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Published in: Journal of Natural Medicines 1/2018

01-01-2018 | Note

Ellagic acid glycosides with hepatoprotective activity from traditional Tibetan medicine Potentilla anserina

Authors: Toshio Morikawa, Katsuya Imura, Yoshinori Akagi, Osamu Muraoka, Kiyofumi Ninomiya

Published in: Journal of Natural Medicines | Issue 1/2018

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Abstract

Two new gallic acid glycosides, potentillanosides G (1) and H (2), were newly isolated from the methanol extract of the tuberous roots of Potentilla anserina (Rosaceae), together with a known compound, ellagic acid 3-O-α-l-rhamnopyranoside (3). Their structures were elucidated on the basis of chemical and physicochemical evidence. Among the constituents, potentillanoside H (2, IC50 = 99.5 μM) was found to show hepatoprotective activity.
Literature
1.
go back to reference 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 102:169–181CrossRef 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 102:169–181CrossRef
2.
go back to reference 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 80:84–93CrossRef 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 80:84–93CrossRef
3.
go back to reference 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 81:1117–1124CrossRef 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 81:1117–1124CrossRef
4.
go back to reference 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 46:1164–1170CrossRef 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 46:1164–1170CrossRef
5.
go back to reference Guo T, Wei JQ, Ma JP (2016) Antitussive and expectorant activities of Potentilla anserina. Pharm Biol 54:807–811CrossRef Guo T, Wei JQ, Ma JP (2016) Antitussive and expectorant activities of Potentilla anserina. Pharm Biol 54:807–811CrossRef
6.
go back to reference Schimmer O, Lindenbaum M (1995) Tannins with antimutagenic properties in the herb of Alchemilla species and Potentilla anserina. Planta Med 61:141–145CrossRef Schimmer O, Lindenbaum M (1995) Tannins with antimutagenic properties in the herb of Alchemilla species and Potentilla anserina. Planta Med 61:141–145CrossRef
7.
go back to reference Kombal R, Glasl H (1995) Flavan-3-ols and flavonoids from Potentilla anserina. Planta Med 61:484–485CrossRef Kombal R, Glasl H (1995) Flavan-3-ols and flavonoids from Potentilla anserina. Planta Med 61:484–485CrossRef
8.
go back to reference 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 55:179–184CrossRef 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 55:179–184CrossRef
9.
go back to reference 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 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
10.
go back to reference 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 15:253–258CrossRef 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 15:253–258CrossRef
11.
go back to reference 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 36:2552–2561CrossRef 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 36:2552–2561CrossRef
12.
go back to reference 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 56:11668–11674CrossRef 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 56:11668–11674CrossRef
13.
go back to reference 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 66:39–48CrossRef 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 66:39–48CrossRef
14.
go back to reference 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 60:62–69CrossRef 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 60:62–69CrossRef
15.
go back to reference 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 20:832–840CrossRef 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 20:832–840CrossRef
16.
go back to reference 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 5:53–58CrossRef 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 5:53–58CrossRef
17.
go back to reference 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 66:486–492CrossRef 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 66:486–492CrossRef
18.
go back to reference 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 66:516–524CrossRef 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 66:516–524CrossRef
19.
go back to reference 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 140:353–360CrossRef 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 140:353–360CrossRef
20.
go back to reference 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 70:89–101CrossRef 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 70:89–101CrossRef
21.
go back to reference 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 70:435–451CrossRef 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 70:435–451CrossRef
22.
go back to reference Ye L, Yang JS (1996) New ellagic glycosides and known triterpenoids from Duchesnea indica Focke. Acta Pharm Sin 31:844–848 Ye L, Yang JS (1996) New ellagic glycosides and known triterpenoids from Duchesnea indica Focke. Acta Pharm Sin 31:844–848
23.
go back to reference Khac DD, Tran-Van S, Campos AM, Lallemand J-Y, Fetizon M (1990) Ellagic compounds from Diplopanax stachyanthus. Phytochemistry 29:251–256CrossRef Khac DD, Tran-Van S, Campos AM, Lallemand J-Y, Fetizon M (1990) Ellagic compounds from Diplopanax stachyanthus. Phytochemistry 29:251–256CrossRef
24.
go back to reference 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 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
