Isolation and Photoinduced Conversion of 6-epi-Stephacidins from Aspergillus taichungensis

Organic Letters
2013.0

Abstract

Three prenylated indole alkaloids with a rare anti bicyclo-[2.2.2]diazaoctane core ring (5-7) were isolated from Aspergillus taichungensis. The structures including absolute configurations were elucidated based on NMR, X-ray, and CD methods. (+)-Versicolamides B and C (8-9) which contain a spiro-center, together with seven analogues (7, 10-15), were isolated as photoinduced conversion products of 6. Biological evaluation indicated that 6 and 7 exhibited significant cytotoxicities with IC50 values in the low micromolar range.

Knowledge Graph

Similar Paper

Isolation and Photoinduced Conversion of 6-<i>epi</i>-Stephacidins from <i>Aspergillus taichungensis</i>
Organic Letters 2013.0
Aspertaichamide a, a novel cytotoxic prenylated indole alkaloid possessing a bicyclo[2.2.2]diazaoctane framework from a marine algal-derived endophytic fungus aspergillus taichungensis 299
Fitoterapia 2024.0
Taichunamides: Prenylated Indole Alkaloids from <i>Aspergillus taichungensis</i> (IBT 19404)
Angewandte Chemie International Edition 2016.0
Taichunamides: Prenylated Indole Alkaloids from <i>Aspergillus taichungensis</i> (IBT 19404)
Angewandte Chemie International Edition 2016.0
21-Epi-taichunamide D and (±)-versicaline A, three unusual alkaloids from the endophytic Aspergillus versicolor F210
Tetrahedron Letters 2020.0
HPLC-DAD-Directed Isolation of Linearly Fused Prenylated Indole Alkaloids from a Soil-Derived <i>Aspergillus versicolor</i>
Journal of Natural Products 2019.0
Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus <i>Aspergillus versicolor</i>
The Journal of Organic Chemistry 2018.0
Asperversiamides, Linearly Fused Prenylated Indole Alkaloids from the Marine-Derived Fungus <i>Aspergillus versicolor</i>
The Journal of Organic Chemistry 2018.0
Isolation, Structure Elucidation, and Biomimetic Total Synthesis of Versicolamide B, and the Isolation of Antipodal (−)‐Stephacidin A and (+)‐Notoamide B from Aspergillus versicolor NRRL 35600
Angewandte Chemie International Edition 2008.0
Versicoamides F–H, Prenylated Indole Alkaloids from <i>Aspergillus tennesseensis</i>
Organic Letters 2017.0