Monoterpenes and flavones from the leaves of Crataegus pinnatifida with anticoagulant activities

• The antithrombotic activities of hawthorn fractions and extracts were observed.
• Five new isolates and 10 known ones were obtained by bioactivity-guided screening.
• In vitro and in vivo antithrombotic assays of compounds 1–15 were carried out.
• One monoterpene and two flavonoids gave significant antithrombotic activity.
• This is the first report of anticoagulant activities of C13-monoterpenes in hawthorn.

Hawthorn is becoming increasingly popular as a functional food that has numerous medicinal and nutritional properties. Antithrombotic activity-guided fractionation of hawthorn leaves resulted in the isolation of four new monoterpene glycosides (1–4) and a new phenolic glycoside (10) in addition to 10 known ones (2–9, 11–15). Based on physicochemical properties and spectral data, such as NMR and HRESIMS, the isolated compounds identified as pinnatifidanoside A–E (1–4, 10), byzantionoside B (5), (3S,5R,6R,7E,9R)-3,6-epoxy-7-megastigmen-5, 9-diol-9-O-β-D-glucopyranoside (6), (6S,7Z,9R)-roseoside (7), icariside B6 (8), linalool oxide β-D-glucoside (9), shanyenoside A (11), dihydrocharcone-2′-β-D-glucopyranoside (12), eriodectyol (13), vitexin (14), and 2″-O-rhamnosyl vitexin (15). In vitro and in vivo antithrombotic assays of compounds 1–15 were carried out and found that compounds 7, 13 and 15 exerted potent antithrombotic activity in vitro, which was in agreement with the in vivo results of their antithrombotic activity in a transgenic zebrafish system.