Involvement of strictosidine as a defensive chemical inCatharanthus roseus (original) (raw)
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Strictosidine activation in Apocynaceae: towards a "nuclear time bomb"?
BMC Plant Biology - BMC PLANT BIOL, 2010
BACKGROUND: The first two enzymatic steps of monoterpene indole alkaloid (MIA) biosynthetic pathway are catalysed by strictosidine synthase (STR) that condensates tryptamine and secologanin to form strictosidine and by strictosidine β-D-glucosidase (SGD) that subsequently hydrolyses the glucose moiety of strictosidine. The resulting unstable aglycon is rapidly converted into a highly reactive dialdehyde, from which more than 2,000 MIAs are derived. Many studies were conducted to elucidate the biosynthesis and regulation of pharmacologically valuable MIAs such as vinblastine and vincristine in Catharanthus roseus or ajmaline in Rauvolfia serpentina. However, very few reports focused on the MIA physiological functions. RESULTS: In this study we showed that a strictosidine pool existed in planta and that the strictosidine deglucosylation product(s) was (were) specifically responsible for in vitro protein cross-linking and precipitation suggesting a potential role for strictosidine acti...
Journal of Biological …, 2000
Strictosidine -D-glucosidase (SGD) is an enzyme involved in the biosynthesis of terpenoid indole alkaloids (TIAs) by converting strictosidine to cathenamine. The biosynthetic pathway toward strictosidine is thought to be similar in all TIA-producing plants. Somewhere downstream of strictosidine formation, however, the biosynthesis diverges to give rise to the different TIAs found. SGD may play a role in creating this biosynthetic diversity. We have studied SGD at both the molecular and enzymatic levels. Based on the homology between different plant -glucosidases, degenerate polymerase chain reaction primers were designed and used to isolate a cDNA clone from a Catharanthus roseus cDNA library. A full-length clone gave rise to SGD activity when expressed in Saccharomyces cerevisiae. SGD shows ϳ60% homology at the amino acid level to other -glucosidases from plants and is encoded by a singlecopy gene. Sgd expression is induced by methyl jasmonate with kinetics similar to those of two other genes acting prior to Sgd in TIA biosynthesis. These results show that coordinate induction of the biosynthetic genes forms at least part of the mechanism for the methyl jasmonate-induced increase in TIA production. Using a novel in vivo staining method, subcellular localization studies of SGD were performed. This showed that SGD is most likely associated with the endoplasmic reticulum, which is in accordance with the presence of a putative signal sequence, but in contrast to previous localization studies. This new insight in SGD localization has significant implications for our understanding of the complex intracellular trafficking of metabolic intermediates during TIA biosynthesis.
Biochemistry, 1979
Strictosidine synthetase, which catalyzes the condensation of tryptamine with secologanin to form strictosidine (isovincoside), was purified 740-fold to homogeneity from cultured cells of Catharanthus roseus in 10% yield. The specific activity is 5.85 nkat/mg. The molecular weight as estimated by gel filtration is 38 000. The isoelectric point is 4.6. Apparent K , values for tryptamine and secologanin are Catharanthus roseus (periwinkle) produces more than 100 indole alkaloids (Scott, 1970), many of which are pharmacologically active, the most notable of these being vinblastine and vincristine, the antitumor alkaloids. As
Advanced Pharmaceutical Bulletin, 2019
Purpose: Strictosidine-β-D-glucosidase (SGD) is considered as a key enzyme in the productionof bisindole alkaloids in Catharanthus roseus. The present study illustrated the production of ashort sequence of this enzyme in Escherichia coli without codon optimization.Methods: Strictosidine-β-D-glucosidase (sgd) gene short sequence (1434 bp), which lacksthe conserved sequence KGFFVWS and the localization peptide sequence at the C-terminal,was amplified from cDNA of C. roseus leaves, cloned and expressed in Escherichia coli. Theactivity of the produced protein in cell free lysate was tested using total alkaloid extract of C.roseus leaves.Results: HPLC and LC-MS analysis of the assay mixture revealed the disappearance of thestrictosidine peak.Conclusion: SGD short sequence can be produced in Escherichia coli in active form withoutcodon optimization.
Insecticidal and antifungal chemicals produced by plants: a review
Environmental Chemistry Letters, 2012
Leaf-cutting ants of the Attini tribe are a major pest of agricultural and forestry productions in the New World. Economic losses caused by these ants were estimated at several million dollars per year. These ants need to live in symbiosis with a basidiomycete fungus. Due to their mutualistic interaction with the symbiotic fungus, management of Attini ants can be done with insecticides or fungicides or both. So far, synthetic pesticides were the main control means, albeit with negative effects on the environment. Very few studies describe alternative methods for the control of leaf-cutting ants such as the use of insecticidal and fungicidal plant extracts. There is therefore a need of knowledge on phytochemicals and plants that could be used as insecticides and fungicides. Here, we review chemicals of plant origin and species with insecticidal and fungicidal activities. We establish a list of plants and phytochemicals that could manage leaf-cutting ants and also other insects, notably insects that use fungusbased agriculture. An exhaustive literature search of 1965 references from 1923 to 2010 was conducted using scientific databases, chemical databases, botanical databases, and books to identify published papers related to insecticidal and fungicidal chemical compounds stemmed from plant species. The major points are the following: (1) 119 and 284 chemicals have been cited in the literature for their insecticidal and fungicidal activities, respectively; (2) 656 and 1,064 plant species have significant insecticidal and fungicidal activities, respectively; (3) 3 main chemical classes were most cited for these activities: alkaloids, phenolics, and terpenoids; (4) 20 interesting chemicals with the both insecticidal and fungicidal activities were found; and (5) 305 plant species containing these chemicals were cited. To conclude, 20 chemicals: caryophyllene oxide, cinnamaldehyde, eugenol, helenalin, linalool, menthone, myristicin, pulegone, thymol, anethole, anisaldehyde, elemicin, isopimpinellin, plumbagin, podophyllotoxin, psoralen, xanthotoxin, anonaine, solamargine, and tomatine; two main plant families, Lamiaceae and Apiaceae; and 17 species of these families were particularly interesting for the management of leaf-cutting ants.
