Published October 31, 2021
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Calyhedins I-VI: Resin glycosides from the rhizomes of Calystegia hederacea
Authors/Creators
- 1. School of Agriculture, Tokai University; 9-1-1 Toroku, Higashi-ku, Kumamoto, 862-8652, Japan
Description
Ono, Masateru, Yuhara, Nobuyoshi, Shimohara, Takaaki, Matsubara, Souta, Yasuda, Shin, Tsuchihashi, Ryota, Okawa, Masafumi, Kinjo, Junei, Zhou, Jian-Rong, Yoshimitsu, Hitoshi, Nohara, Toshihiro (2021): Calyhedins I-VI: Resin glycosides from the rhizomes of Calystegia hederacea. Phytochemistry (112888) 190: 1-9, DOI: 10.1016/j.phytochem.2021.112888, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112888
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- urn:lsid:plazi.org:pub:FFD1912B8D59AA74FFA97D79FFE0FF85
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- Has part
- Figure: 10.5281/zenodo.8258206 (DOI)
- Figure: 10.5281/zenodo.8258208 (DOI)
- Figure: 10.5281/zenodo.8258210 (DOI)
References
- Calystegia hederacea Wall. (Convolvulaceae) is a perennial herb widely distributed throughout India and East Asia (Hotta et al., 1989). Many plants in this family contain resin glycosides as the chemical constituents (Ono, 2017; Pereda-Miranda et al., 2010). They have oligoglycosides of hydroxyl fatty acids (glycosidic acids) partially acylated by some organic acids at the sugar moiety as the core structure and are roughly classified into jalapins (macrolactone structure type) and convolvulins (acylated glycosidic acid with free carboxylic acid form type) (Ono, 2017). The biological effects of jalapins, such as cytotoxicity against cancer cells (Pereda-Miranda et al., 2010), as well as anti-bacterial (Pereda-Miranda et al., 2010), ionophoric (Pereda-Miranda et al., 2010), anti-inflammatory (Yoshikawa et al., 2010), multidrug resistance modulatory (Figueroa-Gonz´alez et al., 2012), and anti-viral (Ono et al., 2014) activities, have been reported.
- garden as the plant material used in this study (Ono et al., 2020b). The absolute configurations of the monosaccharides were determined by HPLC analysis of their thiocarbamoyl-thiazolidine derivatives. Those of 2S -methylbutyric acid and 2R,3R -nilic acid were defined by comparing the specific rotations of their p -bromophenacyl esters and 1H NMR spectral data for ( )-α- methoxy-α- trifluoromethylphenylacetic acid (MTPA) ester of p -bromophenacyl nilate with those of authentic samples. The absolute configurations of 11S -jalapinolic acid and 12S -hydroxyhexadecanoic acid were determined by comparing the 1H NMR spectral data for the (+)-MTPA ester of methyl jalapiniolate with those of an authentic sample and applying Mosher' s method to methyl 12-hydroxyhexadecanoate, respectively (Ono et al., 2020b). We have also reported on the isolation and structures of six previously undescribed glycosidic acids, calyhedic acids A-F, which were obtained along with two known glycosidic acids, calysolic acids A and C. Calysolic acid A and calyhedic acid A, calysolic acid C and calyhedic acid B, calyhedic acid C and calyhedic acid D, and calyhedic acid E and calyhedic acid F were isomers of each other. Only the aglycones were different in 11S -jalapinolic acid and 12S -hydroxyhexadecanoic acid (Ono et al., 2020a, 2020b). The crude resin glycoside fraction obtained from whole plants of C. hederacea demonstrated cytotoxic activity against HL-60 human promyelocytic leukemia cells (Ono et al., 2020b).