An electronic-topological approach has been used to define an active ambergris fragment (AAF) which correctly describes the presence (or absence) of the ambergris odour of all 181 compounds investigated. The AAF consists of one oxygen atom and three carbon atoms (alpha, beta, gamma) which are separated by certain key distances and which possess certain atomic charges. The C(alpha) atom must bear at least one hydrogen atom (H(alpha)) which is located at a certain distance from one of the unshared electronic pairs of the oxygen atom.
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http://dx.doi.org/10.1093/chemse/24.2.171 | DOI Listing |
Nature
August 2024
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany.
Polyene cyclizations are among the most complex and challenging transformations in biology. In a single reaction step, multiple carbon-carbon bonds, ring systems and stereogenic centres are constituted from simple, acyclic precursors. Simultaneously achieving this kind of precise control over product distribution and stereochemistry poses a formidable task for chemists.
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.
View Article and Find Full Text PDFAnimals (Basel)
January 2023
Key Laboratory of Bioresources and Ecoenvironment (Ministry of Education), College of Life Sciences, Sichuan University, Chengdu 610064, China.
Sperm whales are a marine mammal famous for the aromatic substance, the ambergris, produced from its colon. Little is known about the biological processes of ambergris production, and this study aims to investigate the genetic mechanism of ambergris production in the sperm whale based on its chromosome-level genome. Comparative genomics analyses found 1207 expanded gene families and 321 positive selected genes (PSGs) in the sperm whale, and functional enrichment analyses suggested revelatory pathways and terms related to the metabolism of steroids, terpenoids, and aldosterone, as well as microbiota interaction and immune network in the intestine.
View Article and Find Full Text PDFSci Rep
November 2020
Department of Agriculture, Faculty of Agriculture, and Graduate School of Science and Technology, Niigata University, 8050, Ikarashi-2, Nishi-ku, Niigata, Japan.
Ambergris, a sperm whale metabolite, has long been used as a fragrance and traditional medication, but it is now rarely available. The odor components of ambergris result from the photooxidative degradation of the major component, ambrein. The pharmacological activities of ambergris have also been attributed to ambrein.
View Article and Find Full Text PDFMolecules
August 2020
Research Centre for Plant Metabolomics, Department of Biochemistry, University of Johannesburg, P.O. Box 524, Auckland Park 2006, South Africa.
Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components: 40-46% cholestanol type steroids and approximately 25-45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition in the environment to result in odorous compounds, such as ambraoxide, methylambraoxide, and ambracetal.
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