Biotechnology Letters

, Volume 30, Issue 11, pp 2025–2029 | Cite as

Biotransformation of zerumbone by Caragana chamlagu

  • Hiroshi SakamakiEmail author
  • Ken-ichi Itoh
  • Susumu Kitanaka
  • Seiji Sawada
  • C. Akira Horiuchi
Original Research Paper


Suspension cultured cells of Caragana chamlagu (Leguminosae) converted zerumbone (1) into zerumbone epoxide (2) as the intermediate, (2R,3R,7R)-2,3-epoxy-9-humulen-8-one (3) and (2R,3S,7R)-2,3-epoxy-9-humulen-8-one (4) as new sesquiterpenes in 11%, 36% and 21% yields, respectively.


Biotransformation Caragana chamlagu Oxidation-asymmetric reduction Zerumbone 



This work was partially supported by a special research Grant-in-Aid for the promotion and mutual aid corporation for private school of Japan to Nihon University.


  1. Chai W, Sakamaki H, Kitanaka S, Horiuchi CA (2003a) Biotransformation of cycloalkanediones by Caragana chamlagu. Bull Chem Soc Jpn 76:177–182CrossRefGoogle Scholar
  2. Chai W, Sakamaki H, Kitanaka S, Saito M, Horiuchi CA (2003b) Biodegradation of bisphenol A by cultured cells of Caragana chamlagu. Biosci Biotechnol Biochem 67:218–220PubMedCrossRefGoogle Scholar
  3. Dev S (1960) Zerumbone, a monocyclic sesquiterpene ketone. Tetrahedron 8:171–180CrossRefGoogle Scholar
  4. Flitsch S, Gideon G, Ashcroft D (2002) Oxygenation of C–H and C=C bonds. In: Drauz K, Waldman H (eds) Enzyme catalysis in organic synthesis, vol III, 2nd edn. Wiley-VHC Verlag GmbH, Weinheim, pp 1065–1108Google Scholar
  5. Itoh K, Sakamaki H, Nakamura K, Horiuchi CA (2005) Biocatalytic asymmetric reduction of 3-acetylisoxazoles. Tetrahedron Asymmetry 16:1403–1408CrossRefGoogle Scholar
  6. Liao Y-H, Houghton PJ, Hoult JRS (1999) Novel and known constituents from Buddleja species and their activity against leukocyte eicosanoid generation. J Nat Prod 62:1241–1245PubMedCrossRefGoogle Scholar
  7. Matthes HWD, Luu B, Ourisson G (1982) Transannular cyclization of zerumbone epoxide. Tetrahedron 38:3129–3135CrossRefGoogle Scholar
  8. Mukaiyama T, Yamada T, Nagata T, Imagawa K (1993) Asymmetric aerobic epoxidation of unfunctionalized olefins catalyzed by optically active α-ketoiminato manganese(III) complexes. Chem Lett 22:327–330CrossRefGoogle Scholar
  9. Murakami A, Takahashi M, Jiwajinda S, Koshimizu K, Ohigashi H (1999) Identification of zerumbone in Zingiber zerumbet Smith as a potent inhibitor of 12-O-tetradecanoylphorbol-13-acetate-induced Epsein–Barr virus activation. Biosci Biotech Biochem 63:1811–1812CrossRefGoogle Scholar
  10. Sakamaki H, Take M, Matsumoto T, Iwadare T, Ichinohe Y (1988) Transformation of cycloartanyl acetate into B-homo triterpenoids. J Org Chem 53:2622–2624CrossRefGoogle Scholar
  11. Sakamaki H, Kitanaka S, Chai W, Hayashida Y, Takagi Y, Horiuchi CA (2001) Biotransformation of thujopsene by Caragana chamlagu. J Nat Prod 64:630–631PubMedCrossRefGoogle Scholar
  12. Sakamaki H, Itoh K, Chai W, Hayashida Y, Kitanaka S, Horiuchi CA (2004) Biotransformation of (±)-α-ionone and β-ionone by cultured cells of Caragana chamlagu. J Mol Catal B Enzym 27:177–181CrossRefGoogle Scholar
  13. Sakamaki H, Itoh K, Taniai T, Kitanaka S, Takagi Y, Chai W, Horiuchi CA (2005) Biotransformation of valencene by cultured cells of Gynostemma pentaphyllum. J Mol Catal B Enzym 32:103–106CrossRefGoogle Scholar
  14. Sharpless KB, Amberg W, Bennani Y, Crispino G, Hartung J, Jeong K, Kwong H, Morikawa K, Wang Z, Xu D, Zhang X (1992) The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement. J Org Chem 57:2768–2771CrossRefGoogle Scholar
  15. Usia T, Iwata H, Hiratsuka A, Watabe T, Kadota S, Tezuka Y (2004) Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities. J Nat Prod 67:1079–1083PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2008

Authors and Affiliations

  • Hiroshi Sakamaki
    • 1
    Email author
  • Ken-ichi Itoh
    • 1
  • Susumu Kitanaka
    • 2
  • Seiji Sawada
    • 3
  • C. Akira Horiuchi
    • 4
  1. 1.College of Science and TechnologyNihon UniversityFunabashi-shiJapan
  2. 2.College of PharmacyNihon UniversityFunabashi-shiJapan
  3. 3.Kyoto University of EducationKyotoJapan
  4. 4.Department of ChemistryRikkyo (St. Paul’s) UniversityTokyoJapan

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