ノビレチン

ノビレチン
	IUPAC名 2-(3,4-Dimethoxyphenyl)-5,6,7,8-tetramethoxychromen-4-one
	別称 Hexamethoxyflavone
識別情報
CAS登録番号	478-01-3
PubChem	72344
KEGG	C10112
	SMILES COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC;
特性
化学式	C21H22O8
モル質量	402.39 g mol−1
精密質量	402.131468 u
	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。

ノビレチン (Nobiletin) は、柑橘類の果皮等に多く含まれる有機化合物で、フラボンを骨格に持つポリメトキシフラボノイド（O-メチル化フラボノイド）の一種である。

含有食品

主に柑橘類に多く含まれており、特にポンカン、シークヮーサー、橘等に多く含まれている^[1]。可食部分である果実小胞自体にはあまり含まれておらず、果皮部分であるフラベド(外果皮)、アルベド(中果皮)に特に多く含有している。

柑橘類	果実全体	果実小胞	果皮組織	フラベド	アルベド
ポンカン	30.6	0.8	110	198	33.3
シークヮーサー	30.3	2.5	85.2	122	41.0
タチバナ	54.3	0	182	233	46.7
温州みかん(参考)	1.5	0	6.4	10.8	1.8

注：生果の各組織100gあたりの含有量(mg)

薬理作用

in vitroや動物実験で、抗炎症作用や腫瘍の浸潤、拡散、転移を防ぐ作用^[2]^[3]^[4]、皮膚炎抑制作用^[5]、肝炎抑制作用^[6]等が示されている。また、軟骨の分解を抑制する効果も報告されている^[7]。また、培養海馬細胞においてAMPA型グルタミン酸受容体を活性化し、ニューロンの長期増強を促進することが示されている^[8]。

出典

^ Nogata Y, Sakamoto K, Shiratsuchi H, Ishii T, Yano M, Ohta H (2006). “Flavonoid composition of fruit tissues of citrus species”. Biosci Biotechnol Biochem 70: 178-192. doi:10.1271/bbb.70.178. PMID 16428836.
^ Minagawa A, Otani Y, Kubota T, Wada N, Furukawa T, Kumai K, Kameyama K, Okada Y, Fujii M, Yano M, Sato T, Ito A, Kitajima M (2001). “The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice”. Jpn J Cancer Res 92 (12): 1322-1328. PMID 11749698.
^ Sato T, Koike L, Miyata Y, Hirata M, Mimaki Y, Sashida Y, Yano M, Ito A. (2002). “Inhibition of activator protein-1 binding activity and phosphatidylinositol 3-kinase pathway by nobiletin, a polymethoxy flavonoid, results in augmentation of tissue inhibitor of metalloproteinases-1 production and suppression of production of matrix metalloproteinases-1 and -9 in human fibrosarcoma HT-1080 cells”. Cancer Res 62 (4): 1025-1029. PMID 11861377.
^ Yoshimizu N, Otani Y, Saikawa Y, Kubota T, Yoshida M, Furukawa T, Kumai K, Kameyama K, Fujii M, Yano M, Sato T, Ito A, Kitajima M (2004). “Anti-tumour effects of nobiletin, a citrus flavonoid, on gastric cancer include: antiproliferative effects, induction of apoptosis and cell cycle deregulation”. Aliment Pharmacol Ther 1: 95-101. doi:10.1111/j.1365-2036.2004.02082.x. PMID 15298613.
^ Tanaka S, Sato T, Akimoto N, Yano M, Ito A (2004). “Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro”. Biochem Pharmacol 68: 433-439. doi:10.1016/j.bcp.2004.04.006. PMID 15242810.
^ Akachi T, Shiina Y, Ohishi Y, Kawaguchi T, Kawagishi H, Morita T, Mori M, Sugiyama K (2010). “Hepatoprotective effects of flavonoids from shekwasha (Citrus depressa) against D-galactosamine-induced liver injury in rats”. J Nutr Sci Vitaminol 56 (1): 60-67. doi:10.3177/jnsv.56.60. PMID 20354348.
^ Henrotin, Y.; C. Lambert; D. Couchourel; C. Ripoll; E. Chiotelli (January 2011). “Nutraceuticals: do they represent a new era in the management of osteoarthritis? – a narrative review from the lessons taken with five products”. Osteoarthritis and Cartilage 19 (1): 1–21. doi:10.1016/j.joca.2010.10.017. PMID 21035558 2011年12月27日閲覧。.
^ Matsuzaki K, Miyazaki K, Sakai S, Yawo H, Nakata N, Moriguchi S, Fukunaga K, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y (2008). “Nobiletin, a citrus flavonoid with neurotrophic action, augments protein kinase A-mediated phosphorylation of the AMPA receptor subunit, GluR1, and the postsynaptic receptor response to glutamate in murine hippocampus”. Eur J Pharmacol 578 (2-3): 194-200. doi:10.1016/j.ejphar.2007.09.028. PMID 17976577.

