Literature DB >> 20981499

Quantitative analysis of neosalacinol and neokotalanol, another two potent α-glucosidase inhibitors from Salacia species, by LC-MS with ion pair chromatography.

Osamu Muraoka1, Toshio Morikawa, Sohachiro Miyake, Junji Akaki, Kiyofumi Ninomiya, Yutana Pongpiriyadacha, Masayuki Yoshikawa.   

Abstract

A quantitative analytical method for the highly polar sulfonium pseudo-sugar constituents neosalacinol (3) and neokotalanol (4), another two potent α-glucosidase inhibitors isolated from Ayurvedic traditional medicine Salacia species, was developed by employing an ion pair reagent upon chromatographic separation. The optimum conditions for separation and detection of these two constituents were achieved on an ODS column (3-µm particle size, 2.1-mm i.d. × 100 mm) with 5 mM undecafluorohexanoic acid-MeOH (99:1, v/v) as the mobile phase and using MS equipped with an electrospray ionization source. More than ten samples of Salacia from different origins were analyzed, and the results indicated that the assay was reproducible and precise and could be readily utilized for evaluation of α-glucosidase inhibitory activity of Salacia species. By combining this assay with the quantitative analytical method previously developed for salacinol (1) and kotalanol (2), a more precise and strict evaluation of α-glucosidase inhibitory activities of extracts from Salacia species (R = 0.959 for maltase and 0.795 for sucrase) was achieved.

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Year:  2010        PMID: 20981499     DOI: 10.1007/s11418-010-0474-x

Source DB:  PubMed          Journal:  J Nat Med        ISSN: 1340-3443            Impact factor:   2.343


  15 in total

1.  Alpha-glucosidase inhibitor from Kothala-himbutu (Salacia reticulata WIGHT).

Authors:  Sei Ozaki; Hiromi Oe; Shinichi Kitamura
Journal:  J Nat Prod       Date:  2008-06-12       Impact factor: 4.050

2.  Synthesis and biological evaluation of heteroanalogues of kotalanol and de-O-sulfonated kotalanol.

Authors:  Sankar Mohan; Kumarasamy Jayakanthan; Ravindranath Nasi; Douglas A Kuntz; David R Rose; B Mario Pinto
Journal:  Org Lett       Date:  2010-03-05       Impact factor: 6.005

3.  Absolute stereostructure of potent alpha-glucosidase inhibitor, Salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata.

Authors:  Masayuki Yoshikawa; Toshio Morikawa; Hisashi Matsuda; Genzoh Tanabe; Osamu Muraoka
Journal:  Bioorg Med Chem       Date:  2002-05       Impact factor: 3.641

4.  Potent glucosidase inhibitors: de-O-sulfonated ponkoranol and its stereoisomer.

Authors:  Razieh Eskandari; Douglas A Kuntz; David R Rose; B Mario Pinto
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

5.  [Biological activities of Salacia chinensis originating in Thailand: the quality evaluation guided by alpha-glucosidase inhibitory activity].

Authors:  Masayuki Yoshikawa; Yutana Pongpiriyadacha; Akinobu Kishi; Tadashi Kageura; Tao Wang; Toshio Morikawa; Hisashi Matsuda
Journal:  Yakugaku Zasshi       Date:  2003-10       Impact factor: 0.302

Review 6.  Zwitterionic glycosidase inhibitors: salacinol and related analogues.

Authors:  Sankar Mohan; B Mario Pinto
Journal:  Carbohydr Res       Date:  2007-05-18       Impact factor: 2.104

7.  Structure proof and synthesis of kotalanol and de-O-sulfonated kotalanol, glycosidase inhibitors isolated from an herbal remedy for the treatment of type-2 diabetes.

Authors:  Kumarasamy Jayakanthan; Sankar Mohan; B Mario Pinto
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419

8.  Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the alpha-glucosidase inhibitory activity.

Authors:  Genzoh Tanabe; Kazuya Yoshikai; Takanori Hatanaka; Mizuho Yamamoto; Ying Shao; Toshie Minematsu; Osamu Muraoka; Tao Wang; Hisashi Matsuda; Masayuki Yoshikawa
Journal:  Bioorg Med Chem       Date:  2006-10-13       Impact factor: 3.641

9.  Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.

Authors:  Yasuhiro Minami; Chinami Kuriyama; Kyoko Ikeda; Atsushi Kato; Kenji Takebayashi; Isao Adachi; George W J Fleet; Aikkarach Kettawan; Tadashi Okamoto; Naoki Asano
Journal:  Bioorg Med Chem       Date:  2008-01-26       Impact factor: 3.641

10.  Facile synthesis of de-O-sulfated salacinols: revision of the structure of neosalacinol, a potent alpha-glucosidase inhibitor.

