, Volume 218, Issue 3, pp 492–496

Biphenyl synthase from yeast-extract-treated cell cultures of Sorbus aucuparia

  • Benye Liu
  • Till Beuerle
  • Tim Klundt
  • Ludger Beerhues
Rapid Communication


Biphenyls and dibenzofurans are the phytoalexins of the Maloideae, a subfamily of the economically important Rosaceae. The biphenyl aucuparin accumulated in Sorbus aucuparia L. cell cultures in response to yeast extract treatment. Incubation of cell-free extracts from challenged cell cultures with benzoyl-CoA and malonyl-CoA led to the formation of 3,5-dihydroxybiphenyl. This reaction was catalysed by a novel polyketide synthase, which will be named biphenyl synthase. The most efficient starter substrate for the enzyme was benzoyl-CoA. Relatively high activity was also observed with 2-hydroxybenzoyl-CoA but, instead of the corresponding biphenyl, the derailment product 2-hydroxybenzoyltriacetic acid lactone was formed.


Aucuparin Benzoic acid Biphenyl synthase Phytoalexin Polyketide synthase Sorbus 



biphenyl synthase


benzophenone synthase




  1. Akiyama T, Shibuya M, Liu HM, Ebizuka Y (1999) p-Coumaroyltriacetic acid synthase, a new homologue of chalcone synthase, from Hydrangea macrophylla var. thunbergii. Eur J Biochem 263:834–839PubMedGoogle Scholar
  2. Borejsza-Wysocki W, Lester C, Attygalle AB, Hrazdina G (1999) Elicited cell suspension cultures of apple (Malus × domestica) cv. Liberty produce biphenyl phytoalexins. Phytochemistry 50:231–235Google Scholar
  3. Dixon RA (2001) Natural products and plant disease resistance. Nature 411:843–847PubMedGoogle Scholar
  4. Dol GC, Kamer PCJ, van Leeuwen PWNM (1998) Synthesis of 5-substituted resorcinol derivatives via cross-coupling reactions. Eur J Org Chem 2:359–364CrossRefGoogle Scholar
  5. Erdtman H, Eriksson G, Norin T (1963) Aucuparin and methoxyaucuparin, two phenolic biphenyl derivatives from the heartwood of Sorbus aucuparia L. Acta Chem Scand 17:1151–1156Google Scholar
  6. Kokubun T, Harborne JB (1994) A survey of phytoalexin induction in leaves of the Rosaceae by copper ions. Z Naturforsch Teil C 49: 628–634Google Scholar
  7. Kokubun T, Harborne JB (1995) Phytoalexin induction in the sapwood of plants of the Maloideae (Rosaceae): biphenyls or dibenzofurans. Phytochemistry 40:1649–1654Google Scholar
  8. Kokubun T, Harborne JB, Eagles J, Waterman PG (1995) Antifungal biphenyl compounds are the phytoalexins of the sapwood of Sorbus aucuparia. Phytochemistry 40:57–59Google Scholar
  9. Kreuzaler F, Hahlbrock K (1975) Enzymatic synthesis of aromatic compounds in higher plants. Formation of bis-noryangonin (4-hydroxy-6[4-hydroxystyryl]2-pyrone) from p-coumaroyl-CoA and malonyl-CoA. Arch Biochem Biophys 169:84–90PubMedGoogle Scholar
  10. Linsmaier EM, Skoog F (1965) Organic growth factor requirements of tobacco tissue cultures. Physiol Plant 18:100–127Google Scholar
  11. Liu B, Falkenstein-Paul H, Schmidt W, Beerhues L (2003) Benzophenone synthase and chalcone synthase from Hypericum androsaemum cell cultures: cDNA cloning, functional expression, and site-directed mutagenesis of two polyketide synthases. Plant J 34:847–855PubMedGoogle Scholar
  12. Malterud KE, Sandanger Dugstad EK (1985) 4,2′-Dihydroxy-3,5-dimethoxybiphenyl, a new phenol from the wood of Salix caprea L. Z Naturforsch Teil B 40: 853–854Google Scholar
  13. Morita H, Noguchi H, Schröder J, Abe I (2001) Novel polyketides synthesized with a higher plant stilbene synthase. Eur J Biochem 268:3759–3766PubMedGoogle Scholar
  14. Nilsson B, Norin T (1963) Syntheses of aucuparin and methoxyaucuparin. Acta Chem Scand 17:1157–1159Google Scholar
  15. Rupprich N, Kindl H (1978) Stilbene synthases and stilbenecarboxylate synthases I: enzymatic synthesis of 3,5,4′-trihydroxyxstilbene from p-coumaroyl coenzyme A and malonyl coenzyme A. Hoppe-Seyler’s Z Physiol Chem 359:165–172Google Scholar
  16. Schröder J (1999) The chalcone/stilbene synthase-type family of condensing enzymes. In: Sankawa U (ed) Comprehensive natural products chemistry, vol 1. Elsevier, Amsterdam, pp 749–771Google Scholar
  17. Suh DY, Fukuma K, Kagami J, Yamazaki Y, Shibuya M, Ebizuka Y, Sankawa U (2000) Identification of amino acid residues important in the cyclization reactions of chalcone and stilbene synthases. Biochem J 350:229–235PubMedGoogle Scholar
  18. Sultanbawa MUS (1980) Xanthonoids of tropical plants. Tetrahedron 36:1465–1506Google Scholar
  19. Widyastuti SM, Nonaka F, Watanabe K, Sako N, Tanaka K (1992) Isolation and characterization of two aucuparin-related phytoalexins from Photinia glabra. Ann Phytopathol Soc Japan 58:228–233Google Scholar

Copyright information

© Springer-Verlag 2004

Authors and Affiliations

  • Benye Liu
    • 1
    • 2
  • Till Beuerle
    • 1
  • Tim Klundt
    • 1
  • Ludger Beerhues
    • 1
  1. 1.Institut für Pharmazeutische BiologieTechnische Universität BraunschweigBraunschweigGermany
  2. 2.Institute of BotanyChinese Academy of SciencesBeijingChina

Personalised recommendations