Effect of Chemical Constituents from Syzygium cumini (Myrtaceae) on Glucose Uptake in Insulin-resistant L6 Cells *
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1 2009, 31 (5) : Acta Botanica Yunnanica DOI: SP. J , 2, 3, 1, 3, 1 (1, ; 2, ; 3, ) : ( Syzygium cumini) 8, L6, 7, 10 g ml - 1, (1) 17.35% ;, 0.1 g ml - 1, 5, 7, 3, 4, 5 - (8) 51.11% : ; ; ; : Q 946 : A : (2009) Effect of Chemical Constituents from Syzygium cumini (Myrtaceae) on Glucose Uptake in Insulin-resistant L6 Cells * LI Shi-Fei 1, 2, HUANG Nian-Xu 3, HAO Xiao-Jiang 1, LI Ling 3, LI Shun-Lin 1 * * ( 1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming , China ; 2 Graduate University of Chinese Academy of Sciences, Beijing , Ch ina ; 3 Yunnan Pharmacological Laboratories of Natural Products, Kunming Medical College, Kunming , China) Abstract: Eight known compounds isolated from the roots of Syzygium cumini were evaluated for their ability to enhance the glucose consumption in insulin-resistant L6 muscle cells induced by high concentration-insulin and glucose. All of compounds significantly enhanced the glucose consumption of insulin-resistant cells in the presence and absence of insulin. The glucose consumption was increased 17.35% and % by compound 1 ( friedelin) at a concentration of 10 g ml - 1 without insulin and by compound 8 (5, 7, 3, 4, 5 -pentahydroxyflavone) at a concentration of 0.1 g ml - 1 with insulin, respectively. Key words: Syzygium cumini ; Chemical constituents; Insulin resistance ; Glucose uptake ( Syzygium), m, ;, (, 1997),, ( Sagrawat, 2006) 20 60, : : Author for correspondence ; lisl@ mail. kib. ac. cn; Tel: ; Fax: : ( ) ; (2006C009Z) , : ( ),,
2 ( Sigogneau-Jagodzinski, 1967), (Mahapatra, 1985; Teixeira, 1997; Prince, 1998; Sharma, 2003 ), ( Prince, 2004 ),, L6,, 8,, ( 1 ), epifriedelanol ( 2 ), 24 ( S )-stigmast-5-en-3 -ol ( 3), 2 -hydroxybetulinic acid (4 ), arjunolic acid (5 ), 2, 3, 24-trihydroxyolean-12-en-28-oic acid (6 ), ( 7 ), 5, 7, 3, 4, 5 - ( 8) L6, ESI Waters 2695 HPLC-Thermo Finnigan LCQ Advantage API Qstar Pulsar, 5% 1 H, 13 C NMR Bruker AM 400 DRX 500, CDCl 3 CD 3 OD DMSO- d 6 ( Syzygium cumini L.), kg, 95% (3 h, 3 h, 2 h),, (20 g) , - ( ), A-H, B 1 (12 mg), 2 (11 mg), 3 (8 mg), 4 ( 15 mg) ; C 5 (20 mg), 6 (10 mg), H 7 (15 mg), 8 (25 mg) 1.3 (1 ),, C 30 H 50 O, ESIMS ( m z) : 427 [M+ H] + 1 H-NMR; (500 MHz, CDCl 3 ) H : 0.72 (3H, s, H - 24), 0.87 (3H, d, J = 7.0 Hz, H - 23), 0.95 (3H, s, H - 25), 1.00 ( 3H, s, H - 26), 1.01 ( 3H, s, H - 29 ), 1.05 (3H, s, H - 27), 1.18 (3H, s, H - 30 ), 1.25 (3H, s, H - 28) 13 C-NMR (125 MHz, CDCl 3 ) C : 41.2 (C - 1), 41.4 (C - 2), (C - 3 ), 59.4 ( C - 4), 42.1 (C - 5 ), 35.5 (C - 6), 30.5 (C - 7), 53.0 (C - 8), 37.4 (C - 9), 58.1 (C - 10), 32.3 (C - 11), 36.0 ( C - 12), 38.2 (C - 13), 39.6 ( C - 14 ),
