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Published in: Journal of Natural Medicines 3/2021

Open Access 01-06-2021 | Miglitol | Review

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

Published in: Journal of Natural Medicines | Issue 3/2021

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Abstract

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.

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Literature
2.
go back to reference Matsuda H, Yoshikawa M, Morikawa T, Tanabe G, Muraoka O (2005) Antidiabetogenic constituents from Salacia species. J Trad Med 22(Suppl. 1):145–153 Matsuda H, Yoshikawa M, Morikawa T, Tanabe G, Muraoka O (2005) Antidiabetogenic constituents from Salacia species. J Trad Med 22(Suppl. 1):145–153
4.
5.
go back to reference Musini A, Giri A (2015) Salacia oblonga wall: an endangered plant of immenses pharmaceutical value. J Chem Pharm Res 7:1125–1129 Musini A, Giri A (2015) Salacia oblonga wall: an endangered plant of immenses pharmaceutical value. J Chem Pharm Res 7:1125–1129
6.
go back to reference Kushwaha PS, Singh AK, Keshari AK, Maity S, Saha S (2016) An updated review on the phytochemistry, pharmacology, and clinical trials of Salacia oblonga. Pharmacogn Rev 10:109–114PubMedPubMedCentralCrossRef Kushwaha PS, Singh AK, Keshari AK, Maity S, Saha S (2016) An updated review on the phytochemistry, pharmacology, and clinical trials of Salacia oblonga. Pharmacogn Rev 10:109–114PubMedPubMedCentralCrossRef
7.
go back to reference Matsuda H, Morikawa T, Yoshikawa M (2002) Antidiabetogenic constituents from several natural medicines. Pure Appl Chem 74:1301–1308CrossRef Matsuda H, Morikawa T, Yoshikawa M (2002) Antidiabetogenic constituents from several natural medicines. Pure Appl Chem 74:1301–1308CrossRef
8.
go back to reference Chandrasena JPC (1935) The chemistry and pharmacology of Ceylon and Indian medicinal plants. H&C Press, Colombo Chandrasena JPC (1935) The chemistry and pharmacology of Ceylon and Indian medicinal plants. H&C Press, Colombo
9.
go back to reference Jayaweera DMA (1981) Medicinal plants used in ceylon part 1. National Science Council of Sri Lanka, Colombo, p 77 Jayaweera DMA (1981) Medicinal plants used in ceylon part 1. National Science Council of Sri Lanka, Colombo, p 77
10.
go back to reference Vaidyaratnam PS (1996) Indian medicinal plants: a compendium of 500 species. In: Warrier PK, Nambiar VPK, Ramankutty C, (Eds.), Orient Longman, Madras, India, pp. 47–48 Vaidyaratnam PS (1996) Indian medicinal plants: a compendium of 500 species. In: Warrier PK, Nambiar VPK, Ramankutty C, (Eds.), Orient Longman, Madras, India, pp. 47–48
11.
go back to reference Chuakul W, Saralamp P, Paonil W, Temsiririkkul R, Clayton T (1997) Medicinal plants in Thailand (volume II). Department of Pharmaceutical Botany, Faculty of Pharmacy, Mahidol University, Bangkok, pp 192–193 Chuakul W, Saralamp P, Paonil W, Temsiririkkul R, Clayton T (1997) Medicinal plants in Thailand (volume II). Department of Pharmaceutical Botany, Faculty of Pharmacy, Mahidol University, Bangkok, pp 192–193
12.
go back to reference Karunanayake EH, Welihinda J, Sirimanne SR, Sinnadorai G (1984) Oral hypoglycaemic activity of some medicinal plants of Sri Lanka. J Ethnopharmacol 11:223–231PubMedCrossRef Karunanayake EH, Welihinda J, Sirimanne SR, Sinnadorai G (1984) Oral hypoglycaemic activity of some medicinal plants of Sri Lanka. J Ethnopharmacol 11:223–231PubMedCrossRef
13.
go back to reference Serasinghe S, Sirasinghe P, Yamazaki H, Nishiguchi K, Hombhanje F, Nakanishi S, Sewa K, Hattori M, Namba T (1990) Oral hypoglycemic effect of Salacia reticulata in the streptozotocin-induced diabetic rat. Phytother Res 4:205–206CrossRef Serasinghe S, Sirasinghe P, Yamazaki H, Nishiguchi K, Hombhanje F, Nakanishi S, Sewa K, Hattori M, Namba T (1990) Oral hypoglycemic effect of Salacia reticulata in the streptozotocin-induced diabetic rat. Phytother Res 4:205–206CrossRef
14.
go back to reference Augusti KT, Joseph P, Babu TD (1995) Biologically active principles isolated from Salacia oblonga Wall. Indian J Physiol Pharmacol 39:415–417PubMed Augusti KT, Joseph P, Babu TD (1995) Biologically active principles isolated from Salacia oblonga Wall. Indian J Physiol Pharmacol 39:415–417PubMed
15.
go back to reference Pillai NR, Seshadri C, Santhakumari C (1979) Hypoglycaemic activity of the root bark of Salacia prinoides. Indian J Exp Biol 17:1279–1280PubMed Pillai NR, Seshadri C, Santhakumari C (1979) Hypoglycaemic activity of the root bark of Salacia prinoides. Indian J Exp Biol 17:1279–1280PubMed
17.
go back to reference Dash RP, Babu RJ, Srinivas NR (2018) Reappraisal and perspectives of clinical drug-drug interaction potential of a-glucosidase inhibitors such as acarbose, voglibose and miglitol in the treatment of type 2 diabetes mellitus. Xenobiotica 48:89–108PubMedCrossRef Dash RP, Babu RJ, Srinivas NR (2018) Reappraisal and perspectives of clinical drug-drug interaction potential of a-glucosidase inhibitors such as acarbose, voglibose and miglitol in the treatment of type 2 diabetes mellitus. Xenobiotica 48:89–108PubMedCrossRef
18.
go back to reference Ríos JL, Francini F, Schinella GR (2015) Natural products for the treatment of type 2 diabetes mellitus. Plant Med 81:975–994CrossRef Ríos JL, Francini F, Schinella GR (2015) Natural products for the treatment of type 2 diabetes mellitus. Plant Med 81:975–994CrossRef
19.
go back to reference Yoshikawa M, Shimada H, Morikawa T, Yoshizumi S, Matsumura N, Murakami T, Matsuda H, Hori K, Yamahara J (1997) Medicinal foodstuffs. VII. On the saponin constituents with glucose and alcohol absorption-inhibitory activity from a food garnish “tonburi”, the fruit of Japanese Kochia scoparia (L.) Schrad.: structures of scoparianosides A, B, and C. Chem Pharm Bull 45:1300–1305CrossRef Yoshikawa M, Shimada H, Morikawa T, Yoshizumi S, Matsumura N, Murakami T, Matsuda H, Hori K, Yamahara J (1997) Medicinal foodstuffs. VII. On the saponin constituents with glucose and alcohol absorption-inhibitory activity from a food garnish “tonburi”, the fruit of Japanese Kochia scoparia (L.) Schrad.: structures of scoparianosides A, B, and C. Chem Pharm Bull 45:1300–1305CrossRef
20.
