Withanolides from Physalis angulata L.
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ABSTRACT:
SUBMITTER: Okmanov RY
PROVIDER: S-EPMC8340980 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:Physalis angulata L. is a medicinal plant of the Solanaceae family, which is used to produce a variety of steroids. The present study reports on the cytotoxic withanolides of this plant. The species of Physalis angulata L. was identified by DNA barcoding techniques. Two new withanolides (1-2), together with six known analogues (3-8), were isolated from the whole plant of Physalis angulata L. The structures of these new compounds were determined on the basis of extensive spectroscopic data analyses and electronic circular dichroism (ECD) calculations. The withanolides exhibited strong cytotoxic activities against A549, Hela and p388 cell lines. Furthermore, compounds 1 and 2 induced typical apoptotic cell death in A549 cell line according to the evaluation of the apoptosis-inducing activity by flow cytometric analysis.
| S-EPMC6514790 | biostudies-literature
Project description:Five new physalins, including a novel 1,10-seco one, physalin V (1), a tricarboxylic acid cycle one, physalin VIII (5), a rare 11,15-cyclo one, physalin IX (6), and two new ones, physalins VI (2) and VII (4) were isolated from stems and leaves of Physalis angulata together with eleven known analogues (3 and 7-16). Their structures were established by MS, IR, UV, and NMR spectroscopic analysis, together with the X-ray diffraction analysis of neophysalin, physalin P (12), and the structure of physalin D1 (3) has been revised here. These isolated compounds were evaluated for their antiproliferative activities against human cancer cells (C4-2B, 22Rv1, 786-O, A-498, ACHN, and A375-S2) and inhibitory effects on nitric oxide production. Compounds 9 and 10 showed antiproliferative activities against all tested human cancer cells with IC50 values of 0.24-3.17 μM. Compounds 1, 3, 4, 9, 10, 13, 14, and 16 exhibited inhibitory activities against NO production. The IC50 values of compounds 9, 10, 13, and 16 were between 0.32 and 4.03 μM, while compounds 1, 3, 4, and 14 had IC50 values of 12.83-34.19 μM. Herein, plausible biosynthetic pathways for rare structures 1 and 6 and structure-activity relationships on the inhibition of NO production for all isolated compounds are discussed.
| S-EPMC5481415 | biostudies-literature
Project description:Five new withanolides (1-5) along with five known ones (6-10) were isolated from the whole plants of Physalis minima Linn. The chemical structures of the new compounds were identified as (20S,22R) 15a-acetoxy-5β,6β-epoxy-4β,14a,28-trihydroxy-3β-methoxy-1-oxowitha-16,24-dienolide (1), (20S,22R) 15a-acetoxy-5β,6β-epoxy-3β,4β,14β,17β,20β-pentahydroxy-1-oxowitha-24-enolide (2), (20R,22R) 15α-acetoxy-4β,5α,6β,14α,20β-pentahydroxy-1-oxowitha-2,24-dienolide (3), (20R,22R) 15α-acetoxy-5α,6β,14α,20β-tetrahydroxy-1-oxowitha-2,24-dienolide (4), and (20S,22R) 5α,6β,14β-trihydroxy-1,15-dioxowitha-2,16,24-trienolide (5) on the basis of integration combining IR, UV, HR-ESI-MS, 1D-NMR, and 2D-NMR analyses. Biologically, compounds (1-10) were subjected to evaluate their anti-inflammatory activities via inhibiting nitric oxide production in lipopolysaccharide-stimulated murine RAW 264.7 cells in vitro. The activity screening indicated that all of the compounds showed a moderate inhibitory effect against nitric oxide production with IC50 values of 23.53-66.28 μM.
| S-EPMC7271383 | biostudies-literature
Project description:Eleven withanolides including six previously undescribed compounds, 16β-hydroxyixocarpanolide, 24,25-dihydroexodeconolide C, 16,17-dehydro-24-epi-dioscorolide A, 17-epi-philadelphicalactone A, 16-deoxyphiladelphicalactone C, and 4-deoxyixocarpalactone A were isolated from aeroponically grown Physalis philadelphica. Structures of these withanolides were elucidated by the analysis of their spectroscopic (HRMS, 1D and 2D NMR, ECD) data and comparison with published data for related withanolides. Cytotoxic activity of all isolated compounds was evaluated against a panel of five human tumor cell lines (LNCaP, ACHN, UO-31, M14 and SK-MEL-28), and normal (HFF) cells. Of these, 17-epi-philadelphicalactone A, withaphysacarpin, philadelphicalactone C, and ixocarpalactone A exhibited cytotoxicity against ACHN, UO-31, M14 and SK-MEL-28, but showed no toxicity to HFF cells.
