Bioactive xanthones, benzophenones and biphenyls from mangosteen root with potential anti-migration against hepatocellular carcinoma cells

Choodej, Siwattra; Koopklang, Kedkarn; Raksat, Achara; Chuaypen, Natthaya; Pudhom, Khanitha

doi:10.1038/s41598-022-12507-8

Cited by 5 publications

(5 citation statements)

References 40 publications

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“…Moderate cytotoxicity against HepG2 cell line displayed 145 (IC 50 = 9.81 µM) and 138 (IC 50 = 19.41 µM) compared to the positive control sorafenib (IC 50 = 2.66 µM) and doxorubicin (IC 50 = 3.07 µM). [106]. Furthermore, very low cytotoxic activity possessed benzophenones 174, 234, 121 [119], 248 (IC 50 > 50 µM), 249 (IC 50 > 50 µM) [155], and 44, 172, 127, 143 [257].…”

Section: Estrogenic Activitymentioning

confidence: 99%

“…More than twenty O-glycosides of tetraoxygenated benzophenones (Figure 9) have been isolated, so far. Most of these compounds (104)(105)(106)(107)(108)(109)(110)(111)(112)(113)(114)(115)(116)(117)(118)(119)(120)(121) share iriflophenone 59 as their aglycone. The first O-glycoside of iriflophenone 104 was isolated from Coleogyne ramosissima Torr.…”

Section: Tetraoxygenated Bezophenonesmentioning

confidence: 99%

“…ex Benth. [103], G. mangostana [104], G. livingstonei T.Anderson [105], and G. mangostana [106], respectively. Compounds 139 and 140 were the only methylenedioxy-benzophenones with 2,3 ,4,4 ,6-pentaoxygenation pattern originally isolated from Aniba pseudocoto bark [20,22].…”

Section: Pentaoxygenated Benzophenonesmentioning

confidence: 99%

“…ex Buch.-Ham. [109], G. mangostana [106], G. hombroniana Pierre [110], G. speciosa Wall. [111], Hypericum annulatum Moris [8], and H. sampsonii [112], respectively.…”

Section: Pentaoxygenated Benzophenonesmentioning

confidence: 99%

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Naturally Occurring Simple Oxygenated Benzophenones: Structural Diversity, Distribution, and Biological Properties

Marinov,

Kokanova-Nedialkova,

Nedialkov

2023

Diversity

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Naturally occurring benzophenones represent a relatively small group of plant metabolites with narrow distribution, mainly in members of Clusiaceae, Gentianaceae, Hypericaceae, Polygalaceae, Myrtaceae, etc.; however, there were reports of several compounds derived from microorganisms belonging to the Aspergillaceae and Valsaceae families and propolis. Benzophenones exhibit many biological activities, such as antioxidant, anti-inflammatory, cytotoxic, antimicrobial, etc. Few reviews on benzophenones that have appeared in the literature were focused on their prenylated derivatives. Summarized information on structural diversity, distribution, and biological activities of simple oxygenated naturally occurring benzophenones and their glycosides has not been found in the literature. Until 2000, only benzophenone C-glycosides were known to occur in nature. Since then, many O-glycosides have been isolated, structurally, and biologically characterized. This review covers the years from 1850 to 2023 and was compiled using databases such as Chemical Abstracts, Scopus, Google Scholar, PubMed, and ResearchGate. Based on their degree of oxidation, 210 chemical structures of benzophenone derivatives and glycosides were grouped into six categories. In addition, in one group of 40 miscellaneous benzophenones, where one or several protons are replaced by a methyl, alcohol, carboxyl, or acyl group, glycosidic forms with such an aglycone and dimeric compounds with xanthone was included. Simple oxygenated benzophenones and their glycosides were found in 77 plant genera belonging to 44 families. The allergy-associated bezophenone-1, benzophenone-2 and benzophenone-3 have limited distribution across natural sources. A wide range of biological activities (antioxidant, anti-inflammatory, cytotoxic, antitumor, cytoprotective, antimicrobial, MAO-A, antiarthritic, anticholinesterase, anti-atherosclerotic, laxative, etc.) of simple oxygenated benzophenones and their glycosides that appeared in the literature were discussed.

