Abstract
The conversion of β-myrcene to the furanoid flavour compound perillene by Pleurotus ostreatus was investigated using trideutero β-myrcene, trideutero α-(Z)-acaridiol and non-labeled 1,2- and 3,10-epoxy-β-myrcene, α,α-acarilactol, and perillene as substrates. Myrcene diols were formed from the cleavage of myrcene epoxides, but only α-(Z)-acaridiol, a 1,4-butanediol derivative most likely generated through a base-catalysed epoxide opening, was a suitable precursor of perillene. Once formed, this key intermediate was rapidly oxidised and the resulting cyclic lactol was dehydrated to yield perillene. Bioconversion of the supplemented perillene to α,α-acariolide indicated that perillene was another intermediate of the pathway and prone to further oxidative degradation. The data suggest that the fungus converted the cytotoxic β-myrcene in its environment into a metabolically useable carbon source along this route.
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References
Başer KHC, Demirci B, Dönmez AA (2003) Composition of the essential oil Perilla frutescens (L.) britton from Turkey. Flavour Fragr J 18:122–123
Biernacki W, Facile A (1980) Synthesis of methyl (±)-10,11-epoxy-3,7,11-trimethyldodeca-2,6-dienoate, the insect juvenile hormone III. Pol J Chem 54:777–780
Bohlmann F, Zdero C, Jakupovic J, Rourke JP (1985) cis-Guajanolide aus Osmitopsis asteriscoides. Liebigs Ann Chem 12:2342–2351
Busmann D, Berger RG (1994) Conversion of myrcene by submerged cultured basidiomycetes. J Biotechnol 37:39–43
De Vries EJ, Janssen DB (2003) Biocatalytic conversion of epoxides. Curr Opin Biotechnol 14:414–420
Faber K (2004) Biotransformations in organic chemistry. Springer, Berlin
Hua D, Ma C, Song L, Zhang Z, Deng Z, Xu P (2007) Enhanced vanillin production from ferulic acid using adsorbent resin. Appl Microbiol Biotechnol 74:783–790
Krings U, Berger RG (1998) Biotechnological production of flavours and fragrances. Appl Microbiol Biotechnol 49:1–8
Krings U, Hapetta D, Berger RG (2008) Bioconversion of b-myrcene to perillene by Pleurotus ostreatus. Biocatal Biotransform (in press)
Kuwahara Y (1990) Preparation of monoterpene derivatives as agrichemical fungicides. JP patent 02286640 A
Leal WS, Kuwahara Y, Nakano Y, Nakao H, Suzuki T (1989) 2(E)-(4-Methyl-3-pentyl)-butandial, α-acaridial, a novel monoterpene from the Acarid mite Tyrophagus perniciosus (Acarina, Acaridae). Agric Biol Chem 53:1193–1196
Miyazawa M, Ohsawa M (2002) Biotransformation of α-terpineol by the larvae of common cutworm (Spodoptera litura). J Agric Food Chem 50:4916–4918
Mizoguchi A, Mori N, Nishida R, Kuwahara Y (2003) α-Acaridial a female sex pheromone from an alarm pheromone emitting mite Rhizoglyphus robini. J Chem Ecol 29:1681–1690
Ohloff G (1994) Scent and fragrances. Springer, Berlin, Germany
Ohloff G, Giersch W (1980) Stereochemistry-activity relationships in olfaction. Odorants containing a proton donor/proton acceptor unit. Helv Chim Acta 63:76–94
Onken J, Berger RG (1999) Effects of R-(+) limonene on submerged cultures of the terpene transforming basidiomycete Pleurotus sapidus. J Biotechnol 69:163–168
Pinkos R, Fischer R, Müller U (1994) Verfahren zur Herstellung von Butendiolen und Butendiol-Derivaten in Gegenwart oxidischer Katalysatoren. DE patent 4429699 A1
Rito-Polomares M, Negrete A, Miranda L, Flores C, Galindo E, Serrano-Carreón L (2001) The potential application of aqueous two-phase systems for in situ recovery of 6-pentyl-α-pyrone produced by Trichoderma harzianum. Enz Microb Technol 28:625–631
Schewe H, Pescheck M, Sell D, Schrader J (2006) Biotechnological production of terpenoid flavour and fragrance compounds in tailored bioprocesses. In: Bredie WLP, Petersen MA (eds) Flavour science. Elsevier, Amsterdam, The Netherlands, pp 45–48
Schneider C (2006) Synthesis of 1,2-difunctionalised fine chemicals through catalytic, enantioselective ring-opening reactions of epoxides. Synthesis 23:3919–3944
Schrader J (2007) Microbial flavour production. In: Berger RG (ed) Flavour and fragrances. Springer, Berlin, pp 507–566
Schrader J, Berger RG (2001) Biotechnological production of terpenoid flavor and fragrance compounds. In: Rehm HJ (ed) Biotechnology. Wiley, Weinheim, Germany, pp 747–422 vol. 10: special processes
Shimizu N, Tarui H, Mori N, Nishida R (2003) (E)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (α-acariolal) and (E)-2-(2-hydroxyethyl)-6-methyl-2,5-heptadienal (β-acariolal), two new types of isomeric monoterpenes from Caloglyphus polyphyllae (Acari: Acaridae). Biosci Biotechnol Biochem 67:308–313
Smit MS (2004) Fungal epoxide hydrolases: new landmarks in sequence-activity space. Trends Biotechnol 22:123–129
\Steinreiber A, Faber K (2001) Microbial epoxide hydrolases for the preparative biotransformations. Curr Opin Biotechnol 12:552–558
Suzuki T, Haga K, Kuwahara Y (1986) Anal secretion of thrips I. Identification of perillene from Leeuwenia pasanii (Thysanoptera: Phlaeothripidae). Appl Ent Zool 21:461–466
Tarui H, Mori N, Ritsuo N, Okabe K, Kuwahara Y (2002) 3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-acariolide and 4-(4-methyl-3-pentenyl)-2(5H)-furanone, α,β-acariolide: New monoterpene lactones from the astigmatid mites, Schwiebea araujoae and Rhizoglyphus sp. (Astigmata: Acaridae). Biosci Biotechnol Biochem 66:135–140
Taskova RM, Zorn H, Krings U, Berger RG (2006) A comparison of cell wall disruption techniques for the isolation of intracellular metabolites from Pleurotus and Lepista sp. Z Naturforsch C 61:347–350
Wolken AM, ten Have R, van der Werf MJ (2000) Amino-acid-catalyzed conversion of citral: cis–trans isomerization and its conversion into 6-methyl-5-hepten-2-one and acetaldehyde. J Agric Food Chem 48:5401–5405
Yuba A, Yazaki K, Tabata M, Honda G, Croteau R (1996) cDNA cloning, characterization and functional expression of 4S-(−)-limonene synthase from Perilla frutescens. Arch Biochem Biophys 21:280–287
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We are grateful for a grant from the Deutsche Forschungsgemeinschaft (DFG KR 2958/1-1).
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Krings, U., Hapetta, D. & Berger, R.G. A labeling study on the formation of perillene by submerged cultured oyster mushroom, Pleurotus ostreatus . Appl Microbiol Biotechnol 78, 533–541 (2008). https://doi.org/10.1007/s00253-007-1335-8
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DOI: https://doi.org/10.1007/s00253-007-1335-8