Class of aromatic organic chemicals found in plants
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen.[1] When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds.[2] They are the largest class of plant secondary metabolites, representing about 60% of known natural products.[3] Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.[4]
Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes.[5] Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant Salvia divinorum, ginkgolide and bilobalide found in Ginkgo biloba and the cannabinoids found in cannabis. The provitamin beta carotene is a terpene derivative called a carotenoid.
The steroids and sterols in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to proteins, e.g., to enhance their attachment to the cell membrane; this is known as isoprenylation. Terpenoids play a role in plant defense as prophylaxis against pathogens and attractants for the predators of herbivores.[6]
^Chemistry, International Union of Pure and Applied. IUPAC Compendium of Chemical Terminology. IUPAC. doi:10.1351/goldbook.T06279.
^Christianson, David W. (2017). "Structural and Chemical Biology of Terpenoid Cyclases". Chemical Reviews. 117 (17): 11570–11648. doi:10.1021/acs.chemrev.7b00287. PMC 5599884. PMID 28841019.
^Firn R (2010). Nature's Chemicals. Oxford: Biology.
^Ashour, Mohamed; Wink, Michael; Gershenzon, Jonathan (2010). "Biochemistry of Terpenoids: Monoterpenes, Sesquiterpenes and Diterpenes". Biochemistry of Plant Secondary Metabolism. pp. 258–303. doi:10.1002/9781444320503.ch5. ISBN 9781444320503.
^Specter M (September 28, 2009). "A Life of Its Own". The New Yorker.
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives...
predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects...
A cyclase is an enzyme, almost always a lyase, that catalyzes a chemical reaction to form a cyclic compound. Important cyclase enzymes include: Adenylyl...
and even (albeit rarely) including hallucinations. Differences in the terpenoid content of the essential oil may account for some of these differences...
derivatives, phenylpropanoids/benzenoids, amino acid derivatives, and terpenoids. Due to the physical/chemical constraints most VOCs are of low molecular...
Ambroxide, widely known by the brand name Ambroxan, is a naturally occurring terpenoid and one of the key constituents responsible for the odor of ambergris...
known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products...
meroterpene (or meroterpenoid) is a chemical compound having a partial terpenoid structure. Terpenophenolics are compounds that are part terpenes, part...
saturated derivative p-menthane. The biosynthesis of α-terpinene and other terpenoids starts with the isomerization of geranyl pyrophosphate to linalyl pyrophosphate...
pinene with a bacterium. Alpha-pinene is the most widely encountered terpenoid in nature and is highly repellent to insects. Alpha-pinene appears in...
of many terpenoids has been reported. In particular mixture of sesquiterpenes namely carissone and carindone as a novel type of C31 terpenoid have been...
Neryl acetate is a terpenoid found in citrus oils. It is the acetate ester of nerol, an isomer of the more common fragrance geranyl acetate. In flavors...
interrupted spike'), before the commencement of Linnaean taxonomy. The plant terpenoid nepetalactone is the main chemical constituent of the essential oil of...
signature and appear to be involved in terpenoid biosynthesis. The YgbB protein is a putative enzyme thought to aid terpenoid and isoprenoid biosynthesis, a vital...
Geranyl acetate is a terpenoid. It is a colorless liquid with a pleasant floral or fruity rose aroma. It is a colorless liquid but commercial samples...
convulsions, paralysis, and, in rare cases, death. Toxicity occurs due to terpenoid ledol found in all Labrador tea species. R. groenlandicum has the lowest...
(carbocyclic) and more complex natural cyclic compounds Ingenol, a complex, terpenoid natural product, related to but simpler than the paclitaxel that follows...
is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (Cinnamomum...
units present in their structure. Some terpenoids (i.e. many sterols) are primary metabolites. Some terpenoids that may have originated as secondary metabolites...
v t e Types of terpenes and terpenoids (# of isoprene units) Basic forms: Acyclic (linear, cis and trans forms) Monocyclic (single ring) Bicyclic (2 rings)...
(Cucumis sativus) and Their Contribution to Herbivore-induced Volatile Terpenoid Emission". New Phytologist. 233 (2): 862–877. doi:10.1111/nph.17814. hdl:11245...
hemp. Both hops and cannabis contain terpenes and terpenoids; tetrahydrocannabinol (THC) is a terpenoid. Hops lack the enzyme that could convert cannabigerolic...
themselves from herbivores. Major classes of plant toxins include alkaloids, terpenoids, and phenolics. These can be harmful to humans and livestock by ingestion...
phytochemical products are found in the rhizomes are: nardostachysin, a terpenoid ester; nardostachnol; nardostachnone; jatamansic acid and jatamansinone...
oils. Ambergris is relatively nonreactive to acid. White crystals of a terpenoid known as ambrein, discovered by Leopold Ružička and Fernand Lardon in...
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