Flashcards: Diterpenes

Sclareol is a fragrant chemical compound found in clary sage (Salvia sclarea), from which it derives its name.

Phytane is a type of diterpenoid alkane.

Abietic acid (also known as abietinic acid or sylvic acid) is an organic compound that occurs widely in trees.

Forskolin (coleonol) is a labdane diterpene that is produced by the Indian Coleus plant (Coleus forskohlii).

Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1.

Pimaric acid is a carboxylic acid from the resin acid group.

Isopimaric acid (IPA) is a toxin which acts as a large conductance Ca2+-activated K+ channel (BK channel) opener.

Leelamine (dehydroabietylamine) is a diterpene amine that has weak affinity for the cannabinoid receptors CB1 and CB2, as well as being an inhibitor of pyruvate dehydrogenase kinase.

Gibberellins (GAs) are plant hormones that regulate growth and influence various developmental processes, including stem elongation, germination, dormancy, flowering, sex expression, enzyme induction, and leaf and fruit senescence.

Phytanic acid (or 3,7,11,15-tetramethyl hexadecanoic acid) is a branched chain fatty acid that humans can obtain through the consumption of dairy products, ruminant animal fats, and certain fish.

Cafestol is a diterpene molecule present in coffee.

Retinol (Vitamin A1) is one of the animal forms of vitamin A.

Pristane is a natural saturated terpenoid alkane obtained primarily from shark liver oil, from which its name is derived (Latin pristis, "shark").

Shortolide A is a natural product isolated from Solidago shortii.

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum (Bald Cypress), Rosmarinus officinalis (Rosemary), several Salvia species and other plants, along with its oxidized rearrangement product, taxodione.

Tetrahydrocannabinolic acid (THCA, Δ9-THCA, 2-COOH-THC; conjugate base tetrahydrocannabinolate) is a biosynthetic precursor of tetrahydrocannabinol (THC), the active component of cannabis.

Tetrahydrocannabinol-C4, also known as THC-C4 and butyl-THC, is a homologue of tetrahydrocannabinol (THC), the active component of cannabis.

Triptolide is a diterpenoid epoxide which is endogenously produced by the thunder god vine, Tripterygium wilfordii.

Taxamairin A is an non-taxane isolate of Taxus yunnanensis.

Abietane is a diterpene that forms the structural basis for a variety of natural chemical compounds such as abietic acid, carnosic acid, and ferruginol which are collectively known as abietanes or abietane diterpenes.

Phorbol is a natural, plant-derived organic compound.

Panicudine (6-hydroxy-11-deoxy-13-dehydrohetisane) is a C20-diterpene alkaloid of the hetisine type, first isolated from Aconitum paniculatum.

Galanolactone is a diterpenoid lactone first isolated from ginger.

Tripchlorolide is an isolate of Tripterygium wilfordii (雷公藤) that has potential interaction with the NMDA receptor.

Triptolidenol is a bioactive diterpene created by Tripterygium wilfordii.

Tripdiolide is an anti-inflammatory isolate of Tripterygium wilfordii.

Carnosol is a phenolic diterpene found in the herbs rosemary (Rosmarinus officinalis) and Mountain desert sage (Salvia pachyphylla).

β–Araneosene is a molecule first isolated in 1975 from the mold Sordaria araneosa by Borschberg.

Bipinnatin J is a diterpene isolated from the bipinnate sea plume Antillogorgia bipinnata, a sea fan found in the eastern Caribbean Sea.

KM-233 is a drug which is an analogue of Δ8-tetrahydrocannabinol (THC), the less active but more stable isomer of the active component of Cannabis.

Levopimaric acid is an abietane-type of diterpene resin acid.

10-Deacetylbaccatins are a series of closely related natural organic compounds isolated from the Pacific yew tree (Taxus brevifolia) and related species.

Kahweol is a diterpene molecule found in the beans of Coffea arabica.

Menatetrenone (INN), also known as MK-4, is a vitamin K compound used as a hemostatic agent, and also as adjunctive therapy for the pain of osteoporosis.

Pristanic acid (2,6,10,14-tetramethylpentadecanoic acid) is a terpenoid acid present at micromolar concentrations in the blood plasma of healthy individuals.

Momilactone B is an allelopathic agent produced from the roots of rice (Oryza sativa L.) (100 mg from 200 kg dry rice husk).

18-Norabietane is a diterpene perhydrogenated phenanthrene derivative.

Ailanthone is an allelopathic chemical that is produced by the Ailanthus altissima tree which inhibits the growth of other plants.

Carnosic acid is a natural benzenediol abietane diterpene found in rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis).

Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus, Cephalosporum aphidicola with antiviral and antimitotic properties.

12-O-Tetradecanoylphorbol-13-acetate (TPA), also commonly known as tetradecanoylphorbol acetate, tetradecanoyl phorbol acetate, and phorbol 12-myristate 13-acetate (PMA), is a diester of phorbol and a potent tumor promoter often employed in biomedical research to activate the signal transduction enzyme protein kinase C (PKC).

Andrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of Andrographis paniculata.

Pseudopterosin A is a diterpene glycoside isolated from the gorgian sea whip Pseudopterogorgia elisabethae, found in the Bahamas and Florida Keys.

Stemarene is a diterpene hydrocarbon can be produced biosynthetically through enzyme extracts from rice.

Stemodene is a labdane-related diterpene whose corresponding terpene synthase has been discovered in rice and subsequently cloned and functionally characterized.

Guanacastepene A is a compound showing antibiotic activity.

Neotripterifordin is an anti-viral diterpene lactone isolated from Tripterygium wilfordii.

Isocupressic acid is a diterpene acid present in a variety of conifer needles.

Isotuberculosinol, also called nosyberkol or edaxadiene is a diterpene molecule produced by the bacterium Mycobacterium tuberculosis, the causative agent of TB, which aids in its pathogenesis.

Ferruginol is a natural phenol and a meroterpene (a chemical compound containing a terpenoid substructure) that has been isolated from the needles of the redwood Sequoia sempervirens.

Fichtelite is a rare white mineral found in fossilized wood from Bavaria.

Phorbol 12,13-dibutyrate (PDBu) is a phorbol ester which is one of the constituents of croton oil.

Simonellite (1,1-dimethyl-1,2,3,4-tetrahydro-7-isopropyl phenanthrene) is a polycyclic aromatic hydrocarbon with a chemical formula C19H24.

Labdane is a natural bicyclic diterpene.

Taxadiene (taxa-4,11-diene) is a diterpene.

Lagochilin is a bitter diterpene that forms a grey crystalline solid.

Geranylgeraniol is a diterpene alcohol which plays a role in several important biological processes.

Prostratin is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae).

Ryanodine is a poisonous diterpenoide found in the South American plant Ryania speciosa (Salicaceae).

Ingenol mebutate (ingenol-3-angelate, PEP005, LEO Pharma trade name Picato) is a substance found in the sap of the plant Euphorbia peplus and an inducer of cell death.

Steviol is a diterpene first isolated from the plant Stevia rebaudiana in 1931.

Cembrene A, or sometimes neocembrene, is a natural monocyclic diterpene isolated from corals of the genus Nephthea.

EBC-46 is an experimental drug candidate being studied pre-clinically by the Australian company Ecobiotics (specifically its drug discovery subsidiary Qbiotics).

Totarol is a meroterpene, and more precisely a terpenophenolic, a chemical compound that is part terpene and part natural phenol.

Sclarene is a diterpene present in the foliage of Podocarpus hallii.