go back to reference Yoshikawa M, Xu F, Morikawa T, Pongpiriyadacha Y, Nakamura S, Asao Y, Kumahara A, Matsuda H (2007) Medicinal foodstuffs. XII. New spirostane-type steroid saponins with antidiabetogenic activity from Borassus flabellifer. Chem Pharm Bull 55:308–316CrossRef Yoshikawa M, Xu F, Morikawa T, Pongpiriyadacha Y, Nakamura S, Asao Y, Kumahara A, Matsuda H (2007) Medicinal foodstuffs. XII. New spirostane-type steroid saponins with antidiabetogenic activity from Borassus flabellifer. Chem Pharm Bull 55:308–316CrossRef
21.
go back to reference Yoshikawa M, Nakamura S, Ozaki K, Kumahara A, Morikawa T, Matsuda H (2007) Structures of steroid alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solanum lycocarpum. J Nat Prod 70:210–214PubMedCrossRef Yoshikawa M, Nakamura S, Ozaki K, Kumahara A, Morikawa T, Matsuda H (2007) Structures of steroid alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solanum lycocarpum. J Nat Prod 70:210–214PubMedCrossRef
22.
go back to reference Yoshikawa M, Wang T, Morikawa T, Xie H, Matsuda H (2007) Bioactive constituents from Chinese natural medicines. XXIV. Hypoglycemic effects of Sinocrassula indica in sugar-loaded rats and genetically diabetic KK-Ay mice and structures of new acylated flavonol glycosides, sinocrassosides A1, A2, B1, and B2. Chem Pharm Bull 55:1308–1315CrossRef Yoshikawa M, Wang T, Morikawa T, Xie H, Matsuda H (2007) Bioactive constituents from Chinese natural medicines. XXIV. Hypoglycemic effects of Sinocrassula indica in sugar-loaded rats and genetically diabetic KK-Ay mice and structures of new acylated flavonol glycosides, sinocrassosides A1, A2, B1, and B2. Chem Pharm Bull 55:1308–1315CrossRef
23.
go back to reference Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Kon’i H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O (2012) Antidiabetogenic oligstilbenoids and 3-ethyl-4-phynyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii. Bioorg Med Chem 20:832–840PubMedCrossRef Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Kon’i H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O (2012) Antidiabetogenic oligstilbenoids and 3-ethyl-4-phynyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii. Bioorg Med Chem 20:832–840PubMedCrossRef
24.
go back to reference Morikawa T, Ninomiya K, Imamura M, Akaki J, Fujikura S, Pan Y, Yuan D, Yoshikawa M, Jia X, Li Z, Muraoka O (2014) Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice. J Nat Med 68:561–566PubMedCrossRef Morikawa T, Ninomiya K, Imamura M, Akaki J, Fujikura S, Pan Y, Yuan D, Yoshikawa M, Jia X, Li Z, Muraoka O (2014) Acylated phenylethanoid glycosides, echinacoside and acteoside from Cistanche tubulosa, improve glucose tolerance in mice. J Nat Med 68:561–566PubMedCrossRef
25.
go back to reference Morikawa T, Xie H, Pan Y, Ninomiya K, Yuan D, Jia X, Yoshikawa M, Nakamura S, Matsuda H, Muraoka O (2019) A review of biologically active natural products from a desert plant Cistance tubulosa. Chem Pharm Bull 67:675–689CrossRef Morikawa T, Xie H, Pan Y, Ninomiya K, Yuan D, Jia X, Yoshikawa M, Nakamura S, Matsuda H, Muraoka O (2019) A review of biologically active natural products from a desert plant Cistance tubulosa. Chem Pharm Bull 67:675–689CrossRef
26.
go back to reference Morikawa T, Ninomiya K, Akaki J, Kakihara N, Kuramoto H, Matsumoto Y, Hayakawa T, Muraoka O, Wang LB, Wu LJ, Nakamura S, Yoshikawa M, Matsuda H (2015) Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrichalcone glycosides from flowers of Helichrysum arenarium. J Nat Med 69:494–506PubMedPubMedCentralCrossRef Morikawa T, Ninomiya K, Akaki J, Kakihara N, Kuramoto H, Matsumoto Y, Hayakawa T, Muraoka O, Wang LB, Wu LJ, Nakamura S, Yoshikawa M, Matsuda H (2015) Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrichalcone glycosides from flowers of Helichrysum arenarium. J Nat Med 69:494–506PubMedPubMedCentralCrossRef
27.
go back to reference Yoshikawa M, Murakami T, Shimada H, Matsuda H, Yamahara J, Tanabe G, Muraoka O (1997) Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the Ayurvedic traditional medicine Salacia reticulata in Sri Lankan and India. Tetrahedron Lett 48:8367–8370CrossRef Yoshikawa M, Murakami T, Shimada H, Matsuda H, Yamahara J, Tanabe G, Muraoka O (1997) Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the Ayurvedic traditional medicine Salacia reticulata in Sri Lankan and India. Tetrahedron Lett 48:8367–8370CrossRef
28.
go back to reference Yoshikawa M, Morikawa T, Matsuda H, Tanabe G, Muraoka O (2002) Absolute stereostructure of potent α-glucosidase inhibitor, salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata. Bioorg Med Chem 10:1547–1554PubMedCrossRef Yoshikawa M, Morikawa T, Matsuda H, Tanabe G, Muraoka O (2002) Absolute stereostructure of potent α-glucosidase inhibitor, salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata. Bioorg Med Chem 10:1547–1554PubMedCrossRef
29.
go back to reference Yoshikawa M, Murakami T, Yashiro K, Matsuda H (1998) Kotalanol, a potent a-glucosidase inhibitor with thiosugar sulfonium sulfate structure, from antidiabetic Ayurvedic medicine Salacia reticulata. Chem Pharm Bull 46:1339–1340CrossRef Yoshikawa M, Murakami T, Yashiro K, Matsuda H (1998) Kotalanol, a potent a-glucosidase inhibitor with thiosugar sulfonium sulfate structure, from antidiabetic Ayurvedic medicine Salacia reticulata. Chem Pharm Bull 46:1339–1340CrossRef
30.
go back to reference Muraoka O, Xie W, Osaki S, Kagawa A, Tanabe G, Amer MFA, Minematsu T, Morikawa T, Yoshikawa M (2010) Characteristic alkaline catalyzed degradation of kotalanol, a potent α-glucosidase inhibitor isolated from Ayurvedic medicine Salacia reticulata, leading to anhydroheptitols: another structural proof. Thtrahedron 66:3717–3722CrossRef Muraoka O, Xie W, Osaki S, Kagawa A, Tanabe G, Amer MFA, Minematsu T, Morikawa T, Yoshikawa M (2010) Characteristic alkaline catalyzed degradation of kotalanol, a potent α-glucosidase inhibitor isolated from Ayurvedic medicine Salacia reticulata, leading to anhydroheptitols: another structural proof. Thtrahedron 66:3717–3722CrossRef
31.
go back to reference Capon RJ, MacLeod JK (1987) 5-Thio-D-mannose from the marine sponge Clathria pyramida (Lendenfeld). The first example of a naturally occurring 5-thiosugar. Chem Commun 1987:1200–1201CrossRef Capon RJ, MacLeod JK (1987) 5-Thio-D-mannose from the marine sponge Clathria pyramida (Lendenfeld). The first example of a naturally occurring 5-thiosugar. Chem Commun 1987:1200–1201CrossRef
32.
