Conofoline

Last updated
Conofoline
Conofoline.svg
Names
Preferred IUPAC name
Methyl (1aS,1′aS,1bS,1′bS,1b1R,1′b1R,3aS,8bS,8′bR,12′R,12aR,12′aR)-1b,1′b-diethyl-7′-hydroxy-5′,6′-dimethoxy-4-methyl-1a,1′a,1b,1′b,1b1,1′b1,2,2′,3,3a,4,4′,9,9′,10,10′,12a,12′a-octadecahydro-12H,12′H-[7,12′-bioxireno[2′,3′:6,7]indolizino[8,1-cd]carbazole]-3′-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C43H52N4O7/c1-7-40-12-11-28-42(13-15-46(38(40)42)20-27-35(40)53-27)23-17-21(9-10-25(23)45(28)3)30-33-36(54-33)41(8-2)19-22(37(49)52-6)34-43(14-16-47(30)39(41)43)24-18-26(48)31(50-4)32(51-5)29(24)44-34/h9-10,17-18,27-28,30,33,35-36,38-39,44,48H,7-8,11-16,19-20H2,1-6H3/t27-,28+,30-,33-,35-,36-,38+,39+,40-,41-,42+,43+/m1/s1
    Key: AXBZVPIBJWOFHO-XMONSFOZSA-N
  • CC[C@]12CC[C@H]3[C@@]4([C@H]1N(CC4)C[C@@H]5[C@H]2O5)C6=C(N3C)C=CC(=C6)[C@@H]7[C@@H]8[C@@H](O8)[C@]9(CC(=C1[C@@]2([C@H]9N7CC2)C2=CC(=C(C(=C2N1)OC)OC)O)C(=O)OC)CC
Properties
C43H52N4O7
Molar mass 736.910 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 , [1] including Tabernaemontana divaricata , and in Ervatamia peduncularis . [2]

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>Catharanthus</i> Genus of flowering plants

Catharanthus is a genus of flowering plants in the family Apocynaceae. Like the genus Vinca, they are known commonly as periwinkles. There are eight known species. Seven are endemic to Madagascar, though one, C. roseus, is widely naturalized around the world. The eighth species, C. pusillus, is native to India and Sri Lanka. The name Catharanthus comes from the Greek for "pure flower".

<i>Vinca</i> Genus of flowering plants

Vinca is a genus of flowering plants in the family Apocynaceae, native to Europe, northwest Africa and southwest Asia. The English name periwinkle is shared with the related genus Catharanthus.

<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.

<i>Catharanthus roseus</i> Species of flowering plant in the family Apocynaceae

Catharanthus roseus, commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a species of flowering plant in the family Apocynaceae. It is native and endemic to Madagascar, but grown elsewhere as an ornamental and medicinal plant. It is a source of the drugs vincristine and vinblastine, used to treat cancer. It was formerly included in the genus Vinca as Vinca rosea.

<i>Vinca</i> alkaloid

Vinca alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant Catharanthus roseus and other vinca plants. They block beta-tubulin polymerization in a dividing cell.

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.

Vindesine

Vindesine, also termed Eldisine, is a semisynthetic vinca alkaloid derived from the flowering plant Catharanthus roseus. Like the natural and semisynthetic vinca alkaloids derived from this plant, vindesine is an inhibitor of mitosis that is used as a chemotherapy drug. By inhibiting mitosis, vinedsine blocks the proliferation of cells, particularly the rapidly proliferation cells of certain types of cancer. It is used, generally in combination with other chemotherapeutic drugs, in the treatment of various malignancies such as leukaemia, lymphoma, melanoma, breast cancer, and lung cancer.

<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.

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.

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.

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.

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.

References

  1. US 20070232533,"Use of Vinca Alkaloids and Salts Thereof"
  2. Buckingham, John; Baggaley, Keith H.; Roberts, Andrew D.; Szabo, Laszlo F. (2010). Dictionary of Alkaloids with CD-ROM. CRC Press. p. 453. ISBN   978-1-4200-7770-4.