13C NMR spectral studies of entagenic acid to establish its structure.

Okada, Yoshihito; Shibata, Shoji; Kamo, Osamu; Okuyama, Toru

doi:10.1248/cpb.36.5028

Cited by 9 publications

(7 citation statements)

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“…All of these data were confirmed by the fragment ion at m / z 487 present in the FABMS and representing the pseudomolecular ion of this aglycon. Consequently, the aglycon was identified as entagenic acid, for which the structure was revised as 3 β ,15 α ,16 α -trihydroxyolean-12-en-28-oic acid by Okada et al., in contrast to the earlier proposition of Barua et al (3 β ,21 α ,22 α -trihydroxyolean-12-en-28-oic acid). Compound 3 was thus elucidated as 3- O - β - d -xylopyranosyl-(1→3)- O -[ α - l -arabinopyranosyl-(1→6)]-2-acetylamino-2-deoxy- β - d -glucopyranosylentagenic acid 28- O - β - d -apiofuranosyl-(1→2)- β - d -glucopyranoside (pursaethoside C).…”

Section: Resultsmentioning

confidence: 96%

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Pursaethosides A−E, Triterpene Saponins from Entada pursaetha

et al. 2005

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Five new triterpenoid saponins, pursaethosides A-E (1-5), were isolated from the n-BuOH extract of the seed kernels of Entada pursaetha along with the known phaseoloidin. The structures of 1-5 were elucidated mainly by spectroscopic data interpretation and chemical degradation. Pursaethosides C-E (3-5) possess as a common structural feature entagenic acid as aglycon, which is rare among triterpene saponins. Compounds 2-4 and phaesolidin were found to be not cytotoxic when tested against HCT 116 and HT-29 human colon cancer cells.

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Section: Resultsmentioning

confidence: 96%

“…The acid hydrolysis of the prosapogenins resulting from 1 and 2 afforded, respectively, oleanolic acid and echinocystic acid, identified by co-TLC comparison with authentic samples. The same aglycon resulted from the acid hydrolysis of 3 − 5 and was identified as entagenic acid by comparison of its 13 C NMR data with literature values …”

Section: Methodsmentioning

confidence: 93%

Pursaethosides A−E, Triterpene Saponins from Entada pursaetha

et al. 2005

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“…Pharmacological studies on extracts and isolated compounds from this plant displayed cytotoxic [1,3], antidiabetic [4,5], antioxidant [6,7], antimicrobial [6,8], antivirus [9] and anti-inflamatory [10] activities. Besides, studies on chemical constituents of E. phaseoloides showed the presence of triterpenoid saponins [1,3,[10][11][12][13][14], sulfur-containing amides [15][16][17], phenylacetic acid derivatives [9,18] and flavonoids [8]. Herein, we reported the isolation and chemical structural elucidation of four glycosides from the seeds of E. phaseoloides.…”

Section: Introductionmentioning

confidence: 99%

STRUCTURAL ELUCIDATION OF GLYCOSIDES FROM THE SEEDS OF Entada phaseoloides GROWING IN THUA THIEN HUE

Cuong

Lien

Nhi

et al. 2019

JST

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Entada phaseoloides (L.) Merr. belongs to Fabaceae family and widely distributes throughout Vietnam, Thailand, Malaysia, Indonesia, Philippines, China, New Guinea, and Australia. In Vietnamese traditional medicine, the seeds of Entada phaseoloides were used for the treatment of stomachache, haemorrhoids, and hernia diseases. In this article, we report the isolation and structural elucidation of four glycosides from the water extract of seeds of E. phaseoloides including phaseoloideside C (1), phaseoloideside E (2), acanthoside D (3), and 1-(3,4,5-trimethoxyphenyl)prop-7-en-9-ol-O-(6ʹʹ-O-α-L-arabinopyranosyl)-β-D-glucopyranoside (4). To the best of our knowledge, compounds 3-4 were isolated from E. phaseoloides for the first time.

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“…The seed kernels of E. rheedii, 1) and E. pursaetha, 2) and a bark of E. phaseoloides 3,4) were reported to contain a number of N-acetyl-Dglucosamine-containing entagenic acid saponins. Despite these investigations, the chemical constituents of E. rheedei as well as their biological activities have not yet been fully characterized.…”

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confidence: 99%

“…3,4) Judging from the downfield shift of C-3 (d C 89.6) and the upfield shift value observed for C-28 (d C 175.8) (Table 2), 1 was presumed to be a bisdesmosidic glycoside of entagenic acid with sugar linkages at C-3 through a glycosidic bond and at C-28 through an ester bond. Alkaline hydrolysis of 1 liberated a monodesmoside (1a) and a triose, whose sugar composition was analyzed to be Dapiose, D-xylose and D-glucose.…”

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confidence: 99%