Lupane-Type Triterpenoidal Saponins from Pulsatilla chinensis and Their Anticomplement Activities through the Classical Pathway

Abstract

Four (1–4) previously unknown lupane-type triterpenoidal saponins were isolated from the roots of Pulsatilla chinensis, along with six triterpene saponins (5–10). The structures of saponins 1–4 were determined as 23-hydroxy-3β-[(O-β-D-glucopyranosyl-(1 → 4)-α-L-arabinopyranosyl)]lup-20(29)-en-28-oic-acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (1), 23-hydroxy-3β-[(O-α-L-rhamnopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 4)]-α-L-arabinopyranosyl)]lup-20(29)-en-28-oic-acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (2), 3β-[(O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl)]lup-20(29)-en-28-oic-acid 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (3), and 3β-[(O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl)]lup-20(29)-en-28-oic-acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranosyl ester (4), on the basis of hydrolysis and spectral evidence, including 1D- and 2D-NMR and HR-ESI-MS analyses. These pure isolates (1–10) were tested for their anticomplement activity, using an in vitro assay of the complement system of the classical pathway.

Key words

Pulsatilla chinensis - Ranunculaceae - triterpenoidal saponins - lupine - anti-complementary activity - classical pathway

• References

• 1 Editorial Committee of Chinese Pharmacopoeia. Pharmacopoeia of China, Part 1. Beijing: Chemical Industry Press; 2010: 241-242
• 2 Glebko LI, Krasovskaj NP, Strigina LI, Ulanova KP, Denisenko VA, Dmitrenok PS. Triterpene glycosides from Pulsatilla chinensis . Russ Chem Bull 2002; 51: 1945-1950
• 3 Yoshihiro M, Akihito Y, Minpei K, Mari H, Chiseko S, Yutaka S. New bisdesmosidic triterpene saponins from the roots of Pulsatilla chinensis . J Nat Prod 2001; 64: 1226-1229
• 4 Ye WC, Zhang Q, Hsiao WW, Zhao SX, Che CT. New lupane glycosides from Pulsatilla chinensis . Planta Med 2002; 68: 183-186
• 5 Zheng YT, Zhou F, Wu XL, Wen XZ, Li YN, Yan B, Zhang JW, Hao G, Ye WC, Wang GJ. 23-Hydroxybetulinic acid from Pulsatilla chinensis (Bunge) Regel synergizes the antitumor activities of doxorubicin in vitro and in vivo . J Ethnopharmacol 2010; 128: 615-622
• 6 Ye WC, Ji NN, Zhao SX, Liu JH, Ye T, McKervey MA, Stevenson P. Triterpenoids from Pulsatilla chinensis . Phytochemistry 1996; 42: 799-802
• 7 Wu ZJ, Ding LS, Zhao SX. Glycosides from Pulsatilla chinensis (Bunge) Regel. J China Pharm Univ 1991; 22: 265-269
• 8 Yang HJ, Cho YW, Kim SH, Kim YC, Sung SH. Triterpenoidal saponins of Pulsatilla koreana roots. Phytochemistry 2010; 71: 1892-1899
• 9 Bang SC, Kim Y, Lee JH, Ahn BZ. Triterpenoid saponins from the roots of Pulsatilla koreana . J Nat Prod 2005; 68: 268-272
• 10 Siddiqui S, Hafeez F, Begum S, Siddiqui BS. Oleanderol, a new pentacyclic triterpene from the leaves of Nerium oleander . J Nat Prod 1988; 51: 229-233
• 11 Ríos JL. Effects of triterpenes on the immune system. J Ethnopharmacol 2010; 128: 1-14
• 12 Qu H, Ricklin D, Lambris JD. Recent developments in low molecular weight complement inhibitors. Mol Immunol 2009; 47: 185-195