Abstract
Three new triterpenoid saponins, tomentoside A (1), B (2) and C (3), along with four known saponins (4–7) were isolated from the root of Anemone tomentosa. The structures of the new compounds were elucidated as 3-O-β-d-ribopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-α-l-arabinopyranosyl hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (1), 3-O-β-d-ribopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)]-β-d-xylopyranosyl hederagenin 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (2) and 3-O-β-d-galactopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-β-d-xylopyranosyl oleanolic acid 28-O-α-l-rhamnopyranosyl-(1→4)-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (3) on the basis of chemical and spectral evidence. In the oligosaccharide chains of compound 3, the characteristic d-galactose residue is a rare structural feature and secondly encountered among triterpenoid saponins from Anemone.
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References
Sun YX, Li MQ, Liu JC (2008) Haemolytic activities and adjuvant effect of Anemone raddeana saponins (ARS) on the immune responses to ovalbumin in mice. Int Immunopharmacol 8:1095–1102
Fan L, Lu JC, Wang J, Cheng WM, Yao Y, Liu RX, Zhang HF (2010) Two triterpenoid saponins from rhizome of Anemone raddeana Regel. J Nat Med 64:50–54
Zhang LT, Zhang YW, Takaishi Y, Duan HQ (2008) Antitumor triterpene saponins from Anemone flaccida. Chin Chem Lett 19:190–192
Chen X, Li JC, He WF, Chi HD, Yamashita K, Manabe M, Kodama H (2009) Antiperoxidation activity of triterpenoids from rhizome of Anemone raddeana. Fitoterapia 80:105–111
Wang JR, Ma JQ, Peng SL, Feng JT, Ding LS (1998) Chemical constituents and antifeeding activity of Anemone tomentosa. Acta Bot Boreal Occident Sin 18:643–644
Wang XY, Chen XL, Tang HF, Tian XR, Gao H, Zhang PH (2011) Cytotoxic triterpenoid saponins from the rhizomes of Anemone taipaiensis. Planta Med 77:1550–1554
Ding Y, Tang HF, Wang JB, Liu D, Tian XR, Wang XY, Zhou XM (2011) Triterpenoid saponins from Anemone rivularis var. flore-minore. Biochem Syst Ecol 39:236–239
Flora Reipublicae Popularis Sinicae (1980) Chinese flora, vol 28. Science Press, Beijing, pp 29–31
Northwest Institute of Botany (1974) Flora of Qinling, Chinese Academy of Sciences, Science Press, Beijing, pp 278–279
Wang JR, Ma JQ, Peng SL, Feng JT, Ding LS (1998) Chemical constituents of the Anemone tomentosa root. Acta Bot Sin 41:107–110
Liao X, Peng SL, Li BG, Chen YZ, Ding LS (1999) A new triterpenoid saponin from Anemone tomentosa. Chin Chem Lett 10:1035–1036
Hu HB, Zheng XD, Jian YF, Liu JX, Zhu JH (2010) Flavonoids from Anemone tomentosa roots. Chem Nat Compd 46:636–637
Hu HB, Zheng XD, Jian YF, Liu JX, Zhu JH (2011) Constituents of the root of Anemone tomentosa. Arch Pharm Res 34:1097–1105
Hu HB, Zheng XD, Liu JX, Zhu JH, Zhang XD (2011) Study on chemical constituents of the root of Anemone tomentosa. Chin Pharm J 46:252–255
Hu HB, Zheng XD, Zhu JH, Zhang XD (2011) Two glycosides and other constituents from Anemone tomentosa roots. Helv Chim Acta 94:711–718
Mizutani K, Ohtani K, Wei J, Kasai R, Tanaka O (1984) Saponins from Anemone rivular. Planta Med 50:327–331
Sun F, He Q, Xiao PG, Cheng YY (2007) A new triterpenoid saponin from Clematis ganpiniana. Chin Chem Lett 18:1078–1080
Zhong HM, Chen CX, Tian X, Chui YX, Chen YZ (2001) Triterpenoid saponins from Clematis tangutica. Planta Med 67:484–488
Mahato SB, Kundu AP (1994) 13C NMR spectra of pentacyclic triterpenoids—a compilation and some salient features. Phytochemistry 37:1517–1575
Osborn H, Lochey F, Mosley L, Read D (1999) Analysis of polysaccharides and monosaccharides in the root mucilage of maize (Zea mays L.) by gas chromatography. J Chromatogr A 831:267–276
Mimaki Y, Kuroda M, Asano T, Sashida Y (1999) Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells. J Nat Prod 62:1279–1283
Acknowledgments
The authors thank Prof. Ji-tao Wang (Shaanxi University of Chinese Medicine) for the identification of plant materials, and Mr. Min-chang Wang (Nuclear Magnetic Resonance Center, Xi’an Modern Chemistry Research Institute) for the NMR measurements.
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Wang, Y., Kang, W., Hong, Lj. et al. Triterpenoid saponins from the root of Anemone tomentosa . J Nat Med 67, 70–77 (2013). https://doi.org/10.1007/s11418-012-0649-8
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DOI: https://doi.org/10.1007/s11418-012-0649-8