5042-03-5

Usage

Uses

Used in Pharmaceutical Industry:
MESUAXANTHONE-B is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure with hydroxy groups at specific positions may contribute to its bioactivity and interactions with biological targets, making it a candidate for further research and development in the pharmaceutical field.
Used in Cosmetic Industry:
MESUAXANTHONE-B is used as an active ingredient in cosmetic products for its potential skin benefits. The presence of hydroxy groups may provide antioxidant and anti-inflammatory properties, which can be beneficial for skin health and protection against environmental stressors.
Used in Food Industry:
MESUAXANTHONE-B is used as a natural food additive for its potential health-promoting properties. Its antioxidant and anti-inflammatory activities may contribute to the enhancement of food products' nutritional value and overall health benefits.

InChI:InChI=1/C13H8O5/c14-7-2-1-3-9-10(7)11(16)6-4-5-8(15)12(17)13(6)18-9/h1-5,14-15,17H

Upstream product

• 303-07-1 2,6-Dihydroxybenzoic acid 
• 87-66-1 2-hydroxyresorcinol 
• 2150-45-0 methyl 2,6-dihydroxybenzoate 
• 634-36-6 1,2,3-trimethoxybenzene 
• 1989-53-3 2,6-dimethoxybenzoyl chloride 
• 13739-15-6 1,5,6-trimethoxy-9H-xanthen-9-one 
• 1466-76-8 2-6-dimethoxybenzoic acid 

Downstream Products

• 113681-58-6 5,6-dibenzyloxy-1-hydroxyxanthone 
• 113681-59-7 5,6-dibenzyloxy-1-methoxyxanthone 
• 1301159-81-8 7-hydroxy-2,2-diphenyl-6H-[1,3]dioxolo[4,5-c]xanthen-6-one 
• 1301159-87-4 7-(methoxymethoxy)-2,2-diphenyl-6H-[1,3]dioxolo[4,5-c]xanthen-6-one 
• 1338230-32-2 C₂₉H₂₂O₆ 

Relevant academic research and scientific papers

A-ring oxygenation modulates the chemistry and bioactivity of caged Garcinia xanthones

Natural products of the caged Garcinia xanthones (CGX) family are characterized by a unique chemical structure, potent bioactivities and promising pharmacological profiles. We have developed a Claisen/Diels-Alder reaction cascade that, in combination with a Pd(0)-catalyzed reverse prenylation, provides rapid and efficient access to the CGX pharmacophore, represented by the structure of cluvenone. To further explore this pharmacophore, we have synthesized various A-ring oxygenated analogues of cluvenone and have evaluated their bioactivities in terms of growth inhibition, mitochondrial fragmentation, induction of mitochondrial-dependent cell death and Hsp90 client inhibition. We found that installation of an oxygen functionality at various positions of the A-ring influences significantly both the site-selectivity of the Claisen/Diels-Alder reaction and the bioactivity of these compounds, due to remote electronic effects.

GARCINIA DERIVATIVE, ITS PREPARING METHOD AND MEDICINAL USE

The present invention relates to a field of pharmaceutical chemistry, more specifically, the present invention relates to a garcinia derivative Formula (I), its preparing method, and medicinal use. Wherein the definitions of R1 and R2 are disclosed in the specification of the present invention, and the derivative of the present invention is a structurally simplified analogue of the gambogic acid compound; wherein the gambogic acid compound possesses anti-cancer characteristics, and could be used for preparation of anti-tumor drugs.

Synthesis, SAR and biological evaluation of natural and non-natural hydroxylated and prenylated xanthones as antitumor agents

In order to explore the detailed structure-activity relationship (SAR) around xanthone scaffold bearing hydroxyl and prenyl moieties, twenty-nine natural and non-natural hydroxylated and prenylated xanthones have been synthesized and evaluated for their in vitro anti-proliferative activities against five human cancer cell lines, including HepG2 (hepatocelluar carcinoma), HCT-116 (colon carcinoma), A549 (lung carcinoma), BGC823 (gastric carcinoma) and MDAMB- 231 (breast carcinoma). The SAR analysis revealed that the anti-proliferative activity of the xanthones is substantially influenced by the position and number of attached hydroxyl and prenyl groups, and the presence of hydroxyl group ortho to the carbonyl function of xanthone scaffold contributes significantly to their cytotoxicity. The new prenylated xanthone 20 with a relatively simple structure, namely 1,3,8-trihydroxy-2-prenylxanthone, was found to exhibit potent antitumor activities comparable to mangostin against all the five cancer cell lines. Further mechanistic studies suggested that compound 20 induces apoptosis and causes cell cycle arrest at S phase in HepG2 cells. These results have highlighted compound 20 as a new potential lead candidate for future development of novel potent broad-spectrum antitumor agents.

Studies on chemical modification and biology of a natural product, gambogic acid (III): Determination of the essential pharmacophore for biological activity

Caged 4-oxa-tricyclo[4.3.1.03,7]dec-2-one structural motifs are found in Garcinia natural products that demonstrate anti-tumor activity. Gambogic acid (GA, 1), the most abundant caged Garcinia xanthones, has been reported to be a promising anti-cancer agent. To identify the essential pharmacophore for its anti-tumor activity, a series of GA analogues that address potential key structural features for biological activity were synthesized, among which compound 11a displayed comparable in vitro anti-tumor activity as GA. Mechanistic studies on 11a determined that the compound induces apoptosis as well as arrests the G2/M phase of the cell cycle in HepG2 cells. The determination of the essential part of the scaffold found in GA to maintain anti-tumor effects, and the SAR based on the caged pharmacophore are reported and will provide key information for future anti-cancer drug development studies.

A CONVENIENT SYNTHESIS OF NATURALLY OCCURING XANTHONES

Six naturally occuring xanthones are synthesized by the thermal condensation of methyl 2,6-dihydroxybenzoate, methyl 2,4-dihydroxybenzoate and methyl 2,4,6-trihydroxybenzoate with hydroquinone, catechol and pyrogallol.