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The combination of ion mobility mass spectrometry (IM-MS) and chromatography is a valuable tool for identifying compounds in natural products. In this study, using an ultra-performance liquid chromatography system coupled to a high-resolution quadrupole/traveling wave ion mobility spectrometry/time-of-flight MS (UPLC-TWIMS-QTOF), we have established and validated a comprehensive TWCCSN2and MS database for 112 plant specialized metabolites. The database included 15 compounds that were isolated and purified in-house and are not commercially available. We obtained accurate m/z, retention times, fragment ions, and TWIMS-derived CCS (TWCCSN2) values for 207 adducts (ESI+and ESI–). The database included novel 158 TWCCSN2values from 79 specialized metabolites. In the presence of plant matrix, the CCS measurement was reproducible and robust. Finally, we demonstrated the application of the database to extend the metabolite coverage of Ventilago harmandianaPierre. In addition to pyranonaphthoquinones, a group of known specialized metabolites in V. harmandiana, we identified flavonoids, xanthone, naphthofuran, and protocatechuic acid for the first time through targeted analysis. Interestingly, further investigation using IM-MS of unknown features suggested the presence of organonitrogen compounds and lipid and lipid-like molecules, which is also reported for the first time. Data are available on the MassIVE (https://massive.ucsd.edu, data set identifier MSV000090213).

The first phytochemical investigation of the leaves and twigs of Santisukia pagetii(Bignoniaceae) using a bioassay-guided fractionation led to the isolation and identification of seventeen known compounds, including four triterpenoids, 3-O-acetylpomolic acid (1), ursolic acid (2), 3-O-acetylursolic acid (3) and siaresinolic acid (4), three iridoid glycosides, specioside (5), verminoside (6) and ambiguuside (7), three flavonoid glycosides, luteolin-7-O-neohesperidoside (8), apigenin-7-O-neohesperidoside (9) and isoquercitrin (10), two phenolic compounds, p-coumaric acid (11) and caffeic acid (12), one monoterpenoid, (6S)-menthiafolic acid (13), together with α-D-glucose (14), β-D-maltose (15), β-sitosterol 3-O-β-D-glucopyranoside (16), a mixture of β-sitosterol (17A) and stigmasterol (17B). Compounds 1–13were isolated from Santisukiagenus for the first time. In addition, compounds 1–7, 9and 10were found to be active against HIV-1 in anti-syncytium assay, while only compounds 1and 3were found to be active (84.4% and 87.2% inhibition at 200 μg/mL, with IC50values of 290.96 and 210.34 μM, respectively) against HIV-1 reverse transcriptase. Moreover, anti-HIV-1 activities of compounds 1, 3–8, and 13were reported for the first time.