Anonaine
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IUPAC name
1,2-[Methylenebis(oxy)]-12-nor-6aβ-aporphine
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Systematic IUPAC name
(7aR)-6,7,7a,8-Tetrahydro-2H,5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline | |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C17H15NO2 | |
Molar mass | 265.312 g·mol−1 |
Melting point | 122–123 °C (252–253 °F; 395–396 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anonaine is a bioactive benzylisoquinoline alkaloid, present in members of the plant families Magnoliaceae and Annonaceae[1] It is named after the plant it was first extracted from, Annona reticulata, which is commonly known as Anona.[2]
Extraction from Annonaceae
The alkaloid was first isolated from the bark of the
Research
Traditional medicines
Anonaine is found in many species of Annonacae, which have been used as traditional medicines for many years. For example, extracts of Annona squamosa have been used as treatments for epilepsy, dysentery, cardiac problems, worm infection, constipation, bacterial infection, fever and ulcers. It appears, however, that anonaine is not active in the treatment of many of these ailments.[4] Studies into the bioactivity of anonaine have revealed various interesting pharmacological activities including antitumour, vasorelaxation, antioxidative, antiparasitic and antimicrobial effects, as well as having an effect on the central nervous system.[1]
Anti-tumour properties
Anonaine is known to inhibit growth in human cervical cancer[5] and human lung carcinoma H1299 cells in vitro.[6] The mechanism by which anonaine induces apoptosis in these cells is believed to occur by several mechanisms: generation of nitric oxide and reactive oxygen species, reduction in intracellular glutathione concentration, activation of caspases and apoptosis-related proteins, and damage to DNA.
See also
- Apomorphine – a related chemical used in the treatment of Parkinson's disease
- Aporphine – the core alkaloid
- Nuciferine
- Pukateine
References
- ^ PMID 23857128.
- ^ a b Santos, A. C. (1930). "Alkaloid from Anona reticulata L.". Philippine Journal of Science. 43 (4): 561–564.
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- ^ Srivastava, S.; Lal, V. K.; Pant, K. K. (2011). "Medicinal potential of Annona squamosa: At a glance". Journal of Pharmacy Research. 4 (12): 4596–4598.
- PMID 18524447.
- PMID 21361287.