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

Bagri, Priyanka; Chester, Karishma; Khan, Washim; Ahmad, Sayeed

doi:10.1039/c7ra02955a

Cited by 13 publications

(10 citation statements)

References 107 publications

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“…α-Glucosidase inhibition in the small intestine is a simple and effective way by which hyperglycemia treatment can manage type 2 DM . It was reported that different sources of phenolics play a role in inhibiting α-glucosidase; for instance, examples of such phenolics include anthocyanidin derivative from blueberry, blackcurrant, and blue honeysuckle fruits, catechins derivative derived from green tea, and rosmarinic acid derived from Perilla frutescens. , Hence, it was of interest to explore whether the phenolics in the cultivated P.…”

Section: Resultsmentioning

confidence: 99%

Cultivated Fruit Body of Phellinus baumii: A Potentially Sustainable Antidiabetic Resource

Yang

Ying

et al. 2020

ACS Omega

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Previous studies have been reported that the fruit body of wild Phellinus baumii alleviates diabetes, and antioxidants are beneficial to diabetes by protecting the β-cell from damage due to oxidative stress. Large-scale cultivation of P. baumii fruit body has been successful in the past decade. This paper aimed to investigate whether the fruit body of the cultivated P. baumii has the same analogical effects as the wild. The cultivated P. baumii fruit body was extracted by 80% of ethanol extracts, and different fractions were obtained with the successive use of petroleum ether, ethyl acetate (EtOAc), n-butanol (n-BuOH), and water, which yielded 15.98 ± 1.56, 1.74 ± 0.34, 3.31 ± 0.41, 4.12 ± 0.37, and 1.38 ± 0.26% extract recovery, respectively. Results show that the EtOAc fraction exhibits the highest inhibitory effect on α-glucosidase activity (IC 50 = 49.05 ± 3.14 μg mL −1 ), which is an order of magnitude higher than the positive control (acarbose, IC 50 = 645.73 ± 7.86 μg mL −1 ). It was mainly composed of phenolic compounds with a purity of 79.45% and characterized by liquid chromatography-mass spectrometry as osmudacetone, hispidin, davallialactone, 2,5-bis(4,7dihydroxy-8-methyl-2-oxo-2H-chromen-3-yl)cyclohexa-2,5-diene-1,4-dione, hypholomin B, and inoscavin A. Furthermore, the EtOAc fraction increased the glucose consumption of insulin-resistant HepG2 cells at a concentration range of 25−100 μg mL −1 . The EtOAc fraction also demonstrated antioxidant activities by scavenging 1,1-diphenyl-2-picrylhydrazyl, 2,2′-azino-bis(3ethylbenzothiazoline-6-sulfonic acid)diammonium salt, and hydroxyl radicals. In conclusion, the EtOAc fraction of the cultivated P. baumii fruit body exerted effective antidiabetic effects, possibly due to the high content of selective phenolic compounds. Hence, the cultivated fruit body of P. baumii can be a sustainable resource for treating diabetes, and our work also shed some light on its future utilization.

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Section: Resultsmentioning

confidence: 99%

Cultivated Fruit Body of Phellinus baumii: A Potentially Sustainable Antidiabetic Resource

Yang

Ying

et al. 2020

ACS Omega

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“…To date, several research groups have performed synthetic and structure-activity relationship (SAR) studies of salacinol (1) and related analogues regarding α-glucosidase inhibitory activity [39][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55]. We are also performing subsequent studies on the total syntheses of these sulfonium constituents (1-8) and their highly active analogues, as well as more detailed SAR studies [38,[56][57][58][59][60][61][62]; those data will be summarized separately.…”

Section: Thiosugar Sulfoniums (1-6) As a Novel Class Of α-Glucosidase Inhibitorsmentioning

confidence: 99%

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

et al. 2021

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During our studies characterizing functional substances from food resources for the prevention and treatment of lifestyle-related diseases, we isolated the active constituents, salacinol (1) and neokotalanol (4), and related thiosugar sulfoniums, from the roots and stems of the genus Salacia plants [Celastraceae (Hippocrateaceae)] such as Salacia reticulata Wight, S. oblonga Wall., and S. chinensis L., and observed their antidiabetic effects. These plant materials have been used traditionally in Ayurvedic medicine as a specific remedy at the early stage of diabetes, and have been extensively consumed in Japan, the United States, and other countries as a food supplement for the prevention of obesity and diabetes. Here, we review our studies on the antidiabetic effects of plants from the genus Salacia, from basic chemical and pharmacological research to their application and development as new functional food ingredients. Graphic abstract

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“…25−32 biological evaluation of 4−11 indicated an equal α-glucosidase inhibitory potency compared with clinically used α-glucosidase inhibitors. 33 In silico docking clearly demonstrated a strong electrostatic interaction between sulfonium cation and specific carboxylate ion located at a certain catalytic pocket of αglucosidase. 34 Experiment using an in situ rat ligated intestinal loop model revealed that these sulfonium salts are hardly absorbed from the rat intestine.…”

Section: ■ Introductionmentioning

confidence: 98%

“…Ever since the late 1990s, a group of sulfonium salts 4 – 11 (Figure ) have been isolated from genus Salacia , a herbal medicine traditionally used for the treatment of T2DM in South Asian countries. − 4 , 5 , 6 , and 7 present a unique zwitterionic inner salt structure while 8 , 9 , 10 , and 11 are identified as their de- O -sulfonated analogues, respectively. A biological evaluation of 4 – 11 indicated an equal α-glucosidase inhibitory potency compared with clinically used α-glucosidase inhibitors . In silico docking clearly demonstrated a strong electrostatic interaction between sulfonium cation and specific carboxylate ion located at a certain catalytic pocket of α-glucosidase .…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Sulfonium Derivatives: A Novel Class of α-Glucosidase Inhibitors with Potent In Vivo Antihyperglycemic Activities

Chen

Tao

et al. 2023

J. Med. Chem.

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We report the first attempt of double-spot structural modification on a side-chain moiety of sulfonium-type αglucosidase inhibitors isolated from genus Salacia. A series of sulfonium salts with benzylidene acetal linkage at the C3′ and C5′ positions were designed and synthesized. In vitro enzyme inhibition evaluation showed that compounds with a strong electron-withdrawing group attached at the ortho position on the phenyl ring present stronger inhibitory activities. Notably, the most potent inhibitor 21b (1.0 mpk) can exhibit excellent hypoglycemic effects in mice, which can still compete with those of acarbose (20.0 mpk). Molecular docking of 21b demonstrated that besides conventional interacting patterns, the newly introduced benzylidene acetal moiety plays an important role in anchoring the whole molecule in a concave pocket of the enzyme. The successful identification of 21b as a lead compound for new drug discovery may provide a means for structure modification and diversification of the distinguished sulfonium-type α-glucosidase inhibitors.

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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

Abstract: A review of the selective inhibitory activities of sulfonium compounds ofSalaciaagainst intestinal α-glucosidases, structural features important for effective inhibition and the toggling approach for controlling starch digestion and glucose release.

Cited by 13 publications

References 107 publications

Cultivated Fruit Body of Phellinus baumii: A Potentially Sustainable Antidiabetic Resource

Cultivated Fruit Body of Phellinus baumii: A Potentially Sustainable Antidiabetic Resource

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

Design and Synthesis of Sulfonium Derivatives: A Novel Class of α-Glucosidase Inhibitors with Potent In Vivo Antihyperglycemic Activities

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