Chapter 1 Lupine Alkaloids

  title={Chapter 1 Lupine Alkaloids},
  author={Shigeru Ohmiya and Kazuki Saito and Isamu Murakoshi},
Publisher Summary This chapter deals with aspects of the occurrence, the spectroscopic characteristics, and the chemical properties of lupine alkaloids that have been isolated. It includes newly proposed biosynthetic pathway, biotechnological studies, a summary of biological activities, and a discussion of chemotaxonomic aspects of the leguminous plants which accumulate lupine alkaloids. More than 200 naturally occurring lupine alkaloids are known, most of which have been isolated from… Expand
Indolizidine and quinolizidine alkaloids structure and bioactivity
Abstract A review of the structural identification and bioactivity of simple indolizidine and quinolizidine alkaloids isolated from amphibians, ants,fungi, plants and marine sources, covering theExpand
Assessing the genotoxicities of sparteine and compounds isolated from Lupinus mexicanus and L. montanus seeds by using comet assay.
There is evident genotoxic activity in the compounds that were studied, particularly at lower concentrations (0.01 and 0.1 mM). Expand
Quinolizidine Alkaloid Biosynthesis in Lupins and Prospects for Grain Quality Improvement
There is considerable scope to facilitate advances in knowledge on alkaloid biosynthesis in other plant species in recent years, and the recent development of genomic and transcriptomic resources for NLL, leading to the production of improved lupin crops. Expand
Characterization of the genetic factors affecting quinolizidine alkaloid biosynthesis and its response to abiotic stress in narrow-leafed lupin (Lupinus angustifolius L.).
It was demonstrated that sweet accessions are characterized by lower QA biosynthetic gene expression exclusively in leaf and stem tissues than bitter NLL, consistent with the hypothesis that QAs are predominantly produced in aerial tissues and transported to seeds, rather than synthesized within the seed itself. Expand
An acyltransferase-like gene obtained by differential gene expression profiles of quinolizidine alkaloid-producing and nonproducing cultivars of Lupinus angustifolius
It was revealed that LaAT expression was highest in the young leaves but barely detectable in the other organs of the bitter cultivar plant, whereas LaATexpression was undetectable in the sweet cultivar, and LaAT showed the strongest homology to the Arabidopsis thaliana BAHD acyltransferases involved in the formation of conjugated polyamines. Expand
Analysis of Genetic Diversity in the Traditional Chinese Medicine Plant ‘Kushen’ (Sophora flavescens Ait.)
Analysis of dissected flower buds revealed that anthesis occurs before buds fully open suggesting a potential for S. flavescens to be an inbreeding species, however this is not supported by the relatively high level of heterozygosity observed. Expand
The use of hyphenated techniques in comparative phytochemical studies of legumes
The use of GC-MS has provided an extensive data set on the occurrence of quinolizidine alkaloids in legumes and this character is now assuming taxonomic significance at a high level, and LC-MS is likely to play a central role in the analysis of legume proteins. Expand
Microwave-assisted aqueous two-phase extraction of alkaloids from Radix Sophorae Tonkinensis with an ethanol/Na2HPO4 system: Process optimization, composition identification and quantification analysis
Abstract A rapid method for simultaneous extraction and separation of multiple alkaloids from Radix Sophorae Tonkinensis (RST) was developed by microwave-assisted aqueous two-phase extractionExpand
Dynamic kinetic resolution and desymmetrization processes: a straightforward methodology for the enantioselective synthesis of piperidines.
A straightforward procedure for the synthesis of enantiopure polysubstituted piperidines is reported. It involves the direct generation of chiral non-racemic oxazolo[3,2-a]piperidone lactams thatExpand


Chemotaxonomic significance of alkaloids in the genus Lebeckia
The results strongly support the present generic concept of Pearsonia and provide evidence for a close taxonomic affinity with the genus Rothia and confirms the chemotaxonomic value of alkaloids as a generic character. Expand
Alkaloid distribution in seeds of Ormosia, Pericopsis and Haplormosia
Alkaloid profiles were determined by capillary gas chromatography/mass spectrometry in seeds of 15 Ormosia species and in three Pericopsis species and Haplormosia monophylla, finding mainly lupine-type quinolizidine alkaloids of the sparteine/lupanine class. Expand
Observations on the occurrence and distribution of alkaloids in some genera and species of the tribe Crotalarieae (Fabaceae)
A general survey of alkaloids in the tribe Crotalarieae showed that useful chemotaxonomic data may be obtained, and the major alkaloid types seem to be characteristic for each of these genera. Expand
Biogenetic implication of lupin alkaloid biosynthesis in bitter and sweet forms of Lupinus luteus and L. albus
The results suggest that the biosynthetic steps of ring closure forming initial cyclic alkaloids such as (-)-lupinine and (+-lupanine from cadaverine are blocked in sweet plants, but the steps prior to cadaversine and the later steps for modification of the cyclized alkaloid are not altere. Expand
Alkaloidal variation in the genus Pearsonia
In a detailed variation study of quinolizidine alkaloids from the genus Pearsonia, large qualitative and quantitative differences were recorded. Expand
New quinolizidine alkaloids from Lupinus argenteus and its hosted root parasite Castilleja sulphurea. Stereochemistry and conformation of some naturally occurring cyclic carbinolamides
At one Colorado location, Castilleja sulphurea (Scrophulariaceae) is a root parasite on Lupinus argenteus subsp. rubricaulis (Fabaceae). The new carbinolamide quinolizidine alkaloidsExpand
[A new lupin alkaloid, (-)-leontalbinine N-oxide, in Sophora flavescens var. angustifolia seeds and its synthesis by biomimetic transformation from (+)-matrine N-oxide].
The structure of the newly isolated minor lupin alkaloid from the seeds of S. flavescens was determined as (-)-leontalbinine N-oxide from its spectral comparison with the authentic sample, and seems to be specific to the reaction of (+)-matrine N- oxide with ferrous reagents. Expand
The major alkaloids of the genus Argyrolobium
The conclusions are that Argyrolobium is closely related to the genus Polhillia Stirton, that large quantities of anagyrine may be taken as a chemotaxonomic marker for Argyolobium and that a more detailed study of alkaloids may provide valuable taxonomic evidence in a genus without any obvious morphological specializations. Expand
Glycosidic alkaloids from Lupinus hirsutus
Two new glycosidic alkaloid compounds were isolated from the aerial parts of Lupinus hirsutus together with seven known alkaloids and their structures were determined by spectroscopic methods and by chemical transformation. Expand
Site of Lupanine and Sparteine Biosynthesis in Intact Plants and in vitro Organ Cultures
The green aerial parts are the major site of alkaloid biosynthesis in lupins and in other legumes, and no incorporation of cadaverine into lupanine was observed in roots. Expand