Ellagic acid glycosides with hepatoprotective activity from traditional Tibetan medicine Potentilla anserina (original) (raw)
References
Morikawa T, Ninomiya K, Imura K, Yamaguchi T, Akagi Y, Yoshikawa M, Hayakawa T, Muraoka O (2014) Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina. Phytochemistry 102:169–181 ArticleCAS Google Scholar
Wang J, Zhang J, Zhao B, Wang X, Wu Y, Yao J (2010) A comparison study on microwave-assisted extraction of Potentilla anserina L. polysaccharides with conventional method: molecule weight and antioxidant activities evaluation. Carbohydrate Polym 80:84–93 ArticleCAS Google Scholar
Chen J-R, Yang Z-Q, Hu T-J, Yan Z-T, Niu T-X, Wang L, Cui D-A, Wang M (2010) Immunomodulatory activity in vitro and in vivo of polysaccharide from Potentilla anserina. Fitoterapia 81:1117–1124 ArticleCAS Google Scholar
Xia L, You J (2011) The determination of amino acids composition of the traditional food Potentilla anserina L. root by high-performance liquid chromatography via fluorescent determination and mass spectrometry. Int J Food Sci Technol 46:1164–1170 ArticleCAS Google Scholar
Guo T, Wei JQ, Ma JP (2016) Antitussive and expectorant activities of Potentilla anserina. Pharm Biol 54:807–811 ArticleCAS Google Scholar
Schimmer O, Lindenbaum M (1995) Tannins with antimutagenic properties in the herb of Alchemilla species and Potentilla anserina. Planta Med 61:141–145 ArticleCAS Google Scholar
Kombal R, Glasl H (1995) Flavan-3-ols and flavonoids from Potentilla anserina. Planta Med 61:484–485 ArticleCAS Google Scholar
Li Q, Hui J, Shang D, Wu L, Ma X (2003) Investigation of the chemical constituents of the roots of Potentilla anserina L. in Tibet. Chin Pharm J 55:179–184 ArticleCAS Google Scholar
Chu L, Wang L, Zhang Z, Gao H, Huang J, Sun B, Wu L (2008) Studies on the chemical constituents of Potentilla anserine L. Zhongguo Xiandai Zhongyao 10:10–12 CAS Google Scholar
Zhao Y-L, Cai G-M, Hong X, Shan L-M, Xiao X-H (2008) Anti-hepatitis B virus activities of triterpenoid saponin compound from Potentilla anserina L. Phytomedicine 15:253–258 ArticleCAS Google Scholar
Li L, Zhao Y, Liu W, Feng F, Xie N (2013) HPLC with quadrupole TOF-MS and chemometrics analysis for the characterization of Folium Turpiniae from different regions. J Sep Sci 36:2552–2561 ArticleCAS Google Scholar
Bai N, He K, Roller M, Zheng B, Chen X, Shao Z, Peng T, Zheng Q (2008) Active compounds from Lagerstroemia speciosa, insulin-like glucose uptake-stimulatory/inhibitory and adipocyte differentiation-inhibitory activities in 3T3-L1 cells. J Agric Food Chem 56:11668–11674 ArticleCAS Google Scholar
Morikawa T, Imura K, Miyake S, Ninomiya K, Matsuda H, Yamashita C, Muraoka O, Hayakawa T, Yoshikawa M (2012) Promoting the effect of chemical constituents from the flowers of Poacynum hendersonii on adipogenesis in 3T3-L1 cells. J Nat Med 66:39–48 ArticleCAS Google Scholar
Chaipech S, Morikawa T, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O (2012) Structures of two new phenolic glycosides, kaempferiaosides A and B, and hepatoprotective constituents from the rhizomes of Kaempferia parviflora. Chem Pharm Bull 60:62–69 ArticleCAS Google Scholar
Morikawa T, Chaipech S, Matsuda H, Hamao M, Umeda Y, Sato H, Tamura H, Kon’i H, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O (2012) Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii. Bioorg Med Chem 20:832–840 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. Phytochemistry Lett 5:53–58 ArticleCAS Google Scholar
