イカリイン

イカリイン
IUPAC命名法による物質名
	IUPAC名 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7- [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3- [(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one;
臨床データ
法的規制	US: OTC ; Legal;
識別
CAS番号;	489-32-7
ATCコード	none
PubChem	CID: 5318997
ChemSpider	4477421
KEGG	C17555
ChEBI	CHEBI:78420
ChEMBL	CHEMBL553204
日化辞番号	J15.942E
化学的データ
化学式	C33H40O15
分子量	676.662 g/mol
	SMILES O=C3C(\O[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)=C(/Oc4c(c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c34)C\C=C(/C)C)c5ccc(OC)cc5;
	InChI InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 ; Key:TZJALUIVHRYQQB-XLRXWWTNSA-N ;
	テンプレートを表示

イカリイン (Icariin) はフラボノイドの一種であり、フラボノール配糖体に分類される。ケンペリド 3,7-O-ジグルコシドの 8-プレニル誘導体である。ホーニーゴートウィードまたは淫羊藿として知られるメギ科イカリソウ属の数種の植物に由来する^[1]。これらの植物の抽出物は、媚薬の効果を持つと言われ、伝統中国医学において勃起機能を高めるために利用された^[2]。しかし、こうした主張を裏付ける臨床試験データは存在しない^[3]。

研究

ヒトを対象に行われた治験は1つ存在する。この小規模で対照群のない試験は双極性障害を持つ被験者に対して行われ、うつとアルコール消費が低下した^[4]。イカリインはイカリソウエキスの活性成分であると考えられており、西洋医学で勃起不全の治療に用いられる化合物と共通の作用機序を有することが示されている。特に、イカリインはin vitroで弱いPDE5阻害剤であり^[5]^[6]^[7]、一酸化窒素の産生を高め^[8]、ラットではテストステロンの作用を模倣する^[9]。In vitroでは、弱い抗酸化剤であることも示唆されている^[10]^[11]。マウスでは抗うつ薬のような作用を示す^[12]^[13]^[14]。ラットでは神経保護作用も示す^[15]^[16]。

