The role of triterpenes in the management of diabetes mellitus and its complications
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Ahmed N (2005) Advanced glycation endproducts-role in pathology of diabetic complications. Diabetes Res Clin Pract 67:3–21
Alberts P, Engblom L, Edling N, Forsgren M, Klingström G, Larsson C, Rönquist-Nii Y, Öhman B, Abrahmsén L (2002) Selective inhibition of 11β-hydroxysteroid dehydrogenase type 1 decreases blood glucose concentrations in hyperglycaemic mice. Diabetologia 45:1528–1532
Ali MS, Jahangir M, ul Hussan SS, Choudhary MI (2002) Inhibition of α-glucosidase by oleanolic acid and its synthetic derivatives. Phytochemistry 60:295–299
Ali H, Houghton PJ, Soumyanath A (2006) α-Amylase inhibitory activity of some Malaysian plants used to treat diabetes; with particular reference to Phyllanthus amarus. J Ethnopharmacol 107:449–455
Ardiles AE, González-Rodríguez Á, Núñez MJ, Perestelo NR, Pardo V, Jiménez IA, Valverde ÁM, Bazzocchi IL (2012) Studies of naturally occurring friedelane triterpenoids as insulin sensitizers in the treatment type 2 diabetes mellitus. Phytochemistry 84:116–124
Atanasov AG, Dzyakanchuk AA, Schweizer RAS, Nashev LG, Maurer EM, Odermatt A (2006) Coffee inhibits the reactivation of glucocorticoids by 11β-hydroxysteroid dehydrogenase type 1: a glucocorticoid connection in the anti-diabetic action of coffee? FEBS Lett 580:4081–4085
Baker DJ, Timmons JA, Greenhaff PL (2005) Glycogen phosphorylase inhibition in type 2 diabetes therapy. A systematic evaluation of metabolic and functional effects in rat skeletal muscle. Diabetes 54:2453–2459
Baltina LA, Flekhter OB, Nigmatullina LR, Boreko EI, Pavlova NI, Nikolaeva SN, Savinova OV, Tolstikov GA (2003) Lupane triterpenes and derivatives with antiviral activity. Bioorg Med Chem Lett 13:3549–3552
Ban CR, Twigg SM (2008) Fibrosis in diabetes complications: pathogenic mechanisms and circulating and urinary markers. Vasc Health Risk Manag 4:575–596
Basta G, Schmidt AM, De Caterina R (2004) Advanced glycation end products and vascular inflammation: implications for accelerated atherosclerosis in diabetes. Cardiovasc Res 63:582–592
Blum A, Favia AD, Maser E (2009) 11β-hydroxysteroid dehydrogenase type 1 inhibitors with oleanan and ursan scaffolds. Mol Cell Endocrinol 301:132–136
Brala PM, Hagen RL (1983) Effects of sweetness perception and caloric value of a preload on short term intake. Physiol Behav 30:1–9
Cerga O, Borcan F, Ambrus R, Popovici I (2011) Syntheses of new cyclodextrin complexes with oleanolic and ursolic acids. J Agroaliment Proc Technol 17:405–409
Chen X, Lou G, Meng Z, Huang W (2011) TGR5: a novel target for weight maintenance and glucose metabolism. Exp Diabetes Res. Article ID 853501
Cheng HM, González RG (1986) The effect of high glucose and oxidative stress on lens metabolism, aldose reductase, and senile cataractogenesis. Metabolism 35:10–14
Choi YH, Zhou W, Oh J, Choe S, Kim DW, Lee SH, Na MK (2012) Rhododendric acid A, a new ursane-type PTP1B inhibitor from the endangered plant Rhododendron brachycarpum G. Don. Bioorg Med Chem Lett 22:6116–6119
