LC–MS analysis of saponins of Achyranthes root in the Japanese market

Kohei Kuwada, Satoshi Kawase, Karin Nakata, Nodoka Shinya, Yuuji Narukawa, Hiroyuki Fuchino, Nobuo Kawahara, Fumiyuki Kiuchi

Research output: Contribution to journalArticle

Abstract

LC–MS analyses of saponin fractions of Achyranthes roots in the Japanese market revealed that there were three patterns for the saponin fraction of their water extracts, i.e., the saponins with a sugar moiety at position 28 [achyranthosides B (3), C (4) and D (5)] were the major constituents, the saponins without sugar moiety at position 28 [betavulgarosides II (10) and IV (11)] were the major constituents, and mixtures of these saponins. In a decoction prepared from the sample which contained 10 and 11 as the major saponins, their amounts were largely decreased compared with those of the water extract. As large amounts of these saponins were found in the precipitates formed by heating of the water extract, these saponins were seemed to precipitate out under heating. When hot water was used for the extraction, 3, 4 and 5 were detected even from the samples whose water extract did not contain these saponins. This was attributed to inhibition of endogenous esterase which hydrolyzes the ester linkage at position 28. When saponins were extracted with reagent grade 1-butanol, in addition to the decrease of the amounts of highly polar saponins, oxidative decarboxylation of 3 and 10 occurred resulting in formation of achyranthoside E (6) and spinacoside D (12), respectively. As these changes were not observed with HPLC grade 1-butanol, which contain not more than 5 ppm of peroxide impurities, the change was attributable to the peroxide impurities contained in the reagent grade 1-butanol.

Original languageEnglish
JournalJournal of Natural Medicines
DOIs
Publication statusAccepted/In press - 2019 Jan 1

Fingerprint

Achyranthes
Saponins
1-Butanol
Water
Peroxides
Sugars
Heating
Precipitates
Impurities
Decarboxylation
Esterases

Keywords

  • Achyranthes bidentata
  • Achyranthes root
  • Achyranthoside
  • Betavulgaroside
  • LC–MS
  • Saponin composition

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

LC–MS analysis of saponins of Achyranthes root in the Japanese market. / Kuwada, Kohei; Kawase, Satoshi; Nakata, Karin; Shinya, Nodoka; Narukawa, Yuuji; Fuchino, Hiroyuki; Kawahara, Nobuo; Kiuchi, Fumiyuki.

In: Journal of Natural Medicines, 01.01.2019.

Research output: Contribution to journalArticle

Kuwada, Kohei ; Kawase, Satoshi ; Nakata, Karin ; Shinya, Nodoka ; Narukawa, Yuuji ; Fuchino, Hiroyuki ; Kawahara, Nobuo ; Kiuchi, Fumiyuki. / LC–MS analysis of saponins of Achyranthes root in the Japanese market. In: Journal of Natural Medicines. 2019.
@article{21c62d9f03ee47ecace218bb27cad233,
title = "LC–MS analysis of saponins of Achyranthes root in the Japanese market",
abstract = "LC–MS analyses of saponin fractions of Achyranthes roots in the Japanese market revealed that there were three patterns for the saponin fraction of their water extracts, i.e., the saponins with a sugar moiety at position 28 [achyranthosides B (3), C (4) and D (5)] were the major constituents, the saponins without sugar moiety at position 28 [betavulgarosides II (10) and IV (11)] were the major constituents, and mixtures of these saponins. In a decoction prepared from the sample which contained 10 and 11 as the major saponins, their amounts were largely decreased compared with those of the water extract. As large amounts of these saponins were found in the precipitates formed by heating of the water extract, these saponins were seemed to precipitate out under heating. When hot water was used for the extraction, 3, 4 and 5 were detected even from the samples whose water extract did not contain these saponins. This was attributed to inhibition of endogenous esterase which hydrolyzes the ester linkage at position 28. When saponins were extracted with reagent grade 1-butanol, in addition to the decrease of the amounts of highly polar saponins, oxidative decarboxylation of 3 and 10 occurred resulting in formation of achyranthoside E (6) and spinacoside D (12), respectively. As these changes were not observed with HPLC grade 1-butanol, which contain not more than 5 ppm of peroxide impurities, the change was attributable to the peroxide impurities contained in the reagent grade 1-butanol.",
keywords = "Achyranthes bidentata, Achyranthes root, Achyranthoside, Betavulgaroside, LC–MS, Saponin composition",
author = "Kohei Kuwada and Satoshi Kawase and Karin Nakata and Nodoka Shinya and Yuuji Narukawa and Hiroyuki Fuchino and Nobuo Kawahara and Fumiyuki Kiuchi",
year = "2019",
month = "1",
day = "1",
doi = "10.1007/s11418-019-01355-y",
language = "English",
journal = "Journal of Natural Medicines",
issn = "1861-0293",
publisher = "Springer Japan",

