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Volumn 21, Issue 8, 2012, Pages 1762-1770

Synthesis and structure-activity relationships of serotonin derivatives effect on α-glucosidase inhibition

Author keywords

Glucosidase inhibitor; Diabetes; Serotonin derivatives; Structure activity relationship

Indexed keywords

1 DEOXYNOJIRIMYCIN; ACARBOSE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; CAFFEIC ACID; CINNAMIC ACID; N 3,4 DIMETHOXY CINNAMOYL SEROTONIN; N 4 COUMAROYL SEROTONIN; N 4 METHOXY CINNAMOYL SEROTONIN; N CAFFEOYL SEROTONIN; N CAFFEOYLSEROTONIN; N DIHYDRO P COUMAROYLSEROTONIN; N DIHYDROCAFFEOYL SEROTONIN; N DIHYDROCAFFEOYLSEROTONIN; N DIHYDROCINNAMOYL SEROTONIN; N DIHYDROFERULOYL SEROTONIN; N DIHYDROSINAPOYL SEROTONIN; N FERULOYL SEROTONIN; N ISOFERULOYL SEROTONIN; N SINAPOYL SEROTONIN; SEROTONIN DERIVATIVE; SINAPIC ACID; UNCLASSIFIED DRUG;

EID: 84866078672     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9699-9     Document Type: Article
Times cited : (12)

