土曲霉酮

土曲霉酮
	IUPAC名; (4S,5R)-4,5-Dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
识别
CAS号	582-46-7
PubChem	6436830
ChemSpider	4941440
SMILES	C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O;
InChI	1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1;
InChIKey	MHOOPNKRBMHHEC-HZIBQTDNSA-N
性质
化学式	C8H10O3
摩尔质量	154.16 g·mol−1
熔点	125—127 °C（398—400 K）
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

土曲霉酮是曲霉属的一种真菌代谢产物，^[2]可以形成浅黄色的针状晶体，^[2]^[3]它可以L-(+)-酒石酸二甲酯为原料合成得到。^[4]^[5]它对大腸癌的细胞由强细胞毒性。^[2]土曲霉的S020菌株的土曲霉酮的产率最高。^[2]

参考文献

^ E. L. Ghisalberti, M. J. Narbey, C. Y. Rowland. Metabolites of Aspergillus terreus Antagonistic Towards the Take-all Fungus. Journal of Natural Products. 1990-03, 53 (2): 520–522 [2021-03-17]. ISSN 0163-3864. doi:10.1021/np50068a043 （英语）.
^ ^2.0 ^2.1 ^2.2 ^2.3 Asfour, Hani Z.; Awan, Zuhier A.; Bagalagel, Alaa A.; Elfaky, Mahmoud A.; Abdelhameed, Reda F. A.; Elhady, Sameh S. Large-Scale Production of Bioactive Terrein by Aspergillus terreus Strain S020 Isolated from the Saudi Coast of the Red Sea. Biomolecules. 12 September 2019, 9 (9). ISSN 2218-273X. doi:10.3390/biom9090480.
^ Terrein. Biomol GmbH - Life Science Shop （德语）.
^ Saki Nakagawa, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Satoshi Yamamoto, Hiroya Kobayashi, Hidefumi Sako, Kyosuke Sakaida, Hiroshi Yoshimura, Satoki Ishii, Soichiro Ibaragi, Kimito Hirai, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba. The fungal metabolite (+)-terrein abrogates osteoclast differentiation via suppression of the RANKL signaling pathway through NFATc1. International Immunopharmacology. 2020-06, 83: 106429 [2021-03-17]. doi:10.1016/j.intimp.2020.106429 （英语）.
^ Hiroki Mandai, Kazuhiro Omori, Daisuke Yamamoto, Toki Tsumura, Kyouta Murota, Satoshi Yamamoto, Koichi Mitsudo, Soichiro Ibaragi, Akira Sasaki, Hiroshi Maeda, Shogo Takashiba, Seiji Suga. Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts. Bioorganic & Medicinal Chemistry. 2014-10, 22 (19): 5338–5344 [2021-03-17]. doi:10.1016/j.bmc.2014.07.047. （原始内容存档于2020-02-28）（英语）.

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[1] E. L. Ghisalberti, M. J. Narbey, C. Y. Rowland. Metabolites of Aspergillus terreus Antagonistic Towards the Take-all Fungus. Journal of Natural Products. 1990-03, 53 (2): 520–522 [2021-03-17]. ISSN 0163-3864. doi:10.1021/np50068a043 （英语）.

[Terrain-2] 2.0 ^2.1 ^2.2 ^2.3 Asfour, Hani Z.; Awan, Zuhier A.; Bagalagel, Alaa A.; Elfaky, Mahmoud A.; Abdelhameed, Reda F. A.; Elhady, Sameh S. Large-Scale Production of Bioactive Terrein by Aspergillus terreus Strain S020 Isolated from the Saudi Coast of the Red Sea. Biomolecules. 12 September 2019, 9 (9). ISSN 2218-273X. doi:10.3390/biom9090480.

[3] Terrein. Biomol GmbH - Life Science Shop （德语）.

[4] Saki Nakagawa, Kazuhiro Omori, Masaaki Nakayama, Hiroki Mandai, Satoshi Yamamoto, Hiroya Kobayashi, Hidefumi Sako, Kyosuke Sakaida, Hiroshi Yoshimura, Satoki Ishii, Soichiro Ibaragi, Kimito Hirai, Keisuke Yamashiro, Tadashi Yamamoto, Seiji Suga, Shogo Takashiba. The fungal metabolite (+)-terrein abrogates osteoclast differentiation via suppression of the RANKL signaling pathway through NFATc1. International Immunopharmacology. 2020-06, 83: 106429 [2021-03-17]. doi:10.1016/j.intimp.2020.106429 （英语）.

[5] Hiroki Mandai, Kazuhiro Omori, Daisuke Yamamoto, Toki Tsumura, Kyouta Murota, Satoshi Yamamoto, Koichi Mitsudo, Soichiro Ibaragi, Akira Sasaki, Hiroshi Maeda, Shogo Takashiba, Seiji Suga. Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts. Bioorganic & Medicinal Chemistry. 2014-10, 22 (19): 5338–5344 [2021-03-17]. doi:10.1016/j.bmc.2014.07.047. （原始内容存档于2020-02-28）（英语）.

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土曲霉酮

IUPAC名 (4S,5R)-4,5-Dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
识别
CAS号	582-46-7 ^Y
PubChem	6436830
ChemSpider	4941440
SMILES	C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O
InChI	1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1
InChIKey	MHOOPNKRBMHHEC-HZIBQTDNSA-N
性质
化学式	C₈H₁₀O₃
摩尔质量	154.16 g·mol⁻¹
熔点	125—127 °C（398—400 K）^[1]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。