de Sales PM, Monteiro de Souza P, Alberto Simeoni L, de Oliveira Magalhães P, Silveira D (2012) α-Amylase inhibitors: a review of raw material and isolated compounds from plant source. J Pharm Pharmaceut Sci 15:141–183. www.cspsCanada.org
Deutschländera MS, Lall N, Van de Venter M, Hussein AA (2011) Hypoglycemic evaluation of a new triterpene and other compounds isolated from Euclea undulata Thunb. var. myrtina (Ebenaceae) root bark. J Ethnopharmacol 133:1091–1095
Evans JL, Goldfine ID, Maddux BA, Grodsky GM (2002) Oxidative stress and stress-activated signaling pathways: a unifying hypothesis of type 2 diabetes. Endocr Rev 23:599–622
Fröde TS, Medeiros YS (2008) Animal models to test drugs with potential antidiabetic activity. J Ethnopharmacol 115:173–183
Genet C, Strehle A, Schmidt C, Boudjelal G, Lobstein A, Schoonjans K, Souchet M, Auwerx J, Saladin R, Wagner A (2010a) Structure-activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: potential impact in diabetes. J Med Chem 53:178–190
Genet C, Schmidt C, Strehle A, Schoonjans K, Auwerx J, Saladin R, Wagner A (2010b) Redefining the TGR5 triterpenoid binding pocket at the C-3 position. ChemMedChem 5:1983–1988
Ghosh T, Maity TK, Singh J (2011) Antihyperglycemic activity of bacosine, a triterpene from Bacopa monnieri, in alloxan-induced diabetic rats. Planta Med 77:804–808
Goldin A, Beckman JA, Schmidt AM, Creager MA (2006) Advanced glycation end products sparking the development of diabetic vascular injury. Circulation 114:597–605
Goldstein BJ (2002) Protein-tyrosine phosphatases: emerging targets for therapeutic intervention in type 2 diabetes and related states of insulin resistance. J Clin Endocrinol Metab 87:2474–2480
Gowri PM, Tiwari AK, Ali AZ, Rao JM (2007) Inhibition of α-glucosidase and amylase by bartogenic acid isolated from Barringtonia racemosa Roxb. seeds. Phytother Res 21:796–799
Guan T, Qian Y, Tang X, Huang M, Huang L, Li Y, Sun H (2011) Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation. J Neurosci Res 89:1829–1839
Harborne JB, Baxter H (1993) Phytochemical dictionary. A handbook of bioactive compounds from plants. Taylor & Francis, London, pp 728–738
Hou W, Li Y, Zhang Q, Wei X, Peng A, Chen L, Wei Y (2009) Triterpene acids isolated from Lagerstroemia speciosa leaves as α-glucosidase inhibitors. Phytother Res 23:614–618
Huang Y-C, Chang W-L, Huang S-F, Lin C-Y, Lin H-C, Chang T-C (2010) Pachymic acid stimulates glucose uptake through enhanced GLUT4 expression and translocation. Eur J Pharmacol 648:39–49
Ishijima S, Takashima T, Ikemura T, Izutani Y (2008) Gymnemic acid interacts with mammalian glycerol-3-phosphate dehydrogenase. Mol Cell Biochem 310:203–208
Jäger S, Trojan H, Kopp T, Laszczyk MN, Scheffler A (2009) Pentacyclic triterpene distribution in various plants–rich sources for a new group of multi-potent plant extracts. Molecules 14:2016–2031
Jang S-M, Yee S-T, Choi J, Choi M-S, Do G-M, Jeon S-M, Yeo J, Kim M-J, Seo K-I, Lee M-K (2009) Ursolic acid enhances the cellular immune system and pancreatic β-cell function in streptozotocin-induced diabetic mice fed a high-fat diet. Int Immunopharmacol 9:113–119
