Objective: To study the chemical constituents and their anti-angiogenic activities of the fruits of Evodia rutaecarpa. Method: Compounds were isolated and purified by column chromatography using silica gel

Sephadex LH-20

ODS and semi-preparative HPLC. Their structures were identified on the basis of physicochemical properties and spectral data. The anti-angiogenic activities of compounds were evaluated using a zebrafish model. Result: Twenty compounds were isolated and identified from the fruits of E. rutaecarpa

including one degraded limonoids calodendrolide(1)

6 indole alkaloids

i.e. rutaecarpine(2)

evodiamine(3)

goshuyuamide-Ι(4)

N-formyldihydrorutaecarpine(5)

and 7β-hydroxyrutaecarpine(6)

11 quinolone alkaloids

i.e. 2-hydroxy-4-methoxy-3-(3'-methyl-2'-butenyl)-quinoline(7)

1-methyl-2-nonyl-4(1H)-quinolone(8)

1-methyl-2-decyl-4(1H)-quinolone(9)

1-methyl-2-undecyl-4(1H)-quinolone(10)

dihydroevocarpine(11)

1-methyl-2-pentadecenyl-4(1H)-quinolone(12)

1-methyl-2-[(Z)-6-undecyl]-4(1H)-quinolone(13)

evocarpine(14)

1-methyl-2-[(Z)-4-tridecyl]-4(1H)-quinolone(15)

mixture of 1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-quinolone and 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone(16)

1-methyl-2-[(6Z

9Z)-6

9-pentadecenyl]-4(1H)-quinolone(17)

2 amides

i.e. N-methylanthranylamide(18)

acetamide(19)

and one sterol

i.e.β-sitosterol(20). Compounds 1 (20 mg · L-1)

2 (0.5 mg · L-1)

3 (5

10 μg · L-1)

4 (10 mg · L-1)

5 (50 mg · L-1)

10 (20 mg · L-1)

11 (50 mg · L-1)

16 (20 mg · L-1)

and 18 (50 mg · L-1) showed anti-angiogenic effects on internode blood vessels of Zebrafish models. Conclusion: Compounds 1-18 were characteristic constituents of Euodiae Fructus

and compounds 1 and 7 were isolated from this plant for the first time. Compounds 1-5

10

11

16

and 18 showed anti-angiogenic effects on internode blood vessels of Zebrafish models.