Wounding-Induced Increase of Quinolizidine Alkaloid Accumulation in Lupin Leaves

1983 ◽  
Vol 38 (11-12) ◽  
pp. 905-909 ◽  
Author(s):  
M. Wink
Keyword(s):  
Chemical Defense ◽  
Quinolizidine Alkaloids ◽  
Defense System ◽  
Lupinus Polyphyllus ◽  
Quinolizidine Alkaloid ◽  
Wound Induction ◽  
Important Means

Cutting-up leaflets of Lupinus polyphyllus induces a rapid increase of quinolizidine alkaloid accumulation of up to 400% within 2 to 4.5 h. In contrast to the diurnal alkaloid formation, this reaction takes place both in the light and the dark and even at 4°C. The effect is reduced in chloramphenicol-treated samples but unimpaired in cycloheximide-treated assays. Since quinolizidine alkaloids constitute probably an important means of a chemical defense system of lupins against microbes and herbivores, the wound-induction of alkaloid accumulation is discussed as a defense responsf

Enzymatic Synthesis of Quinolizidine Alkaloids in Lupin Chloroplasts

1980 ◽  
Vol 35 (1-2) ◽  
pp. 93-97 ◽  
Author(s):  
M. Wink ◽  
T. Hartmann ◽  
L. Witte
Keyword(s):  
Enzymatic Synthesis ◽  
Osmotic Shock ◽  
Quinolizidine Alkaloids ◽  
Differential Centrifugation ◽  
Alkaloid Biosynthesis ◽  
Lupinus Polyphyllus ◽  
Quinolizidine Alkaloid ◽  
Intact Chloroplasts ◽  
Key Enzyme ◽  
Isolated Chloroplasts

Abstract The enzymatic sequence responsible for the biosynthesis of tetracyclic quinolizidine alkaloids could be localized in chloroplasts isolated from Lupinus polyphyllus leaves and L. albus seedlings by differential centrifugation. Upon feeding of cadaverine to isolated chloroplasts lupanine is produced as the main alkaloid. Chloroplasts treated with digitonine produce sparteine and 17-oxosparteine instead of lupanine, thus indicating that the biosynthetic sequence is interrupted. The intermediacy of 17-oxosparteine could be confirmed since exogeneous 17-oxosparteine is converted into lupanine by intact chloroplasts. 17-Oxosparteine synthase (see Z. Naturforsch. 34 c, 704 1979) the key enzyme of quinolizidine alkaloid biosynthesis could be solubilized from chloro­ plasts treated with detergents or osmotic shock.

Stereoselective Synthesis of Quinolizidine Alkaloids: (–)-Lasubin II

2008 ◽  
Vol 63 (4) ◽  
pp. 425-430 ◽  
Author(s):  
Markus Weymann ◽  
Horst Kunz
Keyword(s):  
Mannich Reaction ◽  
Stereoselective Synthesis ◽  
Pure Form ◽  
Quinolizidine Alkaloids ◽  
Enantiomerically Pure ◽  
Quinolizidine Alkaloid

AbstractBased on a higly diastereoselective Mannich reaction of N-(3,4-dimethoxybenzylidene) 2,3,4,6- tetra-O-pivaloyl-β -D-galactopyranosylamine 3 with the Danishefsky diene the quinolizidine alkaloid lasubin II was synthesized in enantiomerically pure form in six steps.

Chemical Defense of Leguminosae. Are Quinolizidine Alkaloids Part of the Antimicrobial Defense System of Lupins?

1984 ◽  
Vol 39 (6) ◽  
pp. 548-552 ◽  
Author(s):  
M. Wink
Keyword(s):  
Potential Role ◽  
Micrococcus Luteus ◽  
Phytopathogenic Fungi ◽  
Quinolizidine Alkaloids ◽  
Defense System ◽  
Defense Compounds ◽  
Antimicrobial Defense ◽  
Mycobacterium Phlei ◽  
Alternaria Porri ◽  
Total Growth

Growth of 6 bacteria (Serratia marcescens, Bacillus megaterium, Bacillus subtilis, Streptococcus viridis, Micrococcus luteus, and Mycobacterium phlei) was inhibited by 50% if the growth medium contained sparteine at concentrations between 0.5-10mᴍ. Total growth inhibition, which was bacteriostatic in nature, was achieved at 20 mᴍ. The growth of 6 phytopathogenic fungi was also affected: at a sparteine concentration of 15 mᴍ the growth of Alternaria porri was reduced by 40% as compared to the untreated control. Respective values were 18% inhibition for Piricularia oryzae, 33% for Helminthosporium carbonum, 15% for Rhizoctonia solani, 5% for Fusarium oxysporum, and 42% for Asperquillus oryzae. Since the concentrations of quinolizidine alkaloids range from 1-200 mᴍ (roots, leaves, or stems) or 10-200 mmol/kg (seeds) in Leguminosae, it is discussed whether quinolizidine alkaloids are involved in the antimicrobial defense of lupins, in addition to their potential role as allelopathic or herbivore repellent defense compounds.

The Sesquiterpenes of Lactarius vellereus and Their Role in a Proposed Chemical Defense System

1985 ◽  
Vol 48 (2) ◽  
pp. 279-288 ◽  
Author(s):  
Olov Sterner ◽  
Rolf Bergman ◽  
Jan Kihlberg ◽  
Börje Wickberg
Keyword(s):  
Chemical Defense ◽  
Defense System
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