go back to reference Matsuda H, Murakami T, Yashiro K, Yamahara J, Yoshikawa M (1999) Antidiabetic principles of natural medicines. IV. Aldose reductase and a-glucosidase inhibitors from the roots of Salacia oblonga Wall. (Celastraceae): structure of a new friedelane-type triterpene, kotalagenin 16-acetate. Chem Pharm Bull 47:1725–1729CrossRef Matsuda H, Murakami T, Yashiro K, Yamahara J, Yoshikawa M (1999) Antidiabetic principles of natural medicines. IV. Aldose reductase and a-glucosidase inhibitors from the roots of Salacia oblonga Wall. (Celastraceae): structure of a new friedelane-type triterpene, kotalagenin 16-acetate. Chem Pharm Bull 47:1725–1729CrossRef
33.
go back to reference Yoshikawa M, Xu F, Nakamura S, Wang T, Matsuda H, Tanabe G, Muraoka O (2008) Salaprinol and ponkoranol with thiosugar sulfate structure from Salacia prinoides and α-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate. Heterocycles 75:1397–1405CrossRef Yoshikawa M, Xu F, Nakamura S, Wang T, Matsuda H, Tanabe G, Muraoka O (2008) Salaprinol and ponkoranol with thiosugar sulfate structure from Salacia prinoides and α-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate. Heterocycles 75:1397–1405CrossRef
34.
go back to reference Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Yoshikawa M (2010) Quantitative determination of potent α-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography-mass spectrometry. J Pharm Biomed Anal 52:770–773PubMedCrossRef Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Yoshikawa M (2010) Quantitative determination of potent α-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography-mass spectrometry. J Pharm Biomed Anal 52:770–773PubMedCrossRef
35.
go back to reference Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Pongpiriyadacha Y, Yoshikawa M (2011) 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 65:142–148PubMedCrossRef Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Pongpiriyadacha Y, Yoshikawa M (2011) 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 65:142–148PubMedCrossRef
36.
go back to reference Xie W, Tanabe G, Akaki J, Morikawa T, Ninomiya K, Minematsu T, Yoshikawa M, Wu X, Muraoka O (2011) Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors. Bioorg Med Chem 19:2015–2022PubMedCrossRef Xie W, Tanabe G, Akaki J, Morikawa T, Ninomiya K, Minematsu T, Yoshikawa M, Wu X, Muraoka O (2011) Isolation, structure identification and SAR studies on thiosugar sulfonium salts, neosalaprinol and neoponkoranol, as potent α-glucosidase inhibitors. Bioorg Med Chem 19:2015–2022PubMedCrossRef
37.
go back to reference Akaki J, Morikawa T, Miyake S, Ninomiya K, Okada M, Tanabe G, Pongpiriyadacha Y, Yoshikawa M, Muraoka O (2014) Evaluation of Salacia species as anti-diabetic natural resources based on quantitative analysis of eight sulphonium constituents: a new class of α-glucosidase inhibitors. Phytochem Anal 25:544–550PubMedCrossRef Akaki J, Morikawa T, Miyake S, Ninomiya K, Okada M, Tanabe G, Pongpiriyadacha Y, Yoshikawa M, Muraoka O (2014) Evaluation of Salacia species as anti-diabetic natural resources based on quantitative analysis of eight sulphonium constituents: a new class of α-glucosidase inhibitors. Phytochem Anal 25:544–550PubMedCrossRef
38.
go back to reference Morikawa T, Akaki J, Ninomiya K, Kinouchi E, Tanabe G, Pongpiriyadacha Y, Yoshikawa M, Muraoka O (2015) Salacinol and related analogs: new leads for type 2 diabetes therapeutic candidate from the Thai traditional natural medicine Salacia chinensis. Neutrients 7:1480–1493CrossRef Morikawa T, Akaki J, Ninomiya K, Kinouchi E, Tanabe G, Pongpiriyadacha Y, Yoshikawa M, Muraoka O (2015) Salacinol and related analogs: new leads for type 2 diabetes therapeutic candidate from the Thai traditional natural medicine Salacia chinensis. Neutrients 7:1480–1493CrossRef
39.
go back to reference Yuasa H, Takada J, Hashimoto H (2000) Synthesis of salacinol. Tetrahedron Lett 41:6615–6618CrossRef Yuasa H, Takada J, Hashimoto H (2000) Synthesis of salacinol. Tetrahedron Lett 41:6615–6618CrossRef
40.
go back to reference Ghavami A, Johnston BD, Pinto BM (2001) A new class of glycosidase inhibitor: synthesis of salacinol and its stereoisomers. J Org Chem 66:2312–2317PubMedCrossRef Ghavami A, Johnston BD, Pinto BM (2001) A new class of glycosidase inhibitor: synthesis of salacinol and its stereoisomers. J Org Chem 66:2312–2317PubMedCrossRef
41.
go back to reference Johnston BD, Ghavami A, Jensen MT, Svensson B, Pinto BM (2002) Synthesis of selenium analogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors. J Am Chem Soc 124:8245–8250PubMedCrossRef Johnston BD, Ghavami A, Jensen MT, Svensson B, Pinto BM (2002) Synthesis of selenium analogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors. J Am Chem Soc 124:8245–8250PubMedCrossRef
42.
go back to reference Ghavami A, Sadalapure KS, Johnston BD, Lobera M, Snider BB, Pinto BM (2003) Improved syntheses of the naturally occurring glycosidase inhibitor salacinol. Synlett 9:1259–1262 Ghavami A, Sadalapure KS, Johnston BD, Lobera M, Snider BB, Pinto BM (2003) Improved syntheses of the naturally occurring glycosidase inhibitor salacinol. Synlett 9:1259–1262
43.
go back to reference Johnston BD, Jensen HH, Pinto BM (2006) Synthesis of sulfonium sulfate analogues of disaccharides and their conversion to chain-extended homologues of salacinol: new glycosidase inhibitors. J Org Chem 71:1111–1118PubMedCrossRef Johnston BD, Jensen HH, Pinto BM (2006) Synthesis of sulfonium sulfate analogues of disaccharides and their conversion to chain-extended homologues of salacinol: new glycosidase inhibitors. J Org Chem 71:1111–1118PubMedCrossRef
44.
go back to reference Ravindranath HL, Nasi R, Jayakanthan K, Kumarasamy N, Sim JL, Heipel H, Rose DR, Pinto BM (2007) New synthetic routes to chain-extended selenium, sulfer, and nitrogen analogues of the naturally occurring glucosidase inhibitor salacinol and their inhibitory activities against recombinant human maltase glucoamylase. J Org Chem 72:6562–6572CrossRef Ravindranath HL, Nasi R, Jayakanthan K, Kumarasamy N, Sim JL, Heipel H, Rose DR, Pinto BM (2007) New synthetic routes to chain-extended selenium, sulfer, and nitrogen analogues of the naturally occurring glucosidase inhibitor salacinol and their inhibitory activities against recombinant human maltase glucoamylase. J Org Chem 72:6562–6572CrossRef
45.
go back to reference Mohan S, Pinto BM (2007) Zwitterionic glycosidase inhibitors: salacinol and related analogues. Carbohydr Res 342:1551–1580PubMedCrossRef Mohan S, Pinto BM (2007) Zwitterionic glycosidase inhibitors: salacinol and related analogues. Carbohydr Res 342:1551–1580PubMedCrossRef
46.