3 5 : (C - 15), 32.7 ( C - 16), 30.0 (C - 17), 42.7 ( C - 18 ), 39.2 (C - 19), 28.1 ( C - 20), 34.9 (C - 21), 35.2 ( C - 22 ), 6.7 (C - 23), 22.3 ( C - 24), 14.6 ( C - 25), 17.8 ( C - 26 ), 18.1 ( C - 27), 20.3 (C - 28), 32.0 (C - 29), 18.6 (C - 30) Epifriedelanol ( 2 ),, C 30 H 52 O, ESIMS ( m z) : 429 [ M + H ] + 1 H-NMR; (400 MHz, CDCl 3 ) H : 0.72 (3H, s, H - 24), 0.87 ( 3H, d, J = 7.0 Hz, H - 23), 0.95 (3H, s, H - 25), 1.00 (3H, s, H - 26 ), 1.01 (3H, s, H - 29), 1.05 ( 3H, s, H - 27 ), 1.18 ( 3H, s, H - 30), 1.25 (3H, s, H - 28), 3.75 (1H, br d, J = 2.0 Hz, H - 3 ) 13 C- NMR (100 MHz, CDCl 3 ) C : 41.2 ( C - 1 ), 41.4 ( C - 2 ), 72.7 ( C - 3), 49.1 (C - 4), 42.1 (C - 5), 35.5 (C - 6 ), 30.5 (C - 7), 53.1 ( C - 8), 37.4 (C - 9), 61.2 ( C - 10), 32.3 ( C - 11), 36.0 (C - 12), 38.2 ( C - 13), 39.6 (C - 14), 31.7 ( C - 15), 32.7 (C - 16), 30.0 ( C - 17), 42.7 (C - 18), 39.2 ( C - 19), 28.2 (C - 20), 34.9 ( C - 21), 35.2 (C - 22), 11.6 ( C - 23), 16.3 (C - 24), 18.2 ( C - 25), 28.6 (C - 26), 20.1 ( C - 27), 17.5 (C - 28), 32.0 ( C - 29), 15.7 (C - 30 ) 24 ( S ) ( 3),, C 29 H 50 O; ESIMS ( m z) : 415 [ M + H] + 1 H-NMR ( 400 MHz, CDCl 3 ) H : 5.33 (1H, d, J = 4.8 Hz, H - 6), 3.50 (1H, m, H - 3), 0.99 (3H, s, H - 19), (12H, m), 0.67 (3H, s, H - 18) 13 C-NMR (100 MHz, CDCl 3 ) C : 37.2 (C - 1), 31.6 (C - 2), 71.7 ( C - 3), 42.2 (C - 4), (C - 5), (C - 6), 31.8 (C - 7 ), 35.5 ( C - 8), 50.0 ( C - 9 ), 36.5 ( C - 10), 21.0 (C - 11), 39.7 ( C - 12), 42.2 (C - 13 ), 56.7 ( C - 14), 24.2 ( C - 15), 28.2 ( C - 16), 56.0 ( C - 17), 11.8 ( C - 18), 19.4 ( C - 19), 36.1 ( C - 20), 18.7 ( C - 21), 33.8 ( C - 22), 25.9 ( C - 23), 45.7 ( C - 24), 29.0 ( C - 25), 19.0 ( C - 26), 19.8 (C - 27), 23.0 ( C - 28), 11.9 (C - 29 ) 2 -Hydroxybetulinic acid ( 4 ),, C 30 H 48 O 4, ESIMS ( m z) : 473 [M + H ] + 1 H-NMR; (400 MHz, CD 3 OD) H : 0.80, 0.90, 0.93, 0.98, 1.01, 1.69 (each 3H, s, 6 CH 3 ), 4.74 (1H, H - 29a), 4.61 (1H, H - 29b), 4.13 (1H, H - 2 ), 3.67 ( H - 3) 13 C-NMR (100 MHz, CD 3 OD) C : 47.1 (C - 1), 69.6 (C - 2), 84.4 (C - 3), 39.3 ( C - 4), 52.1 ( C - 5), 18.4 (C - 6), 34.3 (C - 7 ), 40.8 ( C - 8), 50.0 (C - 9 ), 37.6 (C - 10), 21.1 ( C - 11), 25.5 (C - 12), 38.3 ( C - 13 ), 42.5 (C - 14), 29.7 ( C - 15), 32.3 (C - 16), 57.5 ( C - 17 ), 49.0 (C - 18), 46.6 (C - 19), (C - 20), 30.6 (C - 21), 37.2 (C - 22), 16.5 ( C - 23), 28.4 (C - 24), 15.9 ( C - 25 ), 17.3 ( C - 26), 14.6 (C - 27 ), ( C - 28), ( C - 29), 19.3 (C - 30 ) Arjunolic acid ( 5 ),, C 30 H 48 O 5, ESIMS ( m z) : 511 [ M+ Na] + 1 H-NMR; (400 MHz, CDCl 3 -CD 3 OD) H : 5.22 (1H, br s, H - 12), 3.68 (1H, dt, J = 9.6, 6.8 Hz, H - 2), 3.47 (1H, d, J = 10.8 Hz, H - 3), 3.29 (2H, m, H - 23), 0.96 ( 3H, s, H - 27), 0.88 ( 3H, s, H - 25 ), 0.85 (3H, s, H - 30), 0.82 (3H, s, H - 29 ), 0.74 (3H, s, H - 26), 0.71 ( 3H, s, H - 24 ) 13 C-NMR ( 100 MHz, CDCl 3 - CD 3 OD) C : 45.8 (C - 1), 68.7 (C - 2 ), 78.8 (C - 3 ), 46.2 (C - 4), 48.6 (C - 5), 18.4 (C - 6 ), 32.4 ( C - 7), 1.7 (C - 8), 47.8 (C - 9), 38.0 ( C - 10), 23.7 ( C - 11), (C - 12), ( C - 13), 39.1 (C - 14 ), 27.0 (C - 15 ), 23.8 ( C - 16), 46.7 (C - 17), 41.1 (C - 18), (C - 19), 30.6 (C - 20), 33.8 (C - 21), 32.1 (C - 22), 67.7 ( C - 23), 13.1 (C - 24), 17.2 (C - 25), 17.1 (C - 26 ), 26.1 (C - 27 ), (C - 28), 32.9 (C - 29), 23.7 ( C - 30) 2, 3, 24-trihydroxyolean 12-en-28-oic acid ( 6 ),, C 30 H 48 O 5, ESIMS ( m z) : 511 [ M + Na] + 1 H-NMR; (400 MHz, DMSO- d 6 ) H : 5.16 ( 1H, br s, H - 12 ), 4.41 (1H, br. d, J = 4.8 Hz, H - 2), 4.24 (1H, d, J = 4.48 Hz, H - 3), 4.17 (2H, m, H - 23), 1.06 (3H, s, H - 27 ), 0.90 (3H, s, H - 25), 0.86 (3H, s, H - 30 ), 0.86 (3H, s, H - 29), 0.69 (3H, s, H - 26), 0.52 (3H, s, H - 24) 13 C-NMR (100 MHz, DMSO- d 6 ) C : 45.8 (C - 1), 67.4 (C - 2 ), 75.4 (C - 3), 46.2 (C - 4), 48.6 (C - 5), 17.4 ( C - 6), 32.4 ( C - 7), 41.7 ( C - 8 ), 47.8 ( C - 9 ), 38.0 ( C - 10 ), 23.7 ( C - 11), (C - 12), ( C - 13), 39.1 (C - 14), 27.0 (C - 15), 23.8 (C - 16), 46.7 (C - 17), 41.1 ( C - 18), 45.8 (C - 19), 30.6 (C - 20), 33.8 (C - 21), 32.1 ( C - 22), 63.8 (C - 23), 13.1 (C - 24), 16.9 (C - 25), 16.7 ( C - 26), 26.1 (C - 27), (C - 28), 32.9 (C - 29), 23.7 ( C - 30) (7 ),, C 15 H 12 O 8, ESIMS ( m z) : 321 [M+ H] + 1 H-NMR (400 MHz, Me 2 CO- d 6 ) H : 6.61 (2H, s, H - 2, 6 ), 5.98 (1H, d, J = 2.5 Hz, H - 6 ), 5.96 (1H, d, J = 2.5 Hz, H - 8), 4.92 ( 1H, d, J = 11.0 Hz, H - 2), 4.55 ( 1H, d, J = 11.0 Hz, H - 3 ) 13 C-NMR ( 100 MHz, Me 2 CO- d 6 ) C : 84.5 ( C - 2), 73.0 ( C - 3 ), (C - 4), (C - 5), 95.9 ( C - 6), ( C - 7 ), 96.9 ( C - 8), (C - 9), (C - 10), (C - 1 ), (C - 2 ), (C - 3 ), (C - 4 ), (C - 5 ), (C - 6 ) 5, 7, 3, 4, 5 - ( 8),, C 15 H 10 O 7, ESIMS ( m z ) : 303 [ M + H ] + 1 H-NMR ( 400 MHz, CD 3 OD) H : 6.87 (2H, s, H -2, 6 ), 6.38 (1H, s, H - 3), 6.32 (1H, d, J = 1.9 Hz, H - 8), 6.09 (1H, d, J = 1.9 Hz, H -6) L6 (L6 muscle cells ),
4 472 31, 2.2 L6 (Mitsumoto, 1992 ) L6,,, ml 96 ( 90 l), 1 2 d, 2% FBS MEM, 1 2 d, 3 4 d, 80% 90%, 2.3 L6, (Carol, 2002; Bailey and Turner, 2004) 25 mmol L nmol L h,, ( 0.1% DM- SO) (0.1% DMSO) ( g ml - 1 ), h, (GOD-PAP) (, 2003),,, 3, t- 3 1, L6,,, 19% 37%, ; L6 24,, 3 5, 6,, ( P < 0.05), -, 10 g ml - 1, %, g ml - 1, 8.21%, 1 L6, 1 (1 8) L6 Table 1 Glucose consumption of compounds ( 1-8 ) in insulin-resistant L6 muscle cells ( mmol L - 1 ) ( mmol L - 1 ) concentration concentration group ( g ml - 1 group ) - Ins (24 h) + Ins (48 h) ( g ml - 1 ) - Ins (24 h) + Ins (48 h) CON Compound * ## # * * ** * Compound * * Compound * * Compound ** * Compound * * * Compound * * * * Compound * * * Compound * * * * * x s, n = 3, # P < 0.05, ## P < 0.01, ( CON) ; * P < 0. 