To date, the only known occurrence of ambrein, an important perfumery organic molecule, is in coproliths found in about one in a hundred sperm whales. Jetsam ambergris coproliths from the whale are also found occasionally on beaches worldwide. Here we report on the surprising occurrence of ambrein in human adipocere. Adipocere is a waxy substance formed post-mortem during incomplete anaerobic decomposition of soft tissues. Adipocere samples obtained from grave exhumations were analysed using gas chromatography-mass spectrometry (GC-MS). In addition to the typical fatty acids of adipocere, lesser amounts of ambrein were identified in the samples, in abundances similar to those of the major accompanying faecal steroids. The distribution of these compounds suggests that ambrein was produced post-mortem during the microbial decomposition of faecal residues and tissues. It is assumed that the adipocere matrix of saturated fatty acidsaided the preservation of ambrein over extended periods of time, because adipocere is stable against degradation. The association of ambrein formation in ageing faecal material, under moist, oxygen-depleted conditions, now requires more attention in studies of other mammalian and geological samples. Indeed, ambrein and its transformation products may be useful novel chemical indicators of aged faecal matter and decomposed bodies.
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http://dx.doi.org/10.1038/s41598-019-54730-w | DOI Listing |
Nat Prod Res
July 2024
Biogeochemistry Research Centre, University of Plymouth, Drake Circus, Plymouth, UK.
Biotechnol Lett
August 2024
Key Laboratory of Digital Quality Evaluation of Chinese Materia Medica of State Administration of TCM, School of Chinese Materia Medica, Guangdong Pharmaceutical University, Guangzhou, 510006, China.
(+)-Ambrein is the primary component of ambergris, a rare product found in sperm whales (Physeter microcephalus). Microbial production using sustainable resources is a promising way to replace animal extraction and chemical synthesis. We constructed an engineered yeast strain to produce (+)-ambrein de novo.
View Article and Find Full Text PDFNat Prod Res
February 2024
School of Environmental Sciences, University of Liverpool, Liverpool, UK.
Sci Rep
January 2024
Graduate School of Science and Technology, Niigata University, Niigata, Japan.
Onoceroids are a rare family of triterpenes. One representative onoceroid is ambrein, which is the main component of ambergris used as a traditional medicine. We have previously identified the onoceroid synthase, BmeTC, in Bacillus megaterium and succeeded in creating ambrein synthase by introducing mutations into BmeTC.
View Article and Find Full Text PDFJ Agric Food Chem
April 2023
Fragrances S&T, Ingredients Research, Givaudan Schweiz AG, Kemptpark 50, CH-8310 Kemptthal, Switzerland.
(-)-Ambrox, the most prominent olfactive component of ambergris is one of the most widely used biodegradable fragrance ingredients. Traditionally it is produced from the diterpene sclareol, modified and cyclized into (-)-ambrox by classical chemistry steps. The availability of the new feedstock ()-β-farnesene produced by fermentation opened new pathways to ()-homofarnesol as a precursor to (-)-ambrox.
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