Full Length Research Paper

Intraspecific variability of dihydrochalcone, chromenes and benzoic acid derivatives in leaves of Piper aduncum L. (Piperaceae)

Andreia de Araújo Morandim¹*, Massuo Jorge Kato², Alberto José Cavalheiro³ and Maysa Furlan³

¹Departamento de Engenharia Química, Centro Universitário da FEI, Av. Humberto de Alencar Castelo Branco, 3972, 09850-901 São Bernardo do Campo - SP, Brazil.

²Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, 05508-000, São Paulo - SP, Brazil.

³Departamento de Química Orgânica, Instituto de Química, Universidade Estadual de São Paulo, Rua Francisco Degni, s/n, 14800-900 Araraquara - SP, Brazil.

*Corresponding author. E-mail: andreia.morandim@gmail.com. Tel: +55-011-43532900. Fax: +55-01141095994.

Accepted 24 February, 2009

Chemical analysis carried out in leaves of 18 specimens of Piper aduncum L. (Piperaceae) occurring at Ripasa Reserve, Araraquara, SP, Brazil indicated two distinct populations when investigated over a period of 14 months (January 2000 to February 2001) and then submitted to cluster analysis. The two groups were characterized by accumulation of prenylated benzoic acids, chromenes and dihydrochalcone, respectively. A total of seven compounds were identified by HPLC analysis and compared with standards including two prenylated benzoic acid [aduncumene (1) and 3-(3’-7’-dimethyl-2’-6’-octadienyl)-4-methoxy-benzoic acid (5)], four chromenes [methyl 2,2-dimethyl-8-(3’-methyl-2’-butenyl)-2H-1-chromene-6-carboxylate (4), methyl 2,2-dimethyl-2H-1-chromene-6-carboxylate (2b), methyl 8-hydroxy-2,2-dimethyl-2H-1-chromene-6-carboxylate (3) and 2,2-dimethyl-2H-1-chromene-6-carboxylic acid (2a)] and one dihydrochalcone [2’,6’-dihydroxy-4’-methoxy-dihydrochalcone (6)].

Key words: Instraspecific variability, Piper aduncum, chemotypes and HPLC analysis.