Vinervine

Last updated
Vinervine
Vinervine.svg
Names
IUPAC name
Methyl (19E)-12-hydroxy-2,16-didehydrocur-19-en-17-oate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H22N2O3/c1-3-11-10-22-8-7-20-13-5-4-6-14(23)17(13)21-18(20)16(19(24)25-2)12(11)9-15(20)22/h3-6,12,15,21,23H,7-10H2,1-2H3/b11-3-/t12-,15-,20+/m0/s1
    Key: FAJVFJABOWWACZ-GGGKWMOSSA-N
  • C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C(=C3NC5=C4C=CC=C5O)C(=O)OC
Properties
C24H39NO7
Molar mass 453.576 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vinervine is a monoterpene indole alkaloid of the Vinca sub-group. It is a derivative of akuammicine, with one additional hydroxy (OH) group in the indole portion, hence it is also known as 12-hydroxyakuammicine.

Contents

History

The alkaloids are a large group of natural products which are classified according to the part-structure which members of a particular group contain. Vinervine is a monoterpene indole alkaloid of the Vinca sub-group which shares a common biosynthesis with other members, namely that they are derived from strictosidine. [1] [2] It was first characterised in 1964 [3] and the structures of closely related materials including akuammicine were confirmed in 1983. [4]

Natural occurrence

Crape Jasmine (Tabernaemontana divaricata), a source of vinervine Crape Jasmine.jpg
Crape Jasmine (Tabernaemontana divaricata), a source of vinervine

Vinervine is found in a variety of plants of the Apocynaceae family, including Vinca erecta , [3] [5] [6] Tabernaemontana divaricata [7] [8] and several other flowering plants species that are native to Africa, Asia, and Europe.

Biosynthesis

As with other indole alkaloids, the biosynthesis of vinervine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration. [1]

Research

Plant metabolites have long been studied for their biological activity and alkaloids in particular are major subjects for ethnobotanical research. [9] However, vinervine has had little reported utility. [8] [10] [11]

See also

Related Research Articles

<span class="mw-page-title-main">Phytochemistry</span> Study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.

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

Voacangine is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in ethanol.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

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

Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose.

Strictosidine synthase (EC 4.3.3.2) is an enzyme in alkaloid biosynthesis that catalyses the condensation of tryptamine with secologanin to form strictosidine in a formal Pictet–Spengler reaction:

<span class="mw-page-title-main">Ibogamine</span> Anti-convulsant, anti-addictive CNS stimulant alkaloid

Ibogamine is an anti-convulsant, anti-addictive, CNS stimulant alkaloid found in Tabernanthe iboga and Crepe Jasmine. Basic research related to how addiction affects the brain has used this chemical.

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

Ajmalicine, also known as δ-yohimbine or raubasine, is an antihypertensive drug used in the treatment of high blood pressure. It has been marketed under numerous brand names including Card-Lamuran, Circolene, Cristanyl, Duxil, Duxor, Hydroxysarpon, Iskedyl, Isosarpan, Isquebral, Lamuran, Melanex, Raunatin, Saltucin Co, Salvalion, and Sarpan. It is an alkaloid found naturally in various plants such as Rauvolfia spp., Catharanthus roseus, and Mitragyna speciosa.

<i>Tabernaemontana divaricata</i> Species of plant

Tabernaemontana divaricata, commonly called pinwheel flower, crape jasmine, East India rosebay, and Nero's crown, is an evergreen shrub or small tree native to South Asia, Southeast Asia and China. In zones where it is not hardy it is grown as a house/glasshouse plant for its attractive flowers and foliage. The stem exudes a milky latex when broken, whence comes the name milk flower

<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">Catharanthine</span> Chemical compound

Catharanthine is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus and Tabernaemontana divaricata. Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown. Catharanthine is one of the two precursors that form vinblastine, the other being vindoline.

