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15.03.2022 | Original Paper

Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.

verfasst von: Akifumi Nagatomo, Naoki Inoue, Takuya Konno, Yin Xu, Chinatsu Sakamoto, Mayuko Sone, Aya Shibasaka, Osamu Muraoka, Kiyofumi Ninomiya, Masayuki Yoshikawa, Yoshiaki Manse, Toshio Morikawa

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2022

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Abstract

The methanol extract from the leaves of Ilex paraguariensis A. St.-Hil. (Aquifoliaceae), popularly known as mate, maté, or yerba maté, inhibits the intracellular triglyceride accumulation in HepG2 cells and suppresses the plasma triglyceride elevation in olive oil-treated mice. Three new triterpene saponins, termed mateosides I (1), II (2), and III (3), were isolated from the extract along with 29 known compounds. The structures of 1–3 were elucidated based on chemical and spectroscopic evidence. Among the isolates, principal saponin constituents, 2 and matesaponins 1 (7) and 2 (9), potently inhibited the triglyceride accumulation in HepG2 cells simultaneously treated with oleic acid and high glucose. In vivo assay of the methanol extract of I. paraguariensis revealed that 7 and 9 showed anti-hyperlipidemic activities in olive oil-treated mice. These results suggested that the saponin constituents of I. paraguariensis could be valuable bioactive marker for the anti-obesogenic activity.

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The Plant List. http://www.theplantlist.org/tpl1.1/record/kew-2861242. Accessed 18 Dec 2021.

Gruenwald J, Brendler T, Jaenicke C (2007) PDR for herbal medicines, 4th edn. Thomson Healthcare Inc., Montvale, pp 572–573

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–R151PubMedCrossRef

Bracesco N, Sanchez AG, Contreras V, Menini T, Gugliucci A (2011) Recent advances on Ilex paraguariensis research: minireview. J Ethnopharmacol 136:378–384PubMedCrossRef

Gambero A, Ribeiro ML (2015) The positive effects of yerba maté (Ilex paraguariensis) in obesity. Nutrients 7:730–750PubMedPubMedCentralCrossRef

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 21:440–454CrossRef

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 10:1682PubMedCentralCrossRef

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 57:257–261CrossRef

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 34:1849–1855PubMedCrossRef

10.

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 19:88–97PubMedCrossRef

11.

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 64:103646CrossRef

12.

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 11:238–248PubMedCrossRef

13.

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 13:14CrossRef

14.

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 12:619535PubMedPubMedCentralCrossRef

15.

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 86:1599–1619PubMedCrossRef

16.

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 65:4142–4148CrossRef

17.

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 5:53–58CrossRef

18.

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 140:353–360PubMedCrossRef

19.

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 20:6322PubMedCentralCrossRef

20.

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 13:223–228PubMedCrossRef

21.

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 68:1360–1365PubMedCrossRef

22.

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 70:689–701PubMedPubMedCentralCrossRef

23.

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 71:828–835PubMedCrossRef

24.

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 130:673–678PubMedCrossRef

25.

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 57:198–203CrossRef

26.

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 66:516–524PubMedCrossRef

27.

Melek FR, Miyase T, El-Gindy MR, Abdel-Khalik SM, Ghaly NS, El-Kady M (2000) Saponins from Fagonia glutinosa. Pharmazie 55:772–776PubMed

28.

Taketa ATC, Breitmaier E, Schenkel EP (2004) Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté). J Braz Chem Soc 15:205–211CrossRef

29.

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 41:183–186CrossRef

30.

Gosmann G, Schenkel EP (1989) A new saponin from mate, Ilex paraguariensis. J Nat Prod 52:1367–1370CrossRef

31.

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 50:255–261CrossRef

32.

Gosmann G, Guillaume D (1995) Triterpenoid saponins from Ilex paraguariensis. J Nat Prod 58:438–441PubMedCrossRef

33.

Kraemer KH, Taketa ATC, Schenkel EP, Gosmann G, Guillaume D (1996) Matesaponin 5, a highly polar saponin from Ilex paraguariensis. Phytochemistry 42:1119–1122PubMedCrossRef

34.

Nishimura K, Miyase T, Noguchi H (1999) Triterpenoid saponins from Ilex kudincha. J Nat Prod 62:1128–1133PubMedCrossRef

35.

Ouyang M-A, Yang C-R, Chen Z-L, Wang H-Q (1996) Tritepenes and triterpenoid glycosides from the leaves of Ilex kudincha. Phytochemistry 41:871–877PubMedCrossRef

36.

Ouyang M-A, Yang C-R, Wu Z-J (2001) Triterpenoid saponins from the leaves of Ilex kudincha. JANPR 3:31–42PubMed

37.

Shimizu S, Ishihara N, Umehara K, Miyase T, Ueno A (1988) Sesquiterpene glycosides and saponins from Cynara cardunculus L. Chem Pharm Bull 36:2466–2474CrossRef

38.

Kinjo J, Uemura H, Nakamura M, Nohara T (1994) Two new triterpenoidal glycosides from Medicago polymorpha L. Chem Pharm Bull 42:1339–1341CrossRef

39.

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 40:1990–1992CrossRef

40.

Ouyang M-A, Wang H-Q, Liu Y-Q, Yang C-R (1997) Triterpenoid saponins from the leaves of Ilex latifolia. Phytochemistry 45:1501–1505CrossRef

41.

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

42.

These isolates were identified by comparison of their physical and spectral data with those of commercially available samples

43.

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 56:547–553CrossRef

44.

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 48:5512–5516PubMedCrossRef

45.

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

46.

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 120:134–139CrossRef

47.

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 106:1195–1201CrossRef

48.

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 125:55–62CrossRef

49.

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 72:317–325PubMedCrossRef

50.

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 169:112185PubMedCrossRef

51.

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 143:104584PubMedCrossRef

52.

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 35:524–529CrossRef

53.

Kakuno T, Yoshikawa K, Arihara S (1992) Triterpenoid saponins from Ilex crenata fruit. Phytochemistry 31:3553–3557CrossRef

54.

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 73:1655–1658PubMedCrossRef

55.

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 102:169–181PubMedCrossRef

56.

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 65:774–778PubMedCrossRef

57.

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 20:1442–1449PubMedCrossRef

58.

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 107:450–455PubMedCrossRef

59.

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 84:1513–1517PubMedCrossRef

60.

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 3:81–89PubMedCrossRef

Titel: Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.
verfasst von: Akifumi Nagatomo
Naoki Inoue
Takuya Konno
Yin Xu
Chinatsu Sakamoto
Mayuko Sone
Aya Shibasaka
Osamu Muraoka
Kiyofumi Ninomiya
Masayuki Yoshikawa
Yoshiaki Manse
Toshio Morikawa
Publikationsdatum: 15.03.2022
Verlag: Springer Nature Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 3/2022
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-022-01614-5

Klimawandel und Gesundheit: Was Sie in der Hausarztpraxis wissen müssen und tun können

Springer Medizin

Ursane-type triterpene oligoglycosides with anti-hepatosteatosis and anti-hyperlipidemic activity from the leaves of Ilex paraguariensis A. St.-Hil.

Abstract

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Klimawandel und Gesundheit: Was Sie in der Hausarztpraxis wissen müssen und tun können

Springer Medizin

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