Download PDF
Planta Med 2013; 79(18): 1730-1735
DOI: 10.1055/s-0033-1351100
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Bioactive Benzofuran Neolignans from Aristolochia fordiana

Zhong-bo Zhou
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, PR China
,
Jian-guang Luo
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, PR China
,
Ke Pan
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, PR China
,
Si-ming Shan
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, PR China
,
Wei Zhang
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, PR China
,
Ling-yi Kong
State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, PR China
› Author Affiliations
Further Information

Publication History

received 31 July 2013
revised 01 October 2013

accepted 24 October 2013

Publication Date:
28 November 2013 (online)

Also available at
    Permissions and Reprints

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

Supporting Information

 

  • References

  • 1 Lee KH, Xiao ZY. Lignans in treatment of cancer and other diseases. Phytochem Rev 2003; 2: 341-362
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    Thieme ConnectPubMedSearch in Google Scholar
  • 4 Maxwell A, Dabideen D, Reynolds WF, McLean S. Neolignans from Piper aequale . Phytochemistry 1999; 50: 499-504
    CrossrefPubMedSearch in Google Scholar
  • 5 Lordelloa ALL, Yoshida M. Neolignans from leaves of Ocotea catharinensis . Phytochemistry 1997; 46: 741-744
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefSearch in Google Scholar
  • 8 Kuo PC, Li YC, Wu TS. Chemical constituents and pharmacology of Aristolochia species. J Trad Complement Med 2012; 2: 249-266
    PubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 10 Jiangsu New Medicine College. Encyclopedia of Chinese Materia Medica. Shanghai: Shanghai Science and Technology Press; 1977: 294
    Search in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 12 Lopes LMX, Bolzani VS, Trevisan LMV, Grigolli TM. Terpenes from Aristolochia triangularis . Phytochemistry 1990; 29: 660-662
    CrossrefPubMedSearch in Google Scholar
  • 13 Lima OA, Gottlieb OR, Magalhães MT. Burchellin, a neolignan from Aniba burchellii . Phytochemistry 1972; 11: 2031-2037
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 15 Aiba CJ, Alvarenga MA, Castro OC, Giesbrecht AM, Gottlieb OR, Pagliosa FM. Benzofuranoid neolignans from Aniba simulans . Phytochemistry 1977; 16: 741-743
    CrossrefPubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 17 Fernandes JB, Gottlieb OR, Maia JGS. Absolute configuration of the benzofuranoid neolignans. Phytochemistry 1977; 15: 1003-1006
    PubMedSearch in Google Scholar
  • 18 Benevides PJC, Sartorelli P, Kato MJ. Phenylpropanoids and neolignans from Piper regnellii . Phytochemistry 1999; 52: 339-343
    CrossrefPubMedSearch in Google Scholar
  • 19 Cheng YX, Zhou J, Tan NH. The chemical constituents of Parakmeria yunnanensis . Acta Bot Yunn 2001; 23: 352-356
    PubMedSearch in Google Scholar
  • 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
    PubMedSearch in Google Scholar
  • 21 Hayashi T, Thomson RH. New lignans in Conocarpus erectus . Phytochemistry 1975; 14: 1085-1087
    CrossrefPubMedSearch in Google Scholar
  • 22 Chauret DC, Bernard CB, Arnason JT, Durst T. Insecticidal neolignans from Piper decurrens . J Nat Prod 1996; 59: 152-155
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 25 Tsai IL, Chen JH, Duh CY, Chen IS. Cytotoxic neolignans and butanolides from Machilus obovatifolia . Planta Med 2001; 67: 559-561
    Thieme ConnectPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar
  • 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
    CrossrefPubMedSearch in Google Scholar