“Terpenes (Isoprenoids)”  

Isoprenoids (Terpenes)

  In phytochemistry, Terpenes (Isoprenoids) are a subclass of compounds composed of repeating 5-carbon units of hemiterpene.

Terpene Classifications

  In biochemistry, the terpenes may be classified by the number of terpene units (C₅H₈) in the molecule; a prefix in the name indicates the number of terpene units needed to assemble the molecule.

Examples of these terpene classifications include:

hemiterpenes (C5 terpenes) hemiterpenoids monoterpenes (C10 terpenes) monoterpenoids sesquiterpenes (C15 terpenes) sesquiterpenoids

diterpenes (C20 terpenes) diterpenoids sesterterpenes (C25 terpenes) sesterterpenoids triterpenes (C30 terpenes) triterpenoids

sesquarterpenes (C35 terpenes) sesquarterpenoids tetraterpenes (C40 terpenes) tetraterpenoids polyterpenes polyterpenoids

  Examples of some other entities related to the terpenes include:

Carotenoids abscisic acid beta carotene lycopenelycopene norisoprenoids retinoids + xanthophylls + zeta carotene

terpene lactones cannabinoids + dolichols gefarnate linalyl anthranilate polyisoprenyl phosphates +

In phytochemistry, Isoprenoids (Terpenes) are a type of prenol lipids. *

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“Sesquiterpenes”  

Sesquiterpene

  In organic chemistry, a Sesquiterpene is a C₁₅ terpene and the parent hydride of the sesquiterpenoids.
  Sesquiterpenes consist of three (3) isoprene units derived from the molecular formula C₁₅H₂₄.

Examples of subsets, concepts, subjects and related entities of the sesquiterpenes include:

monocyclic sesquiterpenes abscisic acid bisabolols Germacrane Sesquiterpenes sesquiterpene lactones

polycyclic sesquiterpenes Eudesmane Sesquiterpenes Guaiane Sesquiterpenes Thapsigargin Santonin

artemisinins Artemether Artesunate farnesol gossypol Trichothecenes O-(Chloroacetylcarbamoyl)fumagillol

  More examples of sesquiterpene subsets include:

alpha-acoradiene beta-acoradiene (-)-alpha-acorenol african-1-ene african-3-ene ambrosane amorpha-4,11-diene aristolane aristolochene (+)-5-epi-aristolochene (+)-alpha-barbatene alpha-bergamotene (+)-endo-beta-bergamotene beta-Bourbonene bicyclogermacrene bisabolanes bisabolenes 6'-bromomelleolide F Cadalene cadinane cadinene caryophyllane beta-caryophyllene 9-epi-caryophyllene cedr-8-ene cedrane

beta-chamigrene alpha-copaene beta-copaene alpha-cubebene beta-cubebene (+)-cubenene (-)-alpha-cuprenene alpha-curcumene beta-curcumene gamma-curcumene 4,5,9,10-dehydroisolongifolene 3,4-Dihydrocadalene dauca-4,7-diene drimane beta-elemene gamma-elemene delta-elemene bicycloelemene epizonarene eremophilane (-)-eremophilene (+)-eremophilene (-)-4-epi-eremophilene (-)-5-epi-eremophilene farnesane farnesene

germacrane germacrene germacrene A germacrene C gibbane guaia-4,6-diene guaiazulene alpha-guaiene beta-guaiene delta-guaiene (-)-alpha-gurjunene (+)-alpha-gurjunene beta-gurjunene gamma-gurjunene himachalane himachalene humulane humulene (-)-alpha-isocomene isolongifolane (+)-epi-isozizaene longifolene alpha-longipinene Lycoposerramine F beta-maaliene cis-muurola-3,5-diene alpha-muurolene gamma-muurolene

beta-Neoclovene pentalenene premnaspirodiene (+)-2-epi-prezizaene (+)-alpha-santalene (-)-beta-santalene sativene selinene beta-sesquiphellandrene sesquisabinene A sesquisabinene B sesquithujene 7-epi-sesquithujene sibirene sodorifen thujopsene trichodiene (+)-valencene beta-Vatirenene vetispirane viridiflorene (+)-vulgraon B beta-ylangene zingiberene ent-zingiberene 7-epi-zingiberene 2,6,10-trimethyldodeca-2,6,10-triene

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“Diterpenes”  

