A New 1,5‐Dihydroxy‐4‐methoxyisoquinoline from Scolopendra subspinipes mutilans

Abstract

A new isoquinoline, 1,5-dihydroxy-4-methoxyisoquinoline (1), was obtained from Scolopendra subspinipes mutilans. Compound 1 showed moderate cytotoxicity on tumour cells with IC values ranging from 13 to 26 μm against five esophageal squamous cancer cells whereas low cytotoxicity against normal human esophageal epithelial cells. Isoquinoline ring oxidized at C(1), C(4), and C(5) can enhance its cytotoxicity. In addition, compound 1 showed potent inhibitory effect (inhibition rate > 50% at 13 μm) on cell migration in human umbilical vein endothelial cells. This article mainly studies the structure and activity of 1, and more modification of 1 as a potential anticancer agent.

Biologically active isoquinoline alkaloids covering 2014–2018

“…22 In another study in the following year, the new isoquinoline alkaloid 1,5-dihydroxy-4-methoxyisoquinoline (3), also isolated from this centipede species, showed moderate cytotoxicity against five cancer cells. 23 Carnegine (4) and N-methylisosalsoline (5), isolated from the plant Hammada scoparia, exhibited antibacterial and antioxidant activities. 24 Also, in 2016, N-methylcorydaldine (6) was isolated from Fumaria officinalis 25 and 6,7dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (7) from Mucuna pruriens seeds.…”

“…236 From 2014 to 2018, many publications have reported the antibacterial and antifungal activities of isoquinoline alkaloids; findings are briefly discussed below or listed in Table 3. 23,57,63,66,78,101 Berberine 161 peroxidation of membrane constituents. 237 Berberine also effectively protected mice infected with Salmonella typhimurium.…”

“…In 2016, two new isoquinoline alkaloids 3,8‐diolisoquinoline ( 1 ) and 1‐methoxy‐4,5‐diolisoquinoline ( 2 ) were isolated from an ethanol extract of the Chinese redheaded centipede Scolopendra subspinipes mutilans 22 . In another study in the following year, the new isoquinoline alkaloid 1,5‐dihydroxy‐4‐methoxyisoquinoline ( 3 ), also isolated from this centipede species, showed moderate cytotoxicity against five cancer cells 23 …”

“…The authors have recently described the significant antifungal activity of sanguinarine ( 299 ) and its possible use as a bio‐fungicide for crop protection 236 . From 2014 to 2018, many publications have reported the antibacterial and antifungal activities of isoquinoline alkaloids; findings are briefly discussed below or listed in Table 3 23,57,63,66,78,101 …”

“…The simple isoquinoline alkaloid carnegine ( 4 ) showed antibacterial activity with MIC ranging from 564 to 2259 µM against various strains. The time‐kill curves indicated potent and rapid bactericidal activity 23 . Michellamine B ( 276 ), a dimeric naphthylisoquinoline alkaloid, inhibited E. coli MraY (IC 50 456 µM) and B. subtilis MraY (IC 50 : 386 µM) and showed antimicrobial activity against B. subtilis 240 …”