References (32)
  • 2
    • 0029078838 scopus 로고
    • N-Alkylated nitrogen-in-the-ring sugars: Conformational basis of inhibition of glycosidases and HIV-1 replication
    • Asano N, Kizu H, Oseki K, Tomioka E, Matsui K, Okamoto M, Baba M (1995) N-Alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication. J Med Chem 38:2349-2356
    • (1995) J Med Chem , vol.38 , pp. 2349-2356
    • Asano, N.1    Kizu, H.2    Oseki, K.3    Tomioka, E.4    Matsui, K.5    Okamoto, M.6    Baba, M.7
  • 3
    • 1842550442 scopus 로고    scopus 로고
    • Cytotoxicity of phenolic compounds isolated from seeds of safflower (Carthamus tinctorius L.)
    • Bae S, Shim S, Park Y, Lee J, Chang E, Choi S (2002) Cytotoxicity of phenolic compounds isolated from seeds of safflower (Carthamus tinctorius L.). Food Sci Biotechnol 11:140-146
    • (2002) Food Sci Biotechnol , vol.11 , pp. 140-146
    • Bae, S.1    Shim, S.2    Park, Y.3    Lee, J.4    Chang, E.5    Choi, S.6
  • 4
    • 0029046739 scopus 로고
    • Hypoglycemic activity and mechanism of extracts from mulberry leaves and cortex mori radices in streptozotocin induced diabetic mice
    • Chen FJ, Nakashima N, Kimura I, Kimura M (1995) Hypoglycemic activity and mechanism of extracts from mulberry leaves and cortex mori radices in streptozotocin induced diabetic mice. Yakugaku Zasshi 115:476-482
    • (1995) Yakugaku Zasshi , vol.115 , pp. 476-482
    • Chen, F.J.1    Nakashima, N.2    Kimura, I.3    Kimura, M.4
  • 5
    • 77956628381 scopus 로고    scopus 로고
    • Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose
    • Choi CW, Choi YH, Mi-ran Cha, Yoo DS, Kim YS, Yon GH, Hong KS, Kim YH, Ryu SY (2010) Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose. J Agric Food Chem 58:9988-9993
    • (2010) J Agric Food Chem , vol.58 , pp. 9988-9993
    • Choi, C.W.1    Choi, Y.H.2    Cha, M.3    Yoo, D.S.4    Kim, Y.S.5    Yon, G.H.6    Hong, K.S.7    Kim, Y.H.8    Ryu, S.Y.9
  • 7
    • 0034170289 scopus 로고    scopus 로고
    • Protection from vascular risk in diabetic hypertension
    • Corry DB, Tuck ML (2000) Protection from vascular risk in diabetic hypertension. Curr Hypertens Rep 2:154-159
    • (2000) Curr Hypertens Rep , vol.2 , pp. 154-159
    • Corry, D.B.1    Tuck, M.L.2
  • 8
    • 0026014062 scopus 로고
    • β1-6 branched oligosaccharides as a marker of tumor progression in human breast and colon neoplasia
    • Fernandes B, Sagman U, Auger M, Demetrio M, Dennis JW (1991) β1-6 branched oligosaccharides as a marker of tumor progression in human breast and colon neoplasia. Cancer Res 51:718-723
    • (1991) Cancer Res , vol.51 , pp. 718-723
    • Fernandes, B.1    Sagman, U.2    Auger, M.3    Demetrio, M.4    Dennis, J.W.5
  • 9
    • 11844294865 scopus 로고    scopus 로고
    • α-Glucosidase inhibitors for patients with type 2 diabetes: Results from a Cochrane systematic review and meta-analysis
    • Floris AL, Peter LL, Reinier PA, Eloy HL, Guy ER, Chris W (2005) α-Glucosidase inhibitors for patients with type 2 diabetes: results from a Cochrane systematic review and meta-analysis. Diabetes Care 28:154-163
    • (2005) Diabetes Care , vol.28 , pp. 154-163
    • Floris, A.L.1    Peter, L.L.2    Reinier, P.A.3    Eloy, H.L.4    Guy, E.R.5    Chris, W.6
  • 10
    • 0031975069 scopus 로고    scopus 로고
    • The effects of improved glycemic control on complications in type 2 diabetes
    • Gaster B, Hirsch IB (1998) The effects of improved glycemic control on complications in type 2 diabetes. Arch Intern Med 158: 134-140
    • (1998) Arch Intern Med , vol.158 , pp. 134-140
    • Gaster, B.1    Hirsch, I.B.2
  • 12
    • 0022475489 scopus 로고
    • Inhibition of experimental metastasis by castanospermine in mice: Blockage of two distinct stages of tumor colonization by oligosaccharide processing inhibitors
    • Humphries MJ, Matsumoto K, White SL, Olden K (1986) Inhibition of experimental metastasis by castanospermine in mice: blockage of two distinct stages of tumor colonization by oligosaccharide processing inhibitors. Cancer Res 46:5215-5222
    • (1986) Cancer Res , vol.46 , pp. 5215-5222
    • Humphries, M.J.1    Matsumoto, K.2    White, S.L.3    Olden, K.4
  • 13
    • 56049105599 scopus 로고    scopus 로고
    • Potent α-glucosidase inhibitors purified from the red alga Grateloupia elliptica