Authors:  Genzoh Tanabe; Weijia Xie; Ai Ogawa; Changnian Cao; Toshie Minematsu; Masayuki Yoshikawa; Osamu Muraoka
Journal:  Bioorg Med Chem Lett       Date:  2009-03-01       Impact factor: 2.823

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  12 in total

1.  Anti-hyperlipidemic constituents from the bark of Shorea roxburghii.

Authors:  Toshio Morikawa; Saowanee Chaipech; Hisashi Matsuda; Makoto Hamao; Yohei Umeda; Hiroki Sato; Haruka Tamura; Kiyofumi Ninomiya; Masayuki Yoshikawa; Yutana Pongpiriyadacha; Takao Hayakawa; Osamu Muraoka
Journal:  J Nat Med       Date:  2012-01-20       Impact factor: 2.343

2.  Salacia chinensis stem extract and its thiosugar sulfonium constituent, neokotalanol, improves HbA1c levels in ob/ob mice.

Authors:  Masakazu Kobayashi; Junji Akaki; Yasuyo Yamaguchi; Hiroo Yamasaki; Kiyofumi Ninomiya; Yutana Pongpiriyadacha; Masayuki Yoshikawa; Osamu Muraoka; Toshio Morikawa
Journal:  J Nat Med       Date:  2019-04-26       Impact factor: 2.343

3.  Two new aromatic glycosides, elengiosides A and B, from the flowers of Mimusops elengi.

Authors:  Toshio Morikawa; Yoshiaki Manse; Mika Koda; Saowanee Chaipech; Yutana Pongpiriyadacha; Osamu Muraoka; Kiyofumi Ninomiya
Journal:  J Nat Med       Date:  2017-12-13       Impact factor: 2.343

4.  Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice.

Authors:  Toshio Morikawa; Kiyofumi Ninomiya; Mio Imamura; Junji Akaki; Shota Fujikura; Yingni Pan; Dan Yuan; Masayuki Yoshikawa; Xiaoguang Jia; Zheng Li; Osamu Muraoka
Journal:  J Nat Med       Date:  2014-04-19       Impact factor: 2.343

Review 5.  A review of antidiabetic active thiosugar sulfoniums, salacinol and neokotalanol, from plants of the genus Salacia.

Authors:  Toshio Morikawa; Kiyofumi Ninomiya; Genzoh Tanabe; Hisashi Matsuda; Masayuki Yoshikawa; Osamu Muraoka
Journal:  J Nat Med       Date:  2021-04-26       Impact factor: 2.343

6.  Salacinol and related analogs: new leads for type 2 diabetes therapeutic candidates from the Thai traditional natural medicine Salacia chinensis.

Authors:  Toshio Morikawa; Junji Akaki; Kiyofumi Ninomiya; Eri Kinouchi; Genzoh Tanabe; Yutana Pongpiriyadacha; Masayuki Yoshikawa; Osamu Muraoka
Journal:  Nutrients       Date:  2015-02-27       Impact factor: 5.717

7.  Salacia Extract Improves Postprandial Glucose and Insulin Response: A Randomized Double-Blind, Placebo Controlled, Crossover Study in Healthy Volunteers.

Authors:  Shankaranarayanan Jeykodi; Jayant Deshpande; Vijaya Juturu
Journal:  J Diabetes Res       Date:  2016-10-10       Impact factor: 4.011

8.  Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium.

Authors:  Toshio Morikawa; Kiyofumi Ninomiya; Junji Akaki; Namiko Kakihara; Hiroyuki Kuramoto; Yurie Matsumoto; Takao Hayakawa; Osamu Muraoka; Li-Bo Wang; Li-Jun Wu; Seikou Nakamura; Masayuki Yoshikawa; Hisashi Matsuda
Journal:  J Nat Med       Date:  2015-04-29       Impact factor: 2.343

9.  Improvement in Human Immune Function with Changes in Intestinal Microbiota by Salacia reticulata Extract Ingestion: A Randomized Placebo-Controlled Trial.

Authors:  Yuriko Oda; Fumitaka Ueda; Masanori Utsuyama; Asuka Kamei; Chihaya Kakinuma; Keiko Abe; Katsuiku Hirokawa
Journal:  PLoS One       Date:  2015-12-02       Impact factor: 3.240

10.  A subchronic oral toxicity study of Salacia reticulata extract powder in rats.

Authors:  Yuriko Oda; Atsuko Yuasa; Fumitaka Ueda; Chihaya Kakinuma
Journal:  Toxicol Rep       Date:  2015-07-26
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