丰原素

丰原素
	IUPAC名; (4S)-5-[[(2R)-5-amino-1-[[(4S,7S,10S,13S,19R,22S,25S,28R)-10-(3-amino-3-oxopropyl)-4-[(2R)-butan-2-yl]-22-(2-carboxyethyl)-25-[(1S)-1-hydroxyethyl]-7-[(4-hydroxyphenyl)methyl]-19-methyl-3,6,9,12,18,21,24,27-octaoxo-2-oxa-5,8,11,17,20,23,26-heptazatricyclo[28.2.2.013,17]tetratriaconta-1(33),30(34),31-trien-28-yl]amino]-1-oxopentan-2-yl]amino]-4-(3-hydroxyhexadecanoylamino)-5-oxopentanoic acid
识别
CAS号	102577-03-7
PubChem	443591
ChemSpider	35518574
SMILES	CCCCCCCCCCCCCC(CC(=O)NC(CCC(=O)O)C(=O)NC(CCCN)C(=O)NC1CC2=CC=C(C=C2)OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C3CCCN3C(=O)C(NC(=O)C(NC(=O)C(NC1=O)C(C)O)CCC(=O)O)C)CCC(=O)N)CC4=CC=C(C=C4)O)C(C)CC)O;
InChIKey	CUOJDWBMJMRDHN-RLLVTFBRSA-N
KEGG	C12042
性质
化学式	C72H110N12O20
摩尔质量	1,462.795934 g·mol⁻¹
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

丰原素（Fengycin）为一种具有抗菌活性的脂多肽。

结构

丰原素属于脂多肽，由β-羟基脂肪酸连结于10颗氨基酸组成的多肽上，其中含有一颗由八颗氨基酸组成的环^[1]。

功能

丰原素具有抑制丝状真菌的功能^[1]。有研究显示，鼻腔及肠道拥有芽孢杆菌属菌丛的个体，检体中的金黄色葡萄球菌较少，推论可能与芽孢杆菌属会分泌丰原素等抑菌物质相关^[2]。

作用机转

丰原素可干扰金黄色葡萄球菌的群聚感应系统，可与自诱导肽（Agr autoinducing-peptide，AIP）竞争AgrC的胞外结合域，进而抑制葡萄球菌移生的能力^[2]。

历史

1977年，台湾中兴大学陈昇明教授在台中县丰原市郊（今台中市丰原区）的马铃薯田中筛选出一株具有抑制立枯丝核菌（Rizoctonia solani）功能的枯草杆菌（Bacillus subtilis），菌株编号定为“F29-3”^[3]^[4]。在经过分析后发现，枯草杆菌F29-3除了具有抑制立枯丝核菌的功能之外，也能抑制其他丝状真菌、细菌，和酵母菌。进一步分析后发现两种抗菌物质，分别命名为“Bacilysin”及“丰原素”（Fengycin）两种抗菌物质^[5]

参考文献

^ ^1.0 ^1.1 Deleu, Magali; Paquot, Michel; Nylander, Tommy. Fengycin interaction with lipid monolayers at the air–aqueous interface—implications for the effect of fengycin on biological membranes. Journal of Colloid and Interface Science. 2005-03-15, 283 (2): 358–365. ISSN 0021-9797. doi:10.1016/j.jcis.2004.09.036 （英语）.
^ ^2.0 ^2.1 Piewngam, Pipat; Zheng, Yue; Nguyen, Thuan H.; Dickey, Seth W.; Joo, Hwang-Soo; Villaruz, Amer E.; Glose, Kyle A.; Fisher, Emilie L.; Hunt, Rachelle L. Pathogen elimination by probiotic Bacillus via signalling interference. Nature. 2018-10, 562 (7728): 532–537 [2020-02-13]. ISSN 1476-4687. doi:10.1038/s41586-018-0616-y. （原始内容存档于2019-11-09）（英语）.
^ Tschen, J. & J.-M. Liu:. Nocardia sp. as antagonists to Rhizoctonia solani.. Plant Protection Bulletin. 1977, 19: 301.
^ Tschen, J. & J.-M. Liu:. Antagonistic effects of Nocardia sp. on Rhizoctonia solani.. 3rd International Congress of Plant Pathology: Abstracts (Miinchen). 1978: 187.
^ Vanittanakom, Nongnuch; Loeffler, Wolfgang; Koch, Ulrike; Jung, Günther. Fengycin - A novel antifungal lipopeptide antibiotic produced by Bacillus subtilis F-29-3.. The Journal of Antibiotics. 1986, 39 (7): 888–901. ISSN 0021-8820. doi:10.7164/antibiotics.39.888 （英语）.

