دورية أكاديمية
Biosynthesis of ambrein in ambergris: evidence from isotopic data and identification of possible intermediates.
| العنوان: | Biosynthesis of ambrein in ambergris: evidence from isotopic data and identification of possible intermediates. |
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| المؤلفون: | Rowland SJ; Biogeochemistry Research Centre, School of Geography, Earth and Environmental Sciences, University of Plymouth, Plymouth, UK., Sutton PA; Biogeochemistry Research Centre, School of Geography, Earth and Environmental Sciences, University of Plymouth, Plymouth, UK., Wolff GA; Department of Earth, Ocean and Ecological Sciences, School of Environmental Sciences, University of Liverpool, Liverpool, UK. |
| المصدر: | Natural product research [Nat Prod Res] 2021 Apr; Vol. 35 (8), pp. 1235-1241. Date of Electronic Publication: 2019 Jul 30. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Taylor & Francis Health Sciences Country of Publication: England NLM ID: 101167924 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1478-6427 (Electronic) Linking ISSN: 14786419 NLM ISO Abbreviation: Nat Prod Res Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Milton Park, UK : Taylor & Francis Health Sciences, c2003- |
| مواضيع طبية MeSH: | Ambergris/*chemistry , Ambergris/*metabolism , Naphthols/*metabolism , Sperm Whale/*metabolism, Animals ; Carbon Isotopes/metabolism ; Cholestanol/metabolism ; Cyclization ; Gas Chromatography-Mass Spectrometry ; Squalene/metabolism ; Sterols/biosynthesis ; Triterpenes/metabolism |
| مستخلص: | Ambrein is found in ambergris, a coprolith occurring in the rectum of the sperm whale. In vitro , ambrein is produced by enzymatic cyclisation of squalene, via a monocyclic intermediate. However, little is known of the in vivo process. In order to find evidence for the reaction in vivo , a comparison was made of the δ 13 C relative isotopic ratios of ambrein in ambergris with those of co-occurring sterols. A statistically significant difference was noted. This suggests that ambrein originates via a different biosynthetic mechanism from that of the sterols. Examination of the minor constituents of a hydrogenolysed extract of ambergris revealed compounds with a bicyclic polypodane nucleus, rather than those with monocyclic structures. It is hypothesised that in vivo biosynthesis of ambrein proceeds, at least in some cases, via bacterial production of bicyclic polypodenols. The latter are known products of non-concerted squalene (or squalene oxide) cyclisations in other organisms. |
| فهرسة مساهمة: | Keywords: Ambergris; Physeter macrocephalus; ambrein; polypodane; sperm whale |
| المشرفين على المادة: | 0 (Ambergris) 0 (Carbon Isotopes) 0 (Naphthols) 0 (Sterols) 0 (Triterpenes) 1N9JB373FJ (ambrein) 7QWM220FJH (Squalene) 8M308U816E (Cholestanol) FDJ0A8596D (Carbon-13) |
| تواريخ الأحداث: | Date Created: 20190731 Date Completed: 20210505 Latest Revision: 20210505 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1080/14786419.2019.1644630 |
| PMID: | 31359775 |
| قاعدة البيانات: | MEDLINE |
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Full Text Finder | تدمد: | 1478-6427 |
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| DOI: | 10.1080/14786419.2019.1644630 |