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Ventilago denticulata is an herbal medicine for the treatment of wound infection; therefore this plant may rich in antibacterial agents. UHPLC-ESI-QTOF-MS/MS-Based molecular networking guided isolation and dereplication led to the identification of antibacterial and antifungal agents in V. denticulata . Nine antimicrobial agents in V. denticulata were isolated and characterized; they are divided into four groups including (I) flavonoid glycosides, rhamnazin 3-rhamninoside ( 7 ), catharticin or rhamnocitrin 3-rhamninoside ( 8 ), xanthorhamnin B or rhamnetin 3-rhamninoside ( 9 ), kaempferol 3-rhamninoside ( 10 ) and flavovilloside or quercetin 3-rhamninoside ( 11 ), (II) benzisochromanquinone, ventilatones B ( 12 ) and A ( 15 ), (III) a naphthopyrone ventilatone C ( 16 ) and (IV) a triterpene lupeol ( 13 ). Among the isolated compounds, ventilatone C ( 16 ) was a new compound. Moreover, kaempferol, chrysoeriol, isopimpinellin, rhamnetin, luteolin, emodin, rhamnocitrin, ventilagodenin A, rhamnazin and mukurozidiol, were tentatively identified as antimicrobial compounds in extracts of V. denticulata by a dereplication method. MS fragmentation of rhamnose-containing compounds gave an oxonium ion, C 6 H 9 O 3  + at m/z 129, while that of galactose-containing glycosides provided the fragment ion at m/z 163 of C 6 H 11 O 5  + . These fragment ions may be used to confirm the presence of rhamnose or galactose in mass spectrometry-based analysis of natural glycosides or oligosaccharide attached to biomolecules, that is, glycoproteins.

antibiotics

UHPLC-ESI-QTOF-MS/MS-Based Molecular Networking Guided Isolation and Dereplication of Antibacterial and Antifungal Constituents of Ventilago denticulata