Diverse Diterpenoids from Microdesmis casearifolia

  • Han Guanghui ,
  • Ren Yuhao ,
  • Fan Yaoyue ,
  • Ji Kailong ,
  • Zhou Bin ,
  • Cao Weiguo ,
  • Yue Jianmin
Expand
  • a Department of Chemistry, College of Science, Shanghai University, Shanghai 200444;
    b State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received date: 2020-05-22

  Revised date: 2020-06-16

  Online published: 2020-07-01

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21532007, 21772213), the Drug Innovation Major Project of China (No. 2018ZX09711001-001-005), the Biological Resources Program of Chinese Academy of Sciences (No. KFJ-BRP-008) and the Youth Innovation Promotion Association, Chinese Academy of Sciences.

Abstract

Four new diterpenoids, casearoids A~D (1~4), including dolabrane, orosane, labdane, and cembrane, were isolated and characterized from Microdesmis casearifolia. Their structures were elucidated by extensive spectroscopic data analysis. The absolute configurations of these diterpenoids were established by analysis of the electronic circular dichroism (ECD) data.

Cite this article

Han Guanghui , Ren Yuhao , Fan Yaoyue , Ji Kailong , Zhou Bin , Cao Weiguo , Yue Jianmin . Diverse Diterpenoids from Microdesmis casearifolia[J]. Chinese Journal of Organic Chemistry, 2020 , 40(9) : 2811 -2816 . DOI: 10.6023/cjoc202005060

References

[1] Li, P. T.; Zhang, Y. T., In Flora of China, Vol. 43, Eds.:Xu, L. R.; Huang, C. J., Science Press, Beijing, 1998, p. 2.
[2] Zamble, A.; Sahpaz, S.; Hennebelle, T.; Carato, P.; Bailleul, F. Chem. Biodiversity 2006, 3, 982.
[3] Zamble, A.; Sahpaz, S.; Brunet, C.; Bailleul, F. Phytomedicine 2008, 15, 625.
[4] Roumy, V.; Hennebelle, T.; Zamble, A.; Yao, J. D.; Sahpaz, S.; Bailleul, F. Eur. J. Mass Spectrom. 2008, 14, 111.
[5] Zamble, A.; Martin-Nizard, F.; Sahpaz, S.; Reynaert, M.-L.; Staels, B.; Bordet, R.; Duriez, P.; Gressier, B.; Bailleul, F. Phytother. Res. 2009, 23, 892.
[6] Zamble, A.; Hennebelle, T.; Sahpaz, S.; Bailleul, F. Chem. Pharm. Bull. 2007, 55, 643.
[7] Akpanyung, E. O.; Ita, S. O.; Opara, K. A.; Davies, K. G.; Ndem, J. I.; Uwah, A. F. J. Med. Plants Res. 2013, 7, 2338.
[8] Ni, S.-J.; Li, J.; Li, M.-Y. Chem. Biodiversity 2018, 15, 1.
[9] Yang, Y.; Zhang, Y.; Liu, D.; Min, L.; Weber; Shao, B.; Lin, W.-H. Fitoterapia 2015, 103, 277.
[10] Bohlmann, F.; Knoll, K. H.; King, R. M.; Robinson, H. Phytochemistry 1979, 18, 1997.
[11] Ansell, S. M.; Pegel, K. H.; Taylor, D. A. H. Phytochemistry 1993, 32, 953.
[12] Jia, R.; Shi, Y.-H.; He, P.-M.; Guo, Y.-W. Chin. J. Nat. Med. 2010, 8, 422.
[13] Duh, C.-Y.; Wang, S.-K.; Weng, Y.-L.; Chiang, M.-Y.; Dai, C.-F. J. Nat. Prod. 1999, 62, 1518.
[14] Kijjoa, A.; Polonia, M. A.; Pinto, M. M. M.; Kitiratakarn, T.; Gedris, T.; Herz, W. Phytochemistry 1994, 37, 197.
[15] Mulholland, D. A.; Langat, M. K.; Crouch, N. R.; Coley, H. M.; Mutambi, E. M.; Nuzillard, J. M. Phytochemistry 2010, 71, 1381.
[16] Langat, M. K.; Crouch, N. R.; Smith, P. J.; Mulholland, D. A. J. Nat. Prod. 2011, 74, 2349.
[17] Kawakami, S.; Matsunami, K.; Otsuka, H.; Lhieochaiphant, D.; Lhieochaiphant, S. J. Nat. Med. 2013, 67, 410.
[18] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M.A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R. E.; Stratmann, O.; Yazyev, A. J.; Austin, R.; Cammi, C.; Pomelli, J. W.; Ochterski, R.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J., Gaussian 09, Rev. B.01, 2010, Gaussian Inc., Wallingford CT.
[19] Bruhn, T.; Schaumloeffel, A.; Hemberger, Y.; Bringmann, G. Chirality 2013, 25, 243.
Outlines

/