go back to reference Nasi R, Patrick BO, Sim L, Rose DR, Pinto BM (2008) Studies directed toward the stereochemical structure determination of the naturally occurring glucosidase inhibitor, kotalanol: synthesis and inhibitory activities against human maltase glucoamylase of seven-carbon, chain-extended homologues of salacinol. J Org Chem 73:6172–6181PubMedCrossRef Nasi R, Patrick BO, Sim L, Rose DR, Pinto BM (2008) Studies directed toward the stereochemical structure determination of the naturally occurring glucosidase inhibitor, kotalanol: synthesis and inhibitory activities against human maltase glucoamylase of seven-carbon, chain-extended homologues of salacinol. J Org Chem 73:6172–6181PubMedCrossRef
47.
go back to reference Jayakanthan K, Mohan S, Pinto BM (2009) 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. J Am Chem Soc 131:5621–5626PubMedCrossRef Jayakanthan K, Mohan S, Pinto BM (2009) 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. J Am Chem Soc 131:5621–5626PubMedCrossRef
48.
go back to reference Mohan S, Pinto BM (2009) Sulfonium-ion glycosidase inhibitors isolated from Salacia species used in traditional medicine, and related compounds. Collect Czech Chem Commun 74:1117–1136CrossRef Mohan S, Pinto BM (2009) Sulfonium-ion glycosidase inhibitors isolated from Salacia species used in traditional medicine, and related compounds. Collect Czech Chem Commun 74:1117–1136CrossRef
49.
go back to reference Mohan S, Pinto BM (2010) Towards the elusive structure of kotalanol, a naturally occurring glucosidase inhibitor. Nat Prod Rep 27:481–488PubMedCrossRef Mohan S, Pinto BM (2010) Towards the elusive structure of kotalanol, a naturally occurring glucosidase inhibitor. Nat Prod Rep 27:481–488PubMedCrossRef
50.
go back to reference Sim L, Jayakanthan K, Mohan S, Nasi R, Johnston BD, Pinto BM, Rose DR (2010) New glucosidase inhibitors from an Ayurvedic herbal treatment for type-2 diabetes: structures and inhibition of human intestinal maltase-glucoamylase with compounds from Salacia reticulata. Biochemistry 49:443–451PubMedCrossRef Sim L, Jayakanthan K, Mohan S, Nasi R, Johnston BD, Pinto BM, Rose DR (2010) New glucosidase inhibitors from an Ayurvedic herbal treatment for type-2 diabetes: structures and inhibition of human intestinal maltase-glucoamylase with compounds from Salacia reticulata. Biochemistry 49:443–451PubMedCrossRef
51.
go back to reference Eskandari R, Jayakanthan K, Kuntz DA, Rose DR, Pinto BM (2010) Synthesis of a biologically active isomer of kotalanol, a naturally occurring glucosidase inhibitor. Bioorg Med Chem 18:2829–2835PubMedCrossRef Eskandari R, Jayakanthan K, Kuntz DA, Rose DR, Pinto BM (2010) Synthesis of a biologically active isomer of kotalanol, a naturally occurring glucosidase inhibitor. Bioorg Med Chem 18:2829–2835PubMedCrossRef
52.
go back to reference Eskandari R, Kuntz DA, Rose DR, Pinto BM (2010) Potent glucosidase inhibitors: de-O-sulfonated ponkoranol and its stereoisomer. Org Lett 12:1632–1635PubMedCrossRef Eskandari R, Kuntz DA, Rose DR, Pinto BM (2010) Potent glucosidase inhibitors: de-O-sulfonated ponkoranol and its stereoisomer. Org Lett 12:1632–1635PubMedCrossRef
53.
go back to reference Eskandari R, Jones K, Rose DR, Pinto BM (2011) The effect of heteroatom substitution of sulfur for selenium in glucosidase inhibitors on intestinal α-glucosidase activities. Chem Commun 47:9134–9136CrossRef Eskandari R, Jones K, Rose DR, Pinto BM (2011) The effect of heteroatom substitution of sulfur for selenium in glucosidase inhibitors on intestinal α-glucosidase activities. Chem Commun 47:9134–9136CrossRef
54.
go back to reference Mohan S, Eskandari R, Pinto BM (2014) Naturally occurring sulfonium-ion glucosidase inhibitors and their derivatives: a promising class of potential antidiabetic agents. Acc Chem Res 47:211–225PubMedCrossRef Mohan S, Eskandari R, Pinto BM (2014) Naturally occurring sulfonium-ion glucosidase inhibitors and their derivatives: a promising class of potential antidiabetic agents. Acc Chem Res 47:211–225PubMedCrossRef
55.
go back to reference Bagri P, Chester K, Khan W, Ahmad S (2017) 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 7:28152–28187CrossRef Bagri P, Chester K, Khan W, Ahmad S (2017) 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 7:28152–28187CrossRef
56.
go back to reference Xie W, Tanabe G, Xu J, Wu X, Morikawa T, Yoshikawa M, Muraoka O (2013) Research progress of synthesis and structure-activity relationship studies on sulfonium-type α-glucosidase inhibitors isolated from Salacia genus plants. Min Rev Org Chem 10:141–159CrossRef Xie W, Tanabe G, Xu J, Wu X, Morikawa T, Yoshikawa M, Muraoka O (2013) Research progress of synthesis and structure-activity relationship studies on sulfonium-type α-glucosidase inhibitors isolated from Salacia genus plants. Min Rev Org Chem 10:141–159CrossRef
57.
go back to reference Nakamura S, Takahira K, Tanabe G, Morikawa T, Sakano M, Ninomiya K, Yoshikawa M, Muraoka O, Nakanishi I (2010) Docking and SAR studies of salacinol derivatives as α-glucosidase inhibitors. Bioorg Med Chem Lett 20:4420–4423PubMedCrossRef Nakamura S, Takahira K, Tanabe G, Morikawa T, Sakano M, Ninomiya K, Yoshikawa M, Muraoka O, Nakanishi I (2010) Docking and SAR studies of salacinol derivatives as α-glucosidase inhibitors. Bioorg Med Chem Lett 20:4420–4423PubMedCrossRef
58.
go back to reference Tanabe G, Nakamura S, Tsutsui N, Balakishan G, Xie W, Tsuchiya S, Akaki J, Morikawa T, Ninomiya K, Nakanishi I, Yoshikawa M, Muraoka O (2012) In silico design, synthesis and evaluation of 3’-O-benzylated analogs of salacinol, a potent α-glucosidase inhibitor isolated from an Ayurvedic traditional medicine “Salacia”. Chem Commun 48:8646–8648CrossRef Tanabe G, Nakamura S, Tsutsui N, Balakishan G, Xie W, Tsuchiya S, Akaki J, Morikawa T, Ninomiya K, Nakanishi I, Yoshikawa M, Muraoka O (2012) In silico design, synthesis and evaluation of 3’-O-benzylated analogs of salacinol, a potent α-glucosidase inhibitor isolated from an Ayurvedic traditional medicine “Salacia”. Chem Commun 48:8646–8648CrossRef
59.
go back to reference Tanabe G, Xie W, Balakishan G, Amer MFA, Tsutsui N, Takemura H, Nakamura S, Akaki J, Ninomiya K, Morikawa T, Nakanishi I, Muraoka O (2016) Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’. Bioorg Med Chem 24:3705–3715PubMedCrossRef Tanabe G, Xie W, Balakishan G, Amer MFA, Tsutsui N, Takemura H, Nakamura S, Akaki J, Ninomiya K, Morikawa T, Nakanishi I, Muraoka O (2016) Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine ‘Salacia’. Bioorg Med Chem 24:3705–3715PubMedCrossRef
60.