25.
go back to reference Nawwar MAM, Hussein SAM, Merfort I (1994) NMR spectral analysis of polyphenols from Punica granatum. Phytochemistry 36:793–798CrossRef Nawwar MAM, Hussein SAM, Merfort I (1994) NMR spectral analysis of polyphenols from Punica granatum. Phytochemistry 36:793–798CrossRef
26.
go back to reference Sato T (1991) Comparative spectroscopic characterization of synthesized isomers of di-O-methylated ellagic acids. Phytochem Anal 2:271–273CrossRef Sato T (1991) Comparative spectroscopic characterization of synthesized isomers of di-O-methylated ellagic acids. Phytochem Anal 2:271–273CrossRef
27.
go back to reference 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 32:4478–4481CrossRef 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 32:4478–4481CrossRef
28.
go back to reference 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 8:339–344CrossRef 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 8:339–344CrossRef
29.
go back to reference 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 9:909–916CrossRef 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 9:909–916CrossRef
30.
go back to reference 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 25:627–631CrossRef 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 25:627–631CrossRef
31.
go back to reference 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 13:1045–1049CrossRef 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 13:1045–1049CrossRef
32.
go back to reference 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 66:922–927CrossRef 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 66:922–927CrossRef
33.
go back to reference 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 67:569–576CrossRef 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 67:569–576CrossRef
34.
go back to reference 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 70:1201–1209CrossRef 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 70:1201–1209CrossRef
35.
go back to reference 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 14:456–463CrossRef 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 14:456–463CrossRef
36.
go back to reference Morikawa T (2007) Search for bioactive constituents from several medicinal food: hepatoprotective, antidiabetic, and antiallergic activities. J Nat Med 61:112–126CrossRef Morikawa T (2007) Search for bioactive constituents from several medicinal food: hepatoprotective, antidiabetic, and antiallergic activities. J Nat Med 61:112–126CrossRef
37.
go back to reference 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 71:1193–1201CrossRef 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 71:1193–1201CrossRef
38.
go back to reference 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 55:1185–1191CrossRef 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 55:1185–1191CrossRef
39.
go back to reference 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 71:1565–1576CrossRef 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 71:1565–1576CrossRef
40.
go back to reference 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 55:1505–1511CrossRef 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 55:1505–1511CrossRef
41.
go back to reference 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 18:2038–2042CrossRef 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 18:2038–2042CrossRef
42.
go back to reference 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 75:1983–1995CrossRef 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 75:1983–1995CrossRef
43.
go back to reference 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 56:1704–1709CrossRef 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 56:1704–1709CrossRef
44.
go back to reference 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 17:7313–7323CrossRef 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 17:7313–7323CrossRef
45.
go back to reference Morikawa T (2010) Search for TNF-α sensitivety degradation principles from medicinal foods—hepatoprotective amide constituents from Thai natural medicine Piper chaba. Yakugaku Zasshi 130:785–791CrossRef Morikawa T (2010) Search for TNF-α sensitivety degradation principles from medicinal foods—hepatoprotective amide constituents from Thai natural medicine Piper chaba. Yakugaku Zasshi 130:785–791CrossRef
46.
go back to reference 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 18:1882–1890CrossRef 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 18:1882–1890CrossRef
47.
go back to reference 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 62:1026–1031CrossRef 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 62:1026–1031CrossRef
48.
go back to reference 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 17:591CrossRef 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 17:591CrossRef
49.
go back to reference 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 18:451CrossRef 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 18:451CrossRef
Metadata
Title
Ellagic acid glycosides with hepatoprotective activity from traditional Tibetan medicine Potentilla anserina
Authors
Toshio Morikawa
Katsuya Imura
Yoshinori Akagi
Osamu Muraoka
Kiyofumi Ninomiya
Publication date
01-01-2018
Publisher
Springer Singapore
Published in
Journal of Natural Medicines / Issue 1/2018
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-017-1137-y

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