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Section: Estrogenic Activitymentioning

confidence: 99%

Section: Tetraoxygenated Bezophenonesmentioning

confidence: 99%

Section: Pentaoxygenated Benzophenonesmentioning

confidence: 99%

“…ex Buch.-Ham. [109], G. mangostana [106], G. hombroniana Pierre [110], G. speciosa Wall. [111], Hypericum annulatum Moris [8], and H. sampsonii [112], respectively.…”

Section: Pentaoxygenated Benzophenonesmentioning

confidence: 99%

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Naturally Occurring Simple Oxygenated Benzophenones: Structural Diversity, Distribution, and Biological Properties

Marinov,

Kokanova-Nedialkova,

Nedialkov

2023

Diversity

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“…The present study represents another attempt to explore the cooling performance of an organic cooling pad made from mangosteen peel waste. Mangosteen (Garcinia mangostana L.) is renowned as one of the world's most exquisite fruits, often referred to as the "Queen of Fruits" due to its sweet-sour taste and unique appearance, with sepals arranged like a crown [36]. Mangosteen is a tropical tree species primarily cultivated in Southeast Asian countries, such as Indonesia, Malaysia, and Thailand [37].…”

Section: Introductionmentioning

confidence: 99%

Performance Evaluation of a Wet Medium Made of Mangosteen Peels for a Direct Evaporative Cooling System

Chaomuang,

Nuangjamnong,

Rakmae

2023

AgriEngineering

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The present study aimed to investigate an alternative evaporative cooling pad material made from mangosteen peel (MP) waste. Mangosteen peels were used to fill a 150 mm thick mesh container with a packing density of 180 kg/m3. A wind tunnel was constructed and utilized to experimentally evaluate the cooling performance of this organic-waste-based pad under hot and humid conditions (31–34 °C and 55–70% RH). The performance parameters assessed included pressure drop, temperature drop, saturation effectiveness, cooling capacity, and coefficient of performance (COP). The influence of air velocity (0.7, 1.0, 1.4, and 1.8 m/s) on these parameters was also examined. The results revealed that the saturation effectiveness of the MP pad ranged from 53% to 77% within the considered air velocity range. The maximum temperature drop (4.6 °C), saturation effectiveness (77%), cooling capacity (0.6 kW), and COP (3.5) were achieved when the system operated at 1.4 m/s. A comparative study showed that, at this velocity, the MP pad provided performance nearly equivalent to that of the commercial cellulose paper pad, except for the pressure drop. This result affirms the potential of mangosteen peels as a suitable wet medium for evaporative cooling applications.

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Development of a Benzophenone-Free Red Propolis Extract and Evaluation of Its Efficacy against Colon Carcinogenesis

Squarisi,

Ribeiro,

Ribeiro

et al. 2024

Pharmaceuticals

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Background/Objectives: Brazilian red propolis has attracted attention for its pharmacological properties. However, signs of toxicity were recently observed in long-term studies using the hydroalcoholic extract of red propolis (RPHE), likely due to polyprenylated benzophenones. This study aimed to develop a benzophenone-free red propolis extract (BFRP) and validate an HPLC-PDA method to quantify its main constituents: isoliquiritigenin, vestitol, neovestitol, medicarpine, and 7-O-methylvestitol. Methods: BFRP’s toxicity was assessed in zebrafish larvae through a vibrational startle response assay (VSRA) and morphological analysis. Genotoxicity was evaluated using the micronucleus test in rodents, and the extract’s effects on chemically induced preneoplastic lesions in rat colon were studied. An HPLC-PDA method was used to quantify BFRP’s main compounds. Results: BFRP primarily contained vestitol (128.24 ± 1.01 μg/mL) along with isoliquiritigenin, medicarpin, neovestitol, and 7-O-methylvestitol. Zebrafish larvae exposed to 40 µg/mL of BFRP exhibited toxicity, higher than the 10 µg/mL for RPHE, though no morphological differences were found. Fluorescent staining in the notochord, branchial arches, and mouth was observed in larvae treated with both BFRP and RPHE. No genotoxic or cytotoxic effects were observed up to 2000 mg/kg in rodents, with no impact on hepatotoxicity or nephrotoxicity markers. Chemoprevention studies showed a 41.6% reduction in preneoplastic lesions in rats treated with 6 mg/kg of BFRP. Conclusions: These findings indicate that BFRP is a safe, effective propolis-based extract with potential applications for human health, demonstrating reduced toxicity and chemopreventive properties.

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Bioactive xanthones, benzophenones and biphenyls from mangosteen root with potential anti-migration against hepatocellular carcinoma cells

Cited by 5 publications

References 40 publications

Naturally Occurring Simple Oxygenated Benzophenones: Structural Diversity, Distribution, and Biological Properties

Naturally Occurring Simple Oxygenated Benzophenones: Structural Diversity, Distribution, and Biological Properties

Performance Evaluation of a Wet Medium Made of Mangosteen Peels for a Direct Evaporative Cooling System

Development of a Benzophenone-Free Red Propolis Extract and Evaluation of Its Efficacy against Colon Carcinogenesis

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