DOLABRANE-TYPE DITERPENOID AND LIGNAN CONSTITUENTS FROM THE STEM BARKS OF CERIOPS DECANDRA (GRIFF.) W. THEOB.

Kieu Thi Phuong Linh, Nguyen Van Chien, Nguyen Quoc Trung, Vu Huy Thong, Nguyen Van Tuyen, Nguyen Phuong Thao

Abstract


Three dolabrane-type diterpenoids (13) and a lignan derivative (4) were isolated from a methanolic extract of C. decandra stem barks using various chromatographic separations. Their structures were elucidated to be tagalsine X (1), tagalsin P (2), ent-5α,2-oxodolabr-3-ene-3,15,16-triol (3), and (+)-pinoresinol (4) by detailed analysis via spectroscopic techniques (1D, 2D NMR, and ESI-MS data) as well as comparison with those reported. This is the first report of compound 4 from the Ceriops genus.


Keywords


Ceriops decandra, Rhizophoraceae, diterpenoid, lignan.

Full Text:

PDF

References


Wu J., Xiao Q., Xu J., Li M.Y., Pana J.Y., Yang M.H. - Natural products from true mangrove flora: source, chemistry and bioactivities. Natural Product Reports 25 (2008) 955-981.

Nebula M., Harisankar H. S., Chandramohanakumar. N. - Metabolites and bioactivities of Rhizophoraceae mangroves. Natural Products and Bioprospecting 3 (2013) 207-232.

Ethnomedicinal, Mahmud I., Shahria N., Yeasmin S., Iqbal A., Mukul E. H., Gain S., Shilpi J. A., Islam M. K. - Ethnomedicinal, phytochemical and pharmacological profile of amangrove plant Ceriops decandra Griff Din Hou. Journal of Complementary and Integrative Medicine 16 (2019) 1-22.

Chen Y., Hou Y., Guo Z., Wenqing W., Zhong C., Zhou R., Shi S. - Applications of multiple nuclear genes to the molecular phylogeny, population genetics and hybrid identification in the mangrove genus Rhizophora. Plos One (2015) e.0145058.

Anjaneyulu A. S. R., Rao V. - Ceriopsins F and G, diterpenoids from Ceriops decandra. Phytochemistry 62 (2003) 1207-1211.

Anjaneyulu A. S. R., Rao V. - Ceriopsins A-D, diterpenoids from Ceriops decandra. Phytochemistry 60 (2002) 777-782.

Anjaneyulu A. S. R., Rao V. L., Lobkovsky E., Clardy J. - Ceriopsin E, a new epoxy ent-kaurene diterpenoid from Ceriops decandra. Journal of Natural Products 65 (2002) 592-594.

Ponglimanont C., Thongdeeying P. - Lupane-triterpene esters from the leaves of Ceriops decandra (Griff.) Ding Hou. Australian Journal of Chemistry 58 (2005) 615-618.

Jiang Z. P., Tian L. W., Shen L., Wu J. - Ent-abietanes from the Godavari mangrove, Ceriops decandra: Absolute configuration and NF-κB inhibitory activity. Fitoterapia 130 (2018) 272-280.

Wang H., Li M. Y., Satyanandamurty T., Wu J. - New diterpenes from a Godavari mangrove, Ceriops decandra. Planta Medica 79 (2013) 666-672.

Wu X., Liao H., Lu H., Zhang C. - A new dolabrane dinorditerpene from Ceriops tagal Open Access Library Journal 3 (2016) e2957.

Hu W. M., Li M. Y., Li J., Xiao Q., Feng G., Wu J. - Dolabranes from the Chinese mangrove, Ceriops tagal. Journal of Natural Products 73 (2010) 1701-1705.

Xie L. H., Akao T., Hamasaki K., Deyama T., Hattori M. - Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol. Chemical and Pharmaceutical Bulletin 51 (2003) 508-515.

Kijjoa A., Pinto M. M. M., Anantachoke C., Gedris T. E., Herz W. - Dolabranes from Endospermum diadenum Phytochemistry 40 (1995) 191-193.

Chang F. R., Chao Y. C., Teng C. M., Wu Y. C. - Chemical constituents from Cassytha filiformis II. Journal of Natural Products 61 (1998) 863-866.

Li C. Y., Chow T. J., Wu T. S. - The epimerization of sesamin and asarinin. Journal of Natural Products 68 (2005) 1622-1624.

Greger H., Hofer O. - New unsymmetrically substituted tetrahydrofurofuran lignans from Artemisia absinthium - Assignment of the relative stereochemistry by lanthanide chemical shifts. Tetrahedron 36 (1980) 3551-3558.

Shao S. Y., Yang Y. N., Feng Z. M., Jiang J. S., Zhang P. C. - An efficient method for determining the relative configuration of furofuran lignans by 1H NMR spectroscopy. Journal of Natural Products 81 (2018) 1023-1028.

Schroeder F. C., Weibel D. B., Meinwald J. - Chiral silylation reagents: determining configuration via NMR-spectroscopic coanalysis. The Journal of Organic Chemistry 6 (2004) 3019-3022.

Pelter A., Ward R. S., Rao E. V., Sastry K. V. - Revised structures for pluviatilol, methyl pluviatilol and xanthoxylol: General methods for the assignment of stereochemistry to 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans. Tetrahedron 32 (1976) 2783-2788.




DOI: https://doi.org/10.15625/2525-2518/58/4/14711 Display counter: Abstract : 88 views. PDF : 6 views.

Refbacks

  • There are currently no refbacks.


budidaya tani

Index: Google Scholar; Crossref; VCGate; Asean Citation Index

Published by Vietnam Academy of Science and Technology