Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil. (original) (raw)
Gruenwald J, Brendler T, Jaenicke C (2007) PDR for herbal medicines, 4th edn. Thomson Healthcare Inc., Montvale, pp 572–573 Google Scholar
Heck CI, de Mejia EG (2007) Yerba mate tea (Ilex paraguariensis): a comprehensive review on chemistry, health implications, and technological considerations. J Food Sci 72:R138–R151 ArticleCASPubMed Google Scholar
Bracesco N, Sanchez AG, Contreras V, Menini T, Gugliucci A (2011) Recent advances on Ilex paraguariensis research: minireview. J Ethnopharmacol 136:378–384 ArticleCASPubMed Google Scholar
Cardozo Junior EL, Morand C (2016) Interest of mate (Ilex paraguariensis A. St.-Hil.) as a new natural functional food to preserve human cardiovascular health—a review. J Funct Foods 21:440–454 ArticleCAS Google Scholar
Gan R-Y, Zhang D, Wang M, Corke H (2018) Health benefits of bioactive compounds from the genus Ilex, a source of traditional caffeinated beverages. Nutrients 10:1682 ArticlePubMed CentralCAS Google Scholar
Sugimoto S, Nakamura S, Yamamoto S, Yamashita C, Oda Y, Matsuda H, Yoshikawa M (2009) Brazilian natural medicines. III. Structures of triterpene oligoglycosides and lipase inhibitors from mate, leaves of Ilex paraguariensis. Chem Pharm Bull 57:257–261 ArticleCAS Google Scholar
Hussein GME, Matsuda H, Nakamura S, Hamao M, Akiyama T, Tamura K, Yoshikawa M (2011) Mate tea (Ilex paraguariensis) promotes satiety and body weight lowering in mice: involvement of glucagon-like peptide-1. Biol Pharm Bull 34:1849–1855 ArticleCASPubMed Google Scholar
Hussein GME, Matsuda H, Nakamura S, Akiyama T, Tamura K, Yoshikawa M (2011) Protective and ameliorative effects of maté (Ilex paraguariensis) on metabolic syndrome in TSOD mice. Phytomedicine 19:88–97 ArticleCASPubMed Google Scholar
Zapata FJ, Rebollo-Hernanz M, Novakofski JE, Nakamura MT, de Mejia EG (2020) Caffeine, but not other phytochemicals, in mate tea (Ilex paraguariensis St. Hilaire) attenuates high-fat-high-sucrose-diet-driven lipogenesis and body fat accumulation. J Funct Foods 64:103646 ArticleCAS Google Scholar
Rocha DS, Model JFA, Von Dentz M, Maschio J, Ohlweiler R, Lima MV, de Souza SK, Sarapio E, Vogt ÉL, Waszczuk M, Martiny S, Bassani VL, Kucharski LC (2021) Adipose tissue of female Wistar rats respond to Ilex paraguariensis treatment after ovariectomy surgery. J Tradit Complement Med 11:238–248 ArticlePubMed Google Scholar
Gebara KS, Gasparotto Junior A, Palozi RAC, Morand C, Bonetti CI, Gozzi PT, de Mello MRF, Costa TA, Cardozo Junior EL (2021) A randomized crossover intervention study on the effect a standardized maté extract (Ilex paraguariensis A. St.-Hil.) in men predisposed to cardiovascular risk. Nutrients 13:14 ArticleCAS Google Scholar
Medeiros MS, Schumacher-Schuh AF, Altmann V, de Mello Rieder CR (2021) A case-control study of the effects of Chimarrão (Ilex paraguariensis) and coffee on Parkinson’s disease. Front Neurol 12:619535 ArticlePubMedPubMed Central Google Scholar
Lorini A, Damin FM, de Oliveira DN, Crizel RL, Godoy HT, Galli V, Meinhart AD (2021) Characterization and quantification of bioactive compounds from Ilex peraguariensis residue by HPLC-ESI-QTOF-MS from plants cultivated under different cultivation systems. J Food Sci 86:1599–1619 ArticleCASPubMed Google Scholar
