Chemical constituents and anti-inflammatory effects of some stilbenoids from Dipterocarpus retusus fruits of Vietnam

Ho Dac Hung, Doan Duy Tien, Nguyen Thi Ngoan, Ba Thi Duong, Do Quoc Viet, Pham Gia Dien, Bui Kim Anh, Do Huu Nghi
Author affiliations

Authors

  • Ho Dac Hung Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam
  • Doan Duy Tien Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam
  • Nguyen Thi Ngoan Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam
  • Ba Thi Duong Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam
  • Do Quoc Viet Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam
  • Pham Gia Dien Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam
  • Bui Kim Anh Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam
  • Do Huu Nghi Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet St. Ha Noi, Viet Nam

DOI:

https://doi.org/10.15625/2525-2518/59/6/14728

Keywords:

Dipterocarpus retusus Blume, fruit, ε-viniferin, paucifloroside, anti-inflammatory activity

Abstract

In this work, the crude MeOH extract of fruits of Dipterocarpus retusus Blume (Dipterocarpaceae) growing in Vietnam was prepared and studied. Five compounds: ε-viniferin, paucifloroside, ursolic acid, quercetin, and (+)-catechin, was isolated. The structures of these compounds were elucidated by spectroscopic methods. The extracts from fruits of D. retusus Blume by metanol and its some isolated stilbene compounds were evaluated for anti-inflammatory effect activities.

Downloads

Download data is not yet available.

References

Aslam M.S., Ahmad M. S., Mamat A. S. - A phytochemical, ethnomedicinal and pharmacological review of Genus dipterocarpus.Int. J. Pharm. Sci., 7 (4) (2015) 27-38.

Xiao K., Zhang H. J., Xuan L. J., Zhang J., Xu Y. M. D. L.- Stilbenoids: chemistry and bioactivities. Stud. Nat. Prod. Chem. 34 (2008) 453-646. DOI: https://doi.org/10.1016/S1572-5995(08)80032-4

Khiev P., Kwon O. K., Song H. H., Oh S. R., Ahn K. S., Lee H. K., et al. Cytotoxic terpenes from the stems of Dipterocarpus obtusifolius collected in Cambodia. Chem. Pharm. Bull. 60 (8) (2012) 955-61. DOI: https://doi.org/10.1248/cpb.c12-00012

Riveiro M. E., De Kimpe N., Moglioni A., Vazquez R., Monczor F., Shayo C., et al.- Coumarins: old compounds with novel promising therapeutic perspectives. Curr. Med. Chem. 17 (13) (2010) 1325-38. DOI: https://doi.org/10.2174/092986710790936284

Ge H. M., Huang B., Tan S. H., Shi D. H., Song Y. C., Tan R. X. - Bioactive oligostilbenoids from the stem bark of Hopea exalata. J. Nat. Prod. 69 (2006) 1800-1802. DOI: https://doi.org/10.1021/np060242y

Yang W. S., Lee B. H., Kim S. H., Kim H. G., Yi Y. S., Htwe K. M. - Dipterocarpus tuberculatus ethanol extract strongly suppresses in vitro macrophage-mediated inflammatory responses and in vivo acute gastritis. J. Ethnopharmacol. 146 (3) (2013)873-80. DOI: https://doi.org/10.1016/j.jep.2013.01.033

Norhayati M., Laily B. D., Sahidin I., Siti F. H., Nazlina I., Zuriati Z., Yaacob W. A.- Acuminatol and other antioxidative resveratrol oligomers from the stem bark of Shorea acuminata. Molecules 17 (2012) 9043-9055. DOI: https://doi.org/10.3390/molecules17089043

Hung H. D, Tien D. D., Ngoan N. T., Duong B. T., Viet D. Q., Dien P. G., Anh K. B. - Study on chemical constituents and bioactivities of the fruits of Dipterocarpus retusus Blume. Diterocarpaceae of Viet Nam. Vietnam Journal of Science and Technology 57 (3) (2019) 294-299. DOI: https://doi.org/10.15625/2525-2518/57/3/13249

