Planta Med 2010; 76 - P44
DOI: 10.1055/s-0030-1251806

Neolignans and ent-Labdane Diterpenoid from the Leaves of Casearia sylvestris (Flacourtiaceae)

W Wang 1, Z Ali 1, XC Li 1, IA Khan 1, 2
  • 1National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, MS 38677, USA
  • 2Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, MS 38677, USA

Casearia sylvestris Swartz (Flacourtiaceae) is a Brazilian and Paraguayan folk medicinal plant called as „Guaçatonga“ or „Chá de Bugre“ and is used to treat snakebite, trauma, ulceration, obesity, and cough [1–5]. Our continued investigation of this species to look for new chemotaxonomic markers has led to the isolation of six new neolignans, casearialignans A-F (1–6) and a new ent-labdane glycoside sylvestin (7) as well as a known lignan glycoside syringaresinol-β-D-glucoside. Compounds 1–6 possessed a 3-(3,5-dimethoxyphenyl)-1,2-propanediol structural moiety. To the best of our knowledge, this is the first time to report the 8-O-4′ type neolignans with such a structure mioety. Therefore, this type of 8-O-4′ neolignans might be considered as chemotaxonomic marker of the title plant. Compound 7 is the first and the only ent-labadane diterpene glycoside found in the title plant. Since many ent-kaurane diterpene glycosides coexist in the same plant [6,7], 1 might be considered as a biosynthetic precursor of the ent-kaurane derivatives.

Fig.1

Acknowledgements: This work is supported by the Food and Drug Administration grant entitled „Science Based Authentication of Dietary Supplements“ and „Botanical Dietary Supplement Research“ Numbers 5U01FD002071–09 and 1U01FD003871–01 and the United States Department of Agriculture Specific Cooperative Research Agreement Number 58–6408–2-0009. References: [1] Cruz GL (1995), Dicionario Das Plantas Uteis Do Brasil, 5th ed., Bertrand: 599. [2] Lorenzi H, Matos FJA. (2002), Plantas medicinais do Brasil:nativas e exóticas. Instituto Plantarum, São Paulo: 220–221. [3] Borges MH, Soares AM, et al. (2001) Toxicon 39: 1863–1869. [4] Ruppett BM, Pereira EF, et al. (1991) Mem Inst Oswaldo Cruz 87: 203–205. [5] Sertié JAA, Carvalho JCT, et al. (2000) Pharmaceut Biol 38: 112–119. [6] Wang W, Zhao J, et al. (2009) Planta Med 75: 1436–1441. [7] Wang W, Ali Z, et al. (2009) Helv Chim Acta 92: 1829–1839.