go back to reference Ishikawa F, Jinno K, Kinouchi E, Ninomiya K, Marumoto S, Xie W, Muraoka O, Morikawa T, Tanabe G (2018) Diastereoselective synthesis of salacinol-type α-glucosidase inhibitors. J Org Chem 83:185–193PubMedCrossRef Ishikawa F, Jinno K, Kinouchi E, Ninomiya K, Marumoto S, Xie W, Muraoka O, Morikawa T, Tanabe G (2018) Diastereoselective synthesis of salacinol-type α-glucosidase inhibitors. J Org Chem 83:185–193PubMedCrossRef
61.
go back to reference Takashima K, Sakano M, Kinouchi E, Nakamura S, Marumoto S, Ishikawa F, Ninomiya K, Nakanishi I, Morikawa T, Tanabe G (2021) Elongation of the side chain by linear alkyl groups increases the potency of salacinol, a potent α-glucosidase inhibitor from the Ayurvedic traditional medicine “Salacia”, against human intestinal maltase. Bioorg Med Chem Lett 33:127751PubMedCrossRef Takashima K, Sakano M, Kinouchi E, Nakamura S, Marumoto S, Ishikawa F, Ninomiya K, Nakanishi I, Morikawa T, Tanabe G (2021) Elongation of the side chain by linear alkyl groups increases the potency of salacinol, a potent α-glucosidase inhibitor from the Ayurvedic traditional medicine “Salacia”, against human intestinal maltase. Bioorg Med Chem Lett 33:127751PubMedCrossRef
62.
go back to reference Ishikawa F, Hirano A, Yoshimori Y, Nishida K, Nakamura S, Takashima K, Marumoto S, Ninomiya K, Nakanishi I, Xie W, Morikawa T, Muraoka O, Tanabe G (2021) Ligand compatibility of salacinol-type α-glucosidase inhibitors toward the GH31 family. RSC Adv 11:3221–3225CrossRef Ishikawa F, Hirano A, Yoshimori Y, Nishida K, Nakamura S, Takashima K, Marumoto S, Ninomiya K, Nakanishi I, Xie W, Morikawa T, Muraoka O, Tanabe G (2021) Ligand compatibility of salacinol-type α-glucosidase inhibitors toward the GH31 family. RSC Adv 11:3221–3225CrossRef
63.
go back to reference Yoshikawa M, Morikawa T, Murakami T, Toguchida I, Harima S, Matsuda H (1999) Medicinal flowers. I. aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L. Chem Pharm Bull 47:340–345CrossRef Yoshikawa M, Morikawa T, Murakami T, Toguchida I, Harima S, Matsuda H (1999) Medicinal flowers. I. aldose reductase inhibitors and three new eudesmane-type sesquiterpenes, kikkanols A, B, and C, from the flowers of Chrysanthemum indicum L. Chem Pharm Bull 47:340–345CrossRef
64.
go back to reference Matsuda H, Morikawa T, Ueda H, Yoshikawa M (2001) Medicinal foodstuffs. XXVI. Inhibitors of aldose reductase and new triterpene and its oligoglycoside, centellasapogenol A and centellasaponin A, from Centella asiatica (Gotu Kola). Heterocycles 55:1499–1504CrossRef Matsuda H, Morikawa T, Ueda H, Yoshikawa M (2001) Medicinal foodstuffs. XXVI. Inhibitors of aldose reductase and new triterpene and its oligoglycoside, centellasapogenol A and centellasaponin A, from Centella asiatica (Gotu Kola). Heterocycles 55:1499–1504CrossRef
65.
go back to reference Matsuda H, Morikawa T, Toguchida I, Yoshikawa M (2002) Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull 50:788–795CrossRef Matsuda H, Morikawa T, Toguchida I, Yoshikawa M (2002) Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity. Chem Pharm Bull 50:788–795CrossRef
66.
go back to reference Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M (2002) Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycosides from the flowers of Chrysanthemum indicum L.: their inhibitory activities of rat lens aldose reductase. Chem Pharm Bull 50:972–975CrossRef Matsuda H, Morikawa T, Toguchida I, Harima S, Yoshikawa M (2002) Medicinal flowers. VI. Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycosides from the flowers of Chrysanthemum indicum L.: their inhibitory activities of rat lens aldose reductase. Chem Pharm Bull 50:972–975CrossRef
67.
go back to reference Yoshikawa M, Murakami T, Ishiwada T, Morikawa T, Kagawa M, Higashi Y, Matsuda H (2002) New flavonol oligoglycosides and polyacylated sucroses with inhibitory effects on aldose reductase and platelet aggregation from the flowers of Prunus mume. J Nat Prod 65:1151–1155PubMedCrossRef Yoshikawa M, Murakami T, Ishiwada T, Morikawa T, Kagawa M, Higashi Y, Matsuda H (2002) New flavonol oligoglycosides and polyacylated sucroses with inhibitory effects on aldose reductase and platelet aggregation from the flowers of Prunus mume. J Nat Prod 65:1151–1155PubMedCrossRef
68.
go back to reference Xie H, Wang T, Matsuda H, Morikawa T, Yoshikawa M, Tani T (2005) Bioactive constituents from Chinese natural medicines. XV. Inhibitory effect on aldose reductase and structures of saussureosides A and B from Saussurea medusa. Chem Pharm Bull 53:1416–1422CrossRef Xie H, Wang T, Matsuda H, Morikawa T, Yoshikawa M, Tani T (2005) Bioactive constituents from Chinese natural medicines. XV. Inhibitory effect on aldose reductase and structures of saussureosides A and B from Saussurea medusa. Chem Pharm Bull 53:1416–1422CrossRef
69.
go back to reference Morikawa T, Xie H, Wang T, Matsuda H, Yoshikawa M (2008) Bioactive constituents from Chinese natural medicines. XXXII. Aminopeptidase N and aldose reductase inhibitors from Sinocrassula indica: structures of sinocrassosides B4, B5, C1, and D1–D3. Chem Pharm Bull 56:1438–1444CrossRef Morikawa T, Xie H, Wang T, Matsuda H, Yoshikawa M (2008) Bioactive constituents from Chinese natural medicines. XXXII. Aminopeptidase N and aldose reductase inhibitors from Sinocrassula indica: structures of sinocrassosides B4, B5, C1, and D1–D3. Chem Pharm Bull 56:1438–1444CrossRef
70.
go back to reference Yoshikawa M, Nishida N, Shimoda H, Takada M, Kawahara Y, Matsuda H (2001) Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with α-glucosidase and aldose reductase inhibitory activity. Yakugaku Zasshi 121:371–378PubMedCrossRef Yoshikawa M, Nishida N, Shimoda H, Takada M, Kawahara Y, Matsuda H (2001) Polyphenol constituents from Salacia species: quantitative analysis of mangiferin with α-glucosidase and aldose reductase inhibitory activity. Yakugaku Zasshi 121:371–378PubMedCrossRef
71.