Jiang B, Yang Y, Jin H, Shang W, Zhou L, Qian L, Chen M (2008) Astragaloside IV attenuates lipolysis and improves insulin resistance induced by TNFα in 3T3-L1 adipocytes. Phytother Res 22:1434–1439
Judy WV, Hari SP, Stogsdill WW, Judy JS, Naguib YMA, Passwater R (2003) Antidiabetic activity of a standardized extract (Glucosol™) from Lagerstroemia speciosa leaves in Type II diabetics. A dose-dependence study. J Ethnopharmacol 87:115–117
Jung SH, Ha YJ, Shim EK, Choi SY, Jin JL, Yun-Choi HS, Lee JR (2007) Insulin-mimetic and insulin-sensitizing activities of a pentacyclic triterpenoid insulin receptor activator. Biochem J 403:243–250
Keller AC, Ma J, Kavalier A, He K, Brillantes A-MB, Kennelly EJ (2011) Saponins from the traditional medicinal plant Momordica charantia stimulate insulin secretion in vitro. Phytomedicine 19:32–37
Kuang H-X, Li H-W, Wang Q-H, Yang B-Y, Wang Z-B, Xia Y-G (2011) Triterpenoids from the roots of Sanguisorba tenuifolia var. alba. Molecules 16:4642–4651
Kwon J-H, Chang M-J, Seo H-W, Lee J-H, Min B-S, Na MK, Kim JC, Woo MH, Choi JS, Lee HK, Bae KH (2008) Triterpenoids and a sterol from the stem-bark of Styrax japonica and their protein tyrosine phosphatase 1B inhibitory activities. Phytother Res 22:1303–1306
Lai Y-C, Chen C-K, Tsai S-F, Lee S-S (2012) Triterpenes as α-glucosidase inhibitors from Fagus hayatae. Phytochemistry 74:206–211
Laszczyk MN (2009) Pentacyclic triterpenes of the lupane, oleanane and ursane group as tools in cancer therapy. Planta Med 75:1549–1560
Lee M-S, Hwang J-T, Kim S-H, Yoon S, Kim M-S, Yang HJ, Kwon DY (2010) Ginsenoside Rc, an active component of Panax ginseng, stimulates glucose uptake in C2C12 myotubes through an AMPK-dependent mechanism. J Ethnopharmacol 127:771–776
Li T-H, Hou C-C, Chang CL-T, Yang W-C (2011) Anti-hyperglycemic properties of crude extract and triterpenes from Poria cocos. Evid base Compl Altern Med. Article ID 128402
Lipson VV, Zamigajlo LL, Petrova ON (2011) Development of 11β-HSD1 inhibitors for the treatment of metabolic syndrome. Ukr Bioorg Acta 2:3–13
Liu J, Sun H, Duan W, Mu D, Zhang L (2007) Maslinic acid reduces blood glucose in KK-Ay mice. Biol Pharm Bull 30:2075–2078
Liu J, He T, Lu Q, Shang J, Sun H, Zhang L (2010) Asiatic acid preserves beta cell mass and mitigates hyperglycemia in streptozocin-induced diabetic rats. Diabetes Metab Res Rev 26:448–454
Lü H, Chen J, Li WL, Ren BR, Wu JL, Kang HY, Zhang HQ, Adams A, De Kimpe N (2009) Hypoglycemic and hypolipidemic effects of the total triterpene acid fraction from folium Eriobotryae. J Ethnopharmacol 122:486–491
Luo J-G, Liu J, Kong L-Y (2008) New pentacyclic triterpenes from Gypsophila oldhamiana and their biological evaluation as glycogen phosphorylase inhibitors. Chem Biodivers 5:751–757
Lv L, Wu S-Y, Wang G-F, Zhang J-J, Pang J-X, Liu Z-Q, Xu W, Wu S-G, Rao J-J (2010) Effect of astragaloside IV on hepatic glucose-regulating enzymes in diabetic mice induced by a high-fat diet and streptozotocin. Phytother Res 24:219–224