外部リンク

Nobiletin, phytochemicals.info

[1] Nogata Y, Sakamoto K, Shiratsuchi H, Ishii T, Yano M, Ohta H (2006). “Flavonoid composition of fruit tissues of citrus species”. Biosci Biotechnol Biochem 70: 178-192. doi:10.1271/bbb.70.178. PMID 16428836.

[2] Minagawa A, Otani Y, Kubota T, Wada N, Furukawa T, Kumai K, Kameyama K, Okada Y, Fujii M, Yano M, Sato T, Ito A, Kitajima M (2001). “The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice”. Jpn J Cancer Res 92 (12): 1322-1328. PMID 11749698.

[3] Sato T, Koike L, Miyata Y, Hirata M, Mimaki Y, Sashida Y, Yano M, Ito A. (2002). “Inhibition of activator protein-1 binding activity and phosphatidylinositol 3-kinase pathway by nobiletin, a polymethoxy flavonoid, results in augmentation of tissue inhibitor of metalloproteinases-1 production and suppression of production of matrix metalloproteinases-1 and -9 in human fibrosarcoma HT-1080 cells”. Cancer Res 62 (4): 1025-1029. PMID 11861377.

[4] Yoshimizu N, Otani Y, Saikawa Y, Kubota T, Yoshida M, Furukawa T, Kumai K, Kameyama K, Fujii M, Yano M, Sato T, Ito A, Kitajima M (2004). “Anti-tumour effects of nobiletin, a citrus flavonoid, on gastric cancer include: antiproliferative effects, induction of apoptosis and cell cycle deregulation”. Aliment Pharmacol Ther 1: 95-101. doi:10.1111/j.1365-2036.2004.02082.x. PMID 15298613.

[5] Tanaka S, Sato T, Akimoto N, Yano M, Ito A (2004). “Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro”. Biochem Pharmacol 68: 433-439. doi:10.1016/j.bcp.2004.04.006. PMID 15242810.

[6] Akachi T, Shiina Y, Ohishi Y, Kawaguchi T, Kawagishi H, Morita T, Mori M, Sugiyama K (2010). “Hepatoprotective effects of flavonoids from shekwasha (Citrus depressa) against D-galactosamine-induced liver injury in rats”. J Nutr Sci Vitaminol 56 (1): 60-67. doi:10.3177/jnsv.56.60. PMID 20354348.

[7] Henrotin, Y.; C. Lambert; D. Couchourel; C. Ripoll; E. Chiotelli (January 2011). “Nutraceuticals: do they represent a new era in the management of osteoarthritis? – a narrative review from the lessons taken with five products”. Osteoarthritis and Cartilage 19 (1): 1–21. doi:10.1016/j.joca.2010.10.017. PMID 21035558 2011年12月27日閲覧。.

[8] Matsuzaki K, Miyazaki K, Sakai S, Yawo H, Nakata N, Moriguchi S, Fukunaga K, Yokosuka A, Sashida Y, Mimaki Y, Yamakuni T, Ohizumi Y (2008). “Nobiletin, a citrus flavonoid with neurotrophic action, augments protein kinase A-mediated phosphorylation of the AMPA receptor subunit, GluR1, and the postsynaptic receptor response to glutamate in murine hippocampus”. Eur J Pharmacol 578 (2-3): 194-200. doi:10.1016/j.ejphar.2007.09.028. PMID 17976577.

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