go back to reference Yoshikawa M, Pongpiriyadacha Y, Kishi A, Kageura T, Wang T, Morikawa T, Matsuda H (2003) Biological activities of Salacia chinensis originating in Thailand: the quality evaluation guided by α-glucosidase inhibitory activity. Yakugaku Zasshi 123:871–880PubMedCrossRef Yoshikawa M, Pongpiriyadacha Y, Kishi A, Kageura T, Wang T, Morikawa T, Matsuda H (2003) Biological activities of Salacia chinensis originating in Thailand: the quality evaluation guided by α-glucosidase inhibitory activity. Yakugaku Zasshi 123:871–880PubMedCrossRef
72.
go back to reference Morikawa T, Kishi A, Pongpiriyadacha Y, Matsuda H, Yoshikawa M (2003) Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpenes and aldose reductase inhibitors from Salacia chinensis. J Nat Prod 66:1191–1196PubMedCrossRef Morikawa T, Kishi A, Pongpiriyadacha Y, Matsuda H, Yoshikawa M (2003) Structures of new friedelane-type triterpenes and eudesmane-type sesquiterpenes and aldose reductase inhibitors from Salacia chinensis. J Nat Prod 66:1191–1196PubMedCrossRef
73.
go back to reference Kishi A, Morikawa T, Matsuda H, Yoshikawa M (2003) Structures of new friedelane- and norfriedelane-type triterpenes and polyacylated eudesmane-type sesquiterpene from Salacia chinensis Linn. (S. prinoides DC., Hippocrateaceae) and radical scavenging activities of principal constituents. Chem Pharm Bull 51:1051–1055CrossRef Kishi A, Morikawa T, Matsuda H, Yoshikawa M (2003) Structures of new friedelane- and norfriedelane-type triterpenes and polyacylated eudesmane-type sesquiterpene from Salacia chinensis Linn. (S. prinoides DC., Hippocrateaceae) and radical scavenging activities of principal constituents. Chem Pharm Bull 51:1051–1055CrossRef
74.
go back to reference Nakamura K, Akaki J, Ishibushi F, Tani K, Morikawa T, Pongpiriyadacha Y, Muraoka O, Hayakawa T, Kakutani K (2015) Discrimination of Salacia chinensis based on the DNA sequence of the rDNA ITS region. Shoyakugaku Zasshi 69:53–58 Nakamura K, Akaki J, Ishibushi F, Tani K, Morikawa T, Pongpiriyadacha Y, Muraoka O, Hayakawa T, Kakutani K (2015) Discrimination of Salacia chinensis based on the DNA sequence of the rDNA ITS region. Shoyakugaku Zasshi 69:53–58
75.
go back to reference Yamada K, Sato-Mito N, Nagata J, Umegaki K (2008) Health claim evidence requirements in Japan. J Nutr 138:1192S-1198SPubMedCrossRef Yamada K, Sato-Mito N, Nagata J, Umegaki K (2008) Health claim evidence requirements in Japan. J Nutr 138:1192S-1198SPubMedCrossRef
76.
go back to reference Tsutani K, Takuma H (2008) Regulatory sciences in herbal medicines and dietary supplements. Yakugaku Zasshi 128:867–880PubMedCrossRef Tsutani K, Takuma H (2008) Regulatory sciences in herbal medicines and dietary supplements. Yakugaku Zasshi 128:867–880PubMedCrossRef
77.
go back to reference Nagata J, Yamada K (2008) Foods with health claims in Japan. Food Sci Technol Res 14:519–524CrossRef Nagata J, Yamada K (2008) Foods with health claims in Japan. Food Sci Technol Res 14:519–524CrossRef
78.
go back to reference Shimizu M (2012) Functional food in Japan: current status and future of gut-modulating food. J Food Drug Anal 20(Suppl. 1):213–216 Shimizu M (2012) Functional food in Japan: current status and future of gut-modulating food. J Food Drug Anal 20(Suppl. 1):213–216
79.
go back to reference Kamioka H, Tsutani K, Origasa H, Yoshizaki T, Kitayuguchi J, Shimada M, Tang W, Takano-Ohmuro H (2017) Quality of systematic reviews of the foods with function claims registered at the consumer affairs agency Web site in Japan: a prospective systematic review. Nutr Res 40:21–31PubMedCrossRef Kamioka H, Tsutani K, Origasa H, Yoshizaki T, Kitayuguchi J, Shimada M, Tang W, Takano-Ohmuro H (2017) Quality of systematic reviews of the foods with function claims registered at the consumer affairs agency Web site in Japan: a prospective systematic review. Nutr Res 40:21–31PubMedCrossRef
80.
go back to reference Kamioka H, Tsutani K, Origasa H, Yoshizaki T, Kitayuguchi J, Shimada M, Wada Y, Takano-Ohmuro H (2019) Quality of systematic reviews of the foods with function claims in Japan: comparative before- and after-evaluation of verification reports by the consumer affairs agency. Nutrients 11:1583PubMedCentralCrossRef Kamioka H, Tsutani K, Origasa H, Yoshizaki T, Kitayuguchi J, Shimada M, Wada Y, Takano-Ohmuro H (2019) Quality of systematic reviews of the foods with function claims in Japan: comparative before- and after-evaluation of verification reports by the consumer affairs agency. Nutrients 11:1583PubMedCentralCrossRef
81.
go back to reference Maeda-Yamamoto M, Ohtani T (2018) Development of functional agricultural products utilizing the new health claim labelling system in Japan. Biosci Boitechnol Biochem 82:554–563CrossRef Maeda-Yamamoto M, Ohtani T (2018) Development of functional agricultural products utilizing the new health claim labelling system in Japan. Biosci Boitechnol Biochem 82:554–563CrossRef
82.
go back to reference Kobayashi M, Akaki J, Yamaguchi Y, Yamasaki H, Ninomiya K, Pongpiriyadacha Y, Yoshikawa M, Muraoka O, Morikawa T (2019) Salacia chinensis stem extract and its thiosugar sulfonium constituent, neokotalanol, improves HbA1c levels in ob/ob mice. J Nat Med 73:584–588PubMedCrossRef Kobayashi M, Akaki J, Yamaguchi Y, Yamasaki H, Ninomiya K, Pongpiriyadacha Y, Yoshikawa M, Muraoka O, Morikawa T (2019) Salacia chinensis stem extract and its thiosugar sulfonium constituent, neokotalanol, improves HbA1c levels in ob/ob mice. J Nat Med 73:584–588PubMedCrossRef
83.
go back to reference Vyas A, Syeda K, Ahmad A, Padhye S, Sarkar FH (2012) Perspectives on medicinal properties of mangiferin. Min Rev Med Chem 12:412–425CrossRef Vyas A, Syeda K, Ahmad A, Padhye S, Sarkar FH (2012) Perspectives on medicinal properties of mangiferin. Min Rev Med Chem 12:412–425CrossRef
84.
go back to reference Matkowski A, Kus P, Góralska E, Wozniak D (2013) Mangiferin—a bioactive xanthanoid, not only from mango and not just antioxidant. Mini-Rev Med Chem 13:439–455PubMed Matkowski A, Kus P, Góralska E, Wozniak D (2013) Mangiferin—a bioactive xanthanoid, not only from mango and not just antioxidant. Mini-Rev Med Chem 13:439–455PubMed
85.
go back to reference Ehianeta TS, Laval S, Yu B (2016) Bio- and chemical syntheses of mangiferin and congeners. BioFactors 42:445–458PubMedCrossRef Ehianeta TS, Laval S, Yu B (2016) Bio- and chemical syntheses of mangiferin and congeners. BioFactors 42:445–458PubMedCrossRef
86.
