Journal
PHYTOCHEMISTRY
Volume 217, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2023.113922
Keywords
Operculina hamiltonii; Convolvulaceae; Cytotoxicity; Cocktail chemotherapy; Glycolipids; Oligosaccharides; Potentiation effects; Recycling HPLC
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This study investigated the roots of Operculina hamiltonii, a traditional medicinal plant in Brazil. Three new acyl sugars or resin glycosides were identified and their structures elucidated. The combination of these compounds with other drugs showed enhanced cytotoxic effects on breast cancer cells.
The jalap roots, Operculina hamiltonii D.F. Austin & Staples (Convolvulaceae), are extensively commercialized as a depurative and laxative remedy in traditional medicine of the north and northeast regions of Brazil. The purification by recycling HPLC and structure elucidation of three new acyl sugars or resin glycosides are described here from a commercial product made of powdered roots. Three macrocyclic structures of a tetrasaccharide of (11S)-hydroxyhexadecanoic acid, operculinic acid C (1), the undescribed hamiltonins II and III (3 and 4), in addition to the known batatinoside III (5), presented a diastereoisomeric relationship as one residue of ndodecanoic acid esterified the oligosaccharide core on a different position in each compound. Furthermore, hamiltonin IV (6) was characterized as an ester-type homodimer of acylated operculinic acid C with the same substitution pattern identified in hamiltonins II (3) and III (4) for each of the dimer subunits. All the isolated resin glycosides did not display any intrinsic cytotoxicity (IC50 > 25 mu M). However, a combination of the individual isolated compounds 3-6 (1-50 mu M) demonstrated an enhancement of cytotoxic effects with sublethal doses of vinblastine and podophyllotoxin (0.003 mu M) in multidrug-resistant breast carcinoma epithelial cells (MCF-7/Vin).
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