Articles

Pentacyclic Triterpenoids from the Roots of Rhodomyrtus tomentosa

  • Xiong Juan ,
  • Huang Ya ,
  • Tang Yu ,
  • You Mei ,
  • Hu Jinfeng
Expand
  • Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai 201203

Received date: 2013-03-19

  Revised date: 2013-04-11

  Online published: 2013-04-17

Supported by

Project supported by the National Natural Science Foundation of China (Nos.81273401, 81202420), the Ph.D.Programs Foundation of Ministry of Education of China (Nos.20120071110049, 20120071120049) and the Grant of Ministry of Science and Technology (MOST, No.2011ZX09307-002-01).

Abstract

Eight pentacyclic triterpenoids were isolated from the methanol extract of the roots of Rhodomyrtus tomentosa.By application of spectroscopic methods (especially 1D-, 2D-NMR, MS), the structures were established as 23-cis-p-coumaroyl- oxy-2α,3β-dihydroxyolean-12-en-28-oic acid (1), 23-trans-p-coumaroyloxy-2α,3β-dihydroxyolean-12-en-28-oic acid (2), 3β- O-trans-ferulyl-2α,23-dihydroxyolean-12-en-28-oic acid (3), 3β-O-trans-p-coumaroyl-2α,23-dihydroxyolean-12-en-28-oic acid (4), 3β-O-cis-p-coumaroyl-2α,23-dihydroxyolean-12-en-28-oic acid (5), maslinic acid (6), arjunolic acid (7), and 2α,3β-dihydroxytaraxer-20-en-28-oic acid (8).Among them, compounds 1 and 3 were new oleanane-type triterpenoids, while compounds 2, 46 and 8 were isolated from this plant for the first time.This is the first report on the chemical constituents from the roots of R.tomentosa.

Cite this article

Xiong Juan , Huang Ya , Tang Yu , You Mei , Hu Jinfeng . Pentacyclic Triterpenoids from the Roots of Rhodomyrtus tomentosa[J]. Chinese Journal of Organic Chemistry, 2013 , 33(06) : 1304 -1308 . DOI: 10.6023/cjoc201303029

References

[1] Zhao, Z.G.; Cheng, W.; Guo, J.J.Guangxi Forestry Sci.2006, 35, 70 (in Chinese).(赵志刚, 程伟, 郭俊杰, 广西林业科学, 2006, 35, 70.)
[2] Jiangsu New Medical College A Dictionary of the Traditional Chinese Medicine, Shanghai Science and Technology Press, Shanghai, 1986, p.200 (in Chinese).(江苏新医学院, 中药大辞典, 科学技术出版社, 上海, 1986, p.200.)
[3] (a) Hiranrat, A.; Mahabusarakam, W.Tetrahedron 2008, 64, 11193.(b) Hiranrat, A.; Mahabusarakam, W.; Carroll, A.R.; Duffy, S.J.Org.Chem.2012, 77, 680.
[4] (a) Hui, W.H.; Li, M.M.; Kong, L.Phytochemistry 1975, 14, 833. (b) Hui, W.H.; Li, M.M.Phytochemistry 1976, 15, 1741.
[5] Hou, A.J.; Liu, Y.Z.; Wu, Y.J.Chin.Trad.Herb. Drugs 1999, 30, 645 (in Chinese).(侯爱君, 刘岩泽, 吴养洁, 中草药, 1999, 30, 645.)
[6] Liu, Y.Z.; Hou, A.J.; Ji, C.R.; Wu, Y.J.Chin.Chem.Lett.1997, 8, 39.
[7] (a) Hiranrat, A.; Chitbankluoi, W.; Mahabusarakam, W.; Limsuwan, S.; Voravuthikunchai, S.P.Nat.Prod.Res.2012, 26, 1904.(b) Huang, M.Q.; Ya, Q.K.; Chen, H.Y.; Tan, X.; Liu, H.D.; Dang, M.Q.Chin.Trad.Herb. Drugs 2010, 41, 1079 (in Chinese).(黄敏琪, 牙启康, 陈海燕, 谭晓, 刘华东, 党美琼, 中草药, 2010, 41, 1079.)
[8] (a) Chen, T.; Yu, C.; Yang, B.Chem.Nat.Compd.2011, 47, 524.(b) Liu, G.-L.; Guo, H.-H.; Sun, Y.-M.Int.J.Mol.Sci.2012, 13, 6292.(c) Lai, T.N.H.; Herent, M.-F.; Quetin-Leclercq, J.; Nguyen, T.B.T.; Rogez, H.; Larondelle, Y.; André, C.M.Food Chem.2013, 138, 1421.
[9] Gu J.-Q.; Park, E.J.; Luyengi, L.; Hawthorne, M.E.; Mehta, R.G.; Farnsworth, N.R.; Pezzuto, J.M.; Kinghorn, A.D.Phytochemistry 2001, 58, 121.
[10] Saimaru, H.; Orihara, Y.; Tansakul, P.; Kang, Y.-H.; Shibuya, M.; Ebizuka, Y.Chem.Pharm.Bull.2007, 55, 784.
[11] Cui, B.S.; Li, S.Chin.Trad.Herb. Drugs 2012, 43, 2132 (in Chinese).(崔保松, 李帅, 中草药, 2012, 43, 2132.)
[12] Kim, D.-H.; Han, K.-M.; Chung, I.-S.; Kim, D.-K.; Kim, S.-H.; Kwon, B.-M.; Jeong, T.-S.; Park, M.-H.; Ahn, E.-M.; Baek, N.-I.Arch.Pharm.Res.2005, 28, 550.
[13] Shao, M.; Wang, Y.; Huang, X.-J.; Fan, C.-L.; Zhang, Q.-W.; Zhang, X.-Q.; Ye, W.-C.J.Asian Nat.Prod.Res.2012, 14, 348.
[14] Ito, H.; Kobayashi, E.; Li, S.-H.; Hatano, T.; Sugita, D.; Kubo, N.; Shimura, S.; Itoh, Y.; Yoshida, T.J.Nat.Prod.2001, 64, 737.
[15] Hu, J.-F.; Eldridge, G.R.; Yu, Y.-H.; O'Neil-Johnson, M.Prog.Chem.2008, 20, 429 (in Chinese).(胡金锋, Eldridge, G.R., 余亦华, O' Neil-Johnson, M.化学进展, 2008, 20, 429.)
[16] Wu, S.-B.; Su, J.-J.; Sun, L.-H.; Wang, W.-X.; Zhao, Y.; Li, H.; Zhang, S.-P.; Dai, G.-H.; Wang, C.-G.; Hu, J.-F.J.Nat.Prod.2010, 73, 1898.
[17] Hong, Z.-L.; Xiong, J.; Wu, S.-B.; Zhu, J.-J.; Hong, J.-L.; Zhao, Y.; Xia, G.; Hu, J.-F.Phytochemistry 2013, 86, 159.
[18] Fan, H.; Zang, Y.; Zhang, Y.; Zhang, H.-F.; Zhao, Z.; Hu, J.-F.Helv.Chim.Acta 2010, 93, 2439.
Outlines

/