingiberaceous plants.Gingerenone A exhibited a moderate anticoccidium activity in vitro and a strong antifungal effect to Pyricularia oryzae.