Habenariol

Last updated
Habenariol
Habenariol 2D.svg
Names
IUPAC name
bis(4-hydroxyphenyl)methyl (2R)-2-ethyl-2-hydroxy-4-methylpentanoate
Other names
Bis-p-hydroxybenzyl-2-isobutylmalate
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/C21H26O5/c1-4-21(25,13-14(2)3)20(24)26-19(15-5-9-17(22)10-6-15)16-7-11-18(23)12-8-16/h5-12,14,19,22-23,25H,4,13H2,1-3H3/t21-/m1/s1
    Key: RXNVZHSSBDLGHI-OAQYLSRUSA-N
  • c1cc(O)ccc1COC(=O)C(O)(CC(C)C)CC(=O)OCc(cc2)ccc2O
Properties
C22H26O7
Molar mass 402.443 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Habenariol is a phenolic compound found in the semi-aquatic orchid Habenaria repens . [1] It acts as a feeding deterrent against the freshwater crayfish Procambarus clarkii . [2]

See also

Related Research Articles

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Vanillin Chemical compound

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<i>Lonicera japonica</i> Flowering shrub known as Japanese honeysuckle

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Adephaga Suborder of beetles

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Ferulic acid Chemical compound

Ferulic acid is a hydroxycinnamic acid, an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans.

<i>p</i>-Cresol Chemical compound

para-Cresol, also 4-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of o-cresol and m-cresol.

Dirigent protein

Dirigent proteins are members of a class of proteins which dictate the stereochemistry of a compound synthesized by other enzymes. The first dirigent protein was discovered in Forsythia intermedia. This protein has been found to direct the stereoselective biosynthesis of (+)-pinoresinol from coniferyl alcohol monomers:

Hordenine Chemical compound

Hordenine is an alkaloid of the phenethylamine class that occurs naturally in a variety of plants, taking its name from one of the most common, barley. Chemically, hordenine is the N-methyl derivative of N-methyltyramine, and the N,N-dimethyl derivative of the well-known biogenic amine tyramine, from which it is biosynthetically derived and with which it shares some pharmacological properties. As of September 2012, hordenine is widely sold as an ingredient of nutritional supplements, with the claims that it is a stimulant of the central nervous system, and has the ability to promote weight loss by enhancing metabolism. In experimental animals, given sufficiently large doses parenterally, hordenine does produce an increase in blood pressure, as well as other disturbances of the cardiovascular, respiratory, and nervous systems. These effects are generally not reproduced by oral administration of the drug in test animals, and virtually no scientific reports of the effects of hordenine in human beings have been published.

Phenanthrenoid

Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.

Triphenyl phosphate Chemical compound

Triphenyl phosphate (TPhP) is the chemical compound with the formula OP(OC6H5)3. This colourless solid is the ester (triester) of phosphoric acid and phenol. It is used as a plasticizer and a fire retardant in a wide variety of settings and products.

Phlorotannin

Phlorotannins are a type of tannins found in brown algae such as kelps and rockweeds or sargassacean species, and in a lower amount also in some red algae. Contrary to hydrolysable or condensed tannins, these compounds are oligomers of phloroglucinol (polyphloroglucinols). As they are called tannins, they have the ability to precipitate proteins. It has been noticed that some phlorotannins have the ability to oxidize and form covalent bonds with some proteins. In contrast, under similar experimental conditions three types of terrestrial tannins apparently did not form covalent complexes with proteins.

Phenolic acid

Phenolic acids or phenolcarboxylic acids are types of aromatic acid compounds. Included in that class are substances containing a phenolic ring and an organic carboxylic acid function. Two important naturally occurring types of phenolic acids are hydroxybenzoic acids and hydroxycinnamic acids, which are derived from non-phenolic molecules of benzoic and cinnamic acid, respectively.

Naturally occurring phenols Group of chemical compounds

In biochemistry, naturally occurring phenols refers to phenol functional group that is found in natural products. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

Gastrodigenin Chemical compound

Gastrodigenin is a phenolic compound found in the rhizome of Gastrodia elata.

Dihydrostilbenoid

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<i>Reticulomyxa</i> Genus of single-celled organisms

Reticulomyxa is a monospecific genus of freshwater foraminiferans. The type species is the unicellular Reticulomyxa filosa. It is found in freshwater environments as well as moist environments, like decomposing matter and damp soils. The heterotrophic naked foraminiferan can feed on microbes as well has larger organisms and is able to be sustained in culture by supplemented nutrients such as wheat germ and oats. The large, multinucleate foraminferan is characteristic for its lack of test and named for the network of connecting pseudopodia surrounding its central body mass. The organism has unique bidirectional cytoplasmic streaming throughout the anastomosing pseudopodia that is some of the fastest reported organelle transport observed. Reticulomyxa was first described in 1949 and is commonly used as a model organism for the unique transport of organelles throughout the cytoplasm of pseudopodia by cytoskeletal mechanisms. Only asexual reproduction of this genus has been observed in culture, but the genome possesses genes related to meiosis suggesting it is capable of sexually reproductive life stages.

<i>Habenaria repens</i> Species of orchid

Habenaria repens, commonly called the water-spider bog orchid or the floating orchid, is an orchid species widespread across Latin America from Mexico and the West Indies south to Argentina, as well as in the Southeastern United States from Texas and Oklahoma east to Florida and the Carolinas plus an isolated population in Virginia.

Pungenin Chemical compound

Pungenin is a phenolic compound found in the needles of Blue Spruce. It is the glucoside of 3,4-dihydroxyacetophenone.

Orchid mycorrhizae are symbiotic relationships between the roots of plants of the family Orchidaceae and a variety of fungi. Nearly all orchids are myco-heterotrophic at some point in their life cycle. Orchid mycorrhizae are critically important during orchid germination, as an orchid seed has virtually no energy reserve and obtains its carbon from the fungal symbiont.

Freshwater salinization

Freshwater salinization is the process of salty runoff contaminating freshwater ecosystems, which can harm aquatic species in certain quantities and contaminate drinking water. It is often measured by the increased amount of dissolved minerals than what is considered usual for the area being observed. Naturally occurring salinization is referred to as primary salinization; this includes rainfall, rock weathering, seawater intrusion, and aerosol deposits. Human-induced salinization is termed as secondary salinization, with the use of de-icing road salts as the most common form of runoff. Approximately 37% of the drainage in the United States has been effected by salinization in the past century. The EPA has defined two thresholds for healthy salinity levels in freshwater ecosystems: 230 mg/L Cl for average salinity levels and 860 mg/L Cl for acute inputs.

References

  1. Johnson, M. K.; Alexander, K. E.; Lindquist, N; Loo, G (1999). "A phenolic antioxidant from the freshwater orchid, Habenaria repens". Comparative Biochemistry and Physiology. Part C, Pharmacology, Toxicology & Endocrinology. 122 (2): 211–4. doi:10.1016/s0742-8413(98)10109-3. PMID   10190047.
  2. Wilson, Dean M; Fenical, William; Hay, Mark; Lindquist, Niels; Bolser, Robin (1999). "Habenariol, a freshwater feeding deterrent from the aquatic orchid Habenaria repens (Orchidaceae)". Phytochemistry. 50 (8): 1333. doi:10.1016/s0031-9422(98)00340-9.