14-Norpseurotin A

14-Norpseurotin A is an alkaloid and a bio-active metabolite of Aspergillus, featuring an oxa-spiro-lactam core.[1][2][3]

14-Norpseurotin A
Names
Preferred IUPAC name
(5S,8S,9R)-8-Benzoyl-2-[(1S,2S,3Z)-1,2-dihydroxypent-3-en-1-yl]-9-hydroxy-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C21H23NO8/c1-4-8-13(23)14(24)15-11(2)16(25)20(30-15)18(27)21(29-3,22-19(20)28)17(26)12-9-6-5-7-10-12/h4-10,13-14,18,23-24,27H,1-3H3,(H,22,28)/b8-4-/t13-,14-,18+,20+,21+/m0/s1
    Key: FCGCMRDADMTJIM-LFDIKFNASA-N
  • C/C=C\[C@@H]([C@@H](C1=C(C(=O)[C@@]2(O1)[C@H]([C@@](NC2=O)(C(=O)C3=CC=CC=C3)OC)O)C)O)O
Properties
C21H23NO8
Molar mass 417.414 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Martínez-Luis S, Cherigo L, Arnold E, Spadafora C, Gerwick WH, Cubilla-Rios L (2012). "Antiparasitic and anticancer constituents of the endophytic fungus Aspergillus sp. strain F1544". Nat Prod Commun. 7 (2): 165–8. PMID 22474943.
  2. Ge HM, Yu ZG, Zhang J, Wu JH, Tan RX (2009). "Bioactive alkaloids from endophytic Aspergillus fumigatus". J Nat Prod. 72 (4): 753–5. doi:10.1021/np800700e. PMID 19256529.
  3. Zhang, Min; Wang, Wen-Liang; Fang, Yu-Chun; Zhu, Tian-Jiao; Gu, Qian-Qun; Zhu, Wei-Ming (2008). "Cytotoxic Alkaloids and Antibiotic Nordammarane Triterpenoids from the Marine-Derived FungusAspergillus sydowi". Journal of Natural Products. 71 (6): 985–989. doi:10.1021/np700737g. ISSN 0163-3864. PMID 18505285.


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