Three New Acylated Glycosidic Acid Methyl Esters from the Crude Resin Glycoside Fraction of <i>Ipomoea lacunosa</i> Seeds by Treatment with Indium(III) Chloride in Methanol

Three new acylated glycosidic acid methyl esters and one known compound were isolated by treating the crude resin glycoside fraction derived from the seeds of Ipomoea lacunosa with indium(III) chloride in methanol, and their structures were elucidated using spectroscopic methods. The new compounds contained methyl 3S,11S-dihydroxytetradecanoate as the aglycone. Two were hexaglycosides and one was a nonaglycoside, with saccharide cores partially acylated by a glycosidic acid, 7S-hydroxydecanoic acid 7-O-β-d-quinovopyranoside (quamoclinic acid B), and/or organic acids, including isobutyric and 2S-methylbutyric acids. Furthermore, the cytotoxic activities of the isolated compounds against HL-60 human promyelocytic leukemia cells were evaluated, and they exhibited moderate activities.

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Journal
Chemical and Pharmaceutical Bulletin
Published
2025-11-25
DOI
https://doi.org/10.1248/cpb.c25-00523
Primary Topic
Carbohydrate Chemistry and Synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

Three New Acylated Glycosidic Acid Methyl Esters from the Crude Resin Glycoside Fraction of Ipomoea lacunosa Seeds by Treatment with Indium(III) Chloride in Methanol

Hiroyuki Miyashita, Hirotaka Nishikawa, Masafumi Okawa, Shin Yasuda et al.
Chemical and Pharmaceutical Bulletin
Carbohydrate Chemistry and Synthesis
article

Three New Acylated Glycosidic Acid Methyl Esters from the Crude Resin Glycoside Fraction of Ipomoea lacunosa Seeds by Treatment with Indium(III) Chloride in Methanol

Hiroyuki Miyashita, Hirotaka Nishikawa, Masafumi Okawa, Shin Yasuda, Kazutaka Uemura, Ryota Tsuchihashi, A. Murata, Masateru Ono
article en

Abstract

Three new acylated glycosidic acid methyl esters and one known compound were isolated by treating the crude resin glycoside fraction derived from the seeds of Ipomoea lacunosa with indium(III) chloride in methanol, and their structures were elucidated using spectroscopic methods. The new compounds contained methyl 3S,11S-dihydroxytetradecanoate as the aglycone. Two were hexaglycosides and one was a nonaglycoside, with saccharide cores partially acylated by a glycosidic acid, 7S-hydroxydecanoic acid 7-O-β-d-quinovopyranoside (quamoclinic acid B), and/or organic acids, including isobutyric and 2S-methylbutyric acids. Furthermore, the cytotoxic activities of the isolated compounds against HL-60 human promyelocytic leukemia cells were evaluated, and they exhibited moderate activities.

Chemical and Pharmaceutical BulletinVol. 73(11)
Sojo University (JP), Fukuoka University (JP), Kyushu Tokai University (JP)
Fukuoka University, Japan Society for the Promotion of Science
Openalex Percentile: Top 72%
Carbohydrate Chemistry and Synthesis
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