Affinine

Last updated
Affinine
Affinine.svg
Names
IUPAC name
(2S,6R,14S,E)-5-ethylidene-14-(hydroxymethyl)-3,14-dimethyl-2,3,4,5,6,7-hexahydro-1H-2,6-methanoazecino[5,4-b]indol-8(9H)-one
Other names
17-hydroxy-vobasan-3-one,
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C21H26N2O2/c1-4-13-11-23(3)19-9-15-14-7-5-6-8-17(14)22-20(15)18(25)10-16(13)21(19,2)12-24/h4-8,16,19,22,24H,9-12H2,1-3H3/b13-4-/t16-,19+,21+/m1/s1
    Key: PROSDVOTXQJUDA-PGVNYQEXSA-N
  • C/C=C1CN(C)[C@H]2CC3=C(C(C[C@H]/1[C@]2(C)CO)=O)NC4=C3C=CC=C4
Properties
C20H24N2O2
Molar mass 324.424 g·mol−1
Melting point 265°C (decomp.) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Affinine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana . [1] [2] Structurally it can be considered a member of the vobasine alkaloid family and may be synthesized from tryptophan. [3] Limited pharmacological testing has indicated that it may be an effective inhibitor of both acetylcholinesterase and butyrylcholinesterase. [4]

See also

Related Research Articles

Voacangine 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.

Indole alkaloid

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.

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

Tabernaemontana corymbosa is a species of plant in the family Apocynaceae. It is found in Brunei, China, Indonesia, Laos, Malaysia, Myanmar, Singapore, Thailand, and Vietnam. Glossy green leaves and faintly sweet scented flower. Flowers continuously all year. Frost tolerant. Grows to about 2metres. Likes full sun to part shade. A number of cultivars are available.

Eletefine Chemical compound

Eletefine is an isoquinoline alkaloid first isolated in 1998 from Cissampelos glaberrima. It is one of few known compounds containing the so-called stephaoxocane skeleton, alongside stephaoxocanidine, excentricine, and the stephalonganines.

Voacamine

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 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.

Conodurine Chemical compound

Conodurine is an acetylcholinesterase inhibitor and butyrylcholinesterase inhibitor isolated from Tabernaemontana.

Affinisine Chemical compound

Affinisine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana. Structurally, it can be considered a member of the sarpagine alkaloid family and may be synthesized from tryptophan via a Pictet-Spengler reaction.

Stemmadenine 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:

Apparicine 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.

<i>Myrcia guianensis</i> Species of flowering plant

Myrcia guianensis (pedra-ume-caá) is a species of the flowering plant family Myrtaceae. It is found in South America.

<i>Annona dioica</i> Species of flowering plant

Annona dioica is a species of plant in the family Annonaceae. It is native to Bolivia, Brazil and Paraguay. Augustin Saint-Hilaire, the French botanist who first formally described the species, named it after its flowers which have different reproductive structures and.

Tabernaemontanine Chemical compound

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

Dregamine Chemical compound

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

Conophylline 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.

Vobasine Chemical compound

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

Voacristine

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

Vinervine 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.

19-Epivoacristine Chemical compound

19-Epivoacristine is an indole alkaloid found in different species of Tabernaemontana, such as Tabernaemontana dichotoma, as well as in Peschiera affinis. It is also known as 20-epivoacangarine and 19-epi-voacangarine.

Conopharyngine Chemical compound

Conopharyngine is the major alkaloid present in the leaves and stem-bark of Tabernaemontana pachysiphon and Conopharyngia durissima. It is closely related voacangine and coronaridine. Conopharyngine pseudoindoxyl, a derivative of it, is also found in the same plant Tabernaemontana pachysiphon.

References

  1. 1 2 Weisbach, Jerry A.; Raffauf, Robert F.; Ribeiro, Oscar; Macko, Edward; Douglas, Bryce (April 1963). "Problems in chemotaxonomy I. Alkaloids ofPeschiera affinis". Journal of Pharmaceutical Sciences. 52 (4): 350–353. doi:10.1002/jps.2600520408. PMID   13999677.
  2. Monnerat, Cecilia Silva; Souza, Jucimar Jorgeane de; Mathias, Leda; Braz-Filho, Raimundo; Vieira, Ivo José C. (November 2005). "A new indole alkaloid isolated from Tabernaemontana hystrix steud (Apocynaceae)". Journal of the Brazilian Chemical Society. 16 (6b): 1331–1335. doi: 10.1590/S0103-50532005000800004 .
  3. Yang, Jie; Rallapalli, Sundari K.; Cook, James M. (February 2010). "The first enantiospecific total synthesis of the 3-oxygenated sarpagine indole alkaloids affinine and 16-epiaffinine, as well as vobasinediol and 16-epivobasinediol". Tetrahedron Letters. 51 (5): 815–817. doi:10.1016/j.tetlet.2009.12.002.
  4. Vieira, IJ; Medeiros, WL; Monnerat, CS; Souza, JJ; Mathias, L; Braz-Filho, R; Pinto, AC; Sousa, PM; Rezende, CM; Epifanio Rde, A (September 2008). "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures". Anais da Academia Brasileira de Ciências. 80 (3): 419–26. doi: 10.1590/S0001-37652008000300003 . PMID   18797794.