サフラナール

Safranal
	IUPAC名 2,6,6-trimethyl-1,3-; cyclohexadiene-1-carboxaldehyde
識別情報
CAS登録番号	116-26-7
PubChem	61041
ChemSpider	55000
UNII	4393FR07EA
ChEBI	CHEBI:53169 ;
	SMILES O=C\C1=C(\C=C/CC1(C)C)C;
	InChI InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 Key: SGAWOGXMMPSZPB-UHFFFAOYSA-N ; InChI=1/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3 Key: SGAWOGXMMPSZPB-UHFFFAOYAY;
特性
化学式	C10H14O
モル質量	150.21 g/mol
密度	0.9734 g/cm3
沸点	70 °C at 1 mmHg
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

サフラナール(Safranal)は、クロッカスの花の雌ずい群であるサフランから単離された有機化合物である。サフランの香りの主成分である。

サフラナールは、カロテノイドのゼアキサンチンがピクロクロシンを介して分解されてできた生成物であると考えられている。

薬理作用

サフラナールは、GABAA受容体のアゴニストとして作用し、効果的な鎮痙剤となる^[1]^[2]。また、in vitroでの悪性腫瘍に対する細胞毒性とともに^[3]、高い抗酸化物質活性、フリーラジカル除去活性を示す^[4]^[5]。抗うつ薬の効果も持つ^[6]^[7]。

天然の存在

天然には、以下のような源に含まれる^[8]。

ルイボス(Aspalathus linearis)
チャノキ(Camellia sinensis)
サフラン(Crocus sativus)
イチジク(Ficus carica)
クコ(Lycium chinense)
クミン(Cuminum cyminum)^[9]
オランダフウロ(Erodium cicutarium)^[10]
セイヨウニワトコ(Sambucus nigra)^[10]
レモン(Citrus limon)^[10]

出典

^ 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.
^ 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.
^ 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.
^ 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: 435-45.
^ 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. 2008年3月2日閲覧。^{[信頼性要検証]}
^ 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]” (Chinese). Se Pu 20 (6): 569-72. PMID 12683011.
^ ^a ^b ^c Ramin Rezaee, Hossein Hosseinzadeh (January 2013). “[Safranal: From an Aromatic Natural Product to a Rewarding Pharmacological Agent”] (English). Iranian Journal of Basic Medical Sciences 16(1): 12-26.

[anticonvulsant-Hosseinzadeh-1] 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.

[protective-effect-Hosseinzadeh-2] 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.

[Crocin-safranal-Escribano-3] 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.

[Safranal-a-constituent-Hosseinzadeh-4] 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.

[Radical-scavenging-Assimopoulou-5] 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.

[6] 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: 435-45.

[7] 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.

[8] “List of Chemicals”. sun.ars-grin.gov. 2008年3月2日閲覧。^{[信頼性要検証]}

[9] 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]” (Chinese). Se Pu 20 (6): 569-72. PMID 12683011.

[rezaee-10] Ramin Rezaee, Hossein Hosseinzadeh (January 2013). “[Safranal: From an Aromatic Natural Product to a Rewarding Pharmacological Agent”] (English). Iranian Journal of Basic Medical Sciences 16(1): 12-26.

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