    • Kim KY, Nam KA, Kurihara H, Kim SM (2008) Potent α-glucosidase inhibitors purified from the red alga Grateloupia elliptica. Phytochemistry 69:2820-2825
    • (2008) Phytochemistry , vol.69 , pp. 2820-2825
    • Kim, K.Y.1    Nam, K.A.2    Kurihara, H.3    Kim, S.M.4
  • 14
    • 38349054049 scopus 로고    scopus 로고
    • Structure and absolute configuration of clerodane diterpene glycosides and a rearranged cadinane sesquiterpene glycoside from the stems of Tinospora sinensis
    • Li W, Wei K, Fu H, Koike K (2007) Structure and absolute configuration of clerodane diterpene glycosides and a rearranged cadinane sesquiterpene glycoside from the stems of Tinospora sinensis. J Nat Prod 70:1971-1976
    • (2007) J Nat Prod , vol.70 , pp. 1971-1976
    • Li, W.1    Wei, K.2    Fu, H.3    Koike, K.4
  • 15
    • 30444438410 scopus 로고    scopus 로고
    • Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: New structures for antivirals and osteoarthritis
    • Liang PH, Cheng WC, Lee YL, Yu HP, Wu YT, Lin YL, Wong CH (2006) Novel five-membered iminocyclitol derivatives as selective and potent glycosidase inhibitors: new structures for antivirals and osteoarthritis. ChemBioChem 7:165-173
    • (2006) ChemBioChem , vol.7 , pp. 165-173
    • Liang, P.H.1    Cheng, W.C.2    Lee, Y.L.3    Yu, H.P.4    Wu, Y.T.5    Lin, Y.L.6    Wong, C.H.7
  • 16
    • 0026558790 scopus 로고
    • Effect of an intestinal disaccharidase inhibitor (AO-128) on obesity and diabetes
    • Matsuo T, Odaka H, Ikeda H (1992) Effect of an intestinal disaccharidase inhibitor (AO-128) on obesity and diabetes. Am J Clin Nutr 55:314s-317s
    • (1992) Am J Clin Nutr , vol.55
    • Matsuo, T.1    Odaka, H.2    Ikeda, H.3
  • 17
    • 0034022660 scopus 로고    scopus 로고
    • Tyrosinase inhibitory and antitumor promoting activities of compunds isolated from safflower (Carthamus tinctorius L.) and cotton (Gossypium hirsutum L.) oil cakes
    • Nagatsu A, Zhang HL, Mizukami H, Okuyama H, Sakakibara J, Tokuda H, Nishino H (2000) Tyrosinase inhibitory and antitumor promoting activities of compunds isolated from safflower (Carthamus tinctorius L.) and cotton (Gossypium hirsutum L.) oil cakes. Nat Prod Lett 14:153-158
    • (2000) Nat Prod Lett , vol.14 , pp. 153-158
    • Nagatsu, A.1    Zhang, H.L.2    Mizukami, H.3    Okuyama, H.4    Sakakibara, J.5    Tokuda, H.6    Nishino, H.7
  • 18
    • 0035112246 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of α-L-fucosidase inhibitors: 5a-carba-a-L-fucopyranosylamine and related compounds
    • Ozawa S, Maruyama A, Odagiri T, Yuasa H, Hashimoto H (2001) Synthesis and biological evaluation of α-L-fucosidase inhibitors: 5a-carba-a-L- fucopyranosylamine and related compounds. Eur J Org Chem 5:967-974
    • (2001) Eur J Org Chem , vol.5 , pp. 967-974
    • Ozawa, S.1    Maruyama, A.2    Odagiri, T.3    Yuasa, H.4    Hashimoto, H.5
  • 19
    • 0000666747 scopus 로고
    • A cathartic lignan glycoside isolated from Carthamus tinctorius
    • Palter R, Lundin RE, Haddon WF (1972a) A cathartic lignan glycoside isolated from Carthamus tinctorius. Phytochemistry 11:2871-2874
    • (1972) Phytochemistry , vol.11 , pp. 2871-2874
    • Palter, R.1    Lundin, R.E.2    Haddon, W.F.3
  • 20
    • 1642494745 scopus 로고
    • Structure of a safflower steroid cellobioside
    • Palter R, Haddon WF, Lundin RE (1972b) Structure of a safflower steroid cellobioside. Phytochemistry 11:2327-2328
    • (1972) Phytochemistry , vol.11 , pp. 2327-2328
    • Palter, R.1    Haddon, W.F.2    Lundin, R.E.3
  • 21
    • 21644477129 scopus 로고    scopus 로고
    • Inhibitory effects of active compounds isolated from safflower (Carthamus tinctorius L.) seeds for melanogenesis
    • Roh JS, Han JY, Kim JH, Hwong JK (2004) Inhibitory effects of active compounds isolated from safflower (Carthamus tinctorius L.) seeds for melanogenesis. Biol Pharm Bull 27:1976-1978
    • (2004) Biol Pharm Bull , vol.27 , pp. 1976-1978
    • Roh, J.S.1    Han, J.Y.2    Kim, J.H.3    Hwong, J.K.4
  • 23
    • 74949102237 scopus 로고    scopus 로고
    • 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
    • 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 49:443-451
    • (2010) Biochemistry , vol.49 , pp. 443-451
    • Sim, L.1    Jayakanthan, K.2    Mohan, S.3    Nasi, R.4    Johnston, B.D.5    Pinto, B.M.6    Rose, D.R.7
  • 24
    • 0034641568 scopus 로고    scopus 로고
