Labdane

Last updated
Labdane
Labdane.svg
Names
IUPAC name
Labdane
Systematic IUPAC name
(4aR,5S,6S,8aS)-1,1,4a,6-Tetramethyl-5-[(3R)-3-methylpentyl]decahydronaphthalene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C20H38/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h15-18H,7-14H2,1-6H3/t15-,16+,17+,18+,20-/m1/s1 Yes check.svgY
    Key: LEWJAHURGICVRE-AISVETHESA-N Yes check.svgY
  • InChI=1/C20H38/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h15-18H,7-14H2,1-6H3/t15-,16+,17+,18+,20-/m1/s1
    Key: LEWJAHURGICVRE-AISVETHEBV
  • C2CC([C@@H]1CC[C@@H]([C@@H]([C@@]1(C)C2)CC[C@H](C)CC)C)(C)C
Properties
C20H38
Molar mass 278.524 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Labdane is a natural bicyclic diterpene. It forms the structural core for a wide variety of natural products collectively known as labdanes or labdane diterpenes. The labdanes were so named because the first members of the class were originally obtained from labdanum, a resin derived from the gum rockrose. [1] [2]

Contents

A variety of biological activities have been determined for labdane diterpenes including antibacterial, antifungal, antiprotozoal, and anti-inflammatory activities. [3]

Example labdane derivatives

See also

Related Research Articles

Combinatorial chemistry comprises chemical synthetic methods that make it possible to prepare a large number of compounds in a single process. These compound libraries can be made as mixtures, sets of individual compounds or chemical structures generated by computer software. Combinatorial chemistry can be used for the synthesis of small molecules and for peptides.

<span class="mw-page-title-main">Resin</span> Solid or highly viscous substance

In polymer chemistry and materials science, a resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on naturally occurring resins.

<span class="mw-page-title-main">Abietic acid</span> Chemical compound

Abietic acid is an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin and is the most abundant of several closely related organic acids that constitute most of rosin, the solid portion of the oleoresin of coniferous trees. Its ester or salt is called an abietate.

<i>Cupressus macrocarpa</i> Species of conifer

Hesperocyparis macrocarpa also known as Cupressus macrocarpa, or the Monterey cypress is a coniferous tree, and is one of several species of cypress trees endemic to California.

<span class="mw-page-title-main">Natural product</span> Chemical compound or substance produced by a living organism, found in nature

A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.

The Passerini reaction is a chemical reaction involving an isocyanide, an aldehyde, and a carboxylic acid to form a α-acyloxy amide. This addition reaction is one of the oldest isocyanide-based multicomponent reactions (IMCR) and was first described in 1921 by Mario Passerini in Florence, Italy. It is typically carried out in aprotic solvents but can also be performed in ionic liquids such as water or Deep Eutectic solvents (DESs). It is a third order reaction; first order in each of the reactants. The Passerini reaction is often used in combinatorial and medicinal chemistry with recent utility in green chemistry and polymer chemistry. As isocyanides exhibit high functional group tolerance, chemoselectivity, regioselectivity, and stereoselectivity, the Passerini reaction has a wide range of synthetic applications.

<span class="mw-page-title-main">Cembrene A</span> Chemical compound

Cembrene A, or sometimes neocembrene, is a natural monocyclic diterpene isolated from corals of the genus Nephthea. It is a colorless oil with a faint wax-like odor.

<span class="mw-page-title-main">Boswellic acid</span> Chemical compound

Boswellic acids are a series of pentacyclic terpenoid molecules that are produced by plants in the genus Boswellia. Like many other terpenes, boswellic acids appear in the resin of the plant that exudes them; it is estimated that they make up 30% of the resin of Boswellia serrata. While boswellic acids are a major component of the resin, the steam or hydro distilled frankincense essential oil does not contain any boswellic acid as these components are non-volatile and too large to come over in the steam distillation process.

<i>Leonotis nepetifolia</i> Species of plant

Leonotis nepetifolia,, is a species of plant in the genus Leonotis and the family Lamiaceae (mint). It is native to tropical Africa and southern India. It can also be found growing abundantly in much of Latin America, the West Indies, and the Southeastern United States. It grows to a height of 3 metres and has whorls of striking lipped flowers, that are most commonly orange, but can vary to red, white, and purple. It has drooping dark green, very soft serrated leaves that can grow up to 10 centimetres (4 in) wide. Sunbirds and ants are attracted to the flowers. It has been found growing on road sides, rubbish heaps or waste land.

Clerodane diterpenes, sometimes referred to as clerodane diterpenoids, are a large group of secondary metabolites that have been isolated from several hundreds of different plant species, as well as fungi, bacteria and marine sponges. They are bicyclic terpenes that contain 20 carbons and a decalin core.

