Advanced search
Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 35, 2021 - Issue 8
Submit an article Journal homepage
542
Views
6
CrossRef citations to date
0
Altmetric
Research Article

Biosynthesis of ambrein in ambergris: evidence from isotopic data and identification of possible intermediates

Steven J. Rowlanda Biogeochemistry Research Centre, School of Geography, Earth and Environmental Sciences, University of Plymouth, Plymouth, UKCorrespondence[email protected]
ORCID Iconhttps://orcid.org/0000-0003-4980-0618
ORCID Icon,
Paul A. Suttona Biogeochemistry Research Centre, School of Geography, Earth and Environmental Sciences, University of Plymouth, Plymouth, UK
&
George A. Wolffb Department of Earth, Ocean and Ecological Sciences, School of Environmental Sciences, University of Liverpool, Liverpool, UK
Pages 1235-1241 | Received 09 May 2019, Accepted 13 Jul 2019, Published online: 30 Jul 2019

References

  • Barrero A, Manzaneda RE, Manzaneda RR, Arseniyadis S, Guittet E. 1990. Achilleol B: a new tricyclic triterpene skeleton from Achillea odorata L. Tetrahedron. 46(24):8161–8168.
  • Bennett GJ, Harrison LJ, Sia G-L, Sim K-Y. 1993. Triterpenoids, tocotrienols and xanthones from the bark of Cratoxylum cochinchinense. Phytochem. 32(5):1245–1251.
  • Clarke R. 2006. The origin of ambergris. LAJAM. 5:7–21.
  • Domingo V, Arteaga JF, Quílez del Moral JF, Barrero AF. 2009. Unusually cyclized triterpenes: occurrence, biosynthesis and chemical synthesis. Nat Prod Rep. 26(1):115–134.
  • Governo TF, Alessandro RT, Pragger MJ. 1977. Gas-liquid chromatographic-mass spectrometric detection and identification of ambergris. J AOAC Int. 60:160–164.
  • Hoshino T, Sato T. 1999. Functional analysis of phenylalanine 365 in hopene synthase, a conserved amino acid in the families of squalene and oxidosqualene cyclises. Chem Commun. (19):2005–2006.
  • Ito R, Mori K, Hashimoto I, Nakano C, Sato T, Hoshino T. 2011. Triterpene cyclases from Oryza sativa L.: Cycloartenol, parkeol and achilleol B synthases. Org Lett. 13(10):2678–2681.
  • Ke D, Caiyin Q, Zhao F, Liu T, Lu W. 2018. Heterologous biosynthesis of triterpenoid ambrein in engineered Escherichia coli. Biotechnol Lett. 40(2):399–340.
  • Lederer E, Marx F, Mercier D, Perot G. 1946. Sur les constituants de l’ambre gris II. Ambreine et coprostanone. Helv Chim Acta. 29(5):1354–1365.
  • Mori K, Tamura H. 1990. Triterpenoid total synthesis I. Synthesis of ambrein and Ambrox®. Liebigs Ann Chem. 1990(4):361–368.
  • Moser S, Strohmeier G, Leitner E, Plocek T, Vanhessche K, Pichler H. 2018. Whole-cell (+)-ambrein production in the yeast Pichia pastoris. Metab Eng Commun. 7:e00077.
  • Nguyen L, Harrison LJ. 1999. Triterpenoid and xanthone constituents of Cratoxylum cochinchinense. Phytochemistry. 50(3):471–476.
  • NIST 2011 [accessed 2018 May]. http://webbook.nist.gov/chemistry/.
  • Robson J, Rowland S. 1994. Synthesis of polypodane (C30) and structurally related C25 bicyclic hydrocarbons. Organic Geochem. 21(8-9):937–942.
  • Rowland SJ, Sutton PA. 2017. Chromatographic and spectral studies of jetsam and archived ambergris. Nat Prod Res. 15:1752–1757.
  • Rowland S, Sutton P, Belt S, Fitzsimmons-Thoss V, Scarlett A. 2018a. Further spectral and chromatographic studies of ambergris. Nat Prod Res. 32(21):2603–2609.
  • Rowland S, Sutton P, Knowles T. 2018b. The age of ambergris. Nat Prod Res:1–9. doi: 10.1080/14786419.2018.1523163.
  • Rowland SJ, Sutton PA. Payne 2018c. Simulated environmental photo- and auto-oxidation of ambrein. Earth. arXiv Pre-Print. Available at https://eartharxiv.org.
  • Sutton P, Rowland S. 2016. Spectral and chromatographic characterisation of the onoceroid, ambrane: a potential novel biological marker. Organic Geochem. 102:106–109.
  • Tenkovskaia L, Murakami M, Okuno K, Ueda D, Sato T. 2017. Analysis of the catalytic mechanism of bifunctional triterpene/sesquarterpene cyclase: Tyr167 functions to terminate cyclization of squalene at the bicyclic step. ChemBioChem. 18(19):1910–1913.
  • Ueda D, Hoshino T, Sato T. 2013. Cyclisation of squalene from both termini: identification of an onoceroid synthase and enzymatic synthesis of ambrein. J Am Chem Soc. 135(49):18335–18338.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.