Ambrein

Last updated
Ambrein
Ambrein.svg
Names
IUPAC name
(1R,2R,4aS,8aS)-1-{(3E)-6-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-4-methylhex-3-en-1-yl}-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
Other names
Ambrein
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.784 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1 Yes check.svgY
    Key: BIADSXOKHZFLSN-CQDHYIGWSA-N Yes check.svgY
  • InChI=1/C30H52O/c1-22(15-16-24-23(2)13-10-18-27(24,3)4)12-9-14-26-29(7)20-11-19-28(5,6)25(29)17-21-30(26,8)31/h12,24-26,31H,2,9-11,13-21H2,1,3-8H3/b22-12+/t24-,25?,26-,29+,30-/m1/s1
    Key: BIADSXOKHZFLSN-CQDHYIGWBE
  • C/C(=C\CC[C@@H]1[C@]2(CCCC(C2CC[C@@]1(C)O)(C)C)C)/CC[C@@H]3C(=C)CCCC3(C)C
  • O[C@@]1(CCC3[C@]([C@H]1CC\C=C(/C)CC[C@@H]2C(=C)\CCCC2(C)C)(C)CCCC3(C)C)C
Properties
C30H52O
Molar mass 428.745 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 ambroxide and is thought to possess fixative properties for other odorants.

Contents

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]

Related Research Articles

<span class="mw-page-title-main">Ambergris</span> Substance produced in the digestive system of sperm whales

Ambergris, ambergrease, or grey amber is a solid, waxy, flammable substance of a dull grey or blackish colour produced in the digestive system of sperm whales. Freshly produced ambergris has a marine, fecal odor. It acquires a sweet, earthy scent as it ages, commonly likened to the fragrance of isopropyl alcohol without the vaporous chemical astringency.

<span class="mw-page-title-main">Aphrodisiac</span> Substance intended to rouse sexual desires

An aphrodisiac is a substance alleged to increase libido, sexual desire, sexual attraction, sexual pleasure, or sexual behavior. These substances range from a variety of plants, spices, and foods to synthetic chemicals. Natural aphrodisiacs, such as cannabis or cocaine, are classified into plant-based and non-plant-based substances. Synthetic aphrodisiacs include MDMA and methamphetamine. Aphrodisiacs can be classified by their type of effects. Aphrodisiacs that contain hallucinogenic properties, such as bufotenin, have psychological effects that can increase sexual desire and sexual pleasure. Aphrodisiacs that have smooth muscle relaxing properties, such as yohimbine, have physiological effects that can affect hormone concentrations and increase blood flow.

<span class="mw-page-title-main">Steroid</span> Polycyclic organic compound having sterane as a core structure

A steroid is an organic compound with four fused rings arranged in a specific molecular configuration.

<span class="mw-page-title-main">Terpene</span> Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

<span class="mw-page-title-main">Cremaster muscle</span> Muscle covering the testicles and spermatic cords

The cremaster muscle is a paired structure made of thin layers of striated and smooth muscle that covers the testicles and the spermatic cords in human males. It consists of the lateral and medial parts. Cremaster is an involuntary muscle, responsible for the cremasteric reflex; a protective and physiologic superficial reflex of the testicles. The reflex raises and lowers the testicles in order to keep them protected. Along with the dartos muscle of the scrotum, it regulates testicular temperature, thus aiding the process of spermatogenesis.

<span class="mw-page-title-main">Leopold Ružička</span> Croatian-Swiss chemist (1887–1976)

Leopold Ružička was a Croatian-Swiss scientist and joint winner of the 1939 Nobel Prize in Chemistry "for his work on polymethylenes and higher terpenes" "including the first chemical synthesis of male sex hormones." He worked most of his life in Switzerland, and received eight doctorates honoris causa in science, medicine, and law; seven prizes and medals; and twenty-four honorary memberships in chemical, biochemical, and other scientific societies.

Uterine contractions are muscle contractions of the uterine smooth muscle that can occur at various intensities in both the non-pregnant and pregnant uterine state. The non-pregnant uterus undergoes small, spontaneous contractions in addition to stronger, coordinated contractions during the menstrual cycle and orgasm. Throughout gestation, the uterus enters a state of uterine quiescence due to various neural and hormonal changes. During this state, the uterus undergoes little to no contractions, though spontaneous contractions still occur for the uterine myocyte cells to experience hypertrophy. The pregnant uterus only contracts strongly during orgasms, labour, and in the postpartum stage to return to its natural size.

<span class="mw-page-title-main">Yohimbine</span> Chemical compound

Yohimbine, also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe; also from the bark of the unrelated South American tree Aspidosperma quebracho-blanco. Yohimbine is an α2-adrenergic receptor antagonist, and has been used in a variety of research projects. It is a veterinary drug used to reverse sedation in dogs and deer.

<span class="mw-page-title-main">Squalene</span> Chemical compound

Squalene is an organic compound. It is a triterpene with the formula C30H50. It is a colourless oil, although impure samples appear yellow. It was originally obtained from shark liver oil (hence its name, as Squalus is a genus of sharks). An estimated 12% of bodily squalene in humans is found in sebum. Squalene has a role in topical skin lubrication and protection.

