白僵菌素

白僵菌素
	IUPAC名; (3S,6R,9S,12R,15S,18R)-3,9,15-Tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
别名	白僵菌毒素
识别
CAS号	26048-05-5
PubChem	3007984
ChemSpider	2277520
SMILES	O=C1N(C)[C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H]1C(C)C)Cc2ccccc2)C)C(C)C)Cc3ccccc3)C)C(C)C)Cc4ccccc4;
InChI	1/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1;
InChIKey	GYSCAQFHASJXRS-FFCOJMSVBB
ChEBI	3000
KEGG	C11590
性质
化学式	C45H57N3O9
摩尔质量	783.95 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

白僵菌素（英語：Beauvericin）是一种具有抗生素和杀虫剂性质的酯肽（缩酚酸肽），隶属于恩镰孢菌素（英语：enniatin）家族。其最早从球孢白僵菌（英语：Beauveria bassiana）（Beauveria bassiana）中分离得到，包括几种镰孢菌在内的其他真菌也会产生白僵菌素^[1]^[2]。其一般出现在受这些真菌污染的谷物中，如玉米、小麦、大麦等^[2]^[3]^[4]。白僵菌素对革兰氏阳性菌和分枝杆菌有抑制活性，也能诱导哺乳动物细胞的程序性死亡^[2]。

从化学结构上看，白僵菌素是一种环状六酯肽，由N-甲基-苯丙氨酰基和D-羟基-异戊酰基交替连接得到。其可与金属离子配位，可与碱金属和碱土金属离子螯合并透过细胞膜^{[來源請求]}。

白僵菌素与抗真菌药物酮康唑联合使用（剂量为 0.1 μg/ml）对近平滑念珠菌（英语：Candida parapsilosis）（Candida parapsilosis）具有体外杀菌作用。在小鼠模型中也显示出提高存活率和低毒性的特性^[5]。

参考文献

^ Hamill RL, Higgens CE, Boaz HE, Gorman M. The structure of beauvericin, a new depsipeptide antibiotic toxic to Artemia salina. Tetrahedron Letters. 1969, 10 (49): 4255–4258. doi:10.1016/S0040-4039(01)88668-8.
^ ^2.0 ^2.1 ^2.2 Logrieco A, Moretti A, Castella G, et al. Beauvericin Production by Fusarium Species. Appl Environ Microbiol. 1998, 64 (8): 3084–8. Bibcode:1998ApEnM..64.3084L. PMC 106821  . PMID 9687479. doi:10.1128/AEM.64.8.3084-3088.1998.
^ Logrieco A, Rizzo A, Ferracane R, Ritieni A. Occurrence of Beauvericin and Enniatins in Wheat Affected by Fusarium avenaceum Head Blight. Appl Environ Microbiol. 2002, 68 (1): 82–5. Bibcode:2002ApEnM..68...82L. PMC 126553  . PMID 11772612. doi:10.1128/AEM.68.1.82-85.2002.
^ Jestoi M, Rokka M, Yli-Mattila T, Parikka P, Rizzo A, Peltonen K. Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples. Food Additives and Contaminants. 2004, 21 (8): 794–802. PMID 15370831. S2CID 19565366. doi:10.1080/02652030410001713906.
^ Zhang L; Yan K; Zhang Y; Huang R; Bian J; Zheng C; Sun H; Chen Z; Sun N; An R; Min F; Zhao W; Zhuo Y; You J; Song Y; Yu Z; Liu Z; Yang K; Gao H; Dai H; Zhang X; Wang J; Fu C; Pei G; Liu J; Zhang S; Goodfellow M; Jiang Y; Kuai J; Zhou G; Chen X.K. High-throughput synergy screening identifies microbial metabolites as combination agents for the treatment of fungal infections. Proc Natl Acad Sci U S A. 2007, 104 (11): 4606–11. Bibcode:2007PNAS..104.4606Z. PMC 1838648  . PMID 17360571. doi:10.1073/pnas.0609370104  .

[1] Hamill RL, Higgens CE, Boaz HE, Gorman M. The structure of beauvericin, a new depsipeptide antibiotic toxic to Artemia salina. Tetrahedron Letters. 1969, 10 (49): 4255–4258. doi:10.1016/S0040-4039(01)88668-8.

[PMID_9687479-2] 2.0 ^2.1 ^2.2 Logrieco A, Moretti A, Castella G, et al. Beauvericin Production by Fusarium Species. Appl Environ Microbiol. 1998, 64 (8): 3084–8. Bibcode:1998ApEnM..64.3084L. PMC 106821  . PMID 9687479. doi:10.1128/AEM.64.8.3084-3088.1998.

[3] Logrieco A, Rizzo A, Ferracane R, Ritieni A. Occurrence of Beauvericin and Enniatins in Wheat Affected by Fusarium avenaceum Head Blight. Appl Environ Microbiol. 2002, 68 (1): 82–5. Bibcode:2002ApEnM..68...82L. PMC 126553  . PMID 11772612. doi:10.1128/AEM.68.1.82-85.2002.

[4] Jestoi M, Rokka M, Yli-Mattila T, Parikka P, Rizzo A, Peltonen K. Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples. Food Additives and Contaminants. 2004, 21 (8): 794–802. PMID 15370831. S2CID 19565366. doi:10.1080/02652030410001713906.

[5] Zhang L; Yan K; Zhang Y; Huang R; Bian J; Zheng C; Sun H; Chen Z; Sun N; An R; Min F; Zhao W; Zhuo Y; You J; Song Y; Yu Z; Liu Z; Yang K; Gao H; Dai H; Zhang X; Wang J; Fu C; Pei G; Liu J; Zhang S; Goodfellow M; Jiang Y; Kuai J; Zhou G; Chen X.K. High-throughput synergy screening identifies microbial metabolites as combination agents for the treatment of fungal infections. Proc Natl Acad Sci U S A. 2007, 104 (11): 4606–11. Bibcode:2007PNAS..104.4606Z. PMC 1838648  . PMID 17360571. doi:10.1073/pnas.0609370104  .

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白僵菌素


IUPAC名 (3S,6R,9S,12R,15S,18R)-3,9,15-Tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
别名	白僵菌毒素
识别
CAS号	26048-05-5 ^Y
PubChem	3007984
ChemSpider	2277520
SMILES	O=C1N(C)[C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H]1C(C)C)Cc2ccccc2)C)C(C)C)Cc3ccccc3)C)C(C)C)Cc4ccccc4
InChI	1/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1
InChIKey	GYSCAQFHASJXRS-FFCOJMSVBB
ChEBI	3000
KEGG	C11590
性质
化学式	C₄₅H₅₇N₃O₉
摩尔质量	783.95 g·mol⁻¹
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。