Coerulescine

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Coerulescine
Coerulescine3.svg
Names
Preferred IUPAC name
(3R)-1'-methylspiro[1H-indole-3,3'-pyrrolidine]-2-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C12H14N2O/c1-14-7-6-12(8-14)9-4-2-3-5-10(9)13-11(12)15/h2-5H,6-8H2,1H3,(H,13,15)
    Key: PNYGHERLKSFRMH-UHFFFAOYSA-N
  • O=C2Nc1c(cccc1)C23CN(CC3)C
Properties
C12H14N2O
Molar mass 202.257 g·mol−1
Density 1.2±0.1 g/cm3
Boiling point 378.8±42.0 °C
Hazards
Flash point 182.9±27.9 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Coerulescine is an oxindole alkaloid found in the plant Phalaris coerulescens . [1]

It is a member of the spiroindolone class. Elacomine and horsfiline have similar chemical structures. [2]

Related Research Articles

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Phalaris arundinacea, or reed canary grass, is a tall, perennial bunchgrass that commonly forms extensive single-species stands along the margins of lakes and streams and in wet open areas, with a wide distribution in Europe, Asia, northern Africa and North America. Other common names for the plant include gardener's-garters and ribbon grass in English, alpiste roseau in French, Rohrglanzgras in German, kusa-yoshi in Japanese, caniço-malhado in Portuguese, and hierba cinta and pasto cinto in Spanish.

<i>Ruta graveolens</i> Species of plant

Ruta graveolens, commonly known as rue, common rue or herb-of-grace, is a species of the genus Ruta grown as an ornamental plant and herb. It is native to the Balkan Peninsula. It is grown throughout the world in gardens, especially for its bluish leaves, and sometimes for its tolerance of hot and dry soil conditions. It is also cultivated as a culinary herb, and to a lesser extent as an insect repellent and incense.

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

Gramine is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.

<span class="mw-page-title-main">Hordenine</span> 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.

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

Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa, commonly known as kratom. As a non-narcotic constituent, it also occurs to a significant amount in the bark of Uncaria tomentosa along with a number of isomeric alkaloids.

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

Oxindole (2-indolone) is an aromatic heterocyclic organic compound with the formula C6H4CHC(O)NH. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Oxindole is a modified indoline with a substituted carbonyl at the second position of the 5-member indoline ring. Classified as a cyclic amide, it is a pale yellow solid.

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

A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+‐ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes.

<i>Senegalia berlandieri</i> Species of plant

Senegalia berlandieri is a shrub native to the Southwestern United States and northeast Mexico that belongs to the Mimosoid clade of Fabaceae. It grows 1 to 5 metres tall, with blossoms that are spherical and white, occurring from February through April. The berlandieri epithet comes from the name of Jean-Louis Berlandier, a French naturalist who studied wildlife native to Texas and Mexico. S. berlandieri contains a wide variety of alkaloids and has been known to cause toxic reactions in domestic animals such as goats.

<i>Alstonia scholaris</i> Species of tree

Alstonia scholaris, commonly called blackboard tree, scholar tree, milkwood or devil's tree in English, is an evergreen tropical tree in the Dogbane Family (Apocynaceae). It is native to southern China, tropical Asia and Australasia, where it is a common ornamental plant. It is a toxic plant, but is used traditionally for myriad diseases and complaints.

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

Horsfiline is an oxindole alkaloid found in the plant Horsfieldia superba, which is used in traditional herbal medicine. It has analgesic effects and has been the subject of research both to produce it synthetically by convenient routes and to develop analogues and derivatives which may have improved analgesic effects.

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

Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and Japanese herbs.

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

Indole is an organic compound with the formula C6H4CCNH3. Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole where one or more of the hydrogen atoms have been replaced by substituent groups. Indoles are widely distributed in nature, most notably as amino acid tryptophan and neurotransmitter serotonin.

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

Senecionine is a toxic pyrrolizidine alkaloid isolated from various botanical sources. It takes its name from the Senecio genus and is produced by many different plants in that genus, including Jacobaea vulgaris. It has also been isolated from several other plants, including Brachyglottis repanda, Emilia, Erechtites hieraciifolius, Petasites, Syneilesis, Crotalaria, Caltha leptosepala, and Castilleja.

<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">Quassinoid</span>

Quassinoids are degraded triterpene lactones of the Simaroubaceae plant family grouped into C-18, C-19, C-20, C-22 and C-25 types. The prototypical member of the group, quassin, was first described in the 19th century from plants of the genus Quassia from which it gets its name. It was isolated in 1937, and its structure elucidated in 1961.

Penicillium paxilli is an anamorph, saprophytic species of the genus Penicillium which produces paxilline, paxisterol, penicillone, pyrenocine A, paspaline B and verruculogene. Penicillium paxilli is used as a model to study the biochemistry of the indol-diterepene biosynthesis

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

Tabernaemontanine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.

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

Speciociliatine is a major alkaloid of the plant Mitragyna speciosa, commonly known as kratom. It is a stereoisomer of Mitragynine and constitutes 0.00156 - 2.9% of the dried leaf material.

<span class="mw-page-title-main">Corymine</span> Chemical compound, neurotoxin

Corymine, also known as NSC381080, is a natural alkaloid found in Hunteria zeylanica.

References

  1. Anderton, N., Cockrum, P. A., Colegate, S. M., Edgar, J. A., Flower, K., Vit, I., Willing, R. I. (June 1998). "Oxindoles from Phalaris coerulescens". Phytochemistry. 48 (3): 437–439. Bibcode:1998PChem..48..437A. doi:10.1016/S0031-9422(97)00946-1. ISSN   0031-9422.
  2. Anderton, N., Cockrum, P. A., Colegate, S. M., Edgar, J. A., Flower, K. (1999). "Assessment of potential for toxicity of Phalaris spp. via alkaloid content determination: P. coerulescens, a case example". Phytochemical Analysis. 10 (3): 113–118. Bibcode:1999PChAn..10..113A. doi:10.1002/(SICI)1099-1565(199905/06)10:3<113::AID-PCA438>3.0.CO;2-#.