<span class="mw-page-title-main">Thujaplicin</span> Chemical compound

Thujaplicins are a series of tropolone-related chemical substances that have been isolated from the softwoods of the trees of Cupressaceae family. These compounds are known for their antibacterial, antifungal, and antioxidant properties. They were the first natural tropolones to be made synthetically.

<span class="mw-page-title-main">Hinokitiol</span> Chemical compound

Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.

<span class="mw-page-title-main">Abietane</span> Chemical compound

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.

<span class="mw-page-title-main">Isocupressic acid</span> Chemical compound

Isocupressic acid is a diterpene acid present in a variety of conifer needles. It induces abortion in cattle. It is found in all parts of the ponderosa pine, especially the needles. This gives its toxic and abortifacient effects. It is also present in the lodgepole pine, the jeffrey pine and possibly in the monterey pine.

<span class="mw-page-title-main">Secalonic acid</span> Group of chemical compounds

Secalonic acids are a group of chiral dimeric tetrahydroxanthones closely related to ergoflavin and ergochrysin A that are collectively called ergochromes and belong to a class of mycotoxins initially isolated as major ergot pigments from the fungi Claviceps purpurea that grows parasitically on rye grasses. From early times and particularly in medieval Europe the consumption of grains containing ergot has repeatedly lead to mass poisonings known as ergotism which was caused by toxic ergot alkaloids and mycotoxins such as the ergochromes, due to contamination of flour by C. purpurea. A cluster of genes responsible for the synthesis of secalonic acids in C. purpurea has been identified. Secalonic acid D the enantiomer of secalonic acid A is a major environmental toxin, isolated from the fungus Penicillium oxalicum, and is a major microbial contaminant of freshly-harvested corn which causes toxicity through contamination of foodstuffs.

<span class="mw-page-title-main">Akuammicine</span> Alkaloid

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.

<span class="mw-page-title-main">Gigactonine</span> Chemical compound

Gigactonine is a naturally occurring diterpene alkaloid first isolated from Aconitum gigas. It occurs widely in the Ranunculaceae plant family. The polycyclic ring system of this chemical compound contains nineteen carbon atoms and one nitrogen atom, which is the same as in aconitine and this is reflected in its preferred IUPAC name.

<span class="mw-page-title-main">Delsoline</span> Naturally occurring chemical compound

Delsoline and delcosine are two closely related naturally occurring diterpene alkaloids first isolated from Delphinium consolida. They occur widely in the Ranunculaceae plant family. The polycyclic ring system containing nineteen carbon atoms and one nitrogen atom in these compounds is the same as in aconitine and this is reflected in their preferred IUPAC name.

Robert Edward Corbett was a New Zealand organic chemist. He is noted for his contribution to natural product chemistry through the isolation and structural elucidation of compounds from New Zealand native plants.

<span class="mw-page-title-main">Sugiol</span> Chemical compound

Sugiol is a phenolic abietane derivative of ferruginol and can be used as a biomarker for specific families of conifers. The presence of sugiol can be used to identify the Cupressaceae s.1., podocarpaceae, and Araucaraiaceae families of conifers. The polar terpenoids are among the most resistant molecules to degradation besides n-alkanes and fatty acids, affording them high viability as biomarkers due to their longevity in the sedimentary record. Significant amounts of sugiol has been detected in fossil wood dated to the Eocene and Miocene periods, as well as a sample of Protopodocarpoxylon dated to the middle Jurassic.

References

  1. Cocker, J. D.; Halsall, T. G.; Bowers, A. (1956). "The chemistry of gum labdanum. I. Some acidic constituents". Journal of the Chemical Society: 4259–62. doi:10.1039/jr9560004259.
  2. Cocker, J. D.; Halsall, T. G. (1956). "The chemistry of gum labdanum. II. The structure of labdanolic acid". Journal of the Chemical Society: 4262–71. doi:10.1039/jr9560004262.
  3. Atta-Ur-Rahman, ed. (1988). Studies in Natural Product Chemistry : Bioactive Natural Products, Part F. ISBN   978-0-08-044001-9.
  4. Kenmogne, Marguerite; Prost, Elise; Harakat, Dominique; Jacquier, Marie-José; Frédérich, Michel; Sondengam, Lucas B.; Zèches, Monique; Waffo-Téguo, Pierre (1 March 2006). "Five labdane diterpenoids from the seeds of Aframomum zambesiacum". Phytochemistry. 67 (5): 433–438. doi:10.1016/j.phytochem.2005.10.015. PMID   16321410.
  5. Parton, K; Gardner, D; Williamson, N.B (1996). "Isocupressic acid, an abortifacient component of Cupressus macrocarpa". New Zealand Veterinary Journal. 44 (3): 109. doi:10.1080/00480169.1996.35946. PMID   16031906.