出典

^ Liu JJ, Li SP, Wang YT (January 2006). “Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design”. J Chromatogr A 1103 (2): 344–9. doi:10.1016/j.chroma.2005.11.036. PMID 16337210.
^ Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP (December 2007). “Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats”. J Ethnopharmacol 114 (3): 412–6. doi:10.1016/j.jep.2007.08.021. PMID 17890032.
^ “Horny Goat Weed Uses, Benefits & Dosage - Drugs.com Herbal Database” (英語). Drugs.com. 2020年5月14日閲覧。
^ Xiao, Heather; Wignall, Nicholas; Brown, E. Sherwood (2016-03). “An open-label pilot study of icariin for co-morbid bipolar and alcohol use disorder”. The American Journal of Drug and Alcohol Abuse 42 (2): 162–167. doi:10.3109/00952990.2015.1114118. ISSN 1097-9891. PMID 26809351.
^ Jiang, Zhaojian; Hu, Benrong; Wang, Jialing; Tang, Qiang; Tan, Yan; Xiang, Jizhou; Liu, Juyan (2006). “Effect of icariin on cyclic GMP levels and on the mRNA expression of cGMP-binding cGMP-specific phosphodiesterase (PDE5) in penile cavernosum”. Journal of Huazhong University of Science and Technology. Medical Sciences = Hua Zhong Ke Ji Da Xue Xue Bao. Yi Xue Ying De Wen Ban = Huazhong Keji Daxue Xuebao. Yixue Yingdewen Ban 26 (4): 460–462. doi:10.1007/s11596-006-0421-y. ISSN 1672-0733. PMID 17120748.
^ Ning, Hongxiu; Xin, Zhong-Cheng; Lin, Guiting; Banie, Lia; Lue, Tom F.; Lin, Ching-Shwun (2006-12). “Effects of icariin on phosphodiesterase-5 activity in vitro and cyclic guanosine monophosphate level in cavernous smooth muscle cells”. Urology 68 (6): 1350–1354. doi:10.1016/j.urology.2006.09.031. ISSN 1527-9995. PMID 17169663.
^ Dell'Agli, Mario; Galli, Germana V.; Dal Cero, Esther; Belluti, Federica; Matera, Riccardo; Zironi, Elisa; Pagliuca, Giampiero; Bosisio, Enrica (2008-09). “Potent inhibition of human phosphodiesterase-5 by icariin derivatives”. Journal of Natural Products 71 (9): 1513–1517. doi:10.1021/np800049y. ISSN 1520-6025. PMID 18778098.
^ Xu, Hai-Bin; Huang, Zhao-Quan (2007-07). “Icariin enhances endothelial nitric-oxide synthase expression on human endothelial cells in vitro”. Vascular Pharmacology 47 (1): 18–24. doi:10.1016/j.vph.2007.03.002. ISSN 1537-1891. PMID 17499557.
^ Zhang, Zhen-Bao; Yang, Qing-Tao (2006-09). “The testosterone mimetic properties of icariin”. Asian Journal of Andrology 8 (5): 601–605. doi:10.1111/j.1745-7262.2006.00197.x. ISSN 1008-682X. PMID 16751992.
^ Xie, J.; Sun, W.; Duan, K.; Zhang, Y. (2007-06). “Chemical constituents of roots of Epimedium wushanense and evaluation of their biological activities”. Natural Product Research 21 (7): 600–605. doi:10.1080/14786410701369680. ISSN 1478-6419. PMID 17613817.
^ Zhao, Feng; Tang, You-Zhi; Liu, Zai-Qun (2007-12). “Protective effect of icariin on DNA against radical-induced oxidative damage”. The Journal of Pharmacy and Pharmacology 59 (12): 1729–1732. doi:10.1211/jpp.59.12.0016. ISSN 0022-3573. PMID 18053336.
^ Pan, Ying; Kong, Lingdong; Xia, Xing; Zhang, Weiyun; Xia, Zhonghao; Jiang, Fuxin (2005-12). “Antidepressant-like effect of icariin and its possible mechanism in mice”. Pharmacology, Biochemistry, and Behavior 82 (4): 686–694. doi:10.1016/j.pbb.2005.11.010. ISSN 0091-3057. PMID 16380159.
^ Pan, Ying; Zhang, Wei-Yun; Xia, Xing; Kong, Ling-Dong (2006-12). “Effects of icariin on hypothalamic-pituitary-adrenal axis action and cytokine levels in stressed Sprague-Dawley rats”. Biological & Pharmaceutical Bulletin 29 (12): 2399–2403. doi:10.1248/bpb.29.2399. ISSN 0918-6158. PMID 17142971.
^ Pan, Ying; Kong, Ling-Dong; Li, Yu-Cheng; Xia, Xing; Kung, Hsiang-Fu; Jiang, Fu-Xing (2007-05). “Icariin from Epimedium brevicornum attenuates chronic mild stress-induced behavioral and neuroendocrinological alterations in male Wistar rats”. Pharmacology, Biochemistry, and Behavior 87 (1): 130–140. doi:10.1016/j.pbb.2007.04.009. ISSN 0091-3057. PMID 17509675.
^ Luo, Yong; Nie, Jing; Gong, Qi-Hai; Lu, Yuan-Fu; Wu, Qin; Shi, Jing-Shan (2007-08). “Protective effects of icariin against learning and memory deficits induced by aluminium in rats”. Clinical and Experimental Pharmacology & Physiology 34 (8): 792–795. doi:10.1111/j.1440-1681.2007.04647.x. ISSN 0305-1870. PMID 17600559.
^ Zheng, Ming; Qu, Linhai; Lou, Yijia (2008-05). “Effects of icariin combined with Panax notoginseng saponins on ischemia reperfusion-induced cognitive impairments related with oxidative stress and CA1 of hippocampal neurons in rat”. Phytotherapy research: PTR 22 (5): 597–604. doi:10.1002/ptr.2276. ISSN 1099-1573. PMID 18398927.

[1] Liu JJ, Li SP, Wang YT (January 2006). “Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design”. J Chromatogr A 1103 (2): 344–9. doi:10.1016/j.chroma.2005.11.036. PMID 16337210.

[2] Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP (December 2007). “Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats”. J Ethnopharmacol 114 (3): 412–6. doi:10.1016/j.jep.2007.08.021. PMID 17890032.

[3] “Horny Goat Weed Uses, Benefits & Dosage - Drugs.com Herbal Database” (英語). Drugs.com. 2020年5月14日閲覧。

[4] Xiao, Heather; Wignall, Nicholas; Brown, E. Sherwood (2016-03). “An open-label pilot study of icariin for co-morbid bipolar and alcohol use disorder”. The American Journal of Drug and Alcohol Abuse 42 (2): 162–167. doi:10.3109/00952990.2015.1114118. ISSN 1097-9891. PMID 26809351.

[5] Jiang, Zhaojian; Hu, Benrong; Wang, Jialing; Tang, Qiang; Tan, Yan; Xiang, Jizhou; Liu, Juyan (2006). “Effect of icariin on cyclic GMP levels and on the mRNA expression of cGMP-binding cGMP-specific phosphodiesterase (PDE5) in penile cavernosum”. Journal of Huazhong University of Science and Technology. Medical Sciences = Hua Zhong Ke Ji Da Xue Xue Bao. Yi Xue Ying De Wen Ban = Huazhong Keji Daxue Xuebao. Yixue Yingdewen Ban 26 (4): 460–462. doi:10.1007/s11596-006-0421-y. ISSN 1672-0733. PMID 17120748.

