Planta Med 2009; 75(1): 76-79
DOI: 10.1055/s-0028-1088344
Natural Products Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Antimicrobially Active Isoquinoline Alkaloids from Litsea cubeba

Tao Feng1 , 2 , Yan Xu3 , Xiang-Hai Cai1 , Zhi-Zhi Du1 , Xiao-Dong Luo1
  • 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
  • 3College of Bioscience and Biotechnology, Yangzhou University, Yangzhou, P.R. China
Further Information

Publication History

Received: June 22, 2008 Revised: July 3, 2008

Accepted: September 24, 2008

Publication Date:
07 November 2008 (online)

Abstract

Bioassay-guided fractionation of the alkaloidal extract of the aerial part of Litsea cubeba led to the isolation of two new isoquinoline alkaloids, (+)-N-(methoxycarbonyl)-N-norboldine (1) and (+)-isoboldine β-N-oxide (2), together with 11 known analogues (3 – 13). Their structures were established by extensive spectroscopic techniques and by comparing spectroscopic data with those in the literature. Compounds 1 and 4 showed antimicrobial activities. This is the first report on the presence of compounds 1, 2, 6, 8, 9, 11, and 12 in this plant and on the antimicrobial activities of 1 and 4. The bioactivities of isoquinoline alkaloids are also at least partly responsible for the pharmacological function of the folk medicinal plant Litsea cubeba.

References

  • 1 Li X W. Delectis Florae Reipublicae Popularis Sinicae Agendae Academiae Sinicae Edita. ”Flora Republicae Popularis Sinicae, Tomus 31”. Beijing; Science Press 1982: 271-2
  • 2 Kunming Insititute of B otany, Chinese Academy of S ciences. ”Flora Yunnanica, Tomus 3”. Beijing; Science Press 1983: 23-5
  • 3 Yu B L. Antibiotic activities of Litsea cubeba oil on molds and effect of Litsea cubeba oil on aflatoxin production.  Weishengwuxue Tongbao. 1998;  25 144-7
  • 4 Wang F, Yang D, Ren S, Zhang H, Li R. Chemical composition of essential oil from leaves of Litsea cubeba and its antifungal activities.  J Chin Med Materials. 1999;  22 400-2
  • 5 Fang F, Lu Z P, Wang Z W, Huang Y L, Li H B. Antifungal susceptibility of Candida spp. to Litsea cubeba oil: a broth microdilution tests and electron microscopy.  Zhonghua Pifuke Zazhi. 2002;  35 349-51
  • 6 Carlson R M, Gibson D J. Anti-fungal formulation of triterpene and essential oil. PCT Int 2004; applied 1997
  • 7 Cai X H, Du Z Z, Luo X D. Unique monoterpenoid indole alkaloids from Alstonia scholaris.  Org Lett. 2007;  9 1817-20
  • 8 Cai X H, Tan Q G, Liu Y P, Feng T, Du Z Z, Li W Q. et al . A cage-monoterpene indole alkaloid from Alstonia scholatis.  Org Lett. 2008;  10 577-80
  • 9 Espine-Ingroff A, White T, Pfaller M A. Manual of clinical microbiology [M], 7th edition. Washington; American Society for Microbiology 1999: 1640-52
  • 10 Castro C O, López V J, Vergara G A. Aporphine alkaloids from Phoebe pittieri.  Phytochemistry. 1985;  24 203-4
  • 11 Jackman L M, Trewella J C, Moniot J L, Shamma M, Stephens R L, Wenkert E. et al . The carbon-13 NMR spectra of aporphine alkaloids.  J Nat Prod. 1979;  42 437-49
  • 12 Marsaioli A J, Reis F AM, Magalhães A F, Rúveda E A, Kuck A M. 13C-NMR analysis of aporphine alkaloids.  Phytochemistry. 1979;  18 165-9
  • 13 Wu Y C. Azafluorene and aporphine alkaloids from Polyalthia longifolia.  Heterocycles. 1989;  29 463-75
  • 14 Vilegas J HY, Gottlieb O R, Kaplan M AC, Gottlieb H E. Aporphine alkaloids from Ocotea caesia.  Phytochemistry. 1989;  28 3577-8
  • 15 Barolo S M, Teng X, Cuny G D, Rossi R A. Syntheses of aporphine and homoaporphine alkaloids by intramolecular ortho-arylation of phenols with aryl halides via SRN1 reactions in liquid ammonia.  J Org Chem. 2006;  71 8493-9
  • 16 Manske R HF. The alkaloids, Vol. 4. New York; Academic Press 1954: 142-3
  • 17 Kimura I, Kimura M, Yoshizaki M, Yanada K, Kadota S, Kikuchi T. Neuromuscular blocking action of alkaloids from a Japanese crude drug ”Shin-1” (Flos Magnoliac) in frog skeletal muscle.  Planta Med. 1983;  48 43-7
  • 18 Shamma M. The isoquinoline alkaloids, Vol. 25. New York; Academic Press 1972: 221
  • 19 Tantisewie B, Pharadai T, Pandhuganont M, Guinaudeau H, Freyer A J, Shamma M. (+)-N-formylnornantenine, a new aporphine alkaloid from Cyclea atjehensis.  J Nat Prod. 1989;  52 652-4
  • 20 Chen Y Y, Chang F R, Wu Y C. Isoquinoline alkaloids and lignans from Rollinia mucosa.  J Nat Prod. 1996;  59 904-6
  • 21 Chang F R, Chen C Y, Wu P H, Kuo R Y, Chang Y C, Wu Y C. New alkaloids from Annona purpurea.  J Nat Prod. 2000;  63 746-8
  • 22 Montgomery C T, Freyer A J, Guinaudeau H, Shamma M. (+)-N-methyllaurotetanine-β-N-oxide from Glossocalyx brevipes.  J Nat Prod. 1985;  48 833-4
  • 23 Lin F W, Wu P L, Wu T S. Alkaloids from the leaves of Cryptocarya chinensis hemsl.  Chem Pharm Bull. 2001;  49 1292-4

Prof. Dr. Xiao-Dong Luo

Kunming Institute of Botany

Chinese Academy of Sciences

134 LanHei Road

Kunming

People’s Republic of China

Phone: +86-871-522-3177

Fax: +86-871-515-0227

Email: xdluo@mail.kib.ac.cn

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