ol9b03796_si_001.pdf (2.11 MB)
(−)- and (+)-Asperginulin A, a Pair of Indole Diketopiperazine Alkaloid Dimers with a 6/5/4/5/6 Pentacyclic Skeleton from the Mangrove Endophytic Fungus Aspergillus sp. SK-28
journal contributionposted on 2019-11-23, 00:03 authored by Runlin Cai, Hongming Jiang, Zeen Xiao, Wenhao Cao, Tao Yan, Zhaoming Liu, Shao’e Lin, Yuhua Long, Zhigang She
A pair of enantiomeric indole diketopiperazine alkaloid dimers [(−)- and (+)-asperginulin A (1a and 1b)] with an unprecedented 6/5/4/5/6 pentacyclic skeleton were isolated from the mangrove endophytic fungus Aspergillus sp. SK-28. The enantiomeric dimers were separated by chiral-phase HPLC. Their structures including absolute configurations were elucidated by spectroscopic analysis, X-ray diffraction, and quantum chemical calculation. (+)-Asperginulin A (1b) exhibited antifouling activity against the barnacle Balanus reticulatus.
chiral-phase HPLCskeletonSK -28.alkaloidspectroscopic analysisasperginulinindoleSK -28X-ray diffractionenantiomeric dimersPentacyclicbarnacle Balanus reticulatusAsperginulinpentacyclicMangrove Endophytic Fungus Aspergillus spantifouling activityconfigurationdiketopiperazineIndole Diketopiperazine Alkaloid DimersSkeletonquantum chemical calculationmangrove endophytic fungus Aspergillus sp1 b