Chemistry and genetics of withanolides in Withania somnifera hybrids
TL;DR: In this paper, the inheritance characteristics of various substituents on the withanolide skeleton were analyzed based on the occurrence in per cent of each substituent in relation to the total withanolides content in the hybrid plants and their respective parents.
About: This article is published in Phytochemistry.The article was published on 1981-01-01. It has received 43 citations till now. The article focuses on the topics: Withania somnifera & Withanolide.
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TL;DR: An overview of the chemical structures of triterpenoid components and their biological activity is presented, focusing on two novel activities, tumor inhibition and antiangiogenic properties of withaferin A and the effects of withanolide A on Alzheimer's disease.
Abstract: Withania somnifera, commonly known as Ashwagandha, is an important medicinal plant that has been used in Ayurvedic and indigenous medicine for over 3,000 years. In view of its varied therapeutic potential, it has also been the subject of considerable modern scientific attention. The major chemical constituents of the Withania genus, the withanolides, are a group of naturally occurring C28-steroidal lactone triterpenoids built on an intact or rearranged ergostane framework, in which C-22 and C-26 are appropriately oxidized to form a six-membered lactone ring. In recent years, numerous pharmacological investigations have been carried out into the components of W. somnifera extracts. We present here an overview of the chemical structures of triterpenoid components and their biological activity, focusing on two novel activities, tumor inhibition and antiangiogenic properties of withaferin A and the effects of withanolide A on Alzheimer's disease. The most recent attempts in biotechnological production of withanolides are also discussed.
470 citations
Cites background from "Chemistry and genetics of withanoli..."
...somnifera are not fully known, and there is very little information about their biogenetic aspects [38-40]....
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01 Jan 1985
TL;DR: From Metabolism and Osmotic Work to Totipotency and Morphogenesis: A Study of Limitations Versus Multiple Interactions.
Abstract: I From Metabolism and Osmotic Work to Totipotency and Morphogenesis: A Study of Limitations Versus Multiple Interactions.- II Primary Metabolism.- Photosynthetic Carbon Metabolism in Photoautotrophic Cell Suspension Cultures of Chenopodium rubrum L..- On the Photosynthetic System and Assimilate Metabolism of Daucus and Arachis Cell Cultures.- Regulation of Carbon and Nitrogen Assimilation Pathways in Tobacco Cell Suspension Cultures in Relation with Ultrastructural and Biochemical Development of the Photosynthetic Apparatus.- Application of Gas Analysis to Continuous Culture.- Carbohydrate Source, Biomass Productivity and Natural Product Yield in Cell Suspension Cultures.- Nitrogen Metabolism of Leaf and Microspore Callus of Betula pendula.- III Secondary Metabolism.- 4-Coumarate: CoA Ligase in Wild Carrot Cell Culture Clones Which Accumulate Different Amounts of Anthocyanin.- Induction of Anthocyanin Synthesis in Relation to Embryogenesis in a Carrot Suspension Culture - A Model System for the Study of Expression and Repression of Secondary Metabolism.- Metabolism of Quinolizidine Alkaloids in Plants and Cell Suspension Cultures: Induction and Degradation.- Production of Alkaloids by Ergot (Claviceps fusiformis Lov.) on Pennisetum typhoides (Burm.) Stapf and Hubb. in Vitro.- Compartmentation of Alkaloids in a Cell Suspension of Catharanthus roseus: A Reappraisal of the Role of pH Gradients.- Studies on Variability of Plant Tissue Cultures for Alkaloid Production in Catharanthus roseus and Papaver somniferum Callus Cultures.- Biosynthesis and Accumulation of Indole Alkaloids in Cell Suspension Cultures of Catharanthus roseus Cultivars.- Formation of Cardenolides in Cell and Organ Cultures of Digitalis lanata.- Metabolism of Caffeoyl Derivatives in Plant Cell Cultures.- Metabolic Relationships of Putrescine, GABA and Alkaloids in Cell and Root Cultures of Solanaceae.- Metabolism and Degradation of Nicotinic Acid in Plant Cell Cultures.- Plant Cell and Tissue Culture of Cinchona Species.- The Production of Pyrethrins by Chrysanthemum cinerariaefolium (Trev) Bocc..- Biosynthesis of Chorismate-Derived Quinones in Plant Cell Cultures.- The Role of Leucine in Terpenoid Metabolism: Incorporation of Leucine into Sesquiterpenoids and Phytosterols by Andrographis Tissue Cultures.- Accumulation of Antineoplastic Agents by Plant Tissue Cultures.- Induction of Enzymes of Phytoalexin Synthesis in Soybean Cells by Fungal Elicitor.- Protoplast Fusion of Secondary Metabolite-Producing Cells.- Conventional and New Approaches to Increase the Alkaloid Production of Plant Cell Cultures.- Multiple Shoot Cultures: A Viable Alternative in Vitro System for the Production of Known and New Biologically Active Plant Constituents.- IV Fermentation and Cryopreservation.- Large-Scale Production of Rosmarinic Acid from Plant Cell Cultures of Coleus blumei Benth..- Immobilised Plant Cell Culture Systems.- Biotransformation of Cardiac Glycosides by Digitalis Cell Cultures in Airlift Reactors.- Cryopreservation of Plant Cell Cultures.- V Herbicides.- Altered Amino Acid Biosynthesis in Amino Acid Analog and Herbicide-Resistant Cells.- Acetohydroxyacid Synthase Inhibitors as Herbicides.- A Glyphosate-Tolerant Plant Tissue Culture.- VI Plant Cell Culture - Future Perspectives.
