土麴黴酮

土麴黴酮
	IUPAC名; (4S,5R)-4,5-Dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
識別
CAS號	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
性質
化學式	C8H10O3
摩爾質量	154.16 g·mol−1
熔點	125—127 °C（398—400 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

土麴黴酮是麴黴屬的一種真菌代謝產物，^[2]可以形成淺黃色的針狀晶體，^[2]^[3]它可以L-(+)-酒石酸二甲酯為原料合成得到。^[4]^[5]它對大腸癌的細胞由強細胞毒性。^[2]土麴黴的S020菌株的土麴黴酮的產率最高。^[2]

參考文獻

^ 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 （英語）.
^ ^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 （德語）.
^ 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 （英語）.
^ 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. （原始內容存檔於2020-02-28）（英語）.

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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 （英語）.

[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 （德語）.

[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 （英語）.

[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. （原始內容存檔於2020-02-28）（英語）.

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土麴黴酮

IUPAC名 (4S,5R)-4,5-Dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
識別
CAS號	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
性質
化學式	C₈H₁₀O₃
摩爾質量	154.16 g·mol⁻¹
熔點	125—127 °C（398—400 K）^[1]
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。