Chaipech S, Morikawa T, Ninomiya K, Yoshikawa M, Pongporiyadacha Y, Hayakawa T, Muraoka O (2012) New flav-3-en-3-ol glycosides, kaempferiaosides C and D, and acetophenone glycosides, kaempferiaosides E and F, from the rhizomes of Keampferia parviflora. J Nat Med 66:486–492 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 constitunets from the bark of Shorea roxburghii. J Nat Med 66:516–524 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 ArticleCAS Google Scholar
Morikawa T, Ninomiya K, Kuramoto H, Kamei I, Yoshikawa M, Muraoka O (2016) Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis. J Nat Med 70:89–101 ArticleCAS Google Scholar
Ninomiya K, Motai C, Nishida E, Kitagawa N, Yoshihara K, Hayakawa T, Muraoka O, Li X, Nakamura S, Yoshikawa M, Matsuda H, Morikawa T (2016) Acylated oleanane-type triterpene saponins from the flowers of Bellis perennis show anti-proliferative activities against human digestive tract carcinoma cell lines. J Nat Med 70:435–451 ArticleCAS Google Scholar
Ye L, Yang JS (1996) New ellagic glycosides and known triterpenoids from Duchesnea indica Focke. Acta Pharm Sin 31:844–848 CAS Google Scholar
Khac DD, Tran-Van S, Campos AM, Lallemand J-Y, Fetizon M (1990) Ellagic compounds from Diplopanax stachyanthus. Phytochemistry 29:251–256 Article Google Scholar
Zhang T, Zhang C-F, Wang Z-T, Xu L-S (2005) Studies on chemical constituents of Dendrobium trigonopus Rchb. f. Chin J Nat Med 3:30–33 Google Scholar
Nawwar MAM, Hussein SAM, Merfort I (1994) NMR spectral analysis of polyphenols from Punica granatum. Phytochemistry 36:793–798 ArticleCAS Google Scholar
Sato T (1991) Comparative spectroscopic characterization of synthesized isomers of di-_O_-methylated ellagic acids. Phytochem Anal 2:271–273 Article Google Scholar
Kosuge T, Ishida H, Yokota M, Yoshida M (1984) Studies on antihemorrhagic substances in herbs classified as hemostatics in Chinese medicine. III. On the antihemorrhagic principle in Sanguisorba officinallis L. Chem Pharm Bull 32:4478–4481 ArticleCAS Google Scholar
Matsuda H, Ninomiya K, Morikawa T, Yoshikawa M (1998) Inhibitory effect and action mechanism of sesquiterpenes from Zedoariae Rhizoma on d-galactosamine/lipopolysaccharide-induced liver injury. Bioorg Med Chem Lett 8:339–344 ArticleCAS Google Scholar
Matsuda H, Morikawa T, Ninomiya K, Yoshikawa M (2001) Hepatoprotective constituents from Zedoariae Rhizoma: absolute stereostructures of three new carabrane-type sesquiterpenes, curcumenolactonea A, B, and C. Bioorg Med Chem 9:909–916 ArticleCAS Google Scholar
Morikawa T, Matsuda H, Ninomiya K, Yoshikawa M (2002) Medicinal foodstuffs. XXIX. potent protective effects of sesquiterpenes and curcumin from Zedoariae Rhizoma on liver injury induced by d-galactosamine/lipopolysaccharide or tumor necrosis factor-α. Biol Pharm Bull 25:627–631 ArticleCAS Google Scholar
Yoshikawa M, Xu F, Morikawa T, Ninomiya K, Matsuda H (2003) Anastatins A and B, new skeletal flavonoids with hepatoprotective activities from the desert plant Anastatica hierochuntica. Bioorg Med Chem Lett 13:1045–1049 ArticleCAS Google Scholar
Yoshikawa M, Morikawa T, Kashima Y, Ninomiya K, Matsuda H (2003) Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins. J Nat Prod 66:922–927 ArticleCAS Google Scholar
Xu F, Morikawa T, Matsuda H, Ninomiya K, Yoshikawa M (2004) Structures of sesquiterpenes and hepatoprotective constituents from the Egyptian herbal medicine Cyperus longus. J Nat Prod 67:569–576 ArticleCAS Google Scholar
Matsuda H, Morikawa T, Xu F, Ninomiya K, Yoshikawa M (2004) New isoflavones and pterocarpanes with hepatoprotective activity from the stems of Erycibe expansa. Planta Med 70:1201–1209 ArticleCAS Google Scholar
Yoshikawa M, Nishida N, Ninomiya K, Ohgushi T, Kubo M, Morikawa T, Matsuda H (2006) Inhibitory effects of coumarin and acetylene constituents from the roots of Angellica furcijuga on d-galactosamine/lipopolysaccharide-induced liver injury in mice and on nitric oxide production in lipopolysaccharide-activated mouse peritoneal macrophages. Bioorg Med Chem 14:456–463 ArticleCAS Google Scholar
