Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Anti-complement Activity of Triterpenoids from the Whole Plant of Patrinia saniculaefolia

  • An, Ren-Bo (College of Pharmacy, Yanbian University) ;
  • Na, Min-Kyun (College of Pharmacy, Yeungnam University) ;
  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu) ;
  • Lee, Hyeong-Kyu (Korea Research Institute of Bioscience and Biotechnology) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
  • Published : 2008.12.31
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Abstract

Two oleanane-type triterpenes (1, 2) and their glycosides (4-6), and one ursane-type triterpene (3) have been isolated from a methanolic extract of Patrinia saniculaefolia Hemsley (Valerianaceae) through repeated silica gel and reversed-phase C-18 column chromatography. Their chemical structures were determined as oleanolic acid (1), oleanonic acid (2), 23-hydroxyursolic acid (3), 3-O-${\alpha}$-L-arabinopyranosyl-oleanolic acid (4), 3-O-${\beta}$-D-glucopyranosyl-oleanolic acid (5), and oleanolic acid 3-O-[${\alpha}$-D-xylopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucuronopyranoside-6-O-butyl-ester] (6) on the basis of their MS, $^1H$-, and $^{13}C$-NMR spectral data. All compounds were isolated from the whole plant of the P. saniculaefolia for the first time. These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 1 - 3 exhibited anti-complement activity with $IC_{50}$ values of 470.1, 212.2, and 121.0 ${\mu}M$, respectively, whereas compounds 4 - 6 were inactive. These results suggest that the carbonyl or hydroxy group at C-3 in the oleananeand/or ursane-triterpenes are important for the anti-complement activity against the classical pathway.

Keywords

References

  1. Abdel-Kader, M.S., Bahler, B.D., Malone, S., Werkhoven, M.C., Wisse, J.H., Neddermann, K.M., Bursuker, I., and Kingston, D. G., Bioactive saponins from Swartzia schomburgkii from the suriname rainforest. J. Nat. Prod. 63, 1461-1464 (2000) https://doi.org/10.1021/np0000926
  2. An, R.-B., Min, B.S., Na, M., Chang, H.W., Son, K.H., Kim, H.P., Lee, H.K., Bae, K., and Kang, S.S., Iridoid Esters from Patrinia saniculaefolia. Chem. Pharm. Bull. 51, 583-585 (2003) https://doi.org/10.1248/cpb.51.583
  3. Bae, K., The Medicinal Plants of Korea, Kyo-Hak Publishing, Seoul, p. 475 (2000)
  4. Do, J.C., Chai, J.Y., and Son, K.H., Studies on the components of Lycopus Iucidus (I) Kor. J. Pharmacogn. 22, 162-165 (1991)
  5. Ju, H.K., Baek, S.-H., An, R.-B., Bae, K., Son, K.H., Kim, H.P., Kang, S.S., Lee, S.H., Son, J.K., and Chang, H.W., Inhibitory effects of nardostachin on nitric oxide, prostaglandin E2, and tumor necrosis factor-$\alpha$ production in lipopolysaccharide activated macrophages. Biol. Pharm. Bull. 26, 1375-1378 (2003a) https://doi.org/10.1248/bpb.26.1375
  6. Ju, H.K., Moon, T.C., Lee, E., Baek, S.-H., An, R.-B., Bae, K., Son, K. H., Kim, H.P., Kang, S.S., Lee, S.H., Son, J.K., and Chang, H.W., Inhibitory effects of a new iridoid, patridoid II and its isomers, on nitric oxide and TNF-$\alpha$ production in cultured murine macrophages. Planta Med. 69, 950-953 (2003b) https://doi.org/10.1055/s-2003-45107
  7. Jung, K.Y., Oh, S.R., Park, S.H., Lee, I.S., Ahn, K.S., Lee, J.J., and Lee, H.K., Anti-complement activity of tiliroside from the flower buds of Magnolia fargesii. Biol. Pharm. Bull. 21, 1077-1078 (1998) https://doi.org/10.1248/bpb.21.1077
  8. Kawamura, N., Watanabe, H., and Oshio, H., Saponins from roots of Momordica cochinchinensis. Phytochemistry 27, 3585-3591 (1988) https://doi.org/10.1016/0031-9422(88)80773-8
  9. Kitanaka, S., Yasuda, I., Kashiwada, Y., Hu, C.Q., Bastow, K.F., Bori, I.D., and Lee, K.H., Antitumor agents, 162. Cell-based assays for identifying novel DNA topoisomerase inhibitors: studies on the constituents of Fatsia japonica. J. Nat. Prod. 58, 1647-1654 (1995) https://doi.org/10.1021/np50125a001
  10. Lee, S.M., Park, J.G., Lee, Y.H., Lee, C.G., Min, B.S., Kim, J.H., and Lee H.K., Anti-complementary activity of triterpenoides from fruits of Zizyphus jujuba. Biol. Pharm. Bull. 27, 1883-1886 (2004) https://doi.org/10.1248/bpb.27.1883
  11. Lee, T. B., Illustrated Flora of Korea. Hyangmoon Publ. Co. Seoul, p. 714 (1980)
  12. Lee, Y. N., Flora of Korea, Kyo-Hak Publishing Co., Ltd.: Seoul, p. 756 (1996)
  13. Li, C.S., Black, W.C., Chan, C.C., Ford-Hutchinson, A.W., Gauthier, J.Y., Gordon, R., Guay, D., Kargman, S., Lau, C.K., and Mancini, J., Cyclooxygenase-2 inhibitors. Synthesis and pharmacological activities of 5-methanesulfonamido-1-indanone derivatives. J. Med. Chem. 38, 4897-4905 (1995) https://doi.org/10.1021/jm00025a007
  14. Li, Y.-F., Lou, F.-C., Tang, Y.-P., and Wang, J.-H., Advances of researches in Patrinia Juss. Nat. Prod. Res. Dev. 13, 71-75 (2001)
  15. Min, B.S., Oh, S.R., Ahn, K.S., Kim, J.H., Lee, J., Kim, D.Y., Kim, E.H., and Lee, H.K., Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica. Planta Med. 70, 1210-1215 (2004) https://doi.org/10.1055/s-2004-835853
  16. Seo, S., Tomita, Y., and Tori, K., Carbon-13 NMR spectra of urs-12-enes and application to structural assignments of components of Isodon japonicus tissue cultures. Tetrahedron Lett. 11, 7-10 (1975)
  17. Thuong, P.T., Min, B.-S., Jin, W., Na, M., Lee, J., Seong, R., Lee, Y.-M., Song, K., Seong, Y., Lee, H.-K., Bae, K., and Kang, S.S., Anticomplementary activity of ursane-type triterpenoids from Weigela subsessilis. Biol. Pharm. Bull. 29, 830-833 (2006) https://doi.org/10.1248/bpb.29.830
  18. Tursch, B., Savoir, R., Ottinger, R., and Chiurdoglu, G., Triterpenes. VII. N M R spectra of triterpenes. Effect of substitution on the chemical shifts of methyl groups in the olean-12-ene series. Tetrahedron Lett. 6, 539-543 (1967)