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. However, efficient production of ambrein and odor compounds has not been achieved. Here, we constructed a system for the synthesis of ambrein and odor components. First, we created a new triterpene synthase, "ambrein synthase," for mass production of ambrein by redesigning a bacterial enzyme. The ambrein yields were approximately 20 times greater than those reported previously. Next, an efficient photooxidative conversion system from ambrein to a range of volatiles of ambergris was established. The yield of volatiles was 8-15%. Finally, two biological activities, promotion of osteoclast differentiation and prevention of amyloid β-induced apoptosis, were discovered using the synthesized ambrein.
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http://dx.doi.org/10.1038/s41598-020-76624-y | 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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