Scientific Journal for Damietta Faculty of Science, 2023
Chromatographic separation of Catharanthus roseus yielded six fractions. Of the sex fractions, the alkaloid and butanol fractions were the most effective fraction against Spodoptera littoralis (Boisd.) larvae in their second instar after seven days of exposure using leaf dipping technique with LC50 value 234.58 and 481.09 ppm, respectively. Toxicological effect guided isolation and elucidation of the most toxic fraction and yielded three monoterpenoid indole alkaloids, vindoline (1), vindorosin (2) and ajmalicine (3) using extensive chromatographic and spectroscopic techniques. The effect of alkaloid and butanol fractions on biochemical aspects including transaminases enzymes (AST and ALT), acelylcolinesterase and chitinase for S. littoralis, 2 nd instar larvae were evaluated. A significant activation on AST and ALT activities were obtained after treatment with LC50 of alkaloid and butanol fractions also, both fractions might be used as AchE inhibitors and suggested an ability in biodegradation of chitin. The sublethal effect of both alkaloid and butanol fractions on the biological aspects of S. littoralis immature and adult stages were studied in details.
New strictosidine β-glucosidase from Strychnos mellodora
Plant Physiology and Biochemistry, 2000
A stable strictosidine glucosidase was isolated from dried powdered material of Strychnos mellodora. The kinetic parameters K m and V max of the purified glucosidases from Catharanthus roseus and S. mellodora towards strictosidine, dolichantoside and palicoside were determined and compared.
Pest Management Science, 2015
BACKGROUND: Tetranychus evansi is an invasive pest of solanaceous crops in Africa, and in the field it differentially attacks edible African nightshades. The chemical basis for the differential attack on these plant species is largely unknown. Using bioassays and chemical analysis, we investigated the differential bioactivity of leaf extracts of three edible African nightshade species, Solanum sarrachoides, S. scabrum and S. villosum, on adult T. evansi females. RESULTS: Only the bioactivity of the leaf extract of S. sarrachoides (LC 50 7.44 mg mL −1) and that of its most polar fraction (LC 50 5.44 mg mL −1) paralleled that of the positive control, neem oil (LC 50 1.89 mg mL −1), across all doses tested. Liquid chromatography-quadruple time of flight-mass spectrometry identified a mixture of steroidal glycoalkaloids (SGAs), including-solasonine,-solamargine and derivatives of tomatine and demissine, which were neither detected in the crude extract nor in any of the fractions obtained from S. scabrum and S. villosum. CONCLUSION: Our results suggest that the presence of SGAs may play a key role in the differential defence of edible African nightshades against attack by T. evansi. These findings may add to the plethora of environmentally friendly tools from natural plant products for management of T. evansi.
In-Vitro Study of Α- Glucosidase Inhibition Activity of Alstonia Scholaris and Catharanthus Roseus
2022
The increasing population of Diabetes Mellitus (DM) in the world has always been concerned by physicians and scientists due to its life-threatening effects including heart diseases and premature death. Out of them, nearly 90-95% population is having type 2 diabetes mellitus (T2DM), characterised by insulin resistance. The available treatments for T2DM includes inhibition of αglucosidase present on the brush border of human intestine that controls post-prandial hyperglycaemia by slower the releasing of glucose in the blood. Adverse effects of the available αglucosidase inhibitors (AGI) such as abdominal discomfort and hypoglycaemia has prompted a search for the newer AGIs from natural compounds. The impact of various plant extracts on the management of medical disorders has recently aroused curiosity of researchers. Alstonia scholaris has set its hight reputation in ethnopharmacological world for treating major health issues including skin carcinoma, lung cancer and also T2DM. Though some research supports the antidiabetic activity of the plant, the mode of action responsible for it has yet to be discovered. At the same time, Catharanthus roseus has also been proved to be effective in diabetic conditions but in vitro study of antidiabetic activity of the plant is yet to be encountered. The presented study investigated different extracts of A. scholaris and C. roseus on αglucosidase isolated from Saccharomyces cerevisiae. The presented research not only gives in-vitro proves of the plants as AGIs but also open ups new pathways in understanding the secondary metabolites as inhibitors.
Antimicrobial and insecticidal activities of essential 2008 Biochemical Syst
The hydrodistillated essential oil of Salvia hydrangea was analyzed by GCeMS. Fifty-four different components representing 95.9% of the compounds in the oil were identified. Camphor (54.2%), a-humulene (4.0%), cis-sesquisabinene hydrate (2.8%), myrtenol (2.6%), b-bisabolol (2.2%) and 1,8-cineole (2.1%) were found to be predominant components. The oil was also characterized by relatively high amount of oxygenated monoterpenes (69.6%). The oil was tested for fungitoxic effects against 33 agricultural pathogenic fungi using in vitro microbial growth inhibition assays. The oil exhibited considerable antifungal activity against a broad spectrum of tested fungi. Antibacterial activity of the oil was determined against 30 bacterial strains using the disc diffusion method. The oil had a very wide spectrum of antibacterial activity. However, it was not as active as penicillin. The oil showed 68.3e75.0% mortality against adults of Sitophilus granarius and Tribolium confusum, the major pests of wheat and wheat products, respectively. It can be concluded that the oil of S. hydrangea has a potential against agricultural pathogenic fungi and two stored pests, S. granarius and T. confusum.