Five new resin glycosides, calyhedins XI–XV, from Calystegia hederacea

• Published in: Journal of natural medicines Vol. 77; no. 4; pp. 774 - 791
• Main Authors: Ono, Masateru, Yamano, Yuki, Shimohara, Takaaki, Yuhara, Nobuyoshi, Misuda, Nodoka, Nishikawa, Hirotaka, Yasuda, Shin, Miyashita, Hiroyuki, Yoshimitsu, Hitoshi, Tsuchihasi, Ryota, Okawa, Masafumi, Kinjo, Junei
• Format: Journal Article
• Language: English
• Published: Singapore Springer Nature Singapore 01.09.2023; Springer Nature B.V
• Subjects: Acids; Aglycones; Biomedical and Life Sciences; Biomedicine; Calystegia - chemistry; Calystegia hederacea; Cisplatin; Complementary & Alternative Medicine; Convolvulaceae - chemistry; Cytotoxicity; Glycosides; Glycosides - chemistry; Glycosides - pharmacology; Gonorrhea; Humans; Medicinal Chemistry; Monosaccharides; Organic acids; Original Paper; Pharmacology/Toxicology; Pharmacy; Plant Sciences; Plants; Promyeloid leukemia; Resins, Plant - chemistry; Rhizomes; Sugars; Resin glycoside; Glycosidic acid; Convolvulaceae; Calyhedin; Cytotoxic activity; Calystegia hederacea
• ISSN: 1340-3443; 1861-0293
• DOI: 10.1007/s11418-023-01720-y

Calystegia hederacea Wall. (Convolvulaceae) is a perennial herbaceous vine that grows widely in India and East Asia. All parts of this plant are used to treat various disorders such as menoxenia and gonorrhea. Four new resin glycosides, calyhedins XI ( 1 )–XIV ( 4 ), were isolated from the rhizomes of C . hederacea . A new glycoside, calyhedin XV ( 5 ), was isolated from its leaves and stems. Alkaline hydrolysis of 1 and 2 furnished a new glycosidic acid, calyhedic acid G ( 1a ), from 1 and a new acid, calyhedic acid H ( 2a ), from 2 along with 2 S -methylbutyric acid and 2 R -methyl-3 R -hydroxybutyric (2 R ,3 R -nilic) acid. The structures of 1 – 5 , 1a , and 2a were determined using MS and NMR spectral analyses. Compounds 1a and 2a had the same sugar moiety, β- d -glucopyranosyl-(1 → 6)- O -β- d -glucopyranosyl-(1 → 6)- O -β- d -glucopyranosyl-(1 → 3)-[ O -β- d -glucopyranosyl-(1 → 3)- O -α- l -rhamnopyranosyl-(1 → 2)]- O -β- d -glucopyranosyl-(1 → 2)-β- d -fucopyranose, while their aglycones were 11 S -dihydroxyhexadecanoic acid and 12 S -dihydroxyhexadecanoic acid, respectively. These compounds are the first glycosidic acids, with fucose as the monosaccharide component obtained from the resin glycosides of C. hederacea . Compounds 1 – 5 , comprising either 1a or 2a , were heptaglycosides with macrolactone structures, and their sugar moieties were partially acylated with 5 mol of organic acids comprising 2 S -methylbutyric, ( E )-2-methylbut-2-enoic, and 2 R ,3 R -nilic acids. Compounds 1 and 5 had 22-membered rings, while 2 – 4 had 28-membered rings. In addition, 1 and 5 exhibited cytotoxic activity against HL-60 human promyelocytic leukemia cells, comparable to that of the positive control cisplatin. Graphical abstract