| 词条 | Dihydromaltophilin |
| 释义 |
| Name = | ImageFile = Heat-Stable Anti-fungal Factor (Dihydromaltophilin).svg | ImageSize = | ImageAlt = | OtherNames = Heat-Stable Anti-fungal Factor (HSAF) | IUPACName = (3E,5S,7S,8R,9S,10S,11S,13R,15R,16S,18Z)-11-Ethyl-7,24,28-trihydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.05,16.08,15.09,13]octacosa-1(28),3,18-triene-2,20,27-trione | SystematicName = (3E,5S,7S,8R,9S,13R,15R,16S)-11-Ethyl-7,28-dihydroxy-8,10-dimethyl-21,26-diazapentacyclo[23.2.1.0⁵,¹⁶.0⁸,¹⁵.0⁹,¹³]octacosa-1(28),3-diene-2,27-dione | Section1 = {{Chembox Identifiers | CASNo = 203304-22-7 | ChemSpiderID = 34227627 | Section2 = {{Chembox Properties | C=29|H=40|N=2|O=6 | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | Section4 = | Section5 = | Section6 = }}Dihydromaltophilin, or heat stable anti-fungal factor (HSAF), is a secondary metabolite of Streptomyces sp. and Lysobacter enzymogenes.[1][2][3] HSAF is a polycyclic tetramate lactam containing a single tetramic acid unit and a 5,5,6-tricyclic system. HSAF has been shown to have anti-fungal activity mediated through the disruption of the biosynthesis of Sphingolipid's by targeting a ceramide synthase unique to fungi.[2][3] BiosynthesisThe backbone of HSAF is formed through a hybrid PKS-NRPS cluster containing one nonribosomal peptide synthase (NRPS) module and one polyketide synthase (PKS) module.[4][5][8][6] The single PKS module functions in a non-canonical fashion in that it is an iterative type I PKS responsible for the generation of the two unique polyketides needed in the backbone of HSAF using malonyl-CoA as both the starter and extender unit, while the NRPS module is responsible for the linking of the polyketides to an L-ornithine unit and the initial cyclization to create the tetramate back bone.[4][7][6] The coding region related to HSAF production contains a PKS-NRPS with a total of 9 domains, (KS-AT-DH-KR-ACP-C-A-PCP-TE), while a cascade of FAD-dependent redox reactions (OX1-OX4) flank the PKS-NRPS cluster proposed to be responsible for formation of the 5,5,6-tricyclic system, there are additional coding regions for a putative regulator, an arginase for L-ornithine production from Arginine, and a transporter which flank the PKS-NRPS.[4][8][7][6] References1. ^{{Cite journal|last=Graupner|first=P. 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E.|date=1997|title=Dihydromaltophilin; a novel fungicidal tetramic acid containing metabolite from Streptomyces sp|journal=The Journal of Antibiotics|volume=50|issue=12|pages=1014–1019|issn=0021-8820|pmid=9510907|via=}} 2. ^{{Cite journal|last=Li|first=Shaojie|last2=Du|first2=Liangcheng|last3=Yuen|first3=Gary|last4=Harris|first4=Steven D.|date=2006|title=Distinct Ceramide Synthases Regulate Polarized Growth in the Filamentous Fungus Aspergillus nidulans|journal=Molecular Biology of the Cell|volume=17|issue=3|pages=1218–1227|doi=10.1091/mbc.E05-06-0533|issn=1059-1524|pmc=1382311|pmid=16394102|via=}} 3. ^{{Cite journal|last=Li|first=Shaojie|last2=Calvo|first2=Ana M.|last3=Yuen|first3=Gary Y.|last4=Du|first4=Liangcheng|last5=Harris|first5=Steven D.|date=2009|title=Induction of cell wall thickening by the antifungal compound dihydromaltophilin disrupts fungal growth and is mediated by sphingolipid biosynthesis|journal=The Journal of Eukaryotic Microbiology|volume=56|issue=2|pages=182–187|issn=1550-7408|pmid=21462551|via=}} 4. ^1 2 3 {{Cite journal|last=Xie|first=Yunxuan|last2=Wright|first2=Stephen|last3=Shen|first3=Yuemao|last4=Du|first4=Liangcheng|date=2012|title=Bioactive natural products from Lysobacter|journal=Natural Product Reports|volume=29|issue=11|pages=1277–1287|doi=10.1039/c2np20064c|issn=1460-4752|pmc=3468324|pmid=22898908|via=}} 5. ^{{Cite journal|last=Yu|first=Fengan|last2=Zaleta-Rivera|first2=Kathia|last3=Zhu|first3=Xiangcheng|last4=Huffman|first4=Justin|last5=Millet|first5=Jeffrey C.|last6=Harris|first6=Steven D.|last7=Yuen|first7=Gary|last8=Li|first8=Xing-Cong|last9=Du|first9=Liangcheng|date=2007-01-01|title=Structure and Biosynthesis of Heat-Stable Antifungal Factor (HSAF), a Broad-Spectrum Antimycotic with a Novel Mode of Action|url=http://aac.asm.org/content/51/1/64|journal=Antimicrobial Agents and Chemotherapy|language=en|volume=51|issue=1|pages=64–72|doi=10.1128/AAC.00931-06|issn=0066-4804|pmid=17074795|via=}} 6. ^1 2 {{Cite journal|last=Chen|first=Haotong|last2=Du|first2=Liangcheng|date=2014|title=Iterative polyketide biosynthesis by modular polyketide synthases in bacteria|journal=Applied Microbiology and Biotechnology|volume=100|issue=2|pages=541–557|doi=10.1007/s00253-015-7093-0|issn=1432-0614|pmc=4706475|pmid=26549236|via=}} 7. ^1 2 {{Cite journal|last=Li|first=Yaoyao|last2=Chen|first2=Haotong|last3=Ding|first3=Yanjiao|last4=Xie|first4=Yunxuan|last5=Wang|first5=Haoxin|last6=Cerny|first6=Ronald L.|last7=Shen|first7=Yuemao|last8=Du|first8=Liangcheng|date=2014-07-14|title=Iterative assembly of two separate polyketide chains by the same single-module bacterial polyketide synthase in the biosynthesis of HSAF|journal=Angewandte Chemie (International Ed. in English)|volume=53|issue=29|pages=7524–7530|doi=10.1002/anie.201403500|issn=1521-3773|pmc=4107061|pmid=24890524}} 8. ^1 {{Cite journal|last=Lou|first=Lili|last2=Qian|first2=Guoliang|last3=Xie|first3=Yunxuan|last4=Hang|first4=Jiliang|last5=Chen|first5=Haotong|last6=Zaleta-Rivera|first6=Kathia|last7=Li|first7=Yaoyao|last8=Shen|first8=Yuemao|last9=Dussault|first9=Patrick H.|date=2011-02-02|title=Biosynthesis of HSAF, a tetramic acid-containing macrolactam from Lysobacter enzymogenes|journal=Journal of the American Chemical Society|volume=133|issue=4|pages=643–645|doi=10.1021/ja105732c|issn=1520-5126|pmc=3078565|pmid=21171605}} 1 : Polyketides |
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