Total synthesis of neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata

Wei-Jia Xie; Genzoh Tanabe; Nozomi Tsutsui; Xiao-Ming Wu; Osamu Muraoka

doi:10.1016/S1875-5364(13)60079-5

Total synthesis of neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata

Chin J Nat Med. 2013 Nov;11(6):676-83. doi: 10.1016/S1875-5364(13)60079-5.

Authors

Wei-Jia Xie¹, Genzoh Tanabe², Nozomi Tsutsui², Xiao-Ming Wu¹, Osamu Muraoka³

Affiliations

¹ Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
² School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
³ School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan. Electronic address: muraoka@phar.kindai.ac.jp.

PMID: 24345510
DOI: 10.1016/S1875-5364(13)60079-5

Abstract

Neokotalanol, a potent α-glucosidase inhibitor isolated from Salacia reticulata, was synthesized through a key coupling reaction between a perbenzylated thiosugar and an appropriately protected perseitol triflate derived from D-mannose. This key step was found to be quite temperature dependent, and a simultaneous cyclization of the triflate leading to a characteristic 2,4,7-trioxabicyclo[4.2.1]nonane system was detected.

Keywords: Neokotalanol; Salacia reticulata; Total synthesis; α-glucosidase inhibitor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Glycoside Hydrolase Inhibitors*
Plant Extracts / chemical synthesis*
Plant Extracts / chemistry
Salacia / chemistry*

Substances

Enzyme Inhibitors
Glycoside Hydrolase Inhibitors
Plant Extracts