Scammonin I

Last updated
Scammonin I
Scammonin I.png
Names
IUPAC name
Hexadecanoic acid, 11-((O-(E)-6-deoxy-4-O-(2-methyl-1-oxo-2-butenyl)-β-D-glucopyranosyl-(1→4)-O-(S)-6-deoxy-2-O-(2-methyl-1-oxobutyl)-α-L-mannopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-6-deoxy-beta-D-glucopyranosyl))
Other names
Jalapin, Scammonium
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C50H84O21/c1-9-12-18-21-30-22-19-16-14-13-15-17-20-23-32(52)66-43-40(69-47-38(58)37(57)39(28(7)62-47)67-45(59)25(4)10-2)29(8)63-50(44(43)68-46(60)26(5)11-3)71-42-36(56)34(54)31(24-51)65-49(42)70-41-35(55)33(53)27(6)61-48(41)64-30/h10,26-31,33-44,47-51,53-58H,9,11-24H2,1-8H3/b25-10+/t26-,27+,28+,29-,30-,31+,33+,34+,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,47-,48-,49-,50-/m0/s1
    Key: DGRGOOVTCYVEDQ-GHYHFUIZSA-N
  • O=C(CCCCCCCCC[C@H](CCCCC)O[C@H]1[C@@]2([H])[C@@H](O)[C@H](O)[C@@H](C)O1)O[C@H]([C@](O[C@@H]3O[C@H](C)[C@@H](OC(/C(C)=C/C)=O)[C@H](O)[C@H]3O)([H])[C@H](C)O4)[C@@H](OC([C@H](CC)C)=O)[C@@H]4O[C@@]5([H])[C@H](O2)O[C@H](CO)[C@@H](O)[C@@H]5O
Properties
C50H84O21
Molar mass 1021.201 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 ?)

Scammonin (also known as jalapin or scammonium [1] ) is a glycoside that has been isolated from the stems of Ipomoea purga (jalap plant) and from Convolvulus scammonia (scammony).

Related Research Articles

<span class="mw-page-title-main">Cardiac glycoside</span> Class of organic compounds

Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses are as treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.

<span class="mw-page-title-main">Stevia</span> Sweetener and sugar substitute

Stevia is a sweet sugar substitute extracted from the leaves of the plant species Stevia rebaudiana native to Paraguay and Brazil.

<span class="mw-page-title-main">Convolvulaceae</span> Family of flowering plants

Convolvulaceae, commonly called the bindweeds or morning glories, is a family of about 60 genera and more than 1,650 species. These species are primarily herbaceous vines, but also include trees, shrubs and herbs. The tubers of several species are edible, the best known of which is the sweet potato.

<i>Convolvulus</i> Genus of flowering plants

Convolvulus is a genus of about 200 to 250 species of flowering plants in the bindweed family Convolvulaceae, with a cosmopolitan distribution. Common names include bindweed and morning glory; both are names shared with other closely related genera.

<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>Fallopia convolvulus</i> Species of flowering plant in the knotweed family Polygonaceae

Fallopia convolvulus, the black-bindweed or wild buckwheat, is a fast-growing annual flowering plant in the family Polygonaceae native throughout Europe, Asia and northern Africa.

<i>Asterix and the Roman Agent</i>

Asterix and the Roman Agent is the fifteenth volume of the Asterix comic book series, by René Goscinny (stories) and Albert Uderzo (illustrations). It first appeared as a serial in Pilote magazine issues 531–552 in 1970 and was translated into English in 1972.

<i>Convolvulus arvensis</i> Species of bindweed

Convolvulus arvensis, or field bindweed, is a species of bindweed in the Convolvulaceae native to Europe and Asia. It is a rhizomatous and climbing or creeping herbaceous perennial plant with stems growing to 0.5–2 metres (1.6–6.6 ft) in length. It is usually found at ground level with small white and pink flowers.

<span class="mw-page-title-main">Glycoside hydrolase</span> Class of enzymes which break glycosidic bonds via hydrolysis

In biochemistry, glycoside hydrolases are a class of enzymes which catalyze the hydrolysis of glycosidic bonds in complex sugars. They are extremely common enzymes, with roles in nature including degradation of biomass such as cellulose (cellulase), hemicellulose, and starch (amylase), in anti-bacterial defense strategies, in pathogenesis mechanisms and in normal cellular function. Together with glycosyltransferases, glycosidases form the major catalytic machinery for the synthesis and breakage of glycosidic bonds.

<span class="mw-page-title-main">Steviol glycoside</span> Sweet chemicals derived from the Stevia plant

Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae) and the main ingredients of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species S. phlebophylla and in the plant Rubus chingii (Rosaceae).

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

Gitoformate is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia. Produced by Madaus, it is not available in the US, and does not seem to be available in Europe either.

<i>Emmelina monodactyla</i> Species of plume moth

Emmelina monodactyla is a moth of the family Pterophoridae found in Africa, Asia, Europe and North America. It was first described by Carl Linnaeus in 1758.

<span class="mw-page-title-main">Flavanonol</span> Class of chemical compounds

The flavanonols are a class of flavonoids that use the 3-hydroxy-2,3-dihydro-2-phenylchromen-4-one backbone.

<i>Stigmella freyella</i> Species of moth

Stigmella freyella is a moth of the family Nepticulidae. It is found from the Netherlands to the Baltic region and Russia, southwards to the Mediterranean region. It is also found in North Africa.

<i>Convolvulus tricolor</i> Species of bindweed

Convolvulus tricolor is a species of flowering plant in the family Convolvulaceae, native to Mediterranean Europe. Common names include dwarf morning-glory, tricolour convolvulus, and belle de jour.

<i>Convolvulus clementii</i> Species of bindweed

Convolvulus clementii, commonly known as desert bindweed, is a trailing perennial plant species, native to inland Australia. Mostly found on flat areas, like dune swales and claypans that are subject to seasonal inundation, in areas of open grassy woodland.

<i>Bedellia somnulentella</i> Species of moth

Bedellia somnulentella, the sweet potato leaf miner, is a moth in the family Bedelliidae.

HMS <i>Convolvulus</i> (K45) Flower-class corvette

HMS Convolvulus was a Flower-class corvette of the Royal Navy in World War II. She was launched in 1940, served in the Battle of the Atlantic and was scrapped in 1947.

References

  1. Noda, N; Kogetsu, H; Kawasaki, T; Miyahara, K (1990). "Scammonins I and II, the resin glycosides of radix scammoniae from Convolvulus scammonia". Phytochemistry. 29 (11): 3565–9. Bibcode:1990PChem..29.3565N. doi:10.1016/0031-9422(90)85277-M. PMID   1367262.