Bioactive Benzofuran Neolignans from Aristolochia fordiana

Abstract

Six new benzofuran neolignans (1–6) were isolated from the EtOAc-soluble fraction of the aerial part of Aristolochia fordiana, together with twelve known analogues (7–18). The structures of the isolated compounds were elucidated by spectroscopic methods. All isolates were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccaride-activated RAW264.7 macrophages and for their cytotoxic activities on three human cancer cell lines. Compound 2 showed significant nitric oxide production inhibitory activity with an IC₅₀ value of 10.00 µM, while compound 16 exhibited cytotoxic activity with an IC₅₀ value of 11.9 µM against MG-63 and compound 18 of 9.15 µM against HepG2 cell lines, respectively.

Key words

neolignans - Aristolochiaceae - Aristolochia fordiana - nitric oxide - cytotoxicity

• References

• 1 Lee KH, Xiao ZY. Lignans in treatment of cancer and other diseases. Phytochem Rev 2003; 2: 341-362
• 2 Juhász L, Dinya Z, Antus S, Gunda TE. A new approach for the synthesis of naturally occurring dihydrobenzo[b]furan-type neolignans of potential biological activity. Tetrahedron Lett 2000; 41: 2491-2494
• 3 Longato GB, Rizzo LY, de Oliveira Sousa IM, Tinti SV, Possenti A, Figueira GM, Ruiz AL, Foglio MA, de Carvalho JE. In vitro and in vivo anticancer activity of extracts, fractions, and eupomatenoid-5 obtained from Piper regnellii leaves. Planta Med 2011; 77: 1482-1488
• 4 Maxwell A, Dabideen D, Reynolds WF, McLean S. Neolignans from Piper aequale . Phytochemistry 1999; 50: 499-504
• 5 Lordelloa ALL, Yoshida M. Neolignans from leaves of Ocotea catharinensis . Phytochemistry 1997; 46: 741-744
• 6 Achenbach H, Utz W, Sánchez VH, Touché EMG, Verde SJ, Domínguez XA. Neolignans, nor-neolignans and other compounds from roots of Krameria grayi . Phytochemistry 1995; 39: 413-415
• 7 Wu TS, Damu AG, Su CR, Kuo PC. Chemical constituents and pharmacology of Aristolochia species. In: Atta-ur-Rahman, editor Studies in natural product chemistry (bioactivenatural proudcts), Volume 40. Amsterdam: Elsevier; 2005: 855-1018
• 8 Kuo PC, Li YC, Wu TS. Chemical constituents and pharmacology of Aristolochia species. J Trad Complement Med 2012; 2: 249-266
• 9 León-Díaz R, Meckes M, Said-Fernández S, Molina-Salinas GM, Vargas-Villarreal J, Torres J, Luna-Herrera J, Jiménez-Arellanes A. Antimycobacterial neolignans isolated from Aristolochia taliscana . Mem Inst Oswaldo Cruz 2010; 105: 45-51
• 10 Jiangsu New Medicine College. Encyclopedia of Chinese Materia Medica. Shanghai: Shanghai Science and Technology Press; 1977: 294
• 11 Yu JQ, Liao ZX, Cai XQ, Lei JC, Zou GL. Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima . Environment Toxicol Pharmacol 2007; 23: 162-167
• 12 Lopes LMX, Bolzani VS, Trevisan LMV, Grigolli TM. Terpenes from Aristolochia triangularis . Phytochemistry 1990; 29: 660-662
• 13 Lima OA, Gottlieb OR, Magalhães MT. Burchellin, a neolignan from Aniba burchellii . Phytochemistry 1972; 11: 2031-2037
• 14 Enriquez RG, Chavez MA, Reynolds WF. Phytochemical investigations of plants of the genus Aristolochia, 1. Isolation and NMR spectral characterization of eupomatenoid derivatives. J Nat Prod 1984; 47: 896-899
• 15 Aiba CJ, Alvarenga MA, Castro OC, Giesbrecht AM, Gottlieb OR, Pagliosa FM. Benzofuranoid neolignans from Aniba simulans . Phytochemistry 1977; 16: 741-743
• 16 Gottlieb OR, Mourão JC, Yoshida M, Mascarenhas YP, Rodrigues M, Resenstein RD, Tomita K. Neolignans from an Aniba species . Phytochemistry 1976; 16: 1033-1036
• 17 Fernandes JB, Gottlieb OR, Maia JGS. Absolute configuration of the benzofuranoid neolignans. Phytochemistry 1977; 15: 1003-1006
• 18 Benevides PJC, Sartorelli P, Kato MJ. Phenylpropanoids and neolignans from Piper regnellii . Phytochemistry 1999; 52: 339-343
• 19 Cheng YX, Zhou J, Tan NH. The chemical constituents of Parakmeria yunnanensis . Acta Bot Yunn 2001; 23: 352-356
• 20 Tsai IL, Chen JH, Duh CY, Chen IS. Two minor 7, 8-dihydrobenzofurans from licarin B via Lemieux-von Rudloff oxidation. Chin Pharm J 2002; 54: 149-153
• 21 Hayashi T, Thomson RH. New lignans in Conocarpus erectus . Phytochemistry 1975; 14: 1085-1087
• 22 Chauret DC, Bernard CB, Arnason JT, Durst T. Insecticidal neolignans from Piper decurrens . J Nat Prod 1996; 59: 152-155
• 23 Achenbacha H, Groba J, Dominguez XA, Cano G, Star JV, Brussolo LDC, Muñoz G, Salgado F, López L. Lignans neolignans and norneolignans from Krameria cystisoides . Phytochemistry 1987; 26: 1159-1166
• 24 Himmelreich U, Ripperger H, Adam G, Anh NH, Sung TV. Eupomatenoids from Caryodaphnosis tonkinensis and their complete NMR assignment. Magn Reson Chem 1995; 33: 280-282
• 25 Tsai IL, Chen JH, Duh CY, Chen IS. Cytotoxic neolignans and butanolides from Machilus obovatifolia . Planta Med 2001; 67: 559-561
• 26 Coy ED, Cuca LE, Sefkow M. COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans. Bioorg Med Chem Lett 2009; 19: 6922-6925
• 27 Yang MH, Wang JS, Luo JG, Wang XB, Kong LY. Chisopanins A–K, 11 new protolimonoids from Chisocheton paniculatus and their anti-inflammatory activities. Bioorg Med Chem 2011; 19: 1409-1417