傘菌氨酸

傘菌氨酸
	IUPAC名; 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide
識別
縮寫	AGT
CAS號	2757-90-6
PubChem	17688; 439517（(2S)-2-amino）; 439516
ChemSpider	388610
SMILES	[O-]C(=O)[C@@H]([NH3+])CCC(=O)NNc1ccc(cc1)CO;
InChI	1/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1;
InChIKey	SRSPQXBFDCGXIZ-JTQLQIEIBZ
Beilstein	757731
ChEBI	15336
RTECS	MA1284000
KEGG	C01550
MeSH	Agaritine
性質
化學式	C12H17N3O4
摩爾質量	267.28 g·mol−1
熔點	203 °C（476 K）
pKa	3.4
危險性
主要危害	有毒
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

傘菌氨酸（英語：Agaritine，AGT），是一種存在於傘菌屬真菌中的芳香聯氨類真菌毒素^[1]。其為α-氨基酸的苯肼衍生物。

分佈

傘菌氨酸作為一種天然產物，其存在於傘菌屬、白環蘑屬和大環柄菇屬下至少24種的新鮮蘑菇中^[1]^[2]。而且這類物種在世界廣泛分佈^[3]。特別是全球都有種植的雙孢蘑菇也含有傘菌氨酸^[4]。

不同物種以及蘑菇不同部位間的傘菌氨酸含量也不相同^[2]。例如，在生孢蘑菇中，傘菌氨酸的含量（鮮重）介於0.033%與0.173%之間^[5]，在菌蓋和菌褶中最高，在菌柄中最低^[6]。傘菌氨酸在蘑菇儲存過程中會迅速氧化。在提取過程中，傘菌氨酸水溶液接觸到水和甲醇48小時後會完全降解^[7]。在蘑菇烹飪過程（可減少90%）和冰凍過程（可減少75%）也會發生降解^[8]。

製備與合成

傘菌氨酸可從種植的雙孢蘑菇中用水或甲醇提取^[1]。

傘菌氨酸也可以通過全合成得到，總收率為33%^[9]。

潛在毒性

儘管在高劑量下時，傘菌氨酸被認為是一種實驗性致癌物，但沒有證據表明在食用蘑菇引起的攝入量對人體產生致癌性^[1]。

參考文獻

^ ^1.0 ^1.1 ^1.2 ^1.3 Agaritine. PubChem, US National Library of Medicine. 24 July 2021 [27 July 2021].
^ ^2.0 ^2.1 Schulzová, V.; Hajslova, J.; Peroutka, R.; Hlavasek, J.; Gry, J.; Andersson, H.C. Agaritine content of 53 Agaricus species collected from nature (PDF). Food Additives & Contaminants: Part A. 2009, 26 (1): 82–93. PMID 19680875. S2CID 427230. doi:10.1080/02652030802039903.
^ Rinaldi, Augusto; Tyndalo, Vassili; Maggiora, Laura Rosano. The complete book of mushrooms : over 1,000 species and varieties of American, European, and Asiatic mushrooms. Crown Publishers. 1974. ISBN 978-0-517-51493-1. ^{[頁碼請求]}
^ Hayes, W. A.; Chang, S. T. The Biology and cultivation of edible mushrooms. Academic Press. 1978. ISBN 978-0-12-168050-3. ^{[頁碼請求]}
^ Liu, J.-W.; Beelman, R. B.; Lineback, D. R.; Speroni, J. J. Agaritine Content of Fresh and Processed Mushrooms [Agaricus bisporus (Lange) Imbach]. Journal of Food Science. 1982, 47 (5): 1542–4. doi:10.1111/j.1365-2621.1982.tb04978.x.
^ Ross, A.E.; Nagel, D.L.; Toth, B. Occurrence, stability and decomposition of β-n[γ-l( + )-glutamyl]-4-hydroxymethylphenylhydrazine (agaritine) from the mushroom Agaricus bisporus. Food and Chemical Toxicology. 1982, 20 (6): 903–7. PMID 6131022. doi:10.1016/S0015-6264(82)80226-5.
^ Hajšlová, J.; Hájková, L.; Schulzová, V.; Frandsen, H.; Gry, J.; Andersson, H. C. Stability of agaritine - a natural toxicant ofAgaricusmushrooms. Food Additives and Contaminants. 2002, 19 (11): 1028–33. PMID 12456273. S2CID 19357429. doi:10.1080/02652030210157691.
^ Schulzová, V.; Hajslová, J.; Peroutka, R.; Gry, J.; Andersson, H. C. Influence of storage and household processing on the agaritine content of the cultivated Agaricus mushroom. Food Additives and Contaminants. 2002, 19 (9): 853–62. PMID 12396396. S2CID 23953741. doi:10.1080/02652030210156340.
^ Datta, Subir; Hoesch, Lienhard. Novel Synthesis of Agaritine, a 4-Hydrazinobenzyl-Alcohol Derivative Occurring in Agaricaceae. Helvetica Chimica Acta. 1987, 70 (5): 1261–7. doi:10.1002/hlca.19870700505.

