Terpenoid


Terpenoid
Chemical structure of the terpenoid isopentenyl pyrophosphate.

The terpenoids (play /ˈtɜrpɨnɔɪd/ tur-pə-noyd), sometimes called isoprenoids, are a large and diverse class of naturally occurring organic chemicals similar to terpenes, derived from five-carbon isoprene units assembled and modified in thousands of ways. Most are multicyclic structures that differ from one another not only in functional groups but also in their basic carbon skeletons. These lipids can be found in all classes of living things, and are the largest group of natural products.

Plant terpenoids are used extensively for their aromatic qualities. They play a role in traditional herbal remedies and are under investigation for antibacterial, antineoplastic, and other pharmaceutical functions. 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.[1] Well-known terpenoids include citral, menthol, camphor, Salvinorin A in the plant Salvia divinorum, and the cannabinoids found in Cannabis.

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.

Many of these are substrates for plant Cytochrome P450.

Contents

Structure and classification

Terpenes are hydrocarbons resulting from the combination of several isoprene units. Terpenoids can be thought of as modified terpenes, wherein methyl groups have been moved or removed, or oxygen atoms added. (Some authors use the term "terpene" more broadly, to include the terpenoids.) Just like terpenes, the terpenoids can be classified according to the number of isoprene units used:

  • Hemiterpenoids, 1 isoprene unit (5 carbons)
  • Monoterpenoids, 2 isoprene units (10C)
  • Sesquiterpenoids, 3 isoprene units (15C)
  • Diterpenoids, 4 isoprene units (20C) (e.g. ginkgolides)
  • Sesterterpenoids, 5 isoprene units (25C)
  • Triterpenoids, 6 isoprene units (30C)
  • Tetraterpenoids, 8 isoprene units (40C) (e.g. carotenoids)
  • Polyterpenoid with a larger number of isoprene units

Terpenoids can also be classified according to the number of cyclic structures they contain. In the year 1995,Julius Anitnec found out that Terpenoids can be test using Salkowski test.

Meroterpenes are any compound, including many natural products, having a partial terpenoid structure

Biosynthesis

Simplified version of the steroid synthesis pathway with the terpenoid intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP), and squalene shown. Some intermediates are omitted for clarity.

There are two metabolic pathways of creating terpenoids:

Mevalonic acid pathway

Many organisms manufacture terpenoids through the HMG-CoA reductase pathway, the pathway that also produces cholesterol. The reactions take place in the cytosol. The pathway was discovered in the 1950s.

MEP/DOXP pathway

The 2-C-methyl-D-erythritol 4-phosphate/1-deoxy-D-xylulose 5-phosphate pathway (MEP/DOXP pathway), also known as [non-mevalonate pathway] or mevalonic acid-independent pathway, takes place in the plastids of plants and apicomplexan protozoa, as well as in many bacteria. It was discovered in the late 1980s.

Pyruvate and glyceraldehyde 3-phosphate are converted by DOXP synthase (Dxs) to 1-deoxy-D-xylulose 5-phosphate, and by DOXP reductase (Dxr, IspC) to 2-C-methyl-D-erythritol 4-phosphate (MEP). The subsequent three reaction steps catalyzed by 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase (YgbP, IspD), 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase (YchB, IspE), and 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase (YgbB, IspF) mediate the formation of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate (MEcPP). Finally, MEcPP is converted to (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) by HMB-PP synthase (GcpE, IspG), and HMB-PP is converted to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) by HMB-PP reductase (LytB, IspH).

IPP and DMAPP are the end-products in either pathway, and are the precursors of isoprene, monoterpenoids (10-carbon), diterpenoids (20-carbon), carotenoids (40-carbon), chlorophylls, and plastoquinone-9 (45-carbon). Synthesis of all higher terpenoids proceeds via formation of geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and geranylgeranyl pyrophosphate (GGPP).

Although both pathways, MVA and MEP, are mutually exclusive in most organisms, interactions between them have been reported in plants and few bacteria species.

Organism Pathways
Bacteria MVA or MEP
Archaea MVA
Green Algae MEP
Plants MVA and MEP
Animals MVA
Fungi MVA

References

External links


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Look at other dictionaries:

  • terpenoid — ter·pe·noid tər pə .nȯid adj resembling a terpene in molecular structure terpenoid n any of a class of compounds that are characterized by an isoprenoid structure like that of the terpene hydrocarbons …   Medical dictionary

  • terpenoid — adjective or noun see terpene …   New Collegiate Dictionary

  • Terpenoid — Zu den Terpenoiden gehören Verbindungen, die auf Isopreneinheiten aufbauen. So gehören zu den Terpenoiden die Untergruppe der Terpene, deren Kohlenstoffatome sich immer durch fünf teilen lassen, aber auch von den Terpenen abgeleitete Verbindungen …   Deutsch Wikipedia

  • terpenoid — See terpenic. * * * …   Universalium

  • terpenoid — noun A very large class of naturally occurring and synthetic organic compounds formally derived from the hydrocarbon isoprene; they include many volatile compounds used in perfume and …   Wiktionary

  • Terpenoid — Ter|pe|no|id [↑ oid], das; s, e: Sammelbez. entweder nur für die Derivate der eigtl. ↑ Terpene (Monoterpene, C10) oder aber für alle Kohlenwasserstoffe u. funktionalisierten Verb., denen ein isoprenoides Bauprinzip (C5n) zugrunde liegt, sodass… …   Universal-Lexikon

  • terpenoid — ter·pe·noid …   English syllables

  • terpenoid — I. ˈtərpəˌnȯid adjective Etymology: terpene + oid : resembling a terpene in molecular structure II. noun ( s) : any of a class of compounds that are characterized by an isoprenoid structure like that of the terpene hydocarbons and that often… …   Useful english dictionary

  • Delta-cadinene synthase — (+) delta cadinene synthase Identifiers EC number 4.2.3.13 CAS number 166800 09 5 …   Wikipedia

  • Cannabis — This article is about the plant genus. For use as a psychoactive drug in the genus, see Cannabis (drug). Cannabis …   Wikipedia


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