Muraoka O, Morikawa T, Zhang Y, Ninomiya K, Nakamura S, Matsuda H, Yoshikawa M (2009) Novel megastigmanes with lipid accumulation inhibitory and lipid metabolism-promoting activities in HepG2 cells from Sedum sarmentosum. Tetrahedron 65:4142–4148 ArticleCAS Google Scholar
Morikawa T, Ninomiya K, Zhang Y, Yamada T, Nakamura S, Matsuda H, Muraoka O, Hayakawa T, Yoshikawa M (2012) Flavonol glycosides with lipid accumulation inhibitory activity from Sedum sarmentosum. Phytochem Lett 5:53–58 ArticleCAS Google Scholar
Morikawa T, Ninomiya K, Miyake S, Miki Y, Okamoto M, Yoshikawa M, Muraoka O (2013) Flavonol glycosides with lipid accumulation inhibitory activity and simultaneous quantitative analysis of 15 polyphenols and caffeine in the flower buds of Camellia sinensis from different regions by LCMS. Food Chem 140:353–360 ArticleCASPubMed Google Scholar
Morikawa T, Nagatomo A, Oka T, Miki Y, Taira N, Shibano-Kitahara M, Hori Y, Muraoka O, Ninomiya K (2019) Glucose tolerance-improving activity of helichrysoside in mice and its structural requirements for promoting glucose and lipid metabolism. Int J Mol Sci 20:6322 ArticleCASPubMed Central Google Scholar
Shimoda H, Ninomiya K, Nishida N, Yoshino T, Morikawa T, Matsuda H, Yoshikawa M (2003) Anti-hyperlipidemic sesquiterpenes and new sesquiterpene glycosides from the leaves of artichoke (Cynara scolymus L.): structure requirement and mode of action. Bioorg Med Chem Lett 13:223–228 ArticleCASPubMed Google Scholar
Yoshikawa M, Morikawa T, Yamamoto K, Kato Y, Nagatomo A, Matsuda H (2005) Floratheasaponins A-C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis). J Nat Prod 68:1360–1365 ArticleCASPubMed Google Scholar
Matsuda H, Nakamura S, Morikawa T, Muraoka O, Yoshikawa M (2016) New biofunctional effects of the flower buds of Camellia sinensis and its bioactive acylated oleanane-type triterpene oligoglycosides. J Nat Med 70:689–701 ArticleCASPubMedPubMed Central Google Scholar
Morikawa T, Li X, Nishida E, Ito Y, Matsuda H, Nakamura S, Muraoka O, Yoshikawa M (2008) Perennisosides I-VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis. J Nat Prod 71:828–835 ArticleCASPubMed Google Scholar
Morikawa T, Muraoka O, Yoshikawa M (2010) Pharmaceutical food science: search for anti-obese constituents from medicinal foods—anti-hyperlipidemic saponin constituents from the flowers of Bellis perennis. Yakugaku Zasshi 130:673–678 ArticleCASPubMed Google Scholar
Asao Y, Morikawa T, Xie Y, Okamoto M, Hamao M, Matsuda H, Muraoka O, Yuan D, Yoshikawa M (2009) Structures of acetylated oleanane-type triterpene saponins, rarasaponins IV, V, and VI, and anti-hyperlipidemic constituents from the pericarps of Sapindus rarak. Chem Pharm Bull 57:198–203 ArticleCAS Google Scholar
Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O (2012) Anti-hyperlipidemic constituents from the bark of Shorea roxburghii. J Nat Med 66:516–524 ArticleCASPubMed Google Scholar
Melek FR, Miyase T, El-Gindy MR, Abdel-Khalik SM, Ghaly NS, El-Kady M (2000) Saponins from Fagonia glutinosa. Pharmazie 55:772–776 CASPubMed Google Scholar
Taketa ATC, Breitmaier E, Schenkel EP (2004) Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté). J Braz Chem Soc 15:205–211 ArticleCAS Google Scholar
