Planta Med 2012; 78(2): 182-185
DOI: 10.1055/s-0031-1280263
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Phenols with Anti-HIV Activity from Daphne acutiloba

Sheng Zhuo Huang1 , 4 , Xing Jie Zhang3 , 4 , Xing Yao Li3 , 4 , He Zhong Jiang1 , 4 , Qing Yun Ma2 , Peng Cheng Wang1 , 4 , Yu Qing Liu1 , Jiang Miao Hu1 , Yong Tang Zheng3 , Jun Zhou1 , You Xing Zhao1 , 2
  • 1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, People's Republic of China
  • 2Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, People's Republic of China
  • 3Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, People's Republic of China
  • 4Graduate School of the Chinese Academy of Sciences, Beijing, People's Republic of China
Further Information

Publication History

received July 7, 2011 revised September 6, 2011

accepted September 8, 2011

Publication Date:
11 October 2011 (online)

Abstract

The present paper describes the study of the phytochemical properties and anti-HIV activity of the phenolic isolates of the plateau medicinal plant Daphne acutiloba Rehd. (Thymelaeceae). Two new lignans named daphnenin (1) and daphnetone (2), along with 11 known ones, were isolated, and their structures were elucidated by 1D and 2D NMR spectroscopy as well as HR-ESI-MS. In the anti-HIV activity study, daphnenin (1) and caffeic acid n-octadecyl ester (13) showed definite anti-HIV activity with EC50 values of 0.39 and 0.16 µg/mL, respectively.

Supporting Information

References

  • 1 Yunnan Institute of Materia Medica .The annals of national medicine in Yunnan. Kunming: the Nationalities Publishing House of Yunnan; 2009
  • 2 Badawi M M, Handa S S, Kinghorn A D, Cordell G A, Farnsworth N R. Plant anticancer agents XXVII: antileukemic and cytotoxic constituents of Dirca occidentalis (Thymelaeaceae).  J Pharm Sci. 1983;  72 1285-1287
  • 3 Carney J R, Krenisky J M, Williamson R T, Luo J, Carlson T J, Hsu V L, Moswa J L. Maprouneacin, a new daphnane diterpenoid with potent antihyperglycemic activity from Maprounea africana.  J Nat Prod. 1999;  62 345-347
  • 4 He W, Cik M, Lesage A, Van der Linden I, De Kimpe N, Appendino G, Bracke J, Mathenge S G, Mudida F P, Leysen J E, Van Puyvelde L. Kirkinine, a new daphnane orthoester with potent neurotrophic activity from Synaptolepis kirkii.  J Nat Prod. 2000;  63 1185-1187
  • 5 Su J, Wu Z, Shen Y, Zhang C, Zhang W. Lignans from Daphne giraldii.  Chem Nat Compd. 2008;  44 648-650
  • 6 Ullah N, Ahmad S, Anis E, Mohammad P, Rabnawaz H, Malik A. A lignan from Daphne oleoides.  Phytochemistry. 1999;  50 147-149
  • 7 Zhuang L, Seligmann O, Jurcic K, Wagner H. Constituents of Daphne tangutica.  Planta Med. 1982;  45 172-176
  • 8 Taniguchi M, Fujiwara A, Baba K, Wang N H. Two biflavonoids from Daphne acutiloba.  Phytochemistry. 1998;  49 863-867
  • 9 Eklund P C, Sundell F J, Smeds A I, Sjoeholm R E. Reactions of the natural lignan hydroxymatairesinol in basic and acidic nucleophilic media: formation and reactivity of a quinone methide intermediate.  Org Biomol Chem. 2004;  2 2229-2235
  • 10 Liang S, Shen Y H, Tian J M, Wu Z J, Jin H Z, Zhang W D, Yan S K. Phenylpropanoids from Daphne feddei and their inhibitory activities against NO production.  J Nat Prod. 2008;  71 1902-1905
  • 11 Yamauchi S, Sugahara T, Nakashima Y, Okada A, Akiyama K, Kishida T, Maruyama M, Masuda T. Radical and superoxide scavenging activities of matairesinol and oxidized matairesinol.  Biosci Biotechnol Biochem. 2006;  70 1934-1940
  • 12 Akiyama K, Maruyama M, Yamauchi S, Nakashima Y, Nakato T, Tago R, Sugahara T, Kishida T, Koba Y. Antimicrobiological activity of lignan: effect of benzylic oxygen and stereochemistry of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on activity.  Biosci Biotechnol Biochem. 2007;  71 1745-1751
  • 13 Evcim U, Gozler B, Freyer A J, Shamma M. Haplomyrtin and (−)-haplomyrfolin: two lignans from Haplophyllum myrtifolium.  Phytochemistry. 1986;  25 1949-1951
  • 14 Xia Y, You J, Zhang Y, Su Z. Synthesis, anti-virus and anti-tumor activities of dibenzylbutyrolactone lignans and their analogues.  J Chem Res. 2009;  565-569
  • 15 Xu Z H, Qin G W, Xu R S. A new bicoumarin from Stellera chamaejasme L.  J Asian Nat Prod Res. 2001;  3 335-340
  • 16 Kiyooka S, Takeshita Y, Tanaka Y, Higaki T, Wada Y. Dicationic [(−)-sparteine]palladium-catalyzed enantioselective aldol reaction of aldehydes with 1-phenyl-1-trimethylsilyloxyethene, proceeding via a palladium enolate.  Tetrahedron Lett. 2006;  47 4453-4456
  • 17 Zhang W, Zhang W D, Liu R H, Shen Y H, Zhang C, Cheng H S, Fu P, Shan L. Two new chemical constituents from Daphne odora Thunb. var. marginata.  Nat Prod Res. 2006;  20 1290-1294
  • 18 Garcia-Argaez A N, Perez-Amador M C, Aguirre-Hernandez E, Martinez-Vazquez M. Two new caffeate esters from roots of Merremia tuberosa and M. dissecta.  Planta Med. 1999;  65 678-679
  • 19 Zhang G H, Wang Q, Chen J J, Zhang X M, Tam S C, Zheng Y T. The anti-HIV-1 effect of scutellarin.  Biochem Biophys Res Commun. 2005;  334 812-816
  • 20 Reed L J, Muench H. A simple method for estimating fifty percent endpoints.  Am J Hyg. 1938;  27 493-497

Prof. Dr. Jun Zhou

State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany
Chinese Academy of Sciences

Kunming 650204

People's Republic of China

Phone: +86 871 5 22 32 61

Fax: +86 871 5 22 32 64

Email: jzhou@mail.kib.ac.cn

Prof. Dr. You Xing Zhao

Institute of Tropical Bioscience and Biotechnology
Chinese Academy of Tropical Agricultural Sciences

Haikou 571101

People's Republic of China

Phone: +86 898 66 98 90 95

Fax: +86 898 66 98 90 95

Email: zhaoyx1011@163.com

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