| S-EPMC8064035 | biostudies-literature
Project description:Physalis pubescens L. plant produces nutritious and healthy fruits, called husk tomato or hairy ground cherry. However, its bioactive components are largely unknown. Four new withanolide steroids (1-4) together with one known withanolide (5) were isolated from the extract of P. pubescens L. and their chemical structures were established by extensive spectroscopic analyses. Compounds 1, 3 and 5 showed potent growth inhibitory effects against four human renal cell carcinoma (RCC) cell lines (i.e. 786-O, A-498, Caki-2 and ACHN). Among them, compound 1 was the most potent one with IC50s ranged from 0.30 to 0.77 μM. Further experiment showed that 1 sensitized human RCC cells 786-O to the tumor necrosis factor related apoptosis ligand (TRAIL)-induced apoptosis and increased the expression of C/EBP-homologous protein (CHOP) and death receptor-5 (DR5), leading to activation of the DR5 and caspase-8/3 mediated apoptosis pathway. Molecular docking analysis revealed that compound 1 could bind stably to the TRAIL/DR5 complex through hydrogen bonds. These results suggest that the new withanolide (1) is a lead anti-cancer compound existing in P. pubescens L. and deserves further investigation for RCC prevention and treatment.
| S-EPMC5095689 | biostudies-literature
Project description:BackgroundThe bone marrow is a hematopoietic tissue that, in the presence of cytokines and growth factors, generates all of the circulating blood cells. These cells are important for protecting the organism against pathogens and for establishing an effective immune response. Previous studies have shown immunomodulatory effects of different products isolated from plant extracts. This study aimed to evaluate the immunomodulatory properties of aqueous Physalis angulata (AEPa) extract on the differentiation of bone marrow cells.ResultsIncreased cellular area, higher spreading ability and several cytoplasmatic projections were observed in the treated cells, using optical microscopy, suggesting cell differentiation. Furthermore, AEPa did not promote the proliferation of lymphocytes and polymorphonuclear leukocytes, however promotes increased the number of macrophages in the culture. The ultrastructural analysis by Transmission Electron Microscopy of treated cells showed spreading ability, high number of cytoplasmatic projections and increase of autophagic vacuoles. Moreover, a high level of LC3b expression by treated cells was detected by flow cytometry, suggesting an autophagic process. Cell surface expression of F4/80 and CD11b also indicated that AEPa may stimulate differentiation of bone marrow cells mainly into macrophages. In addition, AEPa did not differentiate cells into dendritic cells, as assessed by CD11c analysis. Furthermore, no cytotoxic effects were observed in the cells treated with AEPa.ConclusionResults demonstrate that AEPa promotes the differentiation of bone marrow cells, particularly into macrophages and may hold promise as an immunomodulating agent.
| S-EPMC4665300 | biostudies-literature
Project description:Withanolides constitute one of the most interesting classes of natural products due to their diversity of structures and biological activities. Our recent studies on withanolides obtained from plants of Solanaceae including Withania somnifera and a number of Physalis species grown under environmentally controlled aeroponic conditions suggested that this technique is a convenient, reproducible, and superior method for their production and structural diversification. Investigation of aeroponically grown Physalis coztomatl afforded 29 withanolides compared to a total of 13 obtained previously from the wild-crafted plant and included 12 new withanolides, physacoztolides I-M (9-13), 15α-acetoxy-28-hydroxyphysachenolide C (14), 28-oxophysachenolide C (15), and 28-hydroxyphysachenolide C (16), 5α-chloro-6β-hydroxy-5,6-dihydrophysachenolide D (17), 15α-acetoxy-5α-chloro-6β-hydroxy-5,6-dihydrophysachenolide D (18), 28-hydroxy-5α-chloro-6β-hydroxy-5,6-dihydrophysachenolide D (19), physachenolide A-5-methyl ether (20), and 17 known withanolides 3-5, 8, and 21-33. The structures of 9-20 were elucidated by the analysis of their spectroscopic data and the known withanolides 3-5, 8, and 21-33 were identified by comparison of their spectroscopic data with those reported. Evaluation against a panel of prostate cancer (LNCaP, VCaP, DU-145, and PC-3) and renal carcinoma (ACHN) cell lines, and normal human foreskin fibroblast (WI-38) cells revealed that 8, 13, 15, and 17-19 had potent and selective activity for prostate cancer cell lines. Facile conversion of the 5,6-chlorohydrin 17 to its 5,6-epoxide 8 in cell culture medium used for the bioassay suggested that the cytotoxic activities observed for 17-19 may be due to in situ formation of their corresponding 5β,6β-epoxides, 8, 27, and 28.
| S-EPMC8838488 | biostudies-literature
Project description:As part of the search for new bioactive plants from the Colombian Caribbean, the dichloromethane fraction of the calyces of Physalis angulata L. (PADF) was selected for its anti-inflammatory activity. In this work, we investigated the immunomodulatory effect of PADF in activated macrophages and during dextran sulfate sodium (DSS)-induced colitis. PADF displayed a low content of withanolides or phenolic compounds, and a higher content of sucrose esters, representative anti-inflammatory metabolites of the Physalis genus. The PADF fraction at 12.5 ?g/mL prevented the induction of interleukin (IL)-1?, tumor necrosis factor (TNF-?), IL-6, IL-12, cyclooxygenase-2 (COX-2), and inducible nitric oxide synthase (iNOS) by lipopolysaccharide (LPS), while increased the levels of arginase (ARG1), IL-10, and mannose receptor C (MRC1). The polarization towards an anti-inflammatory profile was also observed in resting macrophages, without promoting the typical gene profile induced by IL-4, suggesting that PADF promotes a shift to a regulatory status rather than to an alternative one. In vivo, the administration of PADF to mice with chronic DSS-colitis reduced disease signs (i.e., body weight loss and colon shortening), and improved the histology score by diminishing the levels of pro-inflammatory cