Skip to main content
Log in

Newly Detected Specific Hydrogenation of the Conjugated Double Bond of Unsaturated Alkaloid Lactones by Aspergillus sp.

  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Abstract

A new isolate of Aspergillus sp. hydrogenated the γ,δ-double bond of securinine (143 mg l−1) to give 14,15-dihydrosecurinine at over 98% (w/w) yield after 8 h. It also hydrogenated the C11(13) double bond of 3-hydroxy-1(10),3,11(13)-guaiatriene-12,6-olide-2-one (HGT) (200 mg l−1) to give 3-hydroxy-1(10),3-guaiadiene-12,6-olide-2-one with over 98% (w/w) conversion after 24 h.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • JA Beutler P Livant (1984) ArticleTitleCMR assignments of the securinine alkaloids J. Nat. Prod 47 677–681 Occurrence Handle10.1021/np50034a018

    Article  Google Scholar 

  • JA Beutler EW Karbon AN Brubaker R Malik DR Curtis SJ Enna (1985) ArticleTitleSecurinine alkaloids: a new class of GABA receptor antagonist Brain Res 330 135–140 Occurrence Handle10.1016/0006-8993(85)90014-9 Occurrence Handle2985189

    Article  PubMed  Google Scholar 

  • G Fronza C Fuganti M Pinciroli S Serra (2004) ArticleTitleStereochemical aspects of the bioreduction of the conjugated double bond of perillaldehyde Tetrahedron: Asymmet 15 3073–3077 Occurrence Handle10.1016/j.tetasy.2004.08.025

    Article  Google Scholar 

  • G Fronza C Fuganti P Grasselli S Lanati R Rallo S Tchilibon (1994) ArticleTitleStereochemistry of the baker’s yeast mediated reduction of the C=C bond of (Z)- and (E)-5-ben zoyloxyhex-3-en-2-one J. Chem. Soc., Perkin Trans. 1 1 2927–2930

    Google Scholar 

  • G Han MG Laporte JJ Folmer KM Werner SM Weinreb (2000) ArticleTitleTotal syntheses of the Securinega alkaloids (+)-14,15-dihydronorsecurinine, (−)-norsecurinine, and phyllanthine J. Org. Chem 65 6293–6306 Occurrence Handle10.1021/jo000260z Occurrence Handle11052071

    Article  PubMed  Google Scholar 

  • FL Hsu CC Hou LM Yang JT Cheng TC Chi PC Liu et al. (2002) ArticleTitleMicrobial transformations of isosteviol J. Nat. Prod 65 273–277 Occurrence Handle11908964

    PubMed  Google Scholar 

  • XH Li JL Zhang TH Zhou (2002) ArticleTitleThe metabolic transformation of securinine Acta Pharmaceut. Sin 37 288–293

    Google Scholar 

  • Y Kawai K Saitou K Hida DH Dao A Ohno (1996) ArticleTitleStereochemical control in microbial reduction. X X VIII. Asymmetric reduction of α,β-unsaturated ketones with baker’s yeast Bull. Chem. Soc. Jpn 69 2633–2638

    Google Scholar 

  • JY Ma ZT Wang LS Xu GJ Xu S Kadota T Namba (1997) ArticleTitleSesquiterpene lactones from Ixeris sonchifolia Phytochemistry 48 201–203

    Google Scholar 

  • K Nakamura R Yamanaka T Matsuda T Harada (2003) ArticleTitleRecent developments in asymmetric reduction of ketones with biocatalysts Tetrahedron: Asymmet 14 2659–2681 Occurrence Handle10.1016/S0957-4166(03)00526-3

    Article  Google Scholar 

  • S Saito K Kotera A Ide N Sudmoto Z Horu M Hanaoka et al. (1963) ArticleTitleStructure of Securinine Tetrahedron 19 2085–2099 Occurrence Handle10.1016/0040-4020(63)85024-3 Occurrence Handle5879216

    Article  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Song You.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Guan, H., You, S., Yang, L. et al. Newly Detected Specific Hydrogenation of the Conjugated Double Bond of Unsaturated Alkaloid Lactones by Aspergillus sp.. Biotechnol Lett 27, 1189–1193 (2005). https://doi.org/10.1007/s10529-005-0015-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10529-005-0015-y

Keywords

Navigation