Sulfates

Publication Title: 
Chemical & Pharmaceutical Bulletin

A potent natural alpha-glucosidase inhibitor called kotalanol has been isolated from an antidiabetic traditional Ayurvedic medicine, the roots and stems of Salacia reticulata Wight, through bioassay-guided separation. The structure of kotalanol was elucidated on the basis of chemical and physicochemical evidence to be the inner salt comprised of 1-deoxyheptosyl-3-sulfate anion and 1-deoxy-4-thio-D-arabinofuranosyl sulfonium cation. Kotalanol was found to show more potent inhibitory activity against sucrase than salacinol and acarbose.

Author(s): 
Yoshikawa, M.
Murakami, T.
Yashiro, K.
Matsuda, H.
Publication Title: 
Bioorganic & Medicinal Chemistry

A most potent alpha-glucosidase inhibitor named salacinol has been isolated from an antidiabetic Ayurvedic traditional medicine, Salacia reticulata WIGHT, through bioassay-guided separation.

Author(s): 
Yoshikawa, Masayuki
Morikawa, Toshio
Matsuda, Hisashi
Tanabe, Genzoh
Muraoka, Osamu
Publication Title: 
Carbohydrate Research

Natural products with interesting biological properties and structural diversity have often served as valuable lead drug candidates for the treatment of human diseases. Salacinol, a naturally occurring alpha-glucosidase inhibitor, was shown to be one of the active principles of the aqueous extract of a medicinal plant that has been prescribed traditionally as an Ayurvedic treatment for type II diabetes. Salacinol contains an intriguing zwitterionic sulfonium-sulfate structure that comprises a 1,4-anhydro-4-thio-D-arabinitol core and a polyhydroxylated acyclic chain.

Author(s): 
Mohan, Sankar
Pinto, B. Mario
Publication Title: 
Bioorganic & Medicinal Chemistry Letters

Facile synthesis of de-O-sulfated salacinols (3) was developed by employing the coupling reaction of an epoxide, 1,2-anhydro-3,4-di-O-benzyl-D-erythritol (9) with 2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol (10) as the key reaction. The reported structure of a potent alpha-glucosidase inhibitor named neosalacinol (8), isolated recently from Ayurvedic medicine Salacia oblonga, was proved incorrect, and revised to be de-O-sulfated salacinol formate (3c) by comparison of the spectroscopic properties with those of the authentic specimen synthesized.

Author(s): 
Tanabe, Genzoh
Xie, Weijia
Ogawa, Ai
Cao, Changnian
Minematsu, Toshie
Yoshikawa, Masayuki
Muraoka, Osamu
Publication Title: 
Biochemistry

An approach to controlling blood glucose levels in individuals with type 2 diabetes is to target alpha-amylases and intestinal glucosidases using alpha-glucosidase inhibitors acarbose and miglitol. One of the intestinal glucosidases targeted is the N-terminal catalytic domain of maltase-glucoamylase (ntMGAM), one of the four intestinal glycoside hydrolase 31 enzyme activities responsible for the hydrolysis of terminal starch products into glucose.

Author(s): 
Sim, Lyann
Jayakanthan, Kumarasamy
Mohan, Sankar
Nasi, Ravindranath
Johnston, Blair D.
Pinto, B. Mario
Rose, David R.
Publication Title: 
Journal of Pharmaceutical and Biomedical Analysis

A practical HPLC-MS method for the quantitative determination of salacinol (1) and kotalanol (2), potent alpha-glucosidase inhibitors from Salacia species (Hippocrateaceae) as a specific remedy for diabetes in Ayurvedic system, was developed. The optimum conditions of separation and detection of these two constituents were achieved on a Asahipak NH2P-50 column (5 mcirom particle size, 2.0 mm i.d. x 150 mm) with a CH(3)CN-H(2)O mobile phase, associated with MS using electrospray ionization source.

Author(s): 
Muraoka, Osamu
Morikawa, Toshio
Miyake, Sohachiro
Akaki, Junji
Ninomiya, Kiyofumi
Yoshikawa, Masayuki
Publication Title: 
Natural Product Reports

This Highlight describes the detailed approach used to determine the absolute stereochemistry of the stereogenic centers in the acyclic side chain of kotalanol, a naturally occurring glucosidase inhibitor isolated from the plant Salacia reticulata. The plant extract itself is used in Ayurvedic medicine for the treatment of Type 2 diabetes.

Author(s): 
Mohan, Sankar
Pinto, B. Mario
Publication Title: 
Journal of Natural Medicines

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.

Author(s): 
Muraoka, Osamu
Morikawa, Toshio
Miyake, Sohachiro
Akaki, Junji
Ninomiya, Kiyofumi
Pongpiriyadacha, Yutana
Yoshikawa, Masayuki
Publication Title: 
Bioorganic & Medicinal Chemistry

Synthesis and evaluation of four diastereomers (9a, 9b, 9c and 9d) of kotalanol, a potent α-glucosidase inhibitor isolated from an Ayurvedic medicinal plant Salacia species, are described. Stereo-inversion at C-3' and C-4' of kotalanol (2) caused significant decrease of the inhibitory activities against maltase and sucrase, whereas inhibitory activity against isomaltase sustained, thus resulted in exerting selectivity against isomaltase.

Author(s): 
Xie, Weijia
Tanabe, Genzoh
Matsuoka, Kanjyun
Amer, Mumen F. A.
Minematsu, Toshie
Wu, Xiaoming
Yoshikawa, Masayuki
Muraoka, Osamu
Publication Title: 
Bioorganic & Medicinal Chemistry

Inhibition of intestinal α-glucosidases and pancreatic α-amylases is an approach to controlling blood glucose and serum insulin levels in individuals with Type II diabetes. The two human intestinal glucosidases are maltase-glucoamylase and sucrase-isomaltase. Each incorporates two family 31 glycoside hydrolases responsible for the final step of starch hydrolysis.

Author(s): 
Jones, Kyra
Sim, Lyann
Mohan, Sankar
Kumarasamy, Jayakanthan
Liu, Hui
Avery, Stephen
Naim, Hassan Y.
Quezada-Calvillo, Roberto
Nichols, Buford L.
Pinto, B. Mario
Rose, David R.

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