05, ** P < 0.01, ( t-test) x s, n = 3, # P < 0.05, ## P < 0.01, compare with CON; * P < 0.05, ** P < 0.01, compare with t-test
5 5 : 473 ;,, 2 5, 6,, ( P < 0.05 ), 8 (5, 7, 3, 4, 5 - ) 0.1 g ml - 1, 51.1%, 8 ( 1.78 g ml - 1 ), 10.7%, 8 L6,, 1997., 7 [M]. :, 124 Bailey CJ, Turner SL, Glucosamine i nduced insulin resistance in L6 muscle cells [ J ]. Diabetes, Obesity and Metabolism, 6: Carol H, Romel S, Nish P et al., Sustained exposure of L6 myotubes to high glucose and insulin decreases insulin-stimulated GLUT4 translocation but upregulates GLUT4 activity [ J ]. Diabetes, 51: Maha patra PK, Pal M, Chaudhari AKN et al., Preliminary studies on glycaemic effect of Syzigium cumini seeds. [ J ]. IRCS Medical Science Biochemistry, 13 : Mitsumoto Y, Klip A, Developmental regulation of the subcellular distribution and glycosylation of GLUT1 and GLUT4 glucose transporters during myogenesis of L6 muscle cells [ J ]. Journal of Biological Chemistry, 267: Prince PS, Menon VP, Pari L, Hypoglycaemic activity of Syzygium cumini seeds : effect on lipid peroxidation in alloxon diabetic rats [ J]. Journal of Ethnopharmacology, 61: 1 7 Prince PS, Kamalakkannan N, Menon VP, Antidiabetic and antihyperlipidaemic effect of alcoholic Syzigium cumini seeds in alloxan induced diabetic albino rats [ J ]. Journal of Ethnopharmacology, 91: Sagr awat H, Mann AS, Kharya MD, Pharmacological potential of Eugenia jambolana: A review [ J ]. Pharmacognosy Magazine, 2: Sharma SB, Nasir A, Prabhu KM et al., Hypoglycemic and hypolipidemic effect of ethanolic extract of seeds of Eugenia jambolana in alloxon- induced diabetic rabbits [ J]. Journal of Ethnopharmacology, 85: Sigogneau- Jagodzinski M, Bibal-Prot P, Chanez M et al., Hypoglycaemic and antidiabetic activity of a principle extracted from Eugenia jambolana [ J]. Comptes Rendus Hebdomadaires des S ances de l Acad mie des Sciences. S rie D: Sciences Naturelles, 264: Teixeira CC, Pinto LP, Kessler FHP et al., The effect of Syzygium cumini ( L.) skeels on postprandial blood glucose level in non diabetic rats and rats with streptozotocin induced diabetes mellitus [ J]. Journal of Ethnopharmacology, 56: Yang GZ ( ), Gao XP ( ), Yan JF ( ) et al., Establishment of GOD-POD assay in a minimal way and application to glucose metabolism of 3T3-L1 adipocyte and HepG2 cell in vitro [ J ]. Sichuan Journal of Anatomy ( ), 11: 12 15
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