Triterpene

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Triterpene

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(Redirected from Triterpenoid)

Squalene: One of the most important triterpenes

Hopane: An example of a pentacyclic triterpene

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.^[1]^[2]

Structures

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Triterpenes exist in a great variety of structures. Nearly 200 different skeletons have been identified.^[3] These skeletons may be broadly divided according to the number of rings present. In general pentacyclic structures (5 rings) tend to dominate.

Number of rings	Examples
0	Squalene
1	Achilleol A ^[4]
2	Polypodatetraene
3	Malabaricane
4	Lanostane, Cucurbitacin
5	Hopane, Oleanane, Ursolic acid
6	Chamaecydin

Squalene is biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product. Squalene serves as precursor for the formation of many triterpenoids, including bacterial hopanoids and eukaryotic sterols.

Triterpenoids

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By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The terms triterpene and triterpenoid often are used interchangeably.

Triterpenoids possess a rich chemistry and pharmacology (e.g. cholesterol) with several pentacyclic motifs. Lupane, oleanane and ursane show particular promise as anti-cancer agents.^[5]^[6]

Steroids

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Steroids feature a cucurbitane core, although in practice they are biosynthesised from either lanosterol (animals and fungi) or cycloartenol (plants) via the cyclization of squalene. Steroids have two principal biological functions, being either key components of cell membranes or signaling molecules that activate steroid hormone receptors. Important sub-classes include sterols and cucurbitacins.

Triterpenoid saponins

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Triterpenoid saponins are triterpenes which belong to the saponin group of compounds, making them triterpenoid glycosides. They are produced by plants as part of their self-defense mechanism^[7] with important sub-classes including ginsenosides^[8] and eleutherosides.

References

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^ Eberhard Breitmaier (2006). "Triterpenes". Terpenes: Flavors, Fragrances, Pharmaca, Pheromones. pp. 86–108. doi:10.1002/9783527609949.ch6. ISBN 9783527609949.
^ Davis, Edward M.; Croteau, Rodney (2000). "Cyclization Enzymes in the Biosynthesis of Monoterpenes, Sesquiterpenes, and Diterpenes". Topics in Current Chemistry. 209: 53–95. doi:10.1007/3-540-48146-X_2. ISBN 978-3-540-66573-1.
^ Xu, Ran; Fazio, Gia C.; Matsuda, Seiichi P.T. (February 2004). "On the origins of triterpenoid skeletal diversity". Phytochemistry. 65 (3): 261–291. doi:10.1016/j.phytochem.2003.11.014. PMID 14751299.
^ Barrero, A.F.; Alvarez-Manzaneda, E.J.R.; Alvarez-Manzaneda r, R. (1989-01-01). "Achilleol A: A new monocyclic triterpene skeleton from Achillea odorata L." Tetrahedron Letters. 30 (25): 3351–3352. doi:10.1016/S0040-4039(00)99242-6. ISSN 0040-4039.
^ Laszczyk, Melanie (2009). "Pentacyclic Triterpenes of the Lupane, Oleanane and Ursane Group as Tools in Cancer Therapy". Planta Medica. 75 (15): 1549–60. doi:10.1055/s-0029-1186102. PMID 19742422.
^ Liu, Jie (December 1995). "Pharmacology of oleanolic acid and ursolic acid". Journal of Ethnopharmacology. 49 (2): 57–68. doi:10.1016/0378-8741(95)90032-2. PMID 8847885.
^ Augustin, Jörg M.; Kuzina, Vera; Andersen, Sven B.; Bak, Søren (April 2011). "Molecular activities, biosynthesis and evolution of triterpenoid saponins". Phytochemistry. 72 (6): 435–457. doi:10.1016/j.phytochem.2011.01.015. PMID 21333312.
^ Attele, Anoja S; Wu, Ji An; Yuan, Chun-Su (December 1999). "Ginseng pharmacology". Biochemical Pharmacology. 58 (11): 1685–1693. doi:10.1016/S0006-2952(99)00212-9. PMID 10571242.

Types of terpenes and terpenoids (# of isoprene units)

Basic forms:

Acyclic (linear, cis and trans forms)
Monocyclic (single ring)
Bicyclic (2 rings)
Iridoids (cyclopentane ring)
Iridoid glycosides (iridoids bound to a sugar)
Steroids (4 rings)

Hemiterpenoids (1)

Monoterpenes
(C₁₀H₁₆)(2)

Acyclic	Ocimene Myrcenes
Monocyclic	Limonene Terpinene Phellandrene
Bicyclic	Pinene (α and β) Camphene Thujene Sabinene Carene

Monoterpenoids
(2,modified)

Acyclic	Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool
Monocyclic	Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol) Thymol Perillyl alcohol Carvacrol
Bicyclic	Camphor Borneol Bornyl acetate Eucalyptol Ascaridole Umbellulone

Sesquiterpenoids (3)

Artemisinin
Bisabolol
Cadinene
Cadinol
Cedrene
Chanootin
Farnesyl pyrophosphate
Juniperol
Longifolene
Muurolene
Nootkatin

Diterpenoids (4)

Acyclic	Phytol Geranylgeranyl pyrophosphate Geranyl-linalool
Monocyclic	Retinol Retinal
Bicyclic	cis-Abienol Epimanool Salvinorin A
Tricyclic	Cembrene Forskolin Manoyl oxide Pimaral Pimarol
Tetracyclic	Aphidicolin Gibberellin Paclitaxel
Resin acids	Abietic acid Communic acid Dehydroabietic acid Isopimaric acid Lambertianic acid Levopimaric acid Mercusic acid Neoabietic acid Pimaric acid Sandaracopimaric acid Secodehydroabietic acid Palustric acid

Sesterterpenoids (5)

Geranylfarnesol

Triterpenoids (6)

Steroids	Phytosterols Campesterol Citrostadienol Cycloartenol Sitostanol Sitosterol Stigmasterol Tocopherols Cholesterol Testosterone Cholecalciferol Ecdysones
Other	Betulin Lanosterol Saponins Serratenediol Squalane Acids Oleanolic acid Ursolic acid Betulinic acid Moronic acid

Sesquarterpenes/oids (7)

Ferrugicadiol
Tetraprenylcurcumene

Tetraterpenoids
(Carotenoids) (8)

Carotenes	Alpha-Carotene Beta-Carotene Gamma-Carotene Delta-Carotene Lycopene Neurosporene Phytofluene Phytoene
Xanthophylls:	Canthaxanthin Cryptoxanthin Zeaxanthin Astaxanthin Lutein Rubixanthin

Polyterpenoids (many)

Norisoprenoids (modified)

3-oxo-α-ionol
7,8-dihydroionone

Synthesis

Terpene synthase enzymes (many), having in common a terpene synthase N terminal domain (protein domain)

Activated isoprene forms

Isopentenyl pyrophosphate (IPP)
Dimethylallyl pyrophosphate (DMAPP)

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