Tabernaemontanine

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Tabernaemontanine
Tabernaemontanine.svg
Names
IUPAC name
Methyl (20βH)-3-oxo-19,20-dihydrovobasan-17-oate
Systematic IUPAC name
Methyl (2S,5S,6S,14S)-5-ethyl-3-methyl-8-oxo-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazeceno[5,4-b]indole-14-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C21H26N2O3/c1-4-12-11-23(2)17-9-15-13-7-5-6-8-16(13)22-20(15)18(24)10-14(12)19(17)21(25)26-3/h5-8,12,14,17,19,22H,4,9-11H2,1-3H3/t12-,14+,17+,19+/m1/s1
    Key: FFVRRQMGGGTQRH-DTPILHQWSA-N
  • CC[C@@H]1CN([C@H]2Cc3c4ccccc4[nH]c3C(=O)C[C@@H]1[C@@H]2C(=O)OC)C
Properties [1]
C21H26N2O3
Molar mass 354.450 g·mol−1
Melting point 207 °C (405 °F; 480 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

History

Tabernaemontanine was first reported in 1939 [1] but its structure was only fully confirmed in the 1970s as there was confusion in the original literature regarding the configuration of the ethyl group in the piperidine ring of this alkaloid and its isomer dregamine, so that their identities had been reversed. [2] [3] [4] Both compounds were isolated from plants of the dogbane (Apocynaceae) family including Tabernaemontana coronaria . [5] They have structures that are reduced versions of vobasine.

Biosynthesis

As with other Indole alkaloids, the biosynthesis of tabernaemontanine starts from the amino acid tryptophan. This is converted into strictosidine before further elaboration. [6]

Natural occurrence

Tabernaemontana divaricata, a source of tabernaemontanin Crape Jasmine.jpg
Tabernaemontana divaricata, a source of tabernaemontanin

Tabernaemontanine is found commonly in the genera Tabernaemontana and Kopsia , [7] including the species Ervatamia hirta , [8] Tabernaemontana elegans [9] and Tabernaemontana divaricata . [10] [11] The latter species is known to produce many other alkaloids including catharanthine, ibogamine and voacristine. [12]

Research

Plant metabolites have been of interest for their possible biological activity and alkaloids in particular are major subjects for ethnobotanical research. [13] [14] Tabernaemontanine has been studied, for example as a potential anti-cancer agent, [15] [16] [17] [18] for its antimalarial activity [19] [20] and in antifertility research. [21] However, the alkaloid itself has not been developed as a drug.

See also

Related Research Articles

<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">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">Vincamine</span> Chemical compound

Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor, comprising about 25–65% of its indole alkaloids by weight. It can also be synthesized from related alkaloids.

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

Tabernaemontana corymbosa is a species of plant in the family Apocynaceae. It is native to 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 2 metres. Likes full sun to part shade. A number of cultivars are available.

<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 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">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">Affinine</span> Chemical compound

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

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

<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 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">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">Ervaticine</span> Chemical compound

