Co-occurrence and high-performance liquid chromatographic separation of the glycosides of rhodeasapogenin and its analogs which differ in the f-ring structure

Kazumoto Miyahara, Keiko Kudo, Toshio Kawasaki

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Two spirostanol glycosides (steroid saponins) R-3 (I) and R-8 (II), which were regarded, respectively, as pure 1-0-α-L-rhamnopyranosyl-(1-2)-β-D-xylopyranoside and 3-0-β-D-glucopyranoside of rhodeasapogenin(25S) (III), were shown by 13C-NMR to be accompanied by the corresponding glycosides of isorhodeasapogenin(25R) (IV) and conva-llamarogenin(Δ25(27)) (V). Qualitative and preparative separation by HPLC of the components of I and II were studied and successfully achieved by a combination of two methods. They consisted equally of not three but four compounds, which were isolated in the pure state. Three of them were identified as the glycosides of III (major), IV and V, while the fourth was considered to have the same sugar moiety as I or II combined with a new aglycone different from III - V in the F-ring structure. The methods were applied also to some commonly known sterod saponins.

Original languageEnglish
Pages (from-to)348-351
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume31
Issue number1
DOIs
Publication statusPublished - Jan 1 1983

Fingerprint

Glycosides
Saponins
Spirostans
Liquids
Sugars
Steroids
High Pressure Liquid Chromatography
Nuclear magnetic resonance

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Co-occurrence and high-performance liquid chromatographic separation of the glycosides of rhodeasapogenin and its analogs which differ in the f-ring structure. / Miyahara, Kazumoto; Kudo, Keiko; Kawasaki, Toshio.

In: Chemical and Pharmaceutical Bulletin, Vol. 31, No. 1, 01.01.1983, p. 348-351.

Research output: Contribution to journalArticle

@article{50d0a47496bf43a4a03b0e53a219656a,
title = "Co-occurrence and high-performance liquid chromatographic separation of the glycosides of rhodeasapogenin and its analogs which differ in the f-ring structure",
abstract = "Two spirostanol glycosides (steroid saponins) R-3 (I) and R-8 (II), which were regarded, respectively, as pure 1-0-α-L-rhamnopyranosyl-(1-2)-β-D-xylopyranoside and 3-0-β-D-glucopyranoside of rhodeasapogenin(25S) (III), were shown by 13C-NMR to be accompanied by the corresponding glycosides of isorhodeasapogenin(25R) (IV) and conva-llamarogenin(Δ25(27)) (V). Qualitative and preparative separation by HPLC of the components of I and II were studied and successfully achieved by a combination of two methods. They consisted equally of not three but four compounds, which were isolated in the pure state. Three of them were identified as the glycosides of III (major), IV and V, while the fourth was considered to have the same sugar moiety as I or II combined with a new aglycone different from III - V in the F-ring structure. The methods were applied also to some commonly known sterod saponins.",
author = "Kazumoto Miyahara and Keiko Kudo and Toshio Kawasaki",
year = "1983",
month = "1",
day = "1",
doi = "10.1248/cpb.31.348",
language = "English",
volume = "31",
pages = "348--351",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "The Pharmaceutical Society of Japan",
number = "1",

}

TY - JOUR

T1 - Co-occurrence and high-performance liquid chromatographic separation of the glycosides of rhodeasapogenin and its analogs which differ in the f-ring structure

AU - Miyahara, Kazumoto

AU - Kudo, Keiko

AU - Kawasaki, Toshio

PY - 1983/1/1

Y1 - 1983/1/1

N2 - Two spirostanol glycosides (steroid saponins) R-3 (I) and R-8 (II), which were regarded, respectively, as pure 1-0-α-L-rhamnopyranosyl-(1-2)-β-D-xylopyranoside and 3-0-β-D-glucopyranoside of rhodeasapogenin(25S) (III), were shown by 13C-NMR to be accompanied by the corresponding glycosides of isorhodeasapogenin(25R) (IV) and conva-llamarogenin(Δ25(27)) (V). Qualitative and preparative separation by HPLC of the components of I and II were studied and successfully achieved by a combination of two methods. They consisted equally of not three but four compounds, which were isolated in the pure state. Three of them were identified as the glycosides of III (major), IV and V, while the fourth was considered to have the same sugar moiety as I or II combined with a new aglycone different from III - V in the F-ring structure. The methods were applied also to some commonly known sterod saponins.

AB - Two spirostanol glycosides (steroid saponins) R-3 (I) and R-8 (II), which were regarded, respectively, as pure 1-0-α-L-rhamnopyranosyl-(1-2)-β-D-xylopyranoside and 3-0-β-D-glucopyranoside of rhodeasapogenin(25S) (III), were shown by 13C-NMR to be accompanied by the corresponding glycosides of isorhodeasapogenin(25R) (IV) and conva-llamarogenin(Δ25(27)) (V). Qualitative and preparative separation by HPLC of the components of I and II were studied and successfully achieved by a combination of two methods. They consisted equally of not three but four compounds, which were isolated in the pure state. Three of them were identified as the glycosides of III (major), IV and V, while the fourth was considered to have the same sugar moiety as I or II combined with a new aglycone different from III - V in the F-ring structure. The methods were applied also to some commonly known sterod saponins.

UR - http://www.scopus.com/inward/record.url?scp=0020574893&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0020574893&partnerID=8YFLogxK

U2 - 10.1248/cpb.31.348

DO - 10.1248/cpb.31.348

M3 - Article

AN - SCOPUS:0020574893

VL - 31

SP - 348

EP - 351

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 1

ER -