Bioactive Isoquinoline Alkaloids fromCorydalis saxicola

Abstract

Twelve isoquinoline alkaloids including two new nitro-containing tetrahydroprotoberberines, (-)-2,9-dihydroxyl-3,11-dimethoxy-1,10-dinitrotetrahydroprotoberberine (1) and (+)-4-nitroisoapocavidine (2), were isolated from the whole plant of Corydalis saxicola Bunting. The structures of the new compounds were established by spectroscopic analysis and chemical evidence. The inhibitory activity of these isolates against cholinesterase and canine parvovirus were evaluated. Compounds 1 and 1A, (+)-1-nitroapocavidine (5), berberine (8), palmatine (9), dehydrocavidine (10), and sanguinarine (11) showed potent inhibitory activity against acetylcholinesterase with IC(50) values of less than 10 µM, while only compound 1 possessed weak activity against canine parvovirus. Structure-activity studies demonstrated that the nitro substituents at ring A in the tetrahydroprotoberberines led to an increase in the anti-acetylcholinesterase activity.

Isoquinoline alkaloids as prolyl oligopeptidase inhibitors

“…It seems that quaternary nitrogen could play an important role in the POP inhibition activity. It is known that compounds with quaternary nitrogen are also active AChE inhibitors, such as sanquinarine, chelerythrine [15], berberine [16] and californidine [17]. The quaternary nitrogen plays an important role in binding with the enzyme [18].…”

Finding new sources from “using different plants as the same herb”: A case study of Huang-lian in Northwest Yunnan, China

“…Some other compounds in these species might have similar activities with berberine, jatrorrhizin or palmatine, and the main effective compounds of the species in the present study were in Table 4. According to the previous Phytochemical and Pharmacological studies, some other ingredients in these species, such as swertianolin, gentianine, picroside I, coptisine, tetrandrine, columbamine, magnoflorine, quercetin, rutin, salicylic acid and phellodendrine, also had the similar activities like anti-infection, anti-virus, anti-inflammation, antioxidation and so on (Table 4) (Ye and Wu, 1984;Cuellar et al, 2001;Chen, 2001; State Administration of Traditional Chinese Medicine, 2002a; Qi et al, 2003;Chen et al, 2003;Wu et al, 2007;Kang et al, 2007;Kamath et al, 2009;Li, 2009;The Pharmacopoeia Committee Editorial Department, 2010;Huang et al, 2011;Chen et al, 2012;Li et al, 2013;Wang et al, 2014;Mak et al, 2014;Lu et al, 2014). So the uses of these species without berberine, palmatine or jatrorrhizin as Huang-lian by local people might be reasonable.…”

Prospecting for Bioactive Constituents from Traditional Medicinal Plants through Ethnobotanical Approaches

“…48) This result could provide a pharmacological basis to inhibit PRRSV replication. 27) In addition, many other plant-derived substances from TMPs such as Murraya koenigii, Erythrina caffra, Corydalis saxicola, Larrea tridentate, Holarrhena antidysenterica, and Melampyrum arvense exerted antiviral, 49,50) antibacterial, 51,52) and antiprotozoal 53,54) activities.…”

“…SAR analysis of antitumor carbazole alkaloids showed that the prenyl group at C-4 plays an important role in the inhibitory activity. 72) Moreover, a new nitro-containing tetrahydroprotoberberine, (−)-2,9-dihydroxyl-3,11-dimethoxy-1,10-dinitrotetrahydroprotoberberine (45), and five isoquinoline alkaloids, (+)-1-nitroapocavidine (46), berberine (47), palmatine (48), dehydrocavidine (49), and sanguinarine (50) (Fig. 8), were isolated from the whole plant of C. saxicola.…”

“…65) It is not surprising that SAR studies provide information (41)(42)(43)(44) showed that a prenyl group at C-4 plays an important role in the inhibitory activity. SAR studies on a new nitrocontaining tetrahydroprotoberberine (45) and five isoquinoline alkaloids (46)(47)(48)(49)(50) showed that nitro substituents at ring A improve anti-AchE activity. Comparing the antimicrobial activity of 48, 49, and 51, the SAR results showed that the substituent group on phenyl rings C2 and C3 as well as methylenedioxy improves antimicrobial activity more markedly than methoxyl.…”