Phloroglucinol glycosides from the fresh fruits of Eucalyptus maideni

Five new phloroglucinol glycosides, eucalmainosides A-E (1-5), were isolated from the fresh fruits of Eucalyptus maideni, along with 15 flavonoids (6-20), seven (+)-oleuropeic acid derivatives (15, 16, and 22-26), three hydrolyzable tannins (32-34), and six simple phenolic compounds (21, 27-31). Their structures were determined on the basis of spectroscopic analyses, including HSQC, HMBC, and acidic hydrolysis. The in vitro anti-herpes simplex virus 1 (HSV-1) assay indicated that the flavonols, myricetin (6) and quercetin (7), and the ellagitannin isocoriariin F (33) showed weak anti-HSV-1 activity with TIC values of 0.31, 0.33, and 0.12 mM, respectively.