[:0-1] 1.0 ^1.1 Deleu, Magali; Paquot, Michel; Nylander, Tommy. Fengycin interaction with lipid monolayers at the air–aqueous interface—implications for the effect of fengycin on biological membranes. Journal of Colloid and Interface Science. 2005-03-15, 283 (2): 358–365. ISSN 0021-9797. doi:10.1016/j.jcis.2004.09.036 （英语）.

[:1-2] 2.0 ^2.1 Piewngam, Pipat; Zheng, Yue; Nguyen, Thuan H.; Dickey, Seth W.; Joo, Hwang-Soo; Villaruz, Amer E.; Glose, Kyle A.; Fisher, Emilie L.; Hunt, Rachelle L. Pathogen elimination by probiotic Bacillus via signalling interference. Nature. 2018-10, 562 (7728): 532–537 [2020-02-13]. ISSN 1476-4687. doi:10.1038/s41586-018-0616-y. （原始内容存档于2019-11-09）（英语）.

[3] Tschen, J. & J.-M. Liu:. Nocardia sp. as antagonists to Rhizoctonia solani.. Plant Protection Bulletin. 1977, 19: 301.

[4] Tschen, J. & J.-M. Liu:. Antagonistic effects of Nocardia sp. on Rhizoctonia solani.. 3rd International Congress of Plant Pathology: Abstracts (Miinchen). 1978: 187.

[5] Vanittanakom, Nongnuch; Loeffler, Wolfgang; Koch, Ulrike; Jung, Günther. Fengycin - A novel antifungal lipopeptide antibiotic produced by Bacillus subtilis F-29-3.. The Journal of Antibiotics. 1986, 39 (7): 888–901. ISSN 0021-8820. doi:10.7164/antibiotics.39.888 （英语）.

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丰原素

IUPAC名 (4S)-5-[[(2R)-5-amino-1-[[(4S,7S,10S,13S,19R,22S,25S,28R)-10-(3-amino-3-oxopropyl)-4-[(2R)-butan-2-yl]-22-(2-carboxyethyl)-25-[(1S)-1-hydroxyethyl]-7-[(4-hydroxyphenyl)methyl]-19-methyl-3,6,9,12,18,21,24,27-octaoxo-2-oxa-5,8,11,17,20,23,26-heptazatricyclo[28.2.2.013,17]tetratriaconta-1(33),30(34),31-trien-28-yl]amino]-1-oxopentan-2-yl]amino]-4-(3-hydroxyhexadecanoylamino)-5-oxopentanoic acid
识别
CAS号	102577-03-7
PubChem	443591
ChemSpider	35518574
SMILES	CCCCCCCCCCCCCC(CC(=O)NC(CCC(=O)O)C(=O)NC(CCCN)C(=O)NC1CC2=CC=C(C=C2)OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C3CCCN3C(=O)C(NC(=O)C(NC(=O)C(NC1=O)C(C)O)CCC(=O)O)C)CCC(=O)N)CC4=CC=C(C=C4)O)C(C)CC)O
InChIKey	CUOJDWBMJMRDHN-RLLVTFBRSA-N
KEGG	C12042
性质
化学式	C₇₂H₁₁₀N₁₂O₂₀
摩尔质量	1,462.795934 g·mol⁻¹
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。