Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347.
A novel spirocyclic drimane coupled by two drimane fragment building blocks 2 and a new drimane 1 were identified in mycelia and culture broth of Stachybotrys sp. MF347. Their structures were established by spectroscopic means. This is the first example of spirocyclic drimane coupled by a spirodihydrobenzofuranlactam unit and a spirodihydroisobenzofuran unit; and the connecting position being N-C instead of an N and N connecting unit. Strain MF347 produced also the known spirocyclic drimanes stachybocin A (12) and stachybocin B (11) featured by two sesquiterpene-spirobenzofuran structural units connected by a lysine residue; the known spirocyclic drimanes chartarlactam O (5); chartarlactam K (6); F1839A (7); stachybotrylactam (8); stachybotramide (9); and 2α-acetoxystachybotrylactam acetate (10); as well as ilicicolin B (13), a known sesquiterpene. The relative configuration of two known spirobenzofuranlactams (3 and 4) was determined. All compounds were subjected to biological activity tests. The spirocyclic drimane 2, 11, and 12, as well as the sesquiterpene 13, exhibited antibacterial activity against the clinically relevant methicillin-resistant Staphylococcus aureus (MRSA).
Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz Zentrum für Ozeanforschung Kiel, Kiel 24105, Germany. wubin@zju.edu.cn.
Bin
B
Wu
Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz Zentrum für Ozeanforschung Kiel, Kiel 24105, Germany. vlutz@geomar.de.
Vanessa
V
Oesker
Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz Zentrum für Ozeanforschung Kiel, Kiel 24105, Germany. jwiese@geomar.de.
Jutta
J
Wiese
Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz Zentrum für Ozeanforschung Kiel, Kiel 24105, Germany. smalien@geomar.de.
Susann
S
Malien
Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz Zentrum für Ozeanforschung Kiel, Kiel 24105, Germany. rschmaljohann@geomar.de.
Rolf
R
Schmaljohann
Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz Zentrum für Ozeanforschung Kiel, Kiel 24105, Germany. jimhoff@geomar.de.
Johannes F
JF
Imhoff
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013057:Spectrum Analysis; D013191:Stachybotrys / Q000378:metabolism*
D000900:Anti-Bacterial Agents; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C437376:drimane