Lotaustralin

Last updated
Lotaustralin
Lotaustralin structure.svg
Lotaustralin 3D sticks.png
Names
IUPAC name
(2R)-2-(β-D-Glucopyranosyloxy)-2-methylbutanenitrile
Systematic IUPAC name
(2R)-2-Methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1 X mark.svgN
    Key: WEWBWVMTOYUPHH-QHAQEBJBSA-N X mark.svgN
  • InChI=1/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1
    Key: WEWBWVMTOYUPHH-QHAQEBJBBY
  • CC[C@](C)(C#N)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
Properties
C11H19NO6
Molar mass 261.27 g/mol
Appearancecolorless needles
Density 1.36 g·cm−3
Melting point 139 °C (282 °F; 412 K) [1]
good, also good in Ethyl acetate [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Lotaustralin is a cyanogenic glucoside found in small amounts in Fabaceae austral trefoil (Lotus australis), [1] cassava (Manihot esculenta), lima bean (Phaseolus lunatus), [2] roseroot (Rhodiola rosea) [3] and white clover (Trifolium repens), [4] among other plants. Lotaustralin is the glucoside of methyl ethyl ketone cyanohydrin and is structurally related to linamarin, the acetone cyanohydrin glucoside also found in these plants. Both lotaustralin and linamarin may be hydrolyzed by the enzyme linamarase to form glucose and a precursor to the toxic compound hydrogen cyanide.

Related Research Articles

<span class="mw-page-title-main">Cyanide</span> Any molecule with a cyano group (–C≡N)

In chemistry, a cyanide is a chemical compound that contains a C≡N functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom.

Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure H−C≡N. It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at 25.6 °C (78.1 °F). HCN is produced on an industrial scale and is a highly valued precursor to many chemical compounds ranging from polymers to pharmaceuticals. Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. It is more toxic than solid cyanide compounds due to its volatile nature.

<span class="mw-page-title-main">Cassava</span> Most grown crop in Africa, staple, tuber

Manihot esculenta, commonly called cassava, manioc, or yuca, is a woody shrub of the spurge family, Euphorbiaceae, native to South America, from Brazil and parts of the Andes. Although a perennial plant, cassava is extensively cultivated as an annual crop in tropical and subtropical regions for its edible starchy root tuber, a major source of carbohydrates. Though it is often called yuca in parts of Spanish America and in the United States, it is not related to yucca, a shrub in the family Asparagaceae. Cassava is predominantly consumed in boiled form, but substantial quantities are used to extract cassava starch, called tapioca, which is used for food, animal feed, and industrial purposes. The Brazilian farinha, and the related garri of West Africa, is an edible coarse flour obtained by grating cassava roots, pressing moisture off the obtained grated pulp, and finally drying it.

<span class="mw-page-title-main">Lima bean</span> Species of plant

A lima bean, also commonly known as the butter bean, sieva bean, double bean, Madagascar bean, or wax bean is a legume grown for its edible seeds or beans.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

<i>Trifolium repens</i> Species of flowering plant in the bean family Fabaceae

Trifolium repens, the white clover, is a herbaceous perennial plant in the bean family Fabaceae. It is native to Europe, including the British Isles, and central Asia and is one of the most widely cultivated types of clover. It has been widely introduced worldwide as a forage crop, and is now also common in most grassy areas of North America, Australia and New Zealand. The species includes varieties often classed as small, intermediate and large, according to height, which reflects petiole length. The term 'white clover' is applied to the species in general, 'Dutch clover' is often applied to intermediate varieties, and 'ladino clover' is applied to large varieties.

<span class="mw-page-title-main">Cyanohydrin</span> Functional group in organic chemistry

In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst:

<i>Rhodiola rosea</i> Species of flowering plant in the stonecrop family Crassulaceae

Rhodiola rosea is a perennial flowering plant in the family Crassulaceae. It grows naturally in wild Arctic regions of Europe, Asia, and North America, and can be propagated as a groundcover.

Linamarase, or beta-D-glucosidase, is an enzyme found in many plants including cassava and the butter bean.