321 citations
205 citations
TL;DR: Treatment of the diabetic rats withWSREt, WSLEt and glibenclamide restored the changes of the above parameters to their normal level after eight weeks of treatment, indicating that WSREt and WSLET possess hypoglycaemic and hypolipidaemic activities in alloxan-induced diabetes mellitus (DM) rats.
Abstract: Withania somnifera is an important medicinal plant, which is used in traditional medicine to cure many diseases. Flavonoids were determined in the extracts of W. somnifera root (WSREt) and leaf (WSLEt). The amounts of total flavonoids found in WSREt and WSLEt were 530 and 520 mg/100 g dry weight (DW), respectively. Hypoglycaemic and hypolipidaemic effects of WSREt and WSLEt were also investigated in alloxan-induced diabetic rats. WSREt and WSLEt and the standard drug glibenclamide were orally administered daily to diabetic rats for eight weeks. After the treatment period, urine sugar, blood glucose, haemoglobin (Hb), glycosylated haemoglobin (HbA1C), liver glycogen, serum and tissues lipids, serum and tissues proteins, liver glucose-6-phosphatase (G6P) and serum enzymes like aspartate transaminase (AST), alanine transaminase (ALT), acid phosphatase (ACP) and alkaline phosphatase (ALP) levels were determined. The levels of urine sugar, blood glucose, HbA1C, G6P, AST, ALT, ACP, ALP, serum lipids except high density lipoprotein-bound cholesterol (HDL-c) and tissues like liver, kidney and heart lipids were significantly (p < 0.05) increased, however Hb, total protein, albumin, albumin:globulin (A:G) ratio, tissues protein and glycogen were significantly (p < 0.05) decreased in alloxan-induced diabetic rats. Treatment of the diabetic rats with WSREt, WSLEt and glibenclamide restored the changes of the above parameters to their normal level after eight weeks of treatment, indicating that WSREt and WSLEt possess hypoglycaemic and hypolipidaemic activities in alloxan-induced diabetes mellitus (DM) rats.
159 citations
TL;DR: Shoot multiplication was achieved in vitro from shoot tips of aseptically germinated seedlings of Withania somnifera L. with direct multiple shoot initiation from germinating seeds in the presence of BA alone.
Abstract: Shoot multiplication was achieved in vitro from shoot tips of aseptically germinated seedlings of Withania somnifera L. using low concentrations of 6-benzyladenine (BA), viz. 2.2, 4.4 and 8.9 μM. Maximum number of shoots were obtained when 2.3 μM 2,4-dichlorophenoxyacetic acid (2,4-D) or 2.5 μM indolebutyric acid (IBA) was added to medium containing 4.4 μM BA during initiation of shoot multiplication, but not when added later. Direct multiple shoot initiation was also obtained from germinating seeds in the presence of BA alone. Rooting was successful in excised shoots grown on growth regulator-free MS medium. Rooted shoots were successfully established in soil in a greenhouse.
145 citations
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TL;DR: Withania somnifera Dun (Solanaceae) growing in the southern coastal plane of Israel constitutes a new chemotype and is designated as chemotype III as mentioned in this paper, and the following structures have been assigned to seven of the above compounds: Withanolide G, 20α,27dihydroxy-1-oxo-20R,22R-witha-2,5,8(14),24-tetraenolide (2,2,14)
104 citations
TL;DR: In this article, the effects of hydroxyl substitution in the ring D/side chain part of the molecules were studied and the shift of the heavily functionalized A/B ring system can serve as a fingerprint for different substitution patterns.
Abstract: The 13C NMR spectra of 29 highly oxygenated C, steroids with the withanolide skeleton, 24 of which are naturally occurring substances or acetates thereof, were recorded and the carbon signals fully assigned. The shifts of the heavily functionalized A/B ring system can serve as a ‘fingerprint’ for the different substitution patterns. A study of the effects of hydroxyl substitution in the ring D/side chain part of the molecules leads to conformational information, including preferred rotamers around the 17—20 and 20—22 bonds. Systems with both 17α- and 17β-oriented side chains are thus analysed.
53 citations
TL;DR: In this article, seven steroidal lactones of the withanolide series have been isolated as minor constituents of the leaves of Withania somnifera Dun (Solanaceae) along with the major component withaferin A. The new compounds are: 27-hydroxywithanolide D(4β,20α,27-trihydroxy-1-oxo-5β,6β-epoxy-20 R,22 R -witha-2,24-dienolide) (11a ), 14α-hydroxwith
49 citations
TL;DR: The structure of a new chlorinated withanolide isolated from the hybrid plants of Withania somnifera, chemotypes III (Israel) by Indian I, is established as the chlorohydrin of withanolides D (6α-chloro-4β,5β,20αF-trihydroxy-l-oxo-22R-witha-2,24-dienolide) as discussed by the authors.
48 citations
TL;DR: Three new withanolides (C 28 steroids possessing a 6-membered ring lactone in the side chain) have been isolated from Withania somnifera (Solanaceae) growing in South Africa and characterized as 4β-hydroxy-1-oxo-5β,6β-epoxywitha-2,24-dienolide (IIIa), 4β,20α,(R )dihydroxy- 1-oxoxo,5β-6β -epoxy with-2-enoline (IVa
48 citations