  In organic chemistry, Diterpenes are a subclass of organic compounds in the prenol lipids class within the lipid of lipids and lipid-like molecules superclass, composed of terpene compounds formed by four isoprene units produced mainly via the mevalonic acid (MVA) pathway.   In phytochemistry, Diterpenes (diterpenoids) are twenty-carbon compounds derived from deoxyxylulose phosphate or mevalonic acid (mevalonate) composed of four (4) isoprene units with the molecular formula C₂₀H₃₂.
  Examples of diterpenes and other related diterpenoids include:

diterpenoids diterpene alkaloids aconitine alkaloids diterpene glycosides diterpene lactones

aphidicolin atractyloside abietane diterpenes clerodane diterpenes kaurane diterpenes (kauranes) gibberellins colforsin ginkgolides bilobalides

phorbols phorbol esters + phytanic acid phytol vitamin K + ryanodine taxoids docetaxel paclitaxel +

Examples of more diterpene substances include:

abietadiene abietane abietatriene atisane beta-pinacene beyerane casbane casbene cembrane

cembrene C cycloaraneosene dolabradiene elisabethatriene gibberellane grayanotoxane halimane isoelisabethatriene isopimara-7,15-diene

isopimarane kaurane labdane neophytadiene phomopsene phytane pimaradiene pimarane pseudolaratriene

rhizathalene A rosane sclarene stemar-13-ene taxa-4,11-diene taxane terpentetriene tigliane tsukubadiene

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“Sesterterpenes”  

Sesterterpene

  In Biochemistry, Sesterterpenes consist of 25 carbon (25) and five (5) isoprene units, derived from the molecular formula C₂₅H₄₀.
  Examples of sesterterpenes include:

• Sesterterpene lactones
• Cyclohexane sesterterpenes
• ophiobolane
• scalarane

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“Carotenoids”  

Carotenoid

  In organic chemistry, is one of a class of tetraterpenoids (C₄₀), formally derived from the acyclic parent, ψ,ψ-carotene by hydrogenation, dehydrogenation, cyclization, oxidation, or combination of these processes. This class includes two divisions the carotenes, xanthophylls and certain compounds that arise from rearrangement of the skeleton of ψ,ψ-carotene or by loss of part of this structure. Retinoids are related but generally excluded.
  In our diet and in our body, the Carotenoids are a class of natural fat-soluble pigments, that have an aliphatic hydrocarbons consisting of a polyisoprene (tetraterpenes) backbone, which generally absorb blue light (400 to 500 nm), found principally in plants, algae, photosynthetic bacteria and eggs.
In our diet and in our body, under usual dietary habits over forty Carotenoids get ingested of which six carotenoids and their metabolites can be found in our tissues.

Two Carotenoid Divisions

In and from nature, there are over 600 different carotenoids—fat-soluble pigments, that provide color to plants, most commonly occur in the all-trans form, split into two major distinct divisions, according to their chemical structure, the xanthophylls (oxygen containing) and the carotenes (pure hydrocarbons without oxygen), with the carotene carotenoids including β-carotene and lycopene and the xanthophyll carotenoids including lutein, canthaxanthin, zeaxanthin, violaxanthin, capsorubin and astaxanthin.
  Examples of common carotenoids and related substances many of which are found in the human diet and body tissues include:

carotenes beta Carotene zeta Carotene Also related: norisoprenoids abscisic acid

Xanthophylls Canthaxanthin Cryptoxanthins Beta-Cryptoxanthin Lutein Astaxanthin Zeaxanthins

retinoids Acitretin Etretinate Fenretinide Isotretinoin Retinaldehyde Vitamin A Tretinoin

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“Monoterpenoids subclass (Monoterpenes)”  

Monoterpenoids

  In organic chemistry, monoterpenoids (monoterpenes) are a terpenoid subclass of organic compounds in the prenol lipids class in the lipids and lipid-like molecules superclass, containing a chain of two isoprene units.

Monoterpenes

  In nature, because of the low molecular weight of Monoterpenoids and their parent hydride monoterpenes, exist in the form of plant terpene essential oils.
In biochemistry, Monoterpenes (Monoterpenoids), with a core of 10 carbons, consist of two (2) isoprene units and are derived from the molecular formula C₁₀H₁₆.

