Periglaucines A-D, anti-HBV and -HIV-1 alkaloids from Pericampylus glaucus

Four new hasubanane-type alkaloids, periglaucines A-D (1-4), and three known alkaloids, norruffscine (5), (-)-8-oxotetrahydropalmatine (6), and (-)-8-oxocanadine (7), were isolated from the aerial parts of Pericampylus glaucus. Their structures were elucidated on the basis of extensive NMR and EIMS data, and that of periglaucine A (1) was confirmed by single-crystal X-ray diffraction. Alkaloids 1-4 inhibited hepatitis B virus (HBV) surface antigen (HBsAg) secretion in Hep G2.2.15 cells. (-)-8-Oxotetrahydropalmatine (6) possessed a high selectivity index (SI = 22.4) for HBsAg secretion of the Hep G2.2.15 cell line with an IC(50) value of 0.14 mM. Norruffscine (5) and (-)-8-oxotetrahydropalmatine (6) exhibited inhibitory activity against human immunodeficiency virus (HIV-1) with EC(50) values of 10.9 and 14.1 microM in C8166 cells (SI = 45.7 and 18.8), respectively.