    • Association of glycaemia with macrovascular and microvascular complications of type 2 diabetes (UKPDS 35): Prospective observational study
    • Stratton IM, Adler AI, Neil HA, Matthews DR, Manley SE, Cull CA, Hadden D, Turner RC, Holman RR (2000) Association of glycaemia with macrovascular and microvascular complications of type 2 diabetes (UKPDS 35): prospective observational study. BMJ 321:405-412
    • (2000) BMJ , vol.321 , pp. 405-412
    • Stratton, I.M.1    Adler, A.I.2    Neil, H.A.3    Matthews, D.R.4    Manley, S.E.5    Cull, C.A.6    Hadden, D.7    Turner, R.C.8    Holman, R.R.9
  • 25
    • 78650292529 scopus 로고    scopus 로고
    • Tyrosinase inhibitory activities of cinnamic acid analogues
    • Takahashi T, Miyazawa M (2010) Tyrosinase inhibitory activities of cinnamic acid analogues. Pharmazie 65:913-918
    • (2010) Pharmazie , vol.65 , pp. 913-918
    • Takahashi, T.1    Miyazawa, M.2
  • 26
    • 79952490199 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition
    • Takahashi T, Miyazawa M (2011) Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition. Bioorg Med Chem Lett 21:1983-1986
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 1983-1986
    • Takahashi, T.1    Miyazawa, M.2
  • 27
    • 0032980754 scopus 로고    scopus 로고
    • Serotonin derivative, N-(p-coumaroyl)serotonin, isolated from safflower (Carthamus tinctorius L.) oil cake augments the proliferation of normal human and mouse fibroblasts in synergy with basic fibroblasts growth factor (bFGF) or epidermal growth factor (EGF)
    • Takii T, Hayashi M, Hiroma H, Chiba T, Kawashima S, Zhang HL, Nagatsu A, Sakakibara J, Onozaki K (1999) Serotonin derivative, N-(p-coumaroyl)serotonin, isolated from safflower (Carthamus tinctorius L.) oil cake augments the proliferation of normal human and mouse fibroblasts in synergy with basic fibroblasts growth factor (bFGF) or epidermal growth factor (EGF). J Biochem 125:910-915
    • (1999) J Biochem , vol.125 , pp. 910-915
    • Takii, T.1    Hayashi, M.2    Hiroma, H.3    Chiba, T.4    Kawashima, S.5    Zhang, H.L.6    Nagatsu, A.7    Sakakibara, J.8    Onozaki, K.9
  • 28
    • 0032511583 scopus 로고    scopus 로고
    • Intensive blood-glucose control with sulphonylureas or insulin compared with conventional treatment and risk of complications in patients with type 2 diabetes (UKPDS 33)
    • UK Prospective Diabetes Study (UKPDS) Group
    • UK Prospective Diabetes Study (UKPDS) Group (1998a) Intensive blood-glucose control with sulphonylureas or insulin compared with conventional treatment and risk of complications in patients with type 2 diabetes (UKPDS 33). Lancet 352:837-853
    • (1998) Lancet , vol.352 , pp. 837-853
  • 29
    • 0032511566 scopus 로고    scopus 로고
    • Effects of intensive blood-glucose control with metformin on complications in over weight patients with type 2 diabetes (UKPDS 34)
    • UK Prospective Diabetes Study (UKPDS) Group
    • UK Prospective Diabetes Study (UKPDS) Group (1998b) Effects of intensive blood-glucose control with metformin on complications in over weight patients with type 2 diabetes (UKPDS 34). Lancet 352:854-865
    • (1998) Lancet , vol.352 , pp. 854-865
  • 30
    • 0030662005 scopus 로고    scopus 로고
    • Estimated benefits of glycemic control in microvascular complications in type 2 diabetes
    • Vijan S, Hofer TP, Hayward RA (1997) Estimated benefits of glycemic control in microvascular complications in type 2 diabetes. Ann Intern Med 127:788-795
    • (1997) Ann Intern Med , vol.127 , pp. 788-795
    • Vijan, S.1    Hofer, T.P.2    Hayward, R.A.3
  • 31
    • 77952583265 scopus 로고    scopus 로고
    • α-Glucosidase and a-amylase inhibitory activities of guava leaves
    • Wang H, Du YJ, Song HC (2010) α-Glucosidase and a-amylase inhibitory activities of guava leaves. Food Chem 123:6-13
    • (2010) Food Chem , vol.123 , pp. 6-13
    • Wang, H.1    Du, Y.J.2    Song, H.C.3
  • 32
    • 0038186716 scopus 로고    scopus 로고
    • Antioxidative compounds isolated from safflower (Carthamus tinctorius L.) oil cake
    • Zhang HL, Nagatsu A, Watanabe T, Sakakibara J, Okuyama H (1997) Antioxidative compounds isolated from safflower (Carthamus tinctorius L.) oil cake. Chem Pharm Bull 45:1910-1914
    • (1997) Chem Pharm Bull , vol.45 , pp. 1910-1914
    • Zhang, H.L.1    Nagatsu, A.2    Watanabe, T.3    Sakakibara, J.4    Okuyama, H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.