Safranal is an organic compound isolated from saffron, the spice consisting of the stigmas of crocus flowers (Crocus sativus). It is the constituent primarily responsible for the aroma of saffron.
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Preferred IUPAC name
2,6,6-Trimethylcyclohexa-1,3-diene-1-carbaldehyde | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.003.758 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H14O | |
Molar mass | 150.221 g·mol−1 |
Density | 0.9734 g/cm3 |
Boiling point | 70 °C (158 °F; 343 K) at 1 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is believed that safranal is a degradation product of the carotenoid zeaxanthin via the intermediate picrocrocin.
Pharmacology
editSafranal is an effective anticonvulsant in animal models, shown to act as an agonist at GABAA receptors.[1][2] Safranal also exhibits high antioxidant activity,[3][4] along with cytotoxicity towards cancer cells in vitro.[5] One of its anticancer mechanisms of action involves disruption of the normal assembly dynamics of cellular microtubules.[6] It has also been shown to have antidepressant properties in animals and pilot studies in humans.[7][8]
Natural sources
editNatural sources of safranal include:[9][unreliable source?]
- Microcystis (cyanobacterium)
- Aspalathus linearis (rooibos)
- Camellia sinensis (tea leaf)
- Crocus sativus (saffron)
- Ficus carica (fig leaf)
- Lycium chinense (wolfberry)
- Cuminum cyminum (cumin seed)[10]
- Centaurea sibthorpii [11]
- Centaurea amanicola[11]
- Centaurea consanguinea[11]
- Erodium cicutarium (common stork's-bill or pinweed)[11]
- Calycopteris floribunda (ukshi)[11]
- Sambucus nigra (elderberry)[11]
- Citrus limon (lemon)[11]
- Achillea distans [11]
References
edit- ^ Hosseinzadeh H; Talebzadeh F (December 2005). "Anticonvulsant evaluation of safranal and crocin from Crocus sativus in mice". Fitoterapia. 76 (7–8): 722–4. doi:10.1016/j.fitote.2005.07.008. PMID 16253437.
- ^ Hosseinzadeh H; Sadeghnia HR (April 2007). "Protective effect of safranal on pentylenetetrazol-induced seizures in the rat: involvement of GABAergic and opioids systems". Phytomedicine. 14 (4): 256–62. doi:10.1016/j.phymed.2006.03.007. PMID 16707256.
- ^ Hosseinzadeh H; Sadeghnia HR (2005). "Safranal, a constituent of Crocus sativus (saffron), attenuated cerebral ischemia induced oxidative damage in rat hippocampus". Journal of Pharmacy & Pharmaceutical Sciences. 8 (3): 394–9. PMID 16401389.
- ^ Assimopoulou AN; Sinakos Z; Papageorgiou VP (November 2005). "Radical scavenging activity of Crocus sativus L. extract and its bioactive constituents". Phytotherapy Research. 19 (11): 997–1000. doi:10.1002/ptr.1749. PMID 16317646. S2CID 23907085.
- ^ Escribano J; Alonso GL; Coca-Prados M; Fernandez JA (February 1996). "Crocin, safranal and picrocrocin from saffron (Crocus sativus L.) inhibit the growth of human cancer cells in vitro". Cancer Letters. 100 (1–2): 23–30. doi:10.1016/0304-3835(95)04067-6. PMID 8620447.
- ^ Cheriyamundath S, Choudhary S, and Lopus M (2017) Safranal inhibits HeLa cell viability by perturbing the reassembly potential of microtubules. Phytother Res, 32, 170-173. doi: 10.1002/ptr.5938. PMID 29024138
- ^ Hosseinzadeh H; Karimi G; Niapoor M (2004). "Antidepressant effect of Crocus sativus L. stigma extracts and their constituents, crocin and safranal, in mice". Acta Horticulturae. 650 (650): 435–45. doi:10.17660/ActaHortic.2004.650.54.
- ^ Akhondzadeh S; Fallah-Pour H; Afkham K; Jamshidi AH; Khalighi-Cigaroudi F (September 2004). "Comparison of Crocus sativus L. and imipramine in the treatment of mild to moderate depression: A pilot double-blind randomized trial ISRCTN45683816". BMC Complementary and Alternative Medicine. 4: 12. doi:10.1186/1472-6882-4-12. PMC 517724. PMID 15341662.
- ^ "List of Chemicals". sun.ars-grin.gov. Retrieved 2008-03-02.
- ^ Yan JH; Tang KW; Zhong M; Deng NH (November 2002). "[Determination of chemical components of volatile oil from Cuminum cyminum L. by gas chromatography-mass spectrometry]". Se Pu (in Chinese). 20 (6): 569–72. PMID 12683011.
- ^ a b c d e f g h Ramin Rezaee; Hossein Hosseinzadeh (January 2013). "[Safranal: From an Aromatic Natural Product to a Rewarding Pharmacological Agent]". Iranian Journal of Basic Medical Sciences. 16 (1): 12–26. PMC 3637901. PMID 23638289.