[6] Ning, Hongxiu; Xin, Zhong-Cheng; Lin, Guiting; Banie, Lia; Lue, Tom F.; Lin, Ching-Shwun (2006-12). “Effects of icariin on phosphodiesterase-5 activity in vitro and cyclic guanosine monophosphate level in cavernous smooth muscle cells”. Urology 68 (6): 1350–1354. doi:10.1016/j.urology.2006.09.031. ISSN 1527-9995. PMID 17169663.

[7] Dell'Agli, Mario; Galli, Germana V.; Dal Cero, Esther; Belluti, Federica; Matera, Riccardo; Zironi, Elisa; Pagliuca, Giampiero; Bosisio, Enrica (2008-09). “Potent inhibition of human phosphodiesterase-5 by icariin derivatives”. Journal of Natural Products 71 (9): 1513–1517. doi:10.1021/np800049y. ISSN 1520-6025. PMID 18778098.

[8] Xu, Hai-Bin; Huang, Zhao-Quan (2007-07). “Icariin enhances endothelial nitric-oxide synthase expression on human endothelial cells in vitro”. Vascular Pharmacology 47 (1): 18–24. doi:10.1016/j.vph.2007.03.002. ISSN 1537-1891. PMID 17499557.

[9] Zhang, Zhen-Bao; Yang, Qing-Tao (2006-09). “The testosterone mimetic properties of icariin”. Asian Journal of Andrology 8 (5): 601–605. doi:10.1111/j.1745-7262.2006.00197.x. ISSN 1008-682X. PMID 16751992.

[10] Xie, J.; Sun, W.; Duan, K.; Zhang, Y. (2007-06). “Chemical constituents of roots of Epimedium wushanense and evaluation of their biological activities”. Natural Product Research 21 (7): 600–605. doi:10.1080/14786410701369680. ISSN 1478-6419. PMID 17613817.

[11] Zhao, Feng; Tang, You-Zhi; Liu, Zai-Qun (2007-12). “Protective effect of icariin on DNA against radical-induced oxidative damage”. The Journal of Pharmacy and Pharmacology 59 (12): 1729–1732. doi:10.1211/jpp.59.12.0016. ISSN 0022-3573. PMID 18053336.

[12] Pan, Ying; Kong, Lingdong; Xia, Xing; Zhang, Weiyun; Xia, Zhonghao; Jiang, Fuxin (2005-12). “Antidepressant-like effect of icariin and its possible mechanism in mice”. Pharmacology, Biochemistry, and Behavior 82 (4): 686–694. doi:10.1016/j.pbb.2005.11.010. ISSN 0091-3057. PMID 16380159.

[13] Pan, Ying; Zhang, Wei-Yun; Xia, Xing; Kong, Ling-Dong (2006-12). “Effects of icariin on hypothalamic-pituitary-adrenal axis action and cytokine levels in stressed Sprague-Dawley rats”. Biological & Pharmaceutical Bulletin 29 (12): 2399–2403. doi:10.1248/bpb.29.2399. ISSN 0918-6158. PMID 17142971.

[14] Pan, Ying; Kong, Ling-Dong; Li, Yu-Cheng; Xia, Xing; Kung, Hsiang-Fu; Jiang, Fu-Xing (2007-05). “Icariin from Epimedium brevicornum attenuates chronic mild stress-induced behavioral and neuroendocrinological alterations in male Wistar rats”. Pharmacology, Biochemistry, and Behavior 87 (1): 130–140. doi:10.1016/j.pbb.2007.04.009. ISSN 0091-3057. PMID 17509675.

[15] Luo, Yong; Nie, Jing; Gong, Qi-Hai; Lu, Yuan-Fu; Wu, Qin; Shi, Jing-Shan (2007-08). “Protective effects of icariin against learning and memory deficits induced by aluminium in rats”. Clinical and Experimental Pharmacology & Physiology 34 (8): 792–795. doi:10.1111/j.1440-1681.2007.04647.x. ISSN 0305-1870. PMID 17600559.

[16] Zheng, Ming; Qu, Linhai; Lou, Yijia (2008-05). “Effects of icariin combined with Panax notoginseng saponins on ischemia reperfusion-induced cognitive impairments related with oxidative stress and CA1 of hippocampal neurons in rat”. Phytotherapy research: PTR 22 (5): 597–604. doi:10.1002/ptr.2276. ISSN 1099-1573. PMID 18398927.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]

[16]