Nakanishi T, Tanaka K, Murata H, Somekawa M, Inada A (1993) Phytochemical studies of seeds of medicinal plants. III. Ursolic acid and oleanolic acid glycosides from seeds of Patrinia scabiosaefolia Fischer. Chem Pharm Bull 41:183–186 ArticleCAS Google Scholar
Gosmann G, Schenkel EP (1989) A new saponin from mate, Ilex paraguariensis. J Nat Prod 52:1367–1370 ArticleCAS Google Scholar
De Andrade FDP, Piacente S, Pizza C, Vilegas W (2002) Studies on the constituents of a Brazilian folk infusion. Isolation and structure elucidation of new triterpene saponins from Ilex amara leaves. J Agric Food Chem 50:255–261 ArticleCAS Google Scholar
Gosmann G, Guillaume D (1995) Triterpenoid saponins from Ilex paraguariensis. J Nat Prod 58:438–441 ArticleCASPubMed Google Scholar
Kraemer KH, Taketa ATC, Schenkel EP, Gosmann G, Guillaume D (1996) Matesaponin 5, a highly polar saponin from Ilex paraguariensis. Phytochemistry 42:1119–1122 ArticleCASPubMed Google Scholar
Nishimura K, Miyase T, Noguchi H (1999) Triterpenoid saponins from Ilex kudincha. J Nat Prod 62:1128–1133 ArticleCASPubMed Google Scholar
Ouyang M-A, Yang C-R, Chen Z-L, Wang H-Q (1996) Tritepenes and triterpenoid glycosides from the leaves of Ilex kudincha. Phytochemistry 41:871–877 ArticleCASPubMed Google Scholar
Ouyang M-A, Yang C-R, Wu Z-J (2001) Triterpenoid saponins from the leaves of Ilex kudincha. JANPR 3:31–42 CASPubMed Google Scholar
Shimizu S, Ishihara N, Umehara K, Miyase T, Ueno A (1988) Sesquiterpene glycosides and saponins from Cynara cardunculus L. Chem Pharm Bull 36:2466–2474 ArticleCAS Google Scholar
Kinjo J, Uemura H, Nakamura M, Nohara T (1994) Two new triterpenoidal glycosides from Medicago polymorpha L. Chem Pharm Bull 42:1339–1341 ArticleCAS Google Scholar
Hata C, Kakuno M, Yoshikawa K, Arihara S (1992) Triterpenoid saponins of Aquifoliaceous plants. V. Ilexosides XV–XIX from the barks of Ilex crenata Thunb. Chem Pharm Bull 40:1990–1992 ArticleCAS Google Scholar
Ouyang M-A, Wang H-Q, Liu Y-Q, Yang C-R (1997) Triterpenoid saponins from the leaves of Ilex latifolia. Phytochemistry 45:1501–1505 ArticleCAS Google Scholar
Song N, Xu W, Guan H, Liu X, Wang Y, Nie X (2007) Several flavonoids from Capsella bursa-pastoris (L.) Medic. Asian J Tradit Med 2:218–222 CAS Google Scholar
These isolates were identified by comparison of their physical and spectral data with those of commercially available samples
Zhang Y, Nakamura S, Pongpiriyadacha Y, Matsuda H, Yoshikawa M (2008) Absolute structures of new megastigmane glycosides, foliasalaciosides E1, E2, E3, F, G, H, and I from the leaves of Salacia chinensis. Chem Pharm Bull 56:547–553 ArticleCAS Google Scholar
Nakatani N, Kayano S, Kikuzaki H, Sumino K, Katagiri K, Mitani T (2000) Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in Prune (Prunus domestica L.). J Agric Food Chem 48:5512–5516 ArticleCASPubMed Google Scholar
Grassi-Zampieron R, França LV, Carollo CA, do Carmo Vieira M, Oliveros-Bastidas A, de Siqueira JM (2010) Comparative profiles of Achyrocline alata (Kunth) DC. and A. satureioides (Lam.) DC., Asteraceae, applying HPLC-DAD-MS. Braz J Pharmacogn 20:575–579