go back to reference Miura T, Ichiki H, Hashimoto I, Iwamoto N, Kato M, Kubo M, Ishihara E, Komatsu K, Okada M, Ishida T, Tanigawa K (2001) Antidiabetic activity of a xanthone compound, mangiferin. Phytomedicine 8:85–87PubMedCrossRef Miura T, Ichiki H, Hashimoto I, Iwamoto N, Kato M, Kubo M, Ishihara E, Komatsu K, Okada M, Ishida T, Tanigawa K (2001) Antidiabetic activity of a xanthone compound, mangiferin. Phytomedicine 8:85–87PubMedCrossRef
87.
go back to reference Telang M, Dhulap S, Mandhare A, Hirwani R (2013) Therapeutic and cosmetic application of mangiferin: a patent review. Expert Opin Ther Pat 23:1561–1580PubMedCrossRef Telang M, Dhulap S, Mandhare A, Hirwani R (2013) Therapeutic and cosmetic application of mangiferin: a patent review. Expert Opin Ther Pat 23:1561–1580PubMedCrossRef
89.
go back to reference Singh AK, Raj V, Keshari AK, Rai A, Kumar P, Rawat A, Maity B, Kumar D, Prakash A, De A, Samanta A, Bhattacharya B, Saha S (2018) Isolated mangiferin and naringenin exert antidiabetic effect via PPARγ/GLUT4 dual agonistic action with strong metabolic regulation. Chem-Biol Int 280:33–44CrossRef Singh AK, Raj V, Keshari AK, Rai A, Kumar P, Rawat A, Maity B, Kumar D, Prakash A, De A, Samanta A, Bhattacharya B, Saha S (2018) Isolated mangiferin and naringenin exert antidiabetic effect via PPARγ/GLUT4 dual agonistic action with strong metabolic regulation. Chem-Biol Int 280:33–44CrossRef
90.
go back to reference Yoshikawa M, Ninomiya K, Shimoda H, Nishida N, Matsuda H (2002) Hepatoprotective and antioxidative properties of Salacia reticulata: preventive effects of phenolic constituents on CCl4-induced liver injury in mice. Biol Pharm Bull 25:72–76PubMedCrossRef Yoshikawa M, Ninomiya K, Shimoda H, Nishida N, Matsuda H (2002) Hepatoprotective and antioxidative properties of Salacia reticulata: preventive effects of phenolic constituents on CCl4-induced liver injury in mice. Biol Pharm Bull 25:72–76PubMedCrossRef
91.
go back to reference Saha S, Sadhukhan P, Sil PC (2016) Mangiferin: a xanthanoid with multiportent anti-inflammatory potential. BioFactors 42:459–474PubMedCrossRef Saha S, Sadhukhan P, Sil PC (2016) Mangiferin: a xanthanoid with multiportent anti-inflammatory potential. BioFactors 42:459–474PubMedCrossRef
92.
go back to reference Jyotshna KP, Shanker K (2016) Mangiferin: a review of sources and interventions for biological activeties. BioFactors 42:504–514PubMedCrossRef Jyotshna KP, Shanker K (2016) Mangiferin: a review of sources and interventions for biological activeties. BioFactors 42:504–514PubMedCrossRef
93.
go back to reference Luczkiewicz P, Kokotkiewicz A, Dampc A, Luczkiewicz M (2014) Mangiferin: a promising therapeutic agent for rheumatoid arthritis treatment. Med Hypoth 83:570–574CrossRef Luczkiewicz P, Kokotkiewicz A, Dampc A, Luczkiewicz M (2014) Mangiferin: a promising therapeutic agent for rheumatoid arthritis treatment. Med Hypoth 83:570–574CrossRef
94.
go back to reference Sekiguchi Y, Mano H, Nakatani S, Shimizu J, Kataoka A, Ogura K, Kimira Y, Ebata M, Wada M (2017) Mangiferin positively regulates osteoblast differentiation and suppresses osteoclast differentiation. Mol Med Rep 16:1328–1332PubMedPubMedCentralCrossRef Sekiguchi Y, Mano H, Nakatani S, Shimizu J, Kataoka A, Ogura K, Kimira Y, Ebata M, Wada M (2017) Mangiferin positively regulates osteoblast differentiation and suppresses osteoclast differentiation. Mol Med Rep 16:1328–1332PubMedPubMedCentralCrossRef
95.
go back to reference Salles AJN, Daglia M, Rastrelli L (2016) The potential role of mangiferin in cancer treatment through its immunomodulatory, anti-angiogenic, apoptotic, and gene regulatory effects. BioFactors 42:475–491CrossRef Salles AJN, Daglia M, Rastrelli L (2016) The potential role of mangiferin in cancer treatment through its immunomodulatory, anti-angiogenic, apoptotic, and gene regulatory effects. BioFactors 42:475–491CrossRef
97.
go back to reference Morikawa T, Akaki J, Pongpiriyadacha Y, Yoshikawa M, Ninomiya K, Muraoka O (2018) Simultaneous quantitative determination of polyphenol constituents in Salacia species from different regions by LC-MS. Jpn J Food Chem Saf 25:130–138 Morikawa T, Akaki J, Pongpiriyadacha Y, Yoshikawa M, Ninomiya K, Muraoka O (2018) Simultaneous quantitative determination of polyphenol constituents in Salacia species from different regions by LC-MS. Jpn J Food Chem Saf 25:130–138
98.
go back to reference Shimoda H, Fujimura T, Makino K, Yoshijima K, Naitoh K, Ihota H, Miwa Y (1999) Safety profile of extractive from trunk of Salacia reticulata (Celastraceae). J Food Hyg Soc Jpn 40:198–205CrossRef Shimoda H, Fujimura T, Makino K, Yoshijima K, Naitoh K, Ihota H, Miwa Y (1999) Safety profile of extractive from trunk of Salacia reticulata (Celastraceae). J Food Hyg Soc Jpn 40:198–205CrossRef
99.
go back to reference Shimoda H, Furuhashi T, Naitou K, Nagase T, Okada M (2001) Thirteen-week repeat dose oral toxicity study of Salacia reticulata extract in rats. Jpn J Pharm Sci 46:527–540 Shimoda H, Furuhashi T, Naitou K, Nagase T, Okada M (2001) Thirteen-week repeat dose oral toxicity study of Salacia reticulata extract in rats. Jpn J Pharm Sci 46:527–540
100.
go back to reference Wolf BW, Weisbrode SE (2003) Safety evaluation of an extract from Salacia oblonga. Food Chem Toxicol 41:867–874PubMedCrossRef Wolf BW, Weisbrode SE (2003) Safety evaluation of an extract from Salacia oblonga. Food Chem Toxicol 41:867–874PubMedCrossRef
101.
