| 词条 | Stephacidin |
| 释义 |
Stephacidin A and B are antitumor alkaloids isolated from the fungus Aspergillus ochraceus [1] that belong to a class of naturally occurring 2,5-diketopiperazines.[2] This unusual family of fungal metabolites are complex bridged 2,5-diketopiperazine alkaloids that possess a unique bicyclo[2.2.2]diazaoctane core ring system and are constituted mainly from tryptophan, proline, and substituted proline derivatives where the olefinic unit of the isoprene moiety has been formally oxidatively cyclized across the α-carbon atoms of a 2,5-diketopiperazine ring. The molecular architecture of stephacidin B, formally a dimer of avrainvillamide, reveals a complex dimeric prenylated N-hydroxyindole alkaloid that contains 15 rings and 9 stereogenic centers and is one of the most complex indole alkaloids isolated from fungi. Stephacidin B rapidly converts into the electrophilic monomer avrainvillamide in cell culture, and there is evidence that the monomer avrainvillamide interacts with intracellular thiol-containing proteins, most likely by covalent modification.[3] Avrainvillamide, which contains a 3-alkylidene-3H-indole 1-oxide function, was identified in culture media from various strains of Aspergillus and is reported to exhibit antimicrobial activity against multidrug-resistant bacteria.[4]The avrainvillamide and stephacidins family of structurally complex anticancer natural products are active against the human colon HCT 116 cell line.[5] The signature bicyclo[2.2.2]diazaoctane ring system common to these alkaloids has inspired numerous synthetic approaches.[6] References1. ^{{cite journal |vauthors=Qian-Cutrone J, Huang S, Shu YZ, Vyas D, Fairchild C, Menendez A, Krampitz K, Dalterio R, Klohr SE, Gao Q | title = Stephacidin A and B: two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells | journal = Journal of the American Chemical Society | volume = 124 | issue = 49 | pages = 14556–14557 | date= December 2002 | pmid = 12465964 | doi = 10.1021/ja028538n | url = }} 2. ^{{Cite journal | title = 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products | author = Borthwick AD | journal = Chemical Reviews | year = 2012 | volume = 112 | issue = 7 | pages = 3641–3716 | doi = 10.1021/cr200398y | pmid = 22575049}} 3. ^{{cite journal |vauthors=Wulff JE, Herzon SB, Siegrist R, Myers AG | title = Evidence for the rapid conversion of stephacidin B into the electrophilic monomer avrainvillamide in cell culture | journal = Journal of the American Chemical Society | volume = 129 | issue = 16 | pages = 4898–4899 | date= April 2007 | pmid = 17397160 | doi = 10.1021/ja0690971 | pmc=3175819}} 4. ^{{cite journal |vauthors=Sugie Y, Hirai H, Inagaki T, Ishiguro M, Kim YJ, Kojima Y, Sakakibara T, Sakemi S, Sugiura A, Suzuki Y, Brennan L | title = A new antibiotic CJ-17,665 from Aspergillus ochraceus | journal = The Journal of Antibiotics | volume = 54 | issue = 11 | pages = 911–916 | date= 2001 | pmid = 11827033 | doi = 10.7164/antibiotics.54.911 | url = }} 5. ^{{cite journal |vauthors=Baran PS, Hafensteiner BD, Ambhaikar NB, Guerrero CA, Gallagher JD | title = Enantioselective total synthesis of avrainvillamide and the stephacidins | journal = Journal of the American Chemical Society | volume = 128 | issue = 26 | pages = 8678–8693 | date= July 2006 | pmid = 16802835 | doi = 10.1021/ja061660s | url = }} 6. ^{{cite journal | author = Escolano C | title = Stephacidin B, the avrainvillamide dimer: A formidable synthetic challenge | journal = Angewandte Chemie International Edition | volume = 44 | issue = 47 | pages = 7670–7673 | date= December 2005 | pmid = 16252300 | doi = 10.1002/anie.200502383 | url = }} External links
2 : Diketopiperazines|Alkaloids |
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