Lee EJ, Kim JS, Kim HP, Lee J-H, Kang SS (2010) Phenolic constituents from the flower buds of Lonicera japonica and their 5-lipoxygenase inhibitory activities. Food Chem 120:134–139 ArticleCAS Google Scholar
Gao H, Huang Y-N, Gao B, Xu P-Y, Inagaki C, Kawabata J (2008) α-Glucosidase inhibitory effect by the flower buds of Tussilago farfara L. Food Chem 106:1195–1201 ArticleCAS Google Scholar
Kim JY, Cho J-Y, Ma Y-K, Park KY, Lee S-H, Ham K-S, Lee HJ, Park K-H, Moon J-H (2011) Dicaffeoylquinic acid derivatives and flavonoid glucosides from glasswort (Salicornia herbacea L.) and their antioxidative activity. Food Chem 125:55–62 ArticleCAS Google Scholar
Morikawa T, Imura K, Akagi Y, Muraoka O, Ninomiya K (2018) Ellagic acid glycosides with hepatoprotective activity from traditional Tibetan medicine Potentilla anserina. J Nat Med 72:317–325 ArticleCASPubMed Google Scholar
Morikawa T, Nakanishi Y, Inoue N, Manse Y, Matsuura H, Hamasaki S, Yoshikawa M, Muraoka O, Ninomiya K (2020) Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth. Phytochemistry 169:112185 ArticleCASPubMed Google Scholar
Morikawa T, Inoue N, Nakanishi Y, Manse Y, Matsuura H, Okino K, Hamasaki S, Yoshikawa M, Muraoka O, Ninomiya K (2020) Collagen synthesis-promoting and collagenase inhibitory activities of constituents isolated from the rhizomes of Picrorhiza kurroa Royle ex Benth. Fitoterapia 143:104584 ArticleCASPubMed Google Scholar
Hidaka K, Ito M, Matsuda Y, Kohda H, Yamasaki K, Yamahara J, Chisaka T, Kawakami Y, Sato T, Kagei K (1987) New triterpene saponins from Ilex pubescens. Chem Pharm Bull 35:524–529 ArticleCAS Google Scholar
Kakuno T, Yoshikawa K, Arihara S (1992) Triterpenoid saponins from Ilex crenata fruit. Phytochemistry 31:3553–3557 ArticleCAS Google Scholar
Cheng J-J, Zhang L-J, Cheng H-L, Chiou C-T, Lee I-J, Kuo Y-H (2010) Cytotoxic hexacyclic triterpene acids from Euscaphis japonica. J Nat Prod 73:1655–1658 ArticleCASPubMed Google Scholar
Morikawa T, Ninomiya K, Imura K, Yamaguchi T, Akagi Y, Yoshikawa M, Hayakawa T, Muraoka O (2014) Hepetoprotective triterpenes from traditional Tibetan medicine Potentilla anserina. Phytochemistry 102:169–181 ArticleCASPubMed Google Scholar
El-Hassan AY, Ibrahim EM, Al-Mulhim FA, Nabhan AA, Chammas MY (1992) Fatty infiltration of the liver: analysis of prevalence, radiological and clinical features and influence on patient management. Br J Radiol 65:774–778 ArticleCASPubMed Google Scholar
Bellentani S, Tiribelli C, Saccoccio G, Sodde M, Fratti N, de Martin C, Cristianini G (1994) Prevalence of chronic liver disease in the general population of northern Italy: the dionysos study. Hepatology 20:1442–1449 ArticleCASPubMed Google Scholar
Marchesini G, Brizi M, Morselli-Labate AM, Bianchi G, Bugianesi E, McCullough AJ, Forlani G, Melchionda N (1999) Association of nonalcoholic fatty liver disease with insulin resistance. Am J Med 107:450–455 ArticleCASPubMed Google Scholar
Marceau P, Biron S, Hould F-S, Marceau S, Simard S, Thung SN, Kral JG (1999) Liver pathology and the metabolic syndrome X in severe obesity. J Clin Endocrinol Metab 84:1513–1517 ArticleCASPubMed Google Scholar
Auwerx J, Schoonjans K, Fruchart J-C, Staels B (1996) Regulation of triglyceride metabolism by PPARs: fibrates and thiazolidinediones have distinct effects. J Atheroscler Thromb 3:81–89 ArticleCASPubMed Google Scholar