Abstract
Two new quaternary isoquinoline alkaloids, saxicolalines A (1 ) and N -methylnarceimicine (2 ), together with sixteen known alkaloids (3 - 18 ) were isolated from Corydalis saxicola Bunting. The structures of saxicolalines A (1 ) and N-methylnarceimicine (2 ) were established based on spectral methods including 1D, 2D NMR (COSY, HMQC, HMBC) and HR-ESI-MS. The anti-HBV activities of ten main alkaloids were evaluated. Among the tested compounds, dihydrochelerythrine (8 ) exhibited the most potent activity against HBsAg and HBeAg secretions with IC50 < 0.05 μM, SI > 3.5, respectively.
Key words
Corydalis saxicola Bunting - Fumariaceae - quaternary isoquinoline alkaloids - anti-HBV activity
References
1 Delectis Florae Reipublicae Popularis Sinicae Academiae Sinicae Edita. Flora Reipublicae Popularis Sinicae, Tomus 32. Beijing; Science Press 1999: 418-20.
2 Standards of Chinses Medicinal Material. Nanning; Guangxi Press of science and technology 1990: 64-5.
3
Wei J Q, Jiang S Y, Jiang Y S, Qi X X, Tang H.
A review of Corydalis saxicola Bunting of medicinal plants.
J Gangxi Acad Sci.
2006;
22
108-11.
4
Ke M M, Zhang X D, Wu L Z, Zhao Y, Zhu D Y, Song C Q. et al .
Studies on the active principles of Corydalis saxicola Bunting.
Yaoxue Xuebao.
1982;
24
289-91.
5
Li H L, Zhang W D, Zhang W, Zhang C, Liu R H.
A new nitro alkaloid from Corydalis saxicola Bunting.
Chin Chem Lett.
2005;
16
367-8.
6
Oechslin S M, König G M, Oechslin-Merkel K, Wright A D, Kinghorn A D, Sticher O.
An NMR study of four benzophenanthridine alkaloids.
J Nat Prod.
1991;
54
519-24.
7
Halbsguth C, Meiβner O, Häberlein H.
Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABAA binding site.
Planta Med.
2003;
69
305-9.
8
Iwasa K, Gupta Y P, Cushman M.
Absolute configurations of the cis - and trans -13-methyltetrahydroprotoberberines. Total synthesis of (+)-thalictricavine, (+)-canadine, (±)-, (-)-, and (+)-thalictrifoline, and (±)-, (-)-, and (+)-cavidine.
J Org Chem.
1981;
46
4744-50.
9
Chrzanowska M.
Synthesis of (±) stylopine.
J Nat Prod.
1995;
58
401-7.
10
Koul S, Razdan T K, Andotra C S, Kalla A K, Koul S, Taneja S C.
Benzophenanthridine alkaloiods from Corydalis flabellata
.
Planta Med.
2002;
68
262-5.
11
Blaskö G, Gula D J, Shamma M.
The phthalideisoquinoline alkaloids.
J Nat Prod.
1982;
45
105-22.
12
Sariyar G, Gülgeze H B, Gözler B.
Salutaridine N -oxide from the capsules of Papaver bracteatun
.
Planta Med.
1992;
58
368-9.
13
Wafo P, Nyasse B, Fontaine C.
A 7,8-dihydro-8-hydroxypalmatine from Enantia chlorantha
.
Phytochemistry.
1999;
50l
279-81.
14
Chen C H, Chen T M, Lee C.
Thalifaurine and dehydrodiscretine, new quaternary protoberberine from Talictrum fauriei
.
J Pharm Sci.
1980;
69
1061-5.
15
Barbosa-Filho J M, Da-Cunha E VL, Cornélio M L, Dias C DS, Gray A L.
Cissaglaberrimine, an aporphine alkaloid from Cissampelos glaberrima
.
Phytochemistry.
1997;
44
959-61.
16
Ringdahl B, Chan R PK, Craig J C.
Circular dichroism of aporphines.
J Nat Prod.
1981;
44
80-5.
17
Tripathi Y C, Pandey V B, Pathak N KR, Biswas M.
A seco-phthalideisoquinoline alkaloids from Fumaria indica seeds.
Phytochemistry.
1988;
27
1918-9.
18
Jiang Z Y, Zhang X M, Zhang F X, Liu N, Zhao F, Zhou J. et al .
A new triterpene and anti-Hepatitis B virus active compounds from Alisma orientalis
.
Planta Med.
2006;
72
951-4.
Prof. Dr. Ji-Jun Chen
State Key Laboratory of Phytochemistry and Plant Resources in West China
Kunming Institute of Botany
Chinese Academy of Sciences
Heilongtan
Kunming 650204
People’s Republic of China
Phone: +86-871-522-3265
Fax: +86-871-522-3265
Email: chenjj@mail.kib.ac.cn