Morikawa T (2007) Search for bioactive constituents from several medicinal food: hepatoprotective, antidiabetic, and antiallergic activities. J Nat Med 61:112–126 ArticleCAS Google Scholar
Li N, Morikawa T, Matsuda H, Ninomiya K, Li X, Yoshikawa M (2007) New flavanone oligoglycosides, theaflavanosides I, II, III, and IV, with hepatoprotective activity from the seeds of tea plant (Camellia sinensis). Heterocycles 71:1193–1201 ArticleCAS Google Scholar
Ninomiya K, Morikawa T, Zhang Y, Nakamura S, Matsuda H, Muraoka O, Yoshikawa M (2007) Bioactive constituents from Chinese natural medicines. XXIII. Absolute structures of new megastigmane glycosides, sedumosides A4, A5, A6, H, and I, and hepatoprotective megastigmanes from Sedum sarmentosum. Chem Pharm Bull 55:1185–1191 ArticleCAS Google Scholar
Zhang Y, Morikawa T, Nakamura S, Ninomiya K, Matsuda H, Muraoka O, Yoshikawa M (2007) Bioactive constituents from Chinese natural medicines. XXV. New flavonol bisdesmosides, sarmenosides I, II, III, and IV, with hepatoprotective activity from Sedum sarmentosum. Heterocycles 71:1565–1576 ArticleCAS Google Scholar
Nakamura S, Li X, Matsuda H, Ninomiya K, Morikawa T, Yamaguti K, Yoshikawa M (2007) Bioactive constituents from Chinese natural medicines. XXVI. chemical structures and hepatoprotective effects of constituents from roots of Rhodiola sachalinensis. Chem Pharm Bull 55:1505–1511 ArticleCAS Google Scholar
Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M (2008) Protective effects of amide constituents from the fruit of Piper chaba on d-galactosamine/TNF-_α_-induced cell death in mouse hepatocytes. Bioorg Med Chem Lett 18:2038–2042 ArticleCAS Google Scholar
Ninomiya K, Morikawa T, Xie H, Matsuda H, Yoshikawa M (2008) Bioactive constituents from Chinese natural medicines. XXXI. Hepatoprotective principles from Sinocrassula indica: structres of sinocrassosides A8, A9, A10, A11, and A12. Heterocycles 75:1983–1995 ArticleCAS Google Scholar
Nakamura S, Okazaki Y, Ninomiya K, Morikawa T, Matsuda H, Yoshikawa M (2008) Medicinal flowers. XXIV. Chemical structures and hepatoprotective effects of constituents from flowers of Hedychium coronarium. Chem Pharm Bull 56:1704–1709 ArticleCAS Google Scholar
Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M (2009) Hepatoprotective amide constituents from the fruit of Piper chaba: structural requirements, mode of action, and new amides. Bioorg Med Chem 17:7313–7323 ArticleCAS Google Scholar
Morikawa T (2010) Search for TNF-α sensitivety degradation principles from medicinal foods—hepatoprotective amide constituents from Thai natural medicine Piper chaba. Yakugaku Zasshi 130:785–791 ArticleCAS Google Scholar
Morikawa T, Pan Y, Ninomiya K, Imura K, Matsuda H, Yoshikawa M, Yuan D, Muraoka O (2010) Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa. Bioorg Med Chem 18:1882–1890 ArticleCAS Google Scholar
Nakamura S, Xu F, Ninomiya K, Nakashima S, Oda Y, Morikawa T, Muraoka O, Yoshikawa M, Matsuda H (2014) Chemical structures and hepatoprotective effects of constituents from Cassia auriculata leaves. Chem Pharm Bull 62:1026–1031 ArticleCAS Google Scholar
Ninomiya K, Miyazawa S, Ozeki K, Matsuo N, Muraoka O, Kikuchi T, Yamada T, Tanaka R, Morikawa T (2016) Hepatoprotective limonoids from andiroba (Carapa guianensis). Int J Mol Sci 17:591 Article Google Scholar
Ninomiya K, Chaipech S, Kunikata Y, Yagi R, Pongpiriyadacha Y, Muraoka O, Morikawa T (2017) Quantitative determination of stilbenoids and dihydroisocoumarins in Shorea roxburghii and evaluation of their hepatoprotective activity. Int J Mol Sci 18:451 Article Google Scholar