}

TY - JOUR

T1 - LC–MS analysis of saponins of Achyranthes root in the Japanese market

AU - Kuwada, Kohei

AU - Kawase, Satoshi

AU - Nakata, Karin

AU - Shinya, Nodoka

AU - Narukawa, Yuuji

AU - Fuchino, Hiroyuki

AU - Kawahara, Nobuo

AU - Kiuchi, Fumiyuki

PY - 2019/1/1

Y1 - 2019/1/1

N2 - LC–MS analyses of saponin fractions of Achyranthes roots in the Japanese market revealed that there were three patterns for the saponin fraction of their water extracts, i.e., the saponins with a sugar moiety at position 28 [achyranthosides B (3), C (4) and D (5)] were the major constituents, the saponins without sugar moiety at position 28 [betavulgarosides II (10) and IV (11)] were the major constituents, and mixtures of these saponins. In a decoction prepared from the sample which contained 10 and 11 as the major saponins, their amounts were largely decreased compared with those of the water extract. As large amounts of these saponins were found in the precipitates formed by heating of the water extract, these saponins were seemed to precipitate out under heating. When hot water was used for the extraction, 3, 4 and 5 were detected even from the samples whose water extract did not contain these saponins. This was attributed to inhibition of endogenous esterase which hydrolyzes the ester linkage at position 28. When saponins were extracted with reagent grade 1-butanol, in addition to the decrease of the amounts of highly polar saponins, oxidative decarboxylation of 3 and 10 occurred resulting in formation of achyranthoside E (6) and spinacoside D (12), respectively. As these changes were not observed with HPLC grade 1-butanol, which contain not more than 5 ppm of peroxide impurities, the change was attributable to the peroxide impurities contained in the reagent grade 1-butanol.

AB - LC–MS analyses of saponin fractions of Achyranthes roots in the Japanese market revealed that there were three patterns for the saponin fraction of their water extracts, i.e., the saponins with a sugar moiety at position 28 [achyranthosides B (3), C (4) and D (5)] were the major constituents, the saponins without sugar moiety at position 28 [betavulgarosides II (10) and IV (11)] were the major constituents, and mixtures of these saponins. In a decoction prepared from the sample which contained 10 and 11 as the major saponins, their amounts were largely decreased compared with those of the water extract. As large amounts of these saponins were found in the precipitates formed by heating of the water extract, these saponins were seemed to precipitate out under heating. When hot water was used for the extraction, 3, 4 and 5 were detected even from the samples whose water extract did not contain these saponins. This was attributed to inhibition of endogenous esterase which hydrolyzes the ester linkage at position 28. When saponins were extracted with reagent grade 1-butanol, in addition to the decrease of the amounts of highly polar saponins, oxidative decarboxylation of 3 and 10 occurred resulting in formation of achyranthoside E (6) and spinacoside D (12), respectively. As these changes were not observed with HPLC grade 1-butanol, which contain not more than 5 ppm of peroxide impurities, the change was attributable to the peroxide impurities contained in the reagent grade 1-butanol.

KW - Achyranthes bidentata

KW - Achyranthes root

KW - Achyranthoside

KW - Betavulgaroside

KW - LC–MS

KW - Saponin composition

UR - http://www.scopus.com/inward/record.url?scp=85070897665&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85070897665&partnerID=8YFLogxK

U2 - 10.1007/s11418-019-01355-y

DO - 10.1007/s11418-019-01355-y

M3 - Article

AN - SCOPUS:85070897665

JO - Journal of Natural Medicines

JF - Journal of Natural Medicines

SN - 1861-0293

ER -