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

<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. 1 2 Glasby JS (1975). "T". Encyclopedia of the Alkaloids (PDF). pp. 1282–1352. doi:10.1007/978-1-4615-8729-3_12. ISBN   978-1-4615-8731-6.
  2. ↑ Renner U, Prins DA (1961). "Voacanga-Alkaloide V. Verknüpfung von Vobasin mit Dregamin und Tabernaemontanin". Experientia. 17 (5): 209. doi:10.1007/BF02160617. PMID   13740864. S2CID   35816536.
  3. ↑ Knox JR, Slobbe J (1975). "Indole alkaloids from Ervatamia orientalis. III. The configurations of the ethyl side chains of dregamine and tabernaemontanine and some further chemistry of the vobasine group". Australian Journal of Chemistry. 28 (8): 1843. doi:10.1071/CH9751843.
  4. ↑ Bombardelli E, Bonati A, Gabetta B, Martinelli EM, Mustich G, Danieli B (1976). "Structures of tabernaelegantines A–D and tabernaelegantinines a and B, new indole alkaloids from Tabernaemontana elegans". Journal of the Chemical Society, Perkin Transactions 1 (13): 1432–1438. doi:10.1039/P19760001432.
  5. ↑ Gorman M, Neuss N, Cone NJ, Deyrup JA (1960). "Alkaloids from Apocynaceae. III. Alkaloids of Tabernaemontana and Ervatamia. The Structure of Coronaridine, A New Alkaloid Related to Ibogamine". Journal of the American Chemical Society. 82 (5): 1142–1145. doi:10.1021/ja01490a031.
  6. ↑ Edwin Saxton J (15 September 2009). Indoles, Part 4: The Monoterpenoid Indole Alkaloids. John Wiley & Sons. ISBN   9780470188446.
  7. ↑ Kam TS, Lim KH (2008). Chapter 1 Alkaloids of Kopsia. The Alkaloids: Chemistry and Biology. Vol. 66. pp. 1–111. doi:10.1016/S1099-4831(08)00201-0. ISBN   9780123745200. PMID   19025097.
  8. ↑ Clivio P, Richard B, Deverre JR, Sevenet T, Zeches M, Le Men-Oliver L (January 1991). "Alkaloids from leaves and root bark of Ervatamia hirta". Phytochemistry. 30 (11): 3785–3792. Bibcode:1991PChem..30.3785C. doi:10.1016/0031-9422(91)80111-D.
  9. ↑ Van Der Heijden R, Brouwer R, Verpoorte R, Wijnsma R, Van Beek T, Harkes A, Svendsen A (1986). "Indole alkaloids from a callus culture of Tabernaemontana elegans". Phytochemistry. 25 (4): 843–846. Bibcode:1986PChem..25..843V. doi:10.1016/0031-9422(86)80013-9.
  10. ↑ Arambewela LS, Ranatunge T (1991). "Indole alkaloids from Tabernaemontana divaricata". Phytochemistry. 30 (5): 1740–1741. Bibcode:1991PChem..30.1740A. doi:10.1016/0031-9422(91)84254-P.
  11. ↑ Kam TS, Pang HS, Lim TM (2003). "Biologically active indole and bisindole alkaloids from Tabernaemontana divaricata". Organic & Biomolecular Chemistry. 1 (8): 1292–1297. doi:10.1039/B301167D. PMID   12929658.
  12. ↑ Kulshreshtha A, Saxena J (2019). "Alkaloids and Non Alkaloids of Tabernaemontana divaricata" (PDF). International Journal of Research and Review. 6 (8): 517–524.
  13. ↑ Pratchayasakul W, Pongchaidecha A, Chattipakorn N, Chattipakorn S (April 2008). "Ethnobotany & ethnopharmacology of Tabernaemontana divaricata" (PDF). The Indian Journal of Medical Research. 127 (4): 317–35. PMID   18577786.[ permanent dead link ]
  14. ↑ 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.
  15. ↑ Singh B, a Sharma R, k Vyas G (2011). "Antimicrobial, Antineoplastic and Cytotoxic Activities of Indole Alkaloids from Tabernaemontana divaricata (L.) R.Br". Current Pharmaceutical Analysis. 7 (2): 125–132. doi:10.2174/157341211795684844.
  16. ↑ Paterna A, Kincses A, Spengler G, Mulhovo S, Molnár J, Ferreira MJ (2017). "Dregamine and tabernaemontanine derivatives as ABCB1 modulators on resistant cancer cells". European Journal of Medicinal Chemistry. 128: 247–257. doi: 10.1016/j.ejmech.2017.01.044 . PMID   28189906.
  17. ↑ Ferreira MJ, Paterna A (2019). "Monoterpene indole alkaloids as leads for targeting multidrug resistant cancer cells from the African medicinal plant Tabernaemontana elegans". Phytochemistry Reviews. 18 (4): 971–987. Bibcode:2019PChRv..18..971F. doi:10.1007/s11101-019-09615-1. S2CID   184483520.
  18. ↑ Cardoso D, Kincses A, Nove M, Spengler G, Mulhovo S, Aires-de-Sousa J, Dos Santos D, Ferreira M (January 2021). "Alkylated monoterpene indole alkaloid derivatives as potent P-glycoprotein inhibitors in resistant cancer cells". European Journal of Medicinal Chemistry . 210: 112985. doi: 10.1016/j.ejmech.2020.112985 . PMID   33189435. S2CID   226971895.
  19. ↑ Girardot M, Deregnaucourt C, Imbert C, Rasoanaivo P, Mambu L (2012). "Exploration of the mechanism of action of alkaloids with antiparasitic activities from Muntafara sessilifolia". Planta Medica. 78 (11). doi:10.1055/s-0032-1321055.
  20. ↑ Bapela MJ, Heyman H, Senejoux F, Meyer JM (2019). "1H NMR-based metabolomics of antimalarial plant species traditionally used by Vha-Venda people in Limpopo Province, South Africa and isolation of antiplasmodial compounds". Journal of Ethnopharmacology. 228: 148–155. doi:10.1016/j.jep.2018.07.022. hdl: 2263/75423 . OSTI   1463337. PMID   30048730. S2CID   51725791.
  21. ↑ Jain S, Jain A, Deb L, Dutt K, Jain DK (2010). "Evaluation of anti-fertility activity of Tabernaemontana divaricata(Linn) R.Br. Leaves in rats". Natural Product Research. 24 (9): 855–860. doi:10.1080/14786410903314385. PMID   20306358. S2CID   41422612.

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