Serpentine (alkaloid)

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Serpentine
Serpentine structure.svg
Names
IUPAC name
(19α)-16-(Methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium-1-ide
Other names
Methyl ester of serpentinic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.038.684 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C21H20N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-8,11-12,15-16H,9-10H2,1-2H3/t12-,15-,16+/m0/s1
    Key: WYTGDNHDOZPMIW-VBNZEHGJSA-N
  • C[C@H]1[C@H]2C[n+]3ccc4c5ccccc5[n-]c4c3C[C@@H]2C(=CO1)C(=O)OC
Properties
C21H21N2O3
Molar mass 349.410 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Serpentine is a terpene indole alkaloid produced by several members of the family Apocynaceae (thus an "apocynaceae alkaloid"), including Catharanthus roseus [1] and Rauvolfia serpentina . [2]

See also

Related Research Articles

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Apocynaceae is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison. Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here.

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

Catharanthus is a genus of flowering plants in the family Apocynaceae. Like the genus Vinca, they are known commonly as periwinkles. There are eight known species. Seven are endemic to Madagascar, though one, C. roseus, is widely naturalized around the world. The eighth species, C. pusillus, is native to India and Sri Lanka. The name Catharanthus comes from the Greek for "pure flower".

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<i>Catharanthus roseus</i> Species of flowering plant in the family Apocynaceae

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<i>Vinca</i> alkaloid

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

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

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

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<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">Strictosidine</span> Chemical compound

Strictosidine is a natural chemical compound and is classified as a glucoalkaloid and a vinca alkaloid. It is formed by the Pictet–Spengler condensation reaction of tryptamine with secologanin, catalyzed by the enzyme strictosidine synthase. Thousands of strictosidine derivatives are sometimes referred to by the broad phrase of monoterpene indole alkaloids. Strictosidine is an intermediate in the biosynthesis of numerous pharmaceutically valuable metabolites including quinine, camptothecin, ajmalicine, serpentine, vinblastine, vincristine and mitragynine.

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

Tabersonine is a terpene indole alkaloid found in the medicinal plant Catharanthus roseus and also in the genus Voacanga. Tabersonine is hydroxylated at the 16 position by the enzyme tabersonine 16-hydroxylase (T16H) to form 16-hydroxytabersonine. The enzyme leading to its formation is currently unknown. Tabersonine is the first intermediate leading to the formation of vindoline one of the two precursors required for vinblastine biosynthesis.

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

Stemmadenine is a terpene indole alkaloid. Stemmadenine is believed to be formed from preakuammicine by a carbon-carbon bond cleavage. Cleavage of a second carbon-carbon bond is thought to form dehydrosecodine. The enzymes forming stemmadenine and using it as a substrate remain unknown to date. It is thought to be intermediate compound in many different biosynthetic pathways such as in Aspidosperma species. Many alkaloids are proposed to be produced through intermediate stemmadenine. Some of them are:

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

Lochnericine is a major monoterpene indole alkaloid present in the roots of Catharanthus roseus. It is also present in Tabernaemontana divaricata.

References

  1. Monforte-González, M; Ayora-Talavera, T; Maldonado-Mendoza, I. E; Loyola-Vargas, V. M (1992). "Quantitative analysis of serpentine and ajmalicine in plant tissues of Catharanthus roseus and hyoscyamine and scopolamine in root tissues of Datura stramonium by thin layer chromatography-densitometry". Phytochemical Analysis. 3 (3): 117. Bibcode:1992PChAn...3..117M. doi:10.1002/pca.2800030305.
  2. Leete, Edward (1961). "Biogenesis of the Rauwolfia alkaloids alkaloids—II". Tetrahedron. 14 (1–2): 35–41. doi:10.1016/0040-4020(61)80084-7.