Melicopidine

Last updated

Melicopidine
Melicopidine.png
Names
Preferred IUPAC name
4,11-dimethoxy-5-methyl-[1,3]dioxolo[4,5-b]acridin-10-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.821 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-502-0
PubChem CID
UNII
  • InChI=1S/C17H15NO5/c1-18-10-7-5-4-6-9(10)13(19)11-12(18)15(21-3)17-16(14(11)20-2)22-8-23-17/h4-7H,8H2,1-3H3
    Key: TZZNUDMEMFBPQI-UHFFFAOYSA-N
  • CN1C2=CC=CC=C2C(=O)C3=C1C(=C4C(=C3OC)OCO4)OC
Properties
C17H15NO5
Molar mass 313.309 g·mol−1
Hazards
Lethal dose or concentration (LD, LC):
200 mg/kg (mouse) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Melicopidine is an alkaloid. Its formula is C17H15NO5. It, along with melicopine and melicopicine, is named for the Australian rutaceae ( Melicope fareana ) from which it was first isolated. [2]

Occurrence

As an alkaloid, melicopidine naturally occurs in and has been isolated from Medicosma fareana [3] and Sarcomelicope megistophylla [4] in addition to Melicope fareana. [2]

Related Research Articles

<i>Melicope</i> Genus of plants

Melicope is a genus of about 240 species of shrubs and trees in the family Rutaceae, occurring from the Hawaiian Islands across the Pacific Ocean to tropical Asia, Australia and New Zealand. Plants in the genus Melicope have simple or trifoliate leaves arranged in opposite pairs, flowers arranged in panicles, with four sepals, four petals and four or eight stamens and fruit composed of up to four follicles.

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<span class="mw-page-title-main">Harmala alkaloid</span> Group of chemical compounds

Harmala alkaloids are several alkaloids that act as monoamine oxidase inhibitors (MAOIs). These alkaloids are found in the seeds of Peganum harmala, as well as Banisteriopsis caapi (ayahuasca), leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical structures, hence the name "harmala alkaloids". These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. Harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible inhibitors of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.

<i>Sida cordifolia</i> Species of shrub

Sida cordifolia is a perennial subshrub of the mallow family Malvaceae native to India. It has naturalized throughout the world, and is considered an invasive weed in Africa, Australia, the southern United States, Hawaiian Islands, New Guinea, and French Polynesia. The specific name, cordifolia, refers to the heart-shaped leaf.

<i>Asparagus racemosus</i> Species of flowering plant

Asparagus racemosus is a species of asparagus native from Africa through southern Asia, including the Indian subcontinent, to northern Australia. It grows 1–2 m tall and prefers to take root in gravelly, rocky soils high up in piedmont plains, at 1,300–1,400 m (4,300–4,600 ft) elevation. It was botanically described in 1799. Because of its multiple uses, the demand for Asparagus racemosus is constantly on the rise. Due to destructive harvesting, combined with habitat destruction, and deforestation, the plant is now considered "endangered" in its natural habitat.

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

Medicosma is a genus of shrubs and trees in the family Rutaceae, all native to New Guinea, Australia or New Caledonia. They usually have simple leaves arranged in opposite pairs, flowers arranged in cymes with four sepals, four petals and eight stamens. The fruit is a follicle fused at the base in groups of up to four, each containing one or two brown or black seeds.

Thomas Gordon Hartley was an American botanist.

Platydesma is a formerly recognized genus of plants in family Rutaceae. Evidence from 2009 indicated that Platydesma is nested within the genus Melicope and is sister to all Hawaiian Melicope species, and it is now placed within that genus. The other Melicope species are dioecious, whereas the flowers of species formerly placed in Platydesma are hermaphroditic, suggesting a rare evolutionary reversion away from dioecy. Species included:

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

Sarcomelicope is a genus of about ten species of flowering plants in the family Rutaceae that are endemic to the South Pacific.

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<i>Zanthoxylum zanthoxyloides</i> Species of flowering plant

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<span class="mw-page-title-main">Furoquinoline alkaloid</span> Group of chemical compounds

Furoquinoline alkaloids are a group of alkaloids with simple structure. Distribution of this group of alkaloids is essentially limited to plant family Rutaceae. The simplest member of this group is dictamnine and most widespread member is skimmianine.

<span class="mw-page-title-main">Akuammicine</span> Alkaloid

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<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.

<i>Medicosma fareana</i> Species of tree

Medicosma fareana, commonly known as white aspen, is a species of rainforest small tree in the family Rutaceae and is endemic to north Queensland. It has elliptical leaves and white or cream-coloured flowers borne singly or in small groups in leaf axils.

<i>Medicosma glandulosa</i> Species of shrub

Medicosma glandulosa is a species of shrub or small tree in the family Rutaceae and is endemic to far north Queensland. It has elliptical to egg-shaped leaves and flowers that are white with red tips or cream-coloured, borne singly or in small groups in leaf axils.

<i>Medicosma sessiliflora</i> Species of shrub

Medicosma sessiliflora is a species of shrub or small tree in the family Rutaceae and is endemic to far north Queensland. It has simple elliptical to egg-shaped leaves with the narrower end towards the base and cream-coloured flowers borne singly or in small groups in leaf axils.

<span class="mw-page-title-main">Zanthoxyloideae</span> Subfamily of plants

Zanthoxyloideae is a subfamily of the family Rutaceae. Its most notable member is probably Sichuan pepper.

References

  1. Svoboda GH, Kattau RW (1967). "Alkaloids of Acronychia Baueri (Baurella australiana) III". Lloydia. 30: 364.
  2. 1 2 Crow W, Price J (1949). "Alkaloids of the Australian Rutaceae: Melicope fareana. II. Preliminary Examination of Melicopine, Melicopidine, and Melicopicine". Australian Journal of Chemistry. 2 (2): 255. Bibcode:1949AuSRA...2..255C. doi:10.1071/CH9490255. ISSN   0004-9425.
  3. Habtemariam S, Waterman PG, Hartley T (September 1996). "Fareanine and fareanol from leaves of Medicosma fareana". Phytochemistry. 43 (1): 291–294. Bibcode:1996PChem..43..291H. doi:10.1016/0031-9422(96)00220-8.
  4. Mitaku S, Fokialakis N, Magiatis P, Tillequin F (February 2007). "Alkaloids from Sarcomelicope megistophylla". Fitoterapia. 78 (2): 169–170. doi:10.1016/j.fitote.2006.10.003. PMID   17207940.