Manna P, Sinha M, Sil PC (2009) Prophylactic role of arjunolic acid in response to streptozotocin mediated diabetic renal injury: activation of polyol pathway and oxidative stress responsive signaling cascades. Chem Biol Interact 181:297–308
Manna P, Ghosh J, Das J, Sil PC (2010) Streptozotocin induced activation of oxidative stress responsive splenic cell signaling pathways: protective role of arjunolic acid. Toxicol Appl Pharmacol 244:114–129
Matsuda H, Murakami T, Jashiro K, Yamahara J, Yoshikawa M (1999) Antidiabetic principles of natural medicines. IV. Aldose reductase and α-glucosidase inhibitors from the roots of Salacia oblonga Wall. (Celastraceae): structure of a new friedelane-type triterpene, kotalagenin 16-acetate. Chem Pharm Bull 47:1725–1729
Motomura K, Fujiwara Y, Kiyota N, Tsurushima K, Takeya M, Nohara T, Nagai R, Ikeda T (2009) Astragalosides isolated from the root of Astragalus Radix inhibit the formation of advanced glycation end products. J Agric Food Chem 57:7666–7672
Na MK, Cui L, Min BS, Bae KH, Yoo JK, Kim BY, Oh WK, Ahn JS (2006a) Protein tyrosine phosphatase 1B inhibitory activity of triterpenes isolated from Astilbe koreana. Bioorg Med Chem Lett 16:3273–3276
Na MK, Yang S, He L, Oh H, Kim BS, Oh WK, Kim BY, Ahn JS (2006b) Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata. Planta Med 72:261–263
Na M, Kim BY, Osada H, Ahn JS (2009) Inhibition of protein tyrosine phosphatase 1B by lupeol and lupenone isolated from Sorbus commixta. J Enzym Inhib Med Chem 24:1056–1059
Na MK, Thuong PT, Hwang IH, Bae KH, Kim BY, Osada H, Ahn JS (2010) Protein tyrosine phosphatase 1B inhibitory activity of 24-norursane triterpenes isolated from Weigela subsessilis. Phytother Res 24:1716–1719
Oikonomakos NG, Skamnaki VT, Tsitsanou KE, Gavalas NG, Johnson LN (2000) A new allosteric site in glycogen phosphorylase b as a target for drug interactions structure. Structure 8:575–584
Ono E, Inoue J, Hashidume T, Shimizu M, Sato R (2011) Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet. Biochem Biophys Res Commun 410:677–681
Petrash JM (2004) All in the family: aldose reductase and closely related aldo-ketoreductases. Cell Mol Life Sci 61:737–749
Rahimi R, Nikfar S, Larijani B, Abdollahi M (2005) A review on the role of antioxidants in the management of diabetes and its complications. Biomed Pharmacother 59:365–373
Ramachandran S, Prasad NR (2008) Effect of ursolic acid, a triterpenoid antioxidant, on ultraviolet-B radiation-induced cytotoxicity, lipid peroxidation and DNA damage in human lymphocytes. Chem Biol Interact 176:99–107
Ramírez-Espinosa JJ, Rios MY, López-Martínez S, López-Vallejo F, Medina-Franco JL, Paoli P, Camici G, Navarrete-Vázquez G, Ortiz-Andrade R, Estrada-Soto S (2011) Antidiabetic activity of some pentacyclic acid triterpenoids, role of PTP-1B: in vitro, in silico, and in vivo approaches. Eur J Med Chem 46:2243–2251
Rollinger JM, Kratschmar DV, Schuster D, Pfisterer PH, Gumy C, Aubry EM, Brandstöttera S, Stuppner H, Wolber G, Odermatt A (2010) 11β-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches. Bioorg Med Chem 18:1507–1515
