Discovery of indole alkaloids crienamides A and B from penicillium citrinum by a simulated MS/MS-guided molecular network strategy

The Building blocks-based molecular network (BBMN) strategy is effective
for targeted natural product identification but depends on existing MS/MS
data. To address this, we propose the Simulated MS/MS-Guided Molecular
Network (SMMN) strategy, which combines virtual molecule design and MS/MS
simulation to identify novel compounds containing target building blocks.
We developed the MZmol Analyzer, a user-friendly web tool, to automate the
SMMN strategy. Using this approach and the target 6-methyl-L-pipecolate
(6-MeP), we identified two new indole alkaloid hybrids, crienamides A and
B. In vitro immunosuppressive assays showed that both compounds inhibited
ConA-induced cell proliferation, with IC50 values of 2.86 ± 1.33 μM and
0.96 ± 1.22 μM, respectively.