<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">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">Apparicine</span> Chemical compound

Apparicine is a monoterpenoid indole alkaloid. It is named after Apparicio Duarte, a Brazilian botanist who studied the Aspidosperma species from which apparicine was first isolated. It was the first member of the vallesamine group of alkaloids to be isolated and have its structure established, which was first published in 1965. It has also been known by the synonyms gomezine, pericalline, and tabernoschizine.

<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">Isovoacangine</span> Chemical compound

Isovoacangine is a naturally occurring substance that has action on heart muscles in pigs.

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

Dregamine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Ervatamia hirta and Tabernaemontana divaricata.

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

Conophylline is a autophagy inducing vinca alkaloid found in several species of Tabernaemontana including Ervatamia microphylla and Tabernaemontana divaricata. Among its many functional groups is an epoxide: the compound where that ring is replaced with a double bond is called conophyllidine and this co-occurs in the same plants.

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

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

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

Voacristine is a indole alkaloid occurring in Voacanga and Tabernaemontana genus. It is also an iboga type alkaloid.

<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. 1 2 Dewick, Paul M (2002). Medicinal Natural Products. A Biosynthetic Approach. Second Edition. Wiley. pp. 350–359. ISBN   0-471-49640-5.
  2. Saxton JE (1984). "Recent progress in the chemistry of indole alkaloids and mould metabolites". Natural Product Reports. 1: 21. doi:10.1039/NP9840100021.
  3. 1 2 Abdurakhimova N, Yuldashev PK, Yunusov, SY (1964). "Pseudokopsinine—a new alkaloid from aerial parts of Vinca erecta". Doklady Akademii Nauk SSSR (in Russian). 21 (2): 29–31.
  4. Yagudaev MR (1983). "NMR investigation of alkaloids. IV. 13C NMR spectra and structures of norfluorocurarine, akuammicine, vincanidine, and vinervinine". Chemistry of Natural Compounds. 19 (2): 199–201. doi:10.1007/BF00580558. S2CID   28255077.
  5. Yuldashev PK, Ubaev U, Kuchenkova MA, Yunusov SY (January 1965). "Structure of vincanidine and vinervine". Chemistry of Natural Compounds. 1 (1): 25–30. doi:10.1007/BF00571576. S2CID   27933208.
  6. Kuchenkova MA, Yuldashev PK, Yunusov SY (1965). "Vinervine — A new alkaloid from the aboveground part of Vinca erecta". Bulletin of the Academy of Sciences, USSR Division of Chemical Science. 14 (12): 2119–2121. doi:10.1007/BF00845999.
  7. Pawelka KH, Stöckigt J (April 1983). "Indole alkaloids from cell suspension cultures of Tabernaemontana divaricata and Tabernanthe iboga". Plant Cell Reports. 2 (2): 105–7. doi:10.1007/BF00270178. PMID   24257961. S2CID   23570705.
  8. 1 2 Pratchayasakul W, Pongchaidecha A, Chattipakorn N, Chattipakorn S (April 2008). "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata". The Indian Journal of Medical Research. 127 (4): 317–35. PMID   18577786. S2CID   1119874.
  9. Babiaka SB, Ntie-Kang F, Lifongo LL, Ndingkokhar B, Mbah JA, Yong JN (2015). "The chemistry and bioactivity of Southern African flora I: A bioactivity versus ethnobotanical survey of alkaloid and terpenoid classes". RSC Advances. 5 (54): 43242–43267. Bibcode:2015RSCAd...543242B. doi:10.1039/C5RA01912E.
  10. Ghisalberti EL, Pennacchio M, Alexander E (1998). "Survey of Secondary Plant Metabolites with Cardiovascular Activity". Pharmaceutical Biology. 36 (4): 259. doi:10.1076/phbi.36.4.237.4583.
  11. Heijden R, Jacobs D, Snoeijer W, Hallard D, Verpoorte R (2004). "The Catharanthus Alkaloids:Pharmacognosy and Biotechnology". Current Medicinal Chemistry. 11 (5): 607–628. doi:10.2174/0929867043455846. PMID   15032608.

Further reading