102.
go back to reference Jihong Y, Shaozhong L, Jingfeng S, Kobayashi M, Akaki J, Yamashita K, Tamesada M, Umemura T (2011) Effects of Salacia chinensis extract on reproductive outcome in rats. Food Chem Toxicol 49:57–60PubMedCrossRef Jihong Y, Shaozhong L, Jingfeng S, Kobayashi M, Akaki J, Yamashita K, Tamesada M, Umemura T (2011) Effects of Salacia chinensis extract on reproductive outcome in rats. Food Chem Toxicol 49:57–60PubMedCrossRef
103.
go back to reference Im R, Mano H, Nakatani S, Shimizu J, Wada M (2008) Safety evaluation of the aqueous extract Kothala Himbutu (Salacia reticulata) stem in the hepatic gene expression profile of normal mice using DNA microarrays. Biosci Biotechnol Biochem 72:3075–3083PubMedCrossRef Im R, Mano H, Nakatani S, Shimizu J, Wada M (2008) Safety evaluation of the aqueous extract Kothala Himbutu (Salacia reticulata) stem in the hepatic gene expression profile of normal mice using DNA microarrays. Biosci Biotechnol Biochem 72:3075–3083PubMedCrossRef
104.
go back to reference Shimoda H, Asano I, Yamada Y (2001) Antigenicity and phototoxicity of water-soluble extract from Salacia reticulata (Celastraceae). J Food Hyg Soc Jpn 42:144–147CrossRef Shimoda H, Asano I, Yamada Y (2001) Antigenicity and phototoxicity of water-soluble extract from Salacia reticulata (Celastraceae). J Food Hyg Soc Jpn 42:144–147CrossRef
105.
106.
go back to reference Kobayashi M, Akaki J, Yamaguchi Y, Yamasaki H, Morikawa T, Ninomiya K, Yoshikawa M, Muraoka O (2016) Safety evaluation of long term and excess intake of the tablet containing hot water extract of Salacia chinensis –randomized double-blind placebo-controlled trials. Jpn Pharmacol Ther 44:399–408 Kobayashi M, Akaki J, Yamaguchi Y, Yamasaki H, Morikawa T, Ninomiya K, Yoshikawa M, Muraoka O (2016) Safety evaluation of long term and excess intake of the tablet containing hot water extract of Salacia chinensis –randomized double-blind placebo-controlled trials. Jpn Pharmacol Ther 44:399–408
107.
go back to reference Shimoda H, Kawamori S, Kawahara Y (1998) Effects of an aqueous extract of Salacia reticulata, a useful plant in Sri Lanka, on postprandial hyperglycemia in rats and humans. J Jpn Soc Nutr Food Sci 51:279–287CrossRef Shimoda H, Kawamori S, Kawahara Y (1998) Effects of an aqueous extract of Salacia reticulata, a useful plant in Sri Lanka, on postprandial hyperglycemia in rats and humans. J Jpn Soc Nutr Food Sci 51:279–287CrossRef
108.
go back to reference Kajimoto O, Kawamori S, Shimoda H, Kawahara Y, Hirata H, Takahashi T (2000) Effects of a diet containing Salacia reticulata on mild type 2 diabetes in humans—a placebo-controlled, cross-over trial. J Jpn Soc Nutr Food Sci 53:199–205CrossRef Kajimoto O, Kawamori S, Shimoda H, Kawahara Y, Hirata H, Takahashi T (2000) Effects of a diet containing Salacia reticulata on mild type 2 diabetes in humans—a placebo-controlled, cross-over trial. J Jpn Soc Nutr Food Sci 53:199–205CrossRef
109.
go back to reference Jayawardena MHS, de Alwis NMW, Hettigoda V, Fernando DJS (2005) A double blind randomized placebo controlled cross over study of a herbal preparation containing Salacia reticulata in the treatment of type 2 diabetes. J Ethnopharmacol 97:215–218PubMedCrossRef Jayawardena MHS, de Alwis NMW, Hettigoda V, Fernando DJS (2005) A double blind randomized placebo controlled cross over study of a herbal preparation containing Salacia reticulata in the treatment of type 2 diabetes. J Ethnopharmacol 97:215–218PubMedCrossRef
110.
go back to reference Shivaprasad HN, Bhanumathy M, Sushma G, Midhun T, Raveendra KR, Sushma KR, Venkateshwarlu K (2013) Salacia reticulata improves serum lipid profiles and glycemic control in patients with prediabetes and mild to moderate hyperlipidemia: a double-blind, placebo-controlled, randomized trial. J Med Food 16:564–568PubMedCrossRef Shivaprasad HN, Bhanumathy M, Sushma G, Midhun T, Raveendra KR, Sushma KR, Venkateshwarlu K (2013) Salacia reticulata improves serum lipid profiles and glycemic control in patients with prediabetes and mild to moderate hyperlipidemia: a double-blind, placebo-controlled, randomized trial. J Med Food 16:564–568PubMedCrossRef
111.
go back to reference Collene AL, Hertzler SR, Williams JA, Wolf BW (2005) Effects of a nutritional supplement containing Salacia oblonga extract and insulinogenic amino acids on postprandial glycemia, insulinemia, and breath hydrogen responses in healthy adults. Nutrition 21:848–854PubMedCrossRef Collene AL, Hertzler SR, Williams JA, Wolf BW (2005) Effects of a nutritional supplement containing Salacia oblonga extract and insulinogenic amino acids on postprandial glycemia, insulinemia, and breath hydrogen responses in healthy adults. Nutrition 21:848–854PubMedCrossRef
112.
go back to reference Heacock PM, Hertzler SR, Williams JA, Wolf BW (2005) Effects of a medical food containing an herbal a-glucosidase inhibitor on postprandial glycemia and insulinemia in healthy adults. J Am Diet Assoc 105:66–71CrossRef Heacock PM, Hertzler SR, Williams JA, Wolf BW (2005) Effects of a medical food containing an herbal a-glucosidase inhibitor on postprandial glycemia and insulinemia in healthy adults. J Am Diet Assoc 105:66–71CrossRef
113.
go back to reference Williams JA, Choe YS, Noss MJ, Baumgartner CJ, Mustad VA (2007) Extract of Salacia oblonga lowers acute glycemia in patients with type 2 diabetes. Am J Clin Nutr 86:124–130PubMedCrossRef Williams JA, Choe YS, Noss MJ, Baumgartner CJ, Mustad VA (2007) Extract of Salacia oblonga lowers acute glycemia in patients with type 2 diabetes. Am J Clin Nutr 86:124–130PubMedCrossRef
114.
go back to reference Kobayashi M, Akaki J, Yamashita K, Morikawa T, Ninomiya K, Yoshikawa M, Muraoka O (2010) Suppressive effect of the tablet containing Salacia chinensis extract on postprandial blood glucose. Jpn Pharmacol Ther 38:545–550 Kobayashi M, Akaki J, Yamashita K, Morikawa T, Ninomiya K, Yoshikawa M, Muraoka O (2010) Suppressive effect of the tablet containing Salacia chinensis extract on postprandial blood glucose. Jpn Pharmacol Ther 38:545–550
115.
go back to reference Kobayashi M, Akaki J, Ninomiya K, Yoshikawa M, Muraoka O, Morikawa T, Odawara M (2021) Dose-dependent suppression of postprandial hyperglycemia and improvement of blood glucose parameters by Salacia chinensis extract: two randomized, double-blind, placebo-controlled studies. J Med Food 24:10–17PubMedCrossRef Kobayashi M, Akaki J, Ninomiya K, Yoshikawa M, Muraoka O, Morikawa T, Odawara M (2021) Dose-dependent suppression of postprandial hyperglycemia and improvement of blood glucose parameters by Salacia chinensis extract: two randomized, double-blind, placebo-controlled studies. J Med Food 24:10–17PubMedCrossRef
Metadata
Title
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
Publication date
01-06-2021
Publisher
Springer Singapore
Keyword
Miglitol
Published in
Journal of Natural Medicines / Issue 3/2021
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-021-01522-0

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