Ambrein Explained

Ambrein is a triterpene alcohol that is the chief constituent of ambergris, a secretion from the digestive system of the sperm whale. It has been suggested as the possible active component producing the supposed aphrodisiac effects of ambergris.[1] Although ambrein itself is odorless, it serves as the biological precursor for aromatic derivatives such as ambroxan and is thought to possess fixative properties for other odorants.

It has been shown to act as an analgesic[2] and has been proven to increase sexual behavior in rats,[3] providing some support for its traditional aphrodisiac use.

Apart from its supposed aphrodisiac effects, ambrein has been shown to decrease spontaneous contractions of smooth muscles in rats, guinea pigs, and rabbits. It reduces these contractions by serving as an antagonist and interfering with Ca2+ ions from outside the cell.[4]

Discovery

In 1946, Ruzicka and Lardon "established that the fragrance of ambergris is based on the triterpene (named) ambrein".[5] [6] [7]

Biosynthesis

Ambrein is synthesized from the common triterpenoid precursor squalene. The squalene-hopene cyclase (SHC) catalyzes the cyclization of squalene into the monocyclic 3-deoxyachilleol A. Tetraprenyl-beta-curcumene synthase (BmeTC) converts 3-deoxyachilleol A into the tricyclic ambrein.[8]

Notes and References

  1. Sandroni P . Aphrodisiacs past and present: a historical review . Clinical Autonomic Research . 11 . 5 . 303–7 . October 2001 . 11758796 . 10.1007/BF02332975 . 40455528 .
  2. Taha SA . Studies on the mode of action of ambrein as a new antinociceptive compound . Japanese Journal of Pharmacology . 60 . 2 . 67–71 . October 1992 . 1479744 . 10.1254/jjp.60.67 . free .
  3. Taha SA, Islam MW, Ageel AM . Effect of ambrein, a major constituent of ambergris, on masculine sexual behavior in rats . Archives Internationales de Pharmacodynamie et de Therapie . 329 . 2 . 283–94 . 1995 . 8540767 .
  4. Taha SA, Raza M, El-Khawad IE . Effect of ambrein on smooth muscle responses to various agonists . Journal of Ethnopharmacology . 60 . 1 . 19–26 . February 1998 . 9533428 . 10.1016/s0378-8741(97)00126-8 .
  5. 10.1002/hlca.19460290414. Zur Kenntnis der Triterpene. (105. Mitteilung) Über das Ambreïn, einen Bestandteil des grauen Ambra. 1946. Ruzicka. L.. Lardon. F.. Helvetica Chimica Acta. 29. 4. 912–921.
  6. Prelog . Vladimir . Vladimir Prelog. Jeger . Oskar . 10.1098/rsbm.1980.0013 . Leopold Ruzicka (13 September 1887  - 26 September 1976) . . 26 . 411–501 . 1980 . free .
  7. 10.1530/JOE-19-0084. Terpenes, hormones and life: Isoprene rule revisited. 2019. Hillier. Stephen G.. Lathe. Richard. Journal of Endocrinology. 242. 2. R9–R22. 31051473. free.
  8. Di K, Qinggele C, Fanglong Z, Ting L, Wenyu L . Heterologous biosynthesis of triterpenoid ambrein in engineered Escherichia coli. Biotechnology Letters. 40. 2. 399–404 . February 2018 . 10.1007/s10529-017-2483-2 . 29204767. 3267910. 1573-6776.

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