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Collect. Czech. Chem. Commun. 2009, 74, 1117-1136
https://doi.org/10.1135/cccc2009024
Published online 2009-07-17 23:58:00

Sulfonium-ion glycosidase inhibitors isolated from Salacia species used in traditional medicine, and related compounds

Sankar Mohan and B. Mario Pinto*

Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada, V5A 1S6

Crossref Cited-by Linking

  • Morikawa Toshio, Ninomiya Kiyofumi, Tanabe Genzoh, Matsuda Hisashi, Yoshikawa Masayuki, Muraoka Osamu: A review of antidiabetic active thiosugar sulfoniums, salacinol and neokotalanol, from plants of the genus Salacia. J Nat Med 2021, 75, 449. <https://doi.org/10.1007/s11418-021-01522-0>
  • Merieux Guillaume, Buchotte Marie, Muzard Murielle, Plantier‐Royon Richard: Synthesis of 2‐Substituted Thioglycals from Carbohydrate‐Derived Ketene Dithioacetals. Eur J Org Chem 2020, 2020, 3063. <https://doi.org/10.1002/ejoc.202000312>
  • Mangiavacchi Francesca, Coelho Dias Italo Franco, Di Lorenzo Irene, Grzes Pawel, Palomba Martina, Rosati Ornelio, Bagnoli Luana, Marini Francesca, Santi Claudio, Lenardao Eder Joao, Sancineto Luca: Sweet Selenium: Synthesis and Properties of Selenium-Containing Sugars and Derivatives. Pharmaceuticals 2020, 13, 211. <https://doi.org/10.3390/ph13090211>
  • Lu Lu, Li Xiaoya, Yang Yao, Xie Weijia: Recent Progress in the Construction of Natural De‐O‐Sulfonated Sulfonium Sugars with Antidiabetic Activities. Chemistry A European J 2019, 25, 13458. <https://doi.org/10.1002/chem.201902562>
  • Bagri Priyanka, Chester Karishma, Khan Washim, Ahmad Sayeed: Aspects of extraction and biological evaluation of naturally occurring sugar-mimicking sulfonium-ion and their synthetic analogues as potent α-glucosidase inhibitors from Salacia: a review. RSC Adv. 2017, 7, 28152. <https://doi.org/10.1039/C7RA02955A>
  • Mohan Sankar, Eskandari Razieh, Pinto B. Mario: Naturally Occurring Sulfonium-Ion Glucosidase Inhibitors and Their Derivatives: A Promising Class of Potential Antidiabetic Agents. Acc. Chem. Res. 2014, 47, 211. <https://doi.org/10.1021/ar400132g>
  • Tanabe Genzoh, Matsuoka Kanjyun, Yoshinaga Masahiro, Xie Weijia, Tsutsui Nozomi, A. Amer Mumen F., Nakamura Shinya, Nakanishi Isao, Wu Xiaoming, Yoshikawa Masayuki, Muraoka Osamu: Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2. Bioorganic & Medicinal Chemistry 2012, 20, 6321. <https://doi.org/10.1016/j.bmc.2012.09.006>
  • Lee Byung-Hoo, Eskandari Razieh, Jones Kyra, Reddy Kongara Ravinder, Quezada-Calvillo Roberto, Nichols Buford L., Rose David R., Hamaker Bruce R., Pinto B.Mario: Modulation of Starch Digestion for Slow Glucose Release through “Toggling” of Activities of Mucosal α-Glucosidases. Journal of Biological Chemistry 2012, 287, 31929. <https://doi.org/10.1074/jbc.M112.351858>
  • Eskandari Razieh, Jones Kyra, Ravinder Reddy Kongara, Jayakanthan Kumarasamy, Chaudet Marcia, Rose David R., Pinto B. Mario: Probing the Intestinal α‐Glucosidase Enzyme Specificities of Starch‐Digesting Maltase‐Glucoamylase and Sucrase‐Isomaltase: Synthesis and Inhibitory Properties of 3′‐ and 5′‐Maltose‐Extended De‐O‐sulfonated Ponkoranol. Chemistry A European J 2011, 17, 14817. <https://doi.org/10.1002/chem.201102109>
  • Muraoka Osamu, Morikawa Toshio, Miyake Sohachiro, Akaki Junji, Ninomiya Kiyofumi, Pongpiriyadacha Yutana, Yoshikawa Masayuki: Quantitative analysis of neosalacinol and neokotalanol, another two potent α-glucosidase inhibitors from Salacia species, by LC-MS with ion pair chromatography. J Nat Med 2011, 65, 142. <https://doi.org/10.1007/s11418-010-0474-x>
  • Eskandari Razieh, Jones Kyra, Rose David R., Pinto B. Mario: The effect of heteroatom substitution of sulfur for selenium in glucosidase inhibitors on intestinal α-glucosidase activities. Chemical Communication 2011, 47, 9134. <https://doi.org/10.1039/c1cc13052h>
  • Mohan Sankar, Pinto B. Mario: ChemInform Abstract: Sulfonium‐Ion Glycosidase Inhibitors Isolated from Salacia Species Used in Traditional Medicine, and Related Compounds. ChemInform 2010, 41. <https://doi.org/10.1002/chin.201002249>
  • Eskandari Razieh, Jayakanthan Kumarasamy, Kuntz Douglas A., Rose David R., Mario Pinto B.: Synthesis of a biologically active isomer of kotalanol, a naturally occurring glucosidase inhibitor. biorg med chem 2010, 18, 2829. <https://doi.org/10.1016/j.bmc.2010.03.027>
  • Zandberg Wesley F., Mohan Sankar, Kumarasamy Jayakanthan, Pinto B. Mario: Capillary Zone Electrophoresis Method for the Separation of Glucosidase Inhibitors in Extracts of Salacia reticulata, a Plant Used in Ayurvedic Treatments of Type-2 Diabetes. Anal. Chem. 2010, 82, 5323. <https://doi.org/10.1021/ac100843y>
  • Mohan Sankar, Jayakanthan Kumarasamy, Nasi Ravindranath, Kuntz Douglas A., Rose David R., Pinto B. Mario: Synthesis and Biological Evaluation of Heteroanalogues of Kotalanol and De-O-Sulfonated Kotalanol. Org. Lett. 2010, 12, 1088. <https://doi.org/10.1021/ol100080m>
  • Eskandari Razieh, Kuntz Douglas A., Rose David R., Pinto B. Mario: Potent Glucosidase Inhibitors: De-O-sulfonated Ponkoranol and Its Stereoisomer. Org. Lett. 2010, 12, 1632. <https://doi.org/10.1021/ol1004005>
  • Mohan Sankar, Pinto B. Mario: Towards the elusive structure of kotalanol, a naturally occurring glucosidase inhibitor. Nat. Prod. Rep. 2010, 27, 481. <https://doi.org/10.1039/b925950c>
  • Sim Lyann, Willemsma Carly, Mohan Sankar, Naim Hassan Y., Pinto B. Mario, Rose David R.: Structural Basis for Substrate Selectivity in Human Maltase-Glucoamylase and Sucrase-Isomaltase N-terminal Domains. Journal of Biological Chemistry 2010, 285, 17763. <https://doi.org/10.1074/jbc.M109.078980>