In our body, Monoterpenes & Monoterpenoids), are generally formed via the mevalonate pathway from a combination of 3,3-dimethylallyl pyrophosphate and isopentenyl pyrophosphate.
  Examples of members in the monoterpenoids subclass (monoterpenes) and monoterpenes include:

acyclic monoterpenoids monocyclic monoterpenoids

bicyclic monoterpenoids aromatic monoterpenoids

menthane monoterpenoids monoterpene glycosides

Other monoterpenoid examples include:

Menthol Norbornanes Pyrethrins Acidissiminin Acidissiminol actinopolysporin A actinopolysporin B actinopolysporin C Adhyperforin alpha-Campholene acetate alpha-Terpinyl anthranilate Anhydrofurospongin-1 apo carotenoid monoterpenoid Aristolene epoxide Arnebinone Ascosalitoxin auraptene Auxin b Avasimibe Baliospermin benzylideneacetone BiakamideC,D bismuth camphocarbonate bornane monoterpenoid bornaprine Bornyl butyrate Bornyl isovalerate butibufen calyculin a Camphene hydrate Cannabidivarin cantharidic acid cantharidin chrysanthemol Chrysanthenone cicaprost cis-2-Norbornanol cis-2-Thujen-4-ol cis-4-methoxy thujane cis-8-Hydroxylinalool cis-trans-Iridodial citral dimethyl acetal citronellal citronellic acid citronellol citronellol acetate Citronellyl anthranilate Crispane Curzerenone Darwinol Dehydromyodesmone Dendrolasin dihydromyrcenol Dihydroshikonofuran domitroban ecamsule Empenthrin enzacamene Eucarvone Euphorbiaproliferin I Euphorbiaproliferin J

Evodone fencamfamin fenchane monoterpenoid fenchol Fenchyl acetate fencibutirol Furamethrin Furohyperforin Futoquinol Garcinol geranial geranic acid geraniol geranyl acetate geranyl acetoacetate geranyl benzoate geranyl ethyl ether geranyl isobutyrate glibornuride guttiferone E Hapalindole D Helinorbisabone Heptopargil Hericene A Hericene B Hericenone C Hericenone D homocamfin Humulinone hydroxy-beta-cyclocitral Hydroxygeraniol Hypercalin B ibuprofen guaiacol ester iridoid monoterpenoid (iridoids) iridoid glycosides iridoid glucosides Iridotrial Isobornyl isobutyrate Isobornyl propionate Isocitral isogeraniol Isoleptospermone isoxanthochymol Kolanone L-alpha-bornyl acetate lactinolide lavandulol linalool Linalyl benzoate Linalyl butyrate Linalyl caprylate linalyl ethyl ether Linalyl isobutyrate Linalyl phenylacetate Linalyl propionate Lyngbyatoxin mabuprofen Malyngamide 2 Malyngamide H Mancinellin Mecamylamine hydrochloride

menthofuran meradimate Methyl citronellate Methyl geranate militarinone B Militarinone C Moxisylyte hydrochloride myrcenol Myrigalone A myrtecaine myrtenal myrtenic acid myrtenol neral nerol oxide neryl acetate neryl ethyl ether Norecasantalic acid Norecasantalol Oxepahyperforin Oxocamphor paeoniflorigenone paeonilactinone Panicein A Panicein A hydroquinone Panicein B2 Panicein B3 Panicein C Panicein D Panicein F1 Panicein F2 perillene Photocitral A pi-Oxocamphor Pimilprost pinane monoterpenoid pinaverium Piperochromanoic acid Piperochromenoic acid Piquerol A pyrinoline Pyrohyperforin reparixin Robustadial A rose oxide safranal Teresantalol thiogeraniol thujane monoterpenoid thymol Thymol methyl ether thymol sulfate Thymyl acetate trans-4-methoxy thujane Tricycloekasantal Tricycloekasantalol tschimganine tymazoline Verbenol Vulgarole Vulgarone A

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“Triterpenes”  

Triterpene

  In organic chemistry, a Triterpene consist of six (6) terpenes (isoprenoids) units and have the molecular formula C₃₀H₄₈.
  Examples of some triterpenes include:

triterpenoids pentacyclic triterpenes beta-hexaprene C30 botryococcene

cucurbitacins cucurbitane cycloartane dammarane friedelane

gammacerane ginsenosides hopane lanostane lanosterol

limonins lupanes oleanane protostane sapogenins

squalene quassins taraxastane tirucallane ursane

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