[pubchem-1] 1.0 ^1.1 ^1.2 ^1.3 Agaritine. PubChem, US National Library of Medicine. 24 July 2021 [27 July 2021].

[one-2] 2.0 ^2.1 Schulzová, V.; Hajslova, J.; Peroutka, R.; Hlavasek, J.; Gry, J.; Andersson, H.C. Agaritine content of 53 Agaricus species collected from nature (PDF). Food Additives & Contaminants: Part A. 2009, 26 (1): 82–93. PMID 19680875. S2CID 427230. doi:10.1080/02652030802039903.

[two-3] Rinaldi, Augusto; Tyndalo, Vassili; Maggiora, Laura Rosano. The complete book of mushrooms : over 1,000 species and varieties of American, European, and Asiatic mushrooms. Crown Publishers. 1974. ISBN 978-0-517-51493-1. ^{[頁碼請求]}

[three-4] Hayes, W. A.; Chang, S. T. The Biology and cultivation of edible mushrooms. Academic Press. 1978. ISBN 978-0-12-168050-3. ^{[頁碼請求]}

[four-5] Liu, J.-W.; Beelman, R. B.; Lineback, D. R.; Speroni, J. J. Agaritine Content of Fresh and Processed Mushrooms [Agaricus bisporus (Lange) Imbach]. Journal of Food Science. 1982, 47 (5): 1542–4. doi:10.1111/j.1365-2621.1982.tb04978.x.

[five-6] Ross, A.E.; Nagel, D.L.; Toth, B. Occurrence, stability and decomposition of β-n[γ-l( + )-glutamyl]-4-hydroxymethylphenylhydrazine (agaritine) from the mushroom Agaricus bisporus. Food and Chemical Toxicology. 1982, 20 (6): 903–7. PMID 6131022. doi:10.1016/S0015-6264(82)80226-5.

[six-7] Hajšlová, J.; Hájková, L.; Schulzová, V.; Frandsen, H.; Gry, J.; Andersson, H. C. Stability of agaritine - a natural toxicant ofAgaricusmushrooms. Food Additives and Contaminants. 2002, 19 (11): 1028–33. PMID 12456273. S2CID 19357429. doi:10.1080/02652030210157691.

[seven-8] Schulzová, V.; Hajslová, J.; Peroutka, R.; Gry, J.; Andersson, H. C. Influence of storage and household processing on the agaritine content of the cultivated Agaricus mushroom. Food Additives and Contaminants. 2002, 19 (9): 853–62. PMID 12396396. S2CID 23953741. doi:10.1080/02652030210156340.

[twentyfive-9] Datta, Subir; Hoesch, Lienhard. Novel Synthesis of Agaritine, a 4-Hydrazinobenzyl-Alcohol Derivative Occurring in Agaricaceae. Helvetica Chimica Acta. 1987, 70 (5): 1261–7. doi:10.1002/hlca.19870700505.

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傘菌氨酸


IUPAC名 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide
識別
縮寫	AGT
CAS號	2757-90-6 ^Y
PubChem	17688 439517（(2S)-2-amino） 439516
ChemSpider	388610
SMILES	[O-]C(=O)[C@@H]([NH3+])CCC(=O)NNc1ccc(cc1)CO
InChI	1/C12H17N3O4/c13-10(12(18)19)5-6-11(17)15-14-9-3-1-8(7-16)2-4-9/h1-4,10,14,16H,5-7,13H2,(H,15,17)(H,18,19)/t10-/m0/s1
InChIKey	SRSPQXBFDCGXIZ-JTQLQIEIBZ
Beilstein	757731
ChEBI	15336
RTECS	MA1284000
KEGG	C01550
MeSH	Agaritine
性質
化學式	C₁₂H₁₇N₃O₄
摩爾質量	267.28 g·mol⁻¹
熔點	203 °C（476 K）
pK_a	3.4
危險性
主要危害	有毒
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。