Isovoacangine

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Isovoacangine
Isovoacangine.svg
Isovoacangine 3D ball-and-stick.png
Identifiers
  • methyl 17-ethyl-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C22H28N2O3
Molar mass 368.477 g·mol−1
3D model (JSmol)
  • CCC1CC2CC3(C1N(C2)CCc4c3[nH]c5c4ccc(c5)OC)C(=O)OC
  • InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-17(7-8-24(12-13)20(14)22)16-6-5-15(26-2)10-18(16)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3
  • Key:FPUHKQMDWMVBRI-UHFFFAOYSA-N

Isovoacangine is a naturally occurring substance that has action on heart muscles in pigs.[ citation needed ]

Contents

Chemistry

Derivatives

3-Hydroxyisovoacangine and 3-(2'-oxopropyl)isovoacangine are derivates of isovoacangine. [1]

Natural occurrence

It occurs naturally in many Tabernaemontana (milkwood) species such as Tabernaemontana pachysiphon and Tabernaemontana divaricata . [2] [3]

See also

Related Research Articles

<span class="mw-page-title-main">Apocynaceae</span> Dogbane and oleander family of flowering plants

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>Tabernaemontana</i> Genus of plants

Tabernaemontana is a genus of flowering plants in the family Apocynaceae. It has a pan-tropical distribution, found in Asia, Africa, Australia, North America, South America, and a wide assortment of oceanic islands. These plants are evergreen shrubs and small trees growing to 1–15 m tall. The leaves are opposite, 3–25 cm long, with milky sap; hence it is one of the diverse plant genera commonly called "milkwood". The flowers are fragrant, white, 1–5 cm in diameter.

<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">Coronaridine</span> Chemical compound

Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in Tabernanthe iboga and related species, including Tabernaemontana divaricata for which it was named.

<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">Voacamine</span> Chemical compound

Voacamine, also known under the older names voacanginine and vocamine, is a naturally occurring dimeric indole alkaloid of the secologanin type, found in a number of plants, including Voacanga africana and Tabernaemontana divaricata. It is approved for use as an antimalarial drug in several African countries. Voacamine exhibits cannabinoid CB1 receptor antagonistic activity.

<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

<i>Tabernaemontana elegans</i> African tree species

Tabernaemontana elegans, the toad tree, is a shrub or small tree in the family Apocynaceae. It is native to eastern Africa.

<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">Apparicine</span> Chemical compound

Apparicine is a monoterpenoid tricyclic 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 indole 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">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">Conofoline</span> Chemical compound

Conofoline is an alkaloid of the vinca alkaloid class which is closely related to conophylline. It is found in the leaves of some species in the genus Tabernaemontana, including Tabernaemontana divaricata, and in Ervatamia peduncularis.

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

Ervaticine is a 2-acylindole alkaloid. It occurs in Ervatamia coronaria and Tabernaemontana divaricata.

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

Ervatinine is an anti-corrosive indole alkaloid from Ervatamia coronaria.

<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">Vinervine</span> Vinca alkaloid

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.

<span class="mw-page-title-main">19,20-Dihydroervahanine A</span> Chemical compound

19,20-Dihydroervahanine A is an alkaloid, a natural product which is found in the root of the Southeast Asian plant Tabernaemontana divaricata. It inhibits acetylcholinesterase in vitro more potently than galantamine.

References

  1. Danieli B, Palmisano G (January 1987). "Alkaloids from Tabernaemontana.". In Brossi A (ed.). The alkaloids: Chemistry and Pharmacology. Vol. 27. Academic Press. pp. 1–130 (82). ISBN   978-0-08-086551-5.
  2. "Tabernaemontana undulata - Useful Tropical Plants". tropical.theferns.info.
  3. Kam TS, Loh KY, Wei C (November 1993). "Conophylline and conophyllidine: new dimeric alkaloids from Tabernaemontana divaricata". Journal of Natural Products. 56 (11): 1865–71. doi:10.1021/np50101a001.