<span class="mw-page-title-main">Hopanoids</span> Class of chemical compounds

Hopanoids are a diverse subclass of triterpenoids with the same hydrocarbon skeleton as the compound hopane. This group of pentacyclic molecules therefore refers to simple hopenes, hopanols and hopanes, but also to extensively functionalized derivatives such as bacteriohopanepolyols (BHPs) and hopanoids covalently attached to lipid A.

Not to be confused with the Croatian city of Knin

<span class="mw-page-title-main">Triterpene</span> Class of chemical compounds

Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.

<span class="mw-page-title-main">Calciseptine</span> Neurotoxin

Calciseptine (CaS) is a natural neurotoxin isolated from the black mamba Dendroaspis p. polylepis venom. This toxin consists of 60 amino acids with four disulfide bonds. Calciseptine specifically blocks L-type calcium channels, but not other voltage-dependent Ca2+ channels such as N-type and T-type channels.

<span class="mw-page-title-main">Ursolic acid</span> Pentacyclic chemical compound found in fruits

Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

<span class="mw-page-title-main">Muscle</span> Basic biological tissue

Muscle is a soft tissue, one of the four basic types of animal tissue. There are three types of muscle tissue in vertebrates: skeletal muscle, cardiac muscle, and smooth muscle. Muscle tissue gives skeletal muscles the ability to contract. Muscle tissue contains special contractile proteins called actin and myosin which interact to cause movement. Among many other muscle proteins, present are two regulatory proteins, troponin and tropomyosin. Muscle is formed during embryonic development, in a process known as myogenesis.

<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.

<span class="mw-page-title-main">Ejaculation</span> Semen discharge from the male reproductive tract

Ejaculation is the discharge of semen from the penis through the urethra. It is the final stage and natural objective of male sexual stimulation, and an essential component of natural conception. After forming an erection, many men emit pre-ejaculatory fluid during stimulation prior to ejaculating. Ejaculation involves involuntary contractions of the pelvic floor and is normally linked with orgasm. It is a normal part of male human sexual development.

<span class="mw-page-title-main">Lupeol</span> Chemical compound

Lupeol is a pharmacologically active pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.

<span class="mw-page-title-main">Amyrin</span> Chemical compound

The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton), and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee.

<span class="mw-page-title-main">Diplopterol</span> Chemical compound

Diplopterol is a triterpenoid molecule commonly produced by bacteria, ferns, and a few protozoans. This compound, classified as a member of the hopanoid family, is synthesized from triterpenoid precursor squalene. It is generally believed that hopanoids serve a similar function in bacteria as that of sterols in eukaryotes, which involves modulating membrane fluidity. Diplopterol serves as a useful biomarker for prokaryotic life, along with oxygen content at the time of sediment deposition.

References

Biosynthetic pathway of Ambrein Ambrein biosynthesis.svg
Biosynthetic pathway of Ambrein
  1. Sandroni P (October 2001). "Aphrodisiacs past and present: a historical review". Clinical Autonomic Research. 11 (5): 303–7. doi:10.1007/BF02332975. PMID   11758796. S2CID   40455528.
  2. Taha SA (October 1992). "Studies on the mode of action of ambrein as a new antinociceptive compound". Japanese Journal of Pharmacology. 60 (2): 67–71. doi: 10.1254/jjp.60.67 . PMID   1479744.
  3. Taha SA, Islam MW, Ageel AM (1995). "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. PMID   8540767.
  4. Taha SA, Raza M, El-Khawad IE (February 1998). "Effect of ambrein on smooth muscle responses to various agonists". Journal of Ethnopharmacology. 60 (1): 19–26. doi:10.1016/s0378-8741(97)00126-8. PMID   9533428.
  5. Ruzicka, L.; Lardon, F. (1946). "Zur Kenntnis der Triterpene. (105. Mitteilung) Über das Ambreïn, einen Bestandteil des grauen Ambra". Helvetica Chimica Acta. 29 (4): 912–921. doi:10.1002/hlca.19460290414.
  6. Prelog, Vladimir; Jeger, Oskar (1980). "Leopold Ruzicka (13 September 1887 26 September 1976)". Biogr. Mem. Fellows R. Soc. 26: 411–501. doi: 10.1098/rsbm.1980.0013 .
  7. Hillier, Stephen G.; Lathe, Richard (2019). "Terpenes, hormones and life: Isoprene rule revisited". Journal of Endocrinology. 242 (2): R9 –R22. doi: 10.1530/JOE-19-0084 . PMID   31051473.
  8. Di K, Qinggele C, Fanglong Z, Ting L, Wenyu L (February 2018). "Heterologous biosynthesis of triterpenoid ambrein in engineered Escherichia coli". Biotechnology Letters. 40 (2): 399–404. doi:10.1007/s10529-017-2483-2. ISSN   1573-6776. PMID   29204767. S2CID   3267910.