Presence of the indole alkaloid reserpine in Bignonia capreolata (original) (raw)
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The genuine localization of indole alkaloids in Vinca minor and Catharanthus roseus
Phytochemistry, 2019
Based on the occurrence of indole alkaloids in so-called "chloroform leaf surface extracts", it was previously deduced that these alkaloids are present in the cuticle at the leaf surface of Catharanthus roseus and Vinca minor. As no symplastic markers were found in these extracts this deduction seemed to be sound. However, since chloroform is known to destroy biomembranes very rapidly, these data have to be judged with scepticism. We reanalyzed the alleged apoplastic localization of indole alkaloids by employing slightly acidic aqueous surface extracts and comparing the corresponding alkaloid patterns with those of aqueous total leaf extracts. Whereas in the "chloroform leaf surface extracts" all alkaloids are present in the same manner as in the total leaf extracts, no alkaloids occur in the aqueous leaf surface extracts. These results clearly show that chloroform had rapidly destroyed cell integrity, and the related extracts also contain the alkaloids genuinely accumulated within the protoplasm. The related decompartmentation was verified by the massively enhanced concentration of amino acids in aqueous surface extracts of chloroform treated leaves. Furthermore, the chloroform-induced cell disintegration was vividly visualized by confocal laser scanning microscopical analyses, which clearly displayed a strong decrease in the chlorophyll fluorescence in chloroform treated leaves. These findings unequivocally display that the indole alkaloids are not located in the apoplastic space, but exclusively are present symplastically within the cells of V. minor and C. roseus leaves. Accordingly, we have to presume that also other leaf surface extracts employing organic solvents have to be re-investigated.
Determination of Terpenoid Indole Alkaloids in Hairy Roots of Rhazya stricta (Apocynaceae) by GC-MS
Phytochemical Analysis, 2015
Introduction -Rhazya stricta Decne. (Apocynaceae) is a medicinal plant rich in terpenoid indole alkaloids (TIAs), some of which possess important pharmacological properties. The study material including transgenic hairy root cultures have been developed and their potential for alkaloid production are being investigated. Objective -In this study, a comprehensive GC-MS method for qualitative and quantitative analysis of alkaloids from Rhazya hairy roots was developed. Methods -The composition of alkaloids was determined by using GC-MS. In quantification, the ratio between alkaloid and internal standard was based on extracted ion from total ion current (TIC) analyses. Results -The developed method was validated. An acceptable precision with RSD ≤ 8% over a linear range of 1 to 100 μg/mL was achieved. The accuracy of the method was within 94-107%. Analysis of hairy root extracts indicated the occurrence of a total of 20 TIAs. Six of them, pleiocarpamine, fluorocarpamine, vincamine, ajmalicine and two yohimbine isomers are reported here for the first time in Rhazya. Trimethylsilyl (TMS) derivatisation of the extracts resulted in the separation of two isomers for yohimbine and also for vallesiachotamine. Clearly improved chromatographic profiles of TMS-derivatives were observed for vincanine and for minor compounds vincamine and rhazine. Conclusion -The results show that the present GC-MS method is reliable and well applicable for studying the variation of indole alkaloids in Rhazya samples.
A new indole alkaloid isolated from Tabernaemontana hystrix steud (Apocynaceae
Journal of The Brazilian Chemical Society, 2005
Um novo alcalóide, denominado histrixnina (1), e cinco alcalóides indólicos conhecidos, ibogamina (2), olivacina (3) e affinina (4), affinisina (5) e N b -metilaffinisina (6), foram isolados do extrato metanólico das cascas das raízes de Tabernaemontana hystrix. Os triterpenos conhecidos 3-O-acetil-α-amirina, 3-O-acetil-β-amirina, 3-O-acetil-lupeol foram também identificados. As estruturas dos compostos foram elucidadas com base na análise de dados espectroscópicos.
Induced responses in three alkaloid-containing plant species
Oecologia, 1993
In this paper we test three plant species for the inducibility of their alkaloid production. The plants were heavily damaged by cutting off 50% of their leaf surface using a pair of scissors. The cut-off leaf tips were used as controls for possible diurnal fluctuations. After 3, 6, 12, 24 and 48 h, respectively, the leaf bases of the damaged plants were harvested and the alkaloid concentration was measured. In Senecio jacobaea the pyrrolizidine alkaloid (Pa) concentration in damaged plants decreased within 6-12 h after damage. Within 24 h after damage the Pa concentration of Cynoglossum officinale doubled compared to control values. Indole alkaloid production in Catharanthus roseus was found not to be induced in this experiment. The responses are discussed in a functional context. We hypothesize that the nature of the response is not a feature of the type of secondary metabolite, but is related to whether the plants are damaged mainly by generalist or by specialist herbivores.
Journal of Liquid Chromatography & Related Technologies, 2012
A simple isocratic HPLC method has been developed for the simultaneous quantitation of three antipsychotic indole alkaloid (IA), α-yohimbine (1), isoreserpiline (2), and 10-methoxy tetrahydroalstonine (3) in Rauwolfia tetraphylla leaf. Samples were analyzed by reverse-phase chromatography on a Waters spherisorb ODS2 column using isocratic elution with acetonitrile containing 0.1% TEA and water containing 0.1% TFA (35:65, v/v) at a flow rate of 1 mL/min, a column temperature of 30°C, and UV detection at 210 nm. The method was validated and applied for quantification of individual alkaloids in various leaf extracts of R. tetraphylla. The method allowed simultaneous determination of alkaloids, 1, 2, and 3 in the plant. The limits of detection and quantification were 1.30, 1.16, 1.01, and 4.35, 3.88, and 3.39 µg/mL (20 µL injection) for compounds 1, 2, and 3, respectively. The method is simple, accurate, and precise which may be recommended for the routine quality control analysis of R. tetraphylla leaf extract containing these three IA as antipsychotic principles in the herb.
Alkaloidal Variation in Cissampelos Capensis (Menispermaceae)
2011
Cissampelos capensis, commonly known by the Afrikaans name "dawidjies" or "dawidjieswortel", is the most important and best known medicinal plant of the family Menispermaceae used by the Khoisan and other rural people in the western region of South Africa. The main alkaloids in the leaves, stems and rhizomes were isolated and identified. Several of the main compounds were previously found in species of the related genus Antizoma and this similarity indicates that the two genera are closely related if not congeneric. Bulbocapnine (an aporphine alkaloid), dicentrine (an aporphine alkaloid) and salutaridine (a morphinane alkaloid) were the main alkaloids in the leaves, while bulbocapnine, cissacapine, cycleanine and insularine (the last three are bisbenzyltetrahydroisoquinoline alkaloids) are the major compounds in the stems. The rhizome contains mostly bisbenzyltetrahydroisoquinoline alkaloids, with 12-O-methylcurine, cissacapine and cycleanine as the main ones. Alkaloids appear to be quite variable within different plant parts and different provenances, as confirmed by the difference in alkaloid patterns between coastal and inland forms of Cissampelos capensis (the morphinane alkaloid salutaridine, for example, is the major leaf alkaloid along the coast but is practically absent from the inland form of the species). The variety of alkaloids identified may contribute to the medicinal value of this species. The data on alkaloidal variation in the species has potential value and practical applications in chemotaxonomy, toxicology and pharmacognosy.