Sanchez-Gonzalez M, Lozano-Mena G, Juan ME, Garcia-Granados A, Planas JM (2013) Assessment of the safety of maslinic acid, a bioactive compound from Olea europaea L. Mol Nutr Food Res 57:339–346
Santos FA, Frota JT, Arruda BR, de Melo TS, da Silva AA, Brito GA, Chaves MH, Rao VS (2012) Antihyperglycemic and hypolipidemic effects of α, β-amyrin, a triterpenoid mixture from Protium heptaphyllum in mice. Lipids Health Dis 11:98
Sasaki T, Li W, Morimura H, Li S, Li Q, Asada Y, Koike K (2011) Chemical constituents from Sambucus adnata and their protein-tyrosine phosphatase 1B inhibitory activities. Chem Pharml Bull 59:1396–1399
Sato M, Tai T, Nunoura Y, Yajima Y, Kawashima S, Tanaka K (2002) Dehydrotrametenolic acid induces preadipocyte differentiation and sensitizes animal models of noninsulin-dependent diabetes mellitus to insulin. Biol Pharm Bull 25:81–86
Sato H, Genet C, Strehle A, Thomas C, Lobstein A, Wagner A, Mioskowski C, Auwerx J, Saladin R (2007) Anti-hyperglycemic activity of a TGR5 agonist isolated from Olea europaea. Biochem Biophys Res Commun 362:793–798
Seo C, Yim JH, Lee HK, Oh H (2011) PTP1B inhibitory secondary metabolites from the Antarctic lichen Lecidella carpathica. Mycology 2:18–23
Shi L, Zhang W, Zhou Y-Y, Zhang Y-N, Li J-Y, Hu L-H, Li J (2008) Corosolic acid stimulates glucose uptake via enhancing insulin receptor phosphorylation. Eur J Pharmacol 584:21–29
Shih C-C, Lin C-H, Wu J-B (2010) Eriobotrya japonica improves hyperlipidemia and reverses insulin resistance in high-fat-fed mice. Phytother Res 24:1769–1780
Sticher O (2010) Triterpene einschließlich Steroide. In: Hänsel R, Sticher O (eds) Pharmacognosie–phytopharmazie, 9. Auflage. Springer Medizin Verlag, Heidelberg, pp 833–863
Stulnig TM, Waldhäusl W (2004) 11β-Hydroxysteroid dehydrogenase type 1 in obesity and type 2 diabetes. Diabetologia 47:1–11
Su W, Dai D-Z, Liu H-R, Na T, Dai Y (2007) Upregulated endothelin system in diabetic vascular dysfunction and early retinopathy is reversed by CPU0213 and total triterpene acids from Fructus Corni. Clin Exp Pharmacol Physiol 34:1228–1233
Sudhahar V, Kumar SA, Sudharsan PT, Varalakshmi P (2007) Protective effect of lupeol and its ester on cardiac abnormalities in experimental hypercholesterolemia. Vasc Pharmacol 46:412–418
Suttisri R, Lee I-S, Kinghorn AD (1995) Plant-derived triterpenoid sweetness inhibitors. J Ethnopharmacol 47:9–26
Tahrani AA, Bailey CJ, Del Prato S, Barnett AH (2011) Management of type 2 diabetes: new and future developments in treatment. Lancet 378:182–197
Tan M-J, Ye J-M, Turner N, Hohnen-Behrens C, Ke C-Q, Tang C-P, Chen T, Weiss C-H, Gesing E-R, Rowland A, James DE, Ye Y (2008) Antidiabetic activities of triterpenoids isolated from bitter melon associated with activation of the AMPK pathway. Chem Biol 15:263–273
Thareja S, Aggarwal S, Bhardwaj TR, Kumar M (2012) Protein tyrosine phosphatase 1B inhibitors: a molecular level legitimate approach for the management of diabetes mellitus. Med Res Rev 32:459–517
Uddin G, Rauf A, Al-Othman AM, Collina S, Arfan M, Ali A, Khan I (2012) Pistagremic acid, a glucosidase inhibitor from Pistacia integerrima. Fitoterapia 83:1648–1652
