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Seco -sativene sesquiterpenoids are an important member of phytotoxins and plant growth regulators isolated from a narrow spectrum of fungi. In this report, eight  seco -sativene sesquiterpenoids ( 1 – 8 ) were first analyzed using the UPLC-Q-TOF-MS/MS technique in positive mode, from which their mass fragmentation pathways were suggested. McLafferty rearrangement, 1,3-rearrangement, and neutral losses were considered to be the main fragmentation patterns for the [M+1] +  ions of  1 – 8 . According to the structural features (of different substitutes at C-1, C-2, and C-13) in compounds  1 – 8 , five subtypes (A–E) of  seco -sativene were suggested, from which subtypes A, B/D, and E possessed the diagnostic daughter ions at  m / z  175, 189, and 203, respectively, whereas subtype C had the characteristic daughter ion at  m / z  187 in the UPLC-Q-TOF-MS/MS profiles. Based on the fragmentation patterns of  1 – 8 , several known compounds ( 1 – 8 ) and two new analogues ( 9  and  10 ) were detected in the extract of plant pathogen fungus  Bipolaris sorokiniana  based on UPLC-Q-TOF-MS/MS analysis, of which  1 ,  2 ,  9 , and  10  were then isolated and elucidated by NMR spectra. The UPLC-Q-TOF-MS/MS spectra of these two new compounds ( 9  and  10 ) were consistent with the fragmentation mechanisms of  1 – 8 . Compound  1  displayed moderate antioxidant activities with IC 50  of 0.90 and 1.97 mM for DPPH and ABTS +  scavenging capacity, respectively. The results demonstrated that  seco -sativene sesquiterpenoids with the same subtypes possessed the same diagnostic daughter ions in the UPLC-Q-TOF-MS/MS profiles, which could contribute to structural characterization of  seco -sativene sesquiterpenoids. Our results also further supported that UPLC-Q-TOF-MS/MS is a powerful and sensitive tool for dereplication and detection of new analogues from crude extracts of different biological origins.

UPLC-Q-TOF-MS/MS Analysis of Seco-Sativene Sesquiterpenoids to Detect New and Bioactive Analogues From Plant Pathogen Bipolaris sorokiniana