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

Linamarin is a cyanogenic glucoside found in the leaves and roots of plants such as cassava, lima beans, and flax. It is a glucoside of acetone cyanohydrin. Upon exposure to enzymes and gut flora in the human intestine, linamarin and its methylated relative lotaustralin can decompose to the toxic chemical hydrogen cyanide; hence food uses of plants that contain significant quantities of linamarin require extensive preparation and detoxification. Ingested and absorbed linamarin is rapidly excreted in the urine and the glucoside itself does not appear to be acutely toxic. Consumption of cassava products with low levels of linamarin is widespread in the low-land tropics. Ingestion of food prepared from insufficiently processed cassava roots with high linamarin levels has been associated with dietary toxicity, particularly with the upper motor neuron disease known as konzo to the African populations in which it was first described by Trolli and later through the research network initiated by Hans Rosling. However, the toxicity is believed to be induced by ingestion of acetone cyanohydrin, the breakdown product of linamarin. Dietary exposure to linamarin has also been reported as a risk factor in developing glucose intolerance and diabetes, although studies in experimental animals have been inconsistent in reproducing this effect and may indicate that the primary effect is in aggravating existing conditions rather than inducing diabetes on its own.

Acetone cyanohydrin (ACH) is an organic compound used in the production of methyl methacrylate, the monomer of the transparent plastic polymethyl methacrylate (PMMA), also known as acrylic. It liberates hydrogen cyanide easily, so it is used as a source of such. For this reason, this cyanohydrin is also highly toxic.

In enzymology, a cyanohydrin beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a linamarin synthase is an enzyme that catalyzes the chemical reaction

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

Salidroside (rhodioloside) is a glucoside of tyrosol found in the plant Rhodiola rosea. It has been studied, along with rosavin, as one of the potential compounds responsible for the putative antidepressant and anxiolytic actions of this plant. Salidroside may be more active than rosavin, even though many commercially marketed Rhodiola rosea extracts are standardized for rosavin content rather than salidroside.

Flavonolignans are natural phenols composed of a part flavonoid and a part phenylpropane.

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

Herbacetin is a flavonol, a type of flavonoid.

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

(R)-prunasin is a cyanogenic glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile.

Isoleucine N-monooxygenase (EC 1.14.13.117, CYP79D3, CYP79D4) is an enzyme with systematic name L-isoleucine,NADPH:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction

Valine N-monooxygenase (EC 1.14.13.118, CYP79D1, CYP79D2) is an enzyme with systematic name L-valine,NADPH:oxygen oxidoreductase (N-hydroxylating). This enzyme catalyses the following chemical reaction

(S)-hydroxynitrile lyase (EC 4.1.2.47, (S)-cyanohydrin producing hydroxynitrile lyase, (S)-oxynitrilase, (S)-HbHNL, (S)-MeHNL, hydroxynitrile lyase, oxynitrilase, HbHNL, MeHNL, (S)-selective hydroxynitrile lyase, (S)-cyanohydrin carbonyl-lyase (cyanide forming), hydroxynitrilase) is an enzyme with systematic name (S)-cyanohydrin lyase (cyanide forming). This enzyme catalyses the interconversion between cyanohydrins and the carbonyl compounds derived from the cyanohydrin with free cyanide, as in the following two chemical reactions:

References

  1. 1 2 3 Shmuel Yannai: Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. CRC Press, 2003, ISBN   978-1-58488-416-3, p. 688
  2. Frehner M, Scalet M, Conn EE (1990). "Pattern of the Cyanide-Potential in Developing Fruits : Implications for Plants Accumulating Cyanogenic Monoglucosides (Phaseolus lunatus) or Cyanogenic Diglucosides in Their Seeds (Linum usitatissimum, Prunus amygdalus)". Plant Physiol. 94 (1): 28–34. doi:10.1104/pp.94.1.28. PMC   1077184 . PMID   16667698.
  3. Akgul Y, Ferreira D, Abourashed E, Khan I (2004). "Lotaustralin from Rhodiola rosea roots". Fitoterapia. 75 (6): 612–4. doi:10.1016/j.fitote.2004.06.002. PMID   15351122.
  4. "Notes on poisoning: Trifolium repens". Canadian Poisonous Plants Information System. May 30, 2006. Archived from the original on June 10, 2011. Retrieved 2007-02-11.