Ullevig SL, Zhao Q, Zamora D, Asmis R (2011) Ursolic acid protects diabetic mice against monocyte dysfunction and accelerated atherosclerosis. Atherosclerosis 219:409–416
Wamil M, Seckl JR (2007) Inhibition of 11ß-hydroxysteroid dehydrogenase type 1 as a promising therapeutic target. Drug Discov Today 12:504–520
Wang Z-H, Hsu C-C, Huang C-N, Yin M-C (2010) Anti-glycative effects of oleanolic acid and ursolic acid in kidney of diabetic mice. Eur J Pharmacol 628:255–260
Wang X, Li Y-L, Wu H, Liu J-Z, Hu J-X, Liao N, Peng J, Cao P-P, Liang X, Hai C-X (2011) Antidiabetic effect of oleanolic acid: a promising use of a traditional pharmacological agent. Phytother Res 25:1031–1040
Wen X, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P (2005) Pentacyclic triterpenes. Part 1: the first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Bioorg Med Chem Lett 15:4944–4948
Wen X, Zhang P, Liu J, Zhang L, Wu X, Ni P, Sun H (2006) Pentacyclic triterpenes. Part 2: synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors. Bioorg Med Chem Lett 16:722–726
Xiang M, Wang J, Zhang Y, Ling J, Xu X (2012) Attenuation of aortic injury by ursolic acid through RAGE-Nox-NFκB pathway in streptozocin-induced diabetic rats. Arch Pharm Res 35:877–886
Yamaguchi Y, Yamada K, Yoshikawa N, Nakamura K, Haginaka J, Kunitomo M (2006) Corosolic acid prevents oxidative stress, inflammation and hypertension in SHR/NDmcr-cp rats, a model of metabolic syndrome. Life Sci 79:2474–2479
Yang J, Chen H, Zhang L, Wang Q, Lai M-X (2010) Anti-diabetic effect of standardized extract of Potentilla discolor Bunge and identification of its active components. Drug Dev Res 71:127–132
Yasukawa K, Akihisa T, Oinuma H, Kasahara Y, Kimura Y, Yamanouchi S, Kumaki K, Tamura T, Takido M (1996) Inhibitory effect of di- and trihydroxy triterpenes from the flowers of Compositae on 12-O-tetradecanoylphorbol-13-acetate-induced inflammation in mice. Biol Pharm Bull 19:1329–1331
Yin MC, Chan KC (2007) Nonenzymatic antioxidative and antiglycative effects of oleanolic acid and ursolic acid. J Agric Food Chem 55:7177–7181
Yin M-C, Lin M-C, Mong M-C, Lin C-Y (2012) Bioavailability, distribution, and antioxidative effects of selected triterpenes in mice. J Agric Food Chem 60:7697–7701
Zeng X-Y, Wang Y-P, Cantley J, Iseli TJ, Molero JC, Hegarty BD, Kraegen EW, Ye Y, Ye M (2012) Oleanolic acid reduces hyperglycemia beyond treatment period with Akt/FoxO1-induced suppression of hepatic gluconeogenesis in type-2 diabetic mice. PLoS One 7:1–12
Zhang W, Hong D, Zhou Y, Zhang Y, Shen Q, Li J-Y, Hu L-H, LI J (2006) Ursolic acid and its derivative inhibit protein tyrosine phosphatase 1B, enhancing insulin receptor phosphorylation and stimulating glucose uptake. Biochim Biophys Acta 1760:1505–1512
Zhang XS, Bi X-L, Bi X-L, Wan-Xiao, Cao J-Q, Xia X-C, Diao Y-P, Zhao Y-Q (2013) Protein tyrosine phosphatase 1B inhibitory effect by dammarane-type triterpenes from hydrolyzate of total Gynostemma pentaphyllum saponins. Bioorg Med Chem Lett 23:297–300
Zhou Y, Li J-S, Zhang X, Wu Y-J, Huang K, Zheng L (2010) Ursolic acid inhibits early lesions of diabetic nephropathy. Int J Mol Med 26:565–570