伞菌氨酸

伞菌氨酸
	IUPAC名; 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide
识别
缩写	AGT
CAS号	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
性质
化学式	C12H17N3O4
摩尔质量	267.28 g·mol−1
熔点	203 °C（476 K）
pKa	3.4
危险性
主要危害	有毒
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

伞菌氨酸（英語：Agaritine，AGT），是一种存在于伞菌属真菌中的芳香联氨类真菌毒素^[1]。其为α-氨基酸的苯肼衍生物。

分布

伞菌氨酸作为一种天然产物，其存在于伞菌属、白环蘑属和大环柄菇属下至少24种的新鲜蘑菇中^[1]^[2]。而且这类物种在世界广泛分布^[3]。特别是全球都有种植的双孢蘑菇也含有伞菌氨酸^[4]。

不同物种以及蘑菇不同部位间的伞菌氨酸含量也不相同^[2]。例如，在生孢蘑菇中，伞菌氨酸的含量（鲜重）介于0.033%与0.173%之间^[5]，在菌盖和菌褶中最高，在菌柄中最低^[6]。伞菌氨酸在蘑菇储存过程中会迅速氧化。在提取过程中，伞菌氨酸水溶液接触到水和甲醇48小时后会完全降解^[7]。在蘑菇烹饪过程（可减少90%）和冰冻过程（可减少75%）也会发生降解^[8]。

制备与合成

伞菌氨酸可从种植的双孢蘑菇中用水或甲醇提取^[1]。

伞菌氨酸也可以通过全合成得到，总收率为33%^[9]。

潜在毒性

尽管在高剂量下时，伞菌氨酸被认为是一种实验性致癌物，但没有证据表明在食用蘑菇引起的摄入量对人体产生致癌性^[1]。

参考文献

^ ^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. ^{[页码请求]}
^ Hayes, W. A.; Chang, S. T. The Biology and cultivation of edible mushrooms. Academic Press. 1978. ISBN 978-0-12-168050-3. ^{[页码请求]}
^ 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. ^{[页码请求]}

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

[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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伞菌氨酸


IUPAC名 2-[4-(Hydroxymethyl)phenyl]-glutamohydrazide
识别
缩写	AGT
CAS号	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
性质
化学式	C₁₂H₁₇N₃O₄
摩尔质量	267.28 g·mol⁻¹
熔点	203 °C（476 K）
pK_a	3.4
危险性
主要危害	有毒
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。