Conodurine

Last updated
Conodurine
Conodurine.svg
Names
IUPAC name
methyl 17-ethyl-5-[(15Z)-15-ethylidene-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-6-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene-1-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C43H52N4O5/c1-7-24-17-23-20-43(42(49)52-6)39-28(15-16-47(21-23)40(24)43)27-13-14-34(50-4)36(38(27)45-39)31-18-29-25(8-2)22-46(3)33(35(29)41(48)51-5)19-30-26-11-9-10-12-32(26)44-37(30)31/h8-14,23-24,29,31,33,35,40,44-45H,7,15-22H2,1-6H3/b25-8+
    Key: QJHYXWBJZHUJGS-ZNLRHDTNSA-N
  • CCC1CC2CC3(C1N(C2)CCC4=C3NC5=C4C=CC(=C5C6CC7C(C(CC8=C6NC9=CC=CC=C89)N(CC7=CC)C)C(=O)OC)OC)C(=O)OC
Properties
C43H52N4O5
Molar mass 704.912 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Conodurine is an acetylcholinesterase inhibitor and butyrylcholinesterase inhibitor isolated from Tabernaemontana . [1] [2] [3]

See also

Related Research Articles

Apocynaceae 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.

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.

<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.

Coronaridine 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.

Ibogamine 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.

<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 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.

Catharanthine 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.

Affinine 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.

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.

Heyneanine Chemical compound

Heyneanine is a Tabernaemontana alkaloid with in vitro antitumor activity. It also inhibits butrylcholinesterase.

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.

Ibogaline Alkaloid found in Tabernanthe iboga

Ibogaline is an alkaloid found in Tabernanthe iboga along with the related chemical compounds ibogaine, ibogamine, and other minor alkaloids. It is a relatively smaller component of Tabernanthe iboga root bark total alkaloids (TA) content. It is also present in Tabernaemontana species such as Tabernaemontana australis which shares similar ibogan-biosynthetic pathways. The percentage of ibogaline in T. iboga root bark is up to 15% TA with ibogaine constituting 80% of the alkaloids and ibogamine up to 5%.

Tabernaemontanine Chemical compound

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

19,20-Dihydroervahanine A Chemical compound

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

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.

References

  1. Vieira, IJ; Medeiros, WL; Monnerat, CS; Souza, JJ; Mathias, L; Braz-Filho, R; Pinto, AC; Sousa, PM; Rezende, CM; Epifanio Rde, A (Sep 2008). "Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures". An. Acad. Bras. Ciênc. 80 (3): 419–26. doi: 10.1590/s0001-37652008000300003 . PMID   18797794.
  2. "Annals of the Brazilian Academy of Sciences" (PDF).
  3. Kam TS, Sim KM (July 2003). "Conodurine, conoduramine, and ervahanine derivatives from Tabernaemontana corymbosa". Phytochemistry . 63 (5): 625–9. doi:10.1016/s0031-9422(03)00087-6. PMID   12809725.