Schomburginones A‒J, geranylated benzophenones from the leaves of Garcinia schomburgkiana and their cytotoxic and anti-inflammatory activities

Ten undescribed benzophenones, schomburginones A−J, together with 14 known analogs were isolated from the leaves of Garcinia schomburgkiana, an edible plant native to the Indochina region. The structures of the undescribed compounds were elucidated by NMR combined with HRMS spectroscopy, while their...

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Veröffentlicht in:Phytochemistry (Oxford) 2023-07, Vol.211, p.113701-113701, Article 113701
Hauptverfasser: Sukandar, Edwin R., Kaennakam, Sutin, Wongsuwan, Sutthida, Chatwichien, Jaruwan, Krobthong, Sucheewin, Yingchutrakul, Yodying, Mahatnirunkul, Thanisorn, Mulya, Fadjar, Parasuk, Vudhichai, Harding, David J., Poldorn, Preeyaporn, Rungrotmongkol, Thanyada, Tip-pyang, Santi, Aonbangkhen, Chanat, Chavasiri, Warinthorn
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Sprache:eng
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Zusammenfassung:Ten undescribed benzophenones, schomburginones A−J, together with 14 known analogs were isolated from the leaves of Garcinia schomburgkiana, an edible plant native to the Indochina region. The structures of the undescribed compounds were elucidated by NMR combined with HRMS spectroscopy, while their absolute configurations were determined using ECD and single-crystal X-ray diffraction analysis. The isolated metabolites represent benzophenone derivatives containing a modified monoterpene unit, including tri- and tetracyclic skeletons, which are rarely found in genus Garcinia. The cytotoxic evaluation on three cancerous cell lines demonstrated that schomburginone G, schomburginone H, and 3-geranyl-2,4,6-trihydroxybenzophenone were active against HeLa cells with IC50 values in the range of 12.2–15.7 μM, respectively, and selective compared to the non-cancerous L929 cells (SI > 3.5). In addition, the three cytotoxic compounds together with clusiacyclol A showed significant NO inhibitory activity in RAW 264.7 macrophage cells over 85% inhibition without obvious cytotoxicity at a final concentration of 100 μM. The promising activities of these compounds in cytotoxic and anti-inflammatory assays make them attractive for further study in the development of anticancer drugs. Ten undescribed geranylated benzophenones were isolated from the edible leaves of Garcinia schomburgkiana together with 14 known analogs. Schomburginone H showed selective cytotoxicity against HeLa cells compared to the normal L929 cells. It also exhibited promising nitric oxide inhibition at 100 μM without obvious cytotoxicity to RAW 264.7 cells. [Display omitted] •Ten undescribed geranylated benzophenones were isolated from G. schomburgkiana.•The compounds represent benzophenones containing a modified monoterpene unit.•Schomburginone H was selectively toxic against HeLa cells versus normal L929 cells.•Schomburginones G and H showed promising NO inhibitory activity.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2023.113701