Cuonng N.M., Khanh N. P, Đuc H.V, Huong T. T., Kim Y. C., Long P. Q., Kim Y. H- Flavonoids and triterpenoids from Callistemon citrinus and their inhibitory effect on NO production in LPS - stimulated RAW264.7 macrophages, Vietnam Journal of Science and Technology 54 (2) (2016) 214-223. DOI: https://doi.org/10.15625/0866-708X/54/2/6741

H. Kurihara, J. Kawabata, S. Ichikawa & J. Mizutani- (-)-ɛ-Viniferin and related Oligostilbenes from Carex pumila Thunb., Agric. BioI. Chem., 54 (4) (1990) 1097-1099. DOI: https://doi.org/10.1271/bbb1961.54.1097

Kong Q.J., X.Y. Ren, N. Hu, C.R. Sun, Y.J. Pan - Identification of isomers of resveratrol dimer and their analogues from wine grapes by HPLC/MSn and HPLC/DAD-UV, Food Chem. 127 (2011) 727-734. DOI: https://doi.org/10.1016/j.foodchem.2010.12.133

Amira-Guebailia, H., Valls, J. Richard, T., Vitrac, X., Monti, J.P., Delaunay, J.C., Mérillon, J.M.- Centrifugal partition chromatography followed by HPLC for the isolation of cis-ε-viniferin, a resveratrol dimer newly extracted from a red Algerian wine, Food Chem.113(2009) 320–324. DOI: https://doi.org/10.1016/j.foodchem.2008.07.050

Ito T, Tanaka T, Iinuma M, Iliya I, Nakaya K, Ali Z., Takahashi Y, Sawa R., Shirataki Y, Murata J and Darnaedi D.- New resveratrol oligomers in the stem bark of Vatica pauciflora, Tetrahedron 59 (2003) 5347-5393. DOI: https://doi.org/10.1016/S0040-4020(03)00730-0

Muhtadi, Euis H. Hakim, Yana M. Syah, Lia D. Juliawaty, Laily bin Din, dan Jalifah Latip.-Resveratrol oligomer compounds from thetreebarkofDipterocarpusretusus Blume and cytotoxic effect against murine leukaemia P388, Pharmacon 8 (1)(2007) 6–12.

Woo K. W., Han J. Y., Choi S. U., Kim K. H., and Lee K. R.- Triterpenes from Perilla frutescens var. acuta and their cytotoxic activity, Nat Pro Sci 20 (2) (2014) 71-75.

Doddrell, D., Khong, P.W. and Lewis, K.G. -The Stereochemical Dependence of 13C Chemical shifts in Olean- 12-enes and Urs-12-enes As an Acid to Structural Assignment, Tetrahedron Letters 27 (1974) 2381-2384. DOI: https://doi.org/10.1016/S0040-4039(01)92261-0

Manivannan R. and Shopna R. -Isolation of Quercetin and Isorhamnetin Derivatives and Evaluation of Anti-microbial and Anti-inflammatory Activities of Persicaria glabra. Nat Pro Sci 21(3) (2015) 170-175.

Li Y-L., Li J. , Wang N-L., and Yao X.S.- Flavonoids and a New Polyacetylene from Bidens parviflora Willd., Molecules 13 (2008)1931-1941. DOI: https://doi.org/10.3390/molecules13081931

EL-RAZEK M.H. ABD - NMR Assignments of Four Catechin Epimers, Asian J. Chem. 19 (6) (2007) 4867- 487.

Hye M.A., Taher M. A., Ali M. Y., Ali M. U. and Zaman S. - Isolation of (+)-catechin from Acacia catechu (Cutch tree) by convernient method, J. Sci. Res., I (2) (2009) 300-305. DOI: https://doi.org/10.3329/jsr.v1i2.1635

Downloads

Published

29-12-2021

How to Cite

[1]
H. D. Hung, “Chemical constituents and anti-inflammatory effects of some stilbenoids from <i>Dipterocarpus retusus</i> fruits of Vietnam”, Vietnam J. Sci. Technol., vol. 59, no. 6, pp. 724–733, Dec. 2021.

Issue

Section

Natural Products

Most read articles by the same author(s)