異煙棒麴黴素C

異煙棒麴黴素C
	IUPAC名; (3E,5aS,10bR,11aS)-3-[(1H-Imidazol-5-yl)methylidene]-10b-(2-methylbut-3-en-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
識別
CAS號	58735-64-1 [PubChem]
PubChem	21608802
ChemSpider	10246629
SMILES	CC(C)(C=C)[C@@]12C[C@H]3C(=O)N/C(=C/c4cnc[nH]4)/C(=O)N3[C@@H]1Nc5c2cccc5;
InChI	1/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+/t17-,20-,22+/m0/s1;
InChIKey	SPWSUFUPTSJWNG-JJUKSXGLBA
性質
化學式	C22H23N5O2
莫耳質量	389.5 g·mol⁻¹
外觀	白色或灰白色固態
溶解性（水）	溶於乙醇、甲醇、DMF、DMSO
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

異煙棒麴黴素C（英語：Roquefortine C）是一種真菌毒素，是一種天然2,5-哌嗪二酮（英語：2,5-Diketopiperazine）衍生物^[1]。其由不同真菌產生，特別是青黴菌菌種^[2]。其最初從羅克福青黴菌中提取得到，這種菌種在商業上常被用作藍紋奶酪、洛克福奶酪、丹麥藍奶酪、斯蒂爾頓奶酪和戈貢佐拉奶酪成熟過程中的蛋白水解酶和脂肪分解酶的來源。

異煙棒麴黴素C是一種環狀二肽，從哌嗪二酮環（色氨酸-脫氫組氨酸）二肽結構母體衍生得到，是幾種青黴菌中常見的代謝產物。其被視為飲料、啤酒、紅酒、肉、奶酪和麵包中一種真菌污染物^[3]。高濃度的異煙棒麴黴素C被歸類為有毒化合物^[4]，特別是其具有強神經毒性^[5]^[6]。義大利研究學者發在義大利本土奶酪中一般含有0.05至1.47 mg/kg異煙棒麴黴素C，但認為該含量範圍「對消費者是安全的」^[7]。研究人員通過研究其與哺乳動物的細胞色素P450酶的相互作用，其毒性機理和代謝過程得以知曉^[4]。此外，異煙棒麴黴素C還對革蘭氏陽性菌展現出抑菌活性^[8]，但僅限於含有血紅素蛋白（英語：Hemoprotein）的菌類^[4]^[9]。

異煙棒麴黴素C含有不常見的E-脫氫組氨酸殘基，這使得其在酸性、鹼性以及光照條件下容易異構化成其異構體異異煙棒麴黴素C（isoroquefortine C），即連接在2,5-哌嗪二酮環上的雙鍵從E構型變成Z構型^[10]。

其異構體不同於天然產生的異煙棒麴黴素C，在自然界中並不存在，且不能與鐵離子結合。但兩者均可以通過人工合成得到^[10]。

參考文獻

^ Borthwick AD. 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products. Chemical Reviews. 2012, 112 (7): 3641–3716. PMID 22575049. doi:10.1021/cr200398y.
^ Kokkonen M, Jestoi M, Rizzo A. The effect of substrate on mycotoxin production of selected Penicillium strains. International Journal of Food Microbiology. 2005, 99 (2): 207–14. PMID 15734568. doi:10.1016/j.ijfoodmicro.2004.08.014.
^ Borthwick AD, Da Costa NC. 2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity. Critical Reviews in Food Science and Nutrition. 2017, 57 (4): 718–742. PMID 25629623. S2CID 1334464. doi:10.1080/10408398.2014.911142.
^ ^4.0 ^4.1 ^4.2 Aninat C, Hayashi Y, André F, Delaforge M. Molecular requirements for inhibition of cytochrome P450 activities by roquefortine. Chemical Research in Toxicology. July 2001, 14 (9): 1259–1265. PMID 11559041. doi:10.1021/tx015512l.
^ SCBT. Roquefortine - A potent neurotoxin produced most notably by Penicillium species. [2024-07-25]. （原始內容存檔於2016-03-16）.
^ EPA. Penicillium roqueforti Final Risk Assessment. [2024-07-25]. （原始內容存檔於2015-09-24）.
^ Finoli C, Vecchio A, Galli A, Dragoni I. Roquefortine C occurrence in blue cheese.. J. Food Prot. February 2001, 64 (2): 246–51. PMID 11271775. doi:10.4315/0362-028x-64.2.246 .
^ Kopp-Holtwiesche B, Rehm HJ. Antimicrobial action of roquefortine. Journal of Environmental Pathology, Toxicology and Oncology. December 1989, 10 (1–2): 41–44. PMID 2231314.
^ Aninat C, Andre F, Delaforge M. Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity. Food Additives and Contaminants. April 2005, 22 (4): 361–368. PMID 16019806. S2CID 9880652. doi:10.1080/02652030500073287.
^ ^10.0 ^10.1 Shangguan N, Hehre WJ, Ohlinger WS, Beavers MP, Joullie MM. The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C. Journal of the American Chemical Society. April 2008, 130 (19): 6281–6287. PMID 18412344. doi:10.1021/ja800067q.

[1] Borthwick AD. 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products. Chemical Reviews. 2012, 112 (7): 3641–3716. PMID 22575049. doi:10.1021/cr200398y.

[pmid15734568-2] Kokkonen M, Jestoi M, Rizzo A. The effect of substrate on mycotoxin production of selected Penicillium strains. International Journal of Food Microbiology. 2005, 99 (2): 207–14. PMID 15734568. doi:10.1016/j.ijfoodmicro.2004.08.014.

[pmid25629623-3] Borthwick AD, Da Costa NC. 2,5-Diketopiperazines in Food and Beverages: Taste and Bioactivity. Critical Reviews in Food Science and Nutrition. 2017, 57 (4): 718–742. PMID 25629623. S2CID 1334464. doi:10.1080/10408398.2014.911142.

[pmid111559041-4] 4.0 ^4.1 ^4.2 Aninat C, Hayashi Y, André F, Delaforge M. Molecular requirements for inhibition of cytochrome P450 activities by roquefortine. Chemical Research in Toxicology. July 2001, 14 (9): 1259–1265. PMID 11559041. doi:10.1021/tx015512l.

[5] SCBT. Roquefortine - A potent neurotoxin produced most notably by Penicillium species. [2024-07-25]. （原始內容存檔於2016-03-16）.

[6] EPA. Penicillium roqueforti Final Risk Assessment. [2024-07-25]. （原始內容存檔於2015-09-24）.

[7] Finoli C, Vecchio A, Galli A, Dragoni I. Roquefortine C occurrence in blue cheese.. J. Food Prot. February 2001, 64 (2): 246–51. PMID 11271775. doi:10.4315/0362-028x-64.2.246 .

[pmid2231314-8] Kopp-Holtwiesche B, Rehm HJ. Antimicrobial action of roquefortine. Journal of Environmental Pathology, Toxicology and Oncology. December 1989, 10 (1–2): 41–44. PMID 2231314.

[pmid16019806-9] Aninat C, Andre F, Delaforge M. Oxidative metabolism by P450 and function coupling to efflux systems: modulation of mycotoxin toxicity. Food Additives and Contaminants. April 2005, 22 (4): 361–368. PMID 16019806. S2CID 9880652. doi:10.1080/02652030500073287.

[pmid18412344-10] 10.0 ^10.1 Shangguan N, Hehre WJ, Ohlinger WS, Beavers MP, Joullie MM. The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C. Journal of the American Chemical Society. April 2008, 130 (19): 6281–6287. PMID 18412344. doi:10.1021/ja800067q.

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參考文獻