Planta Med 2007; 73(8): 787-791
DOI: 10.1055/s-2007-981549
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Two New Quaternary Alkaloids and Anti-Hepatitis B Virus Active Constituents from Corydalis saxicola

Ying-Rui Wu1 , 2 , Yun-Bao Ma1 , You-Xing Zhao1 , Shu-Ying Yao1 , 2 , Jun Zhou1 , Ying Zhou3 , Ji-Jun Chen1
  • 1State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, P. R. China
  • 2Graduate School of Chinese Academy of Sciences, Beijing, P. R. China
  • 3Guangxi Institue of Chinese Medicine & Pharmaceutical Science, Nanning, P. R. China
Further Information

Publication History

Received: February 26, 2007 Revised: May 17, 2007

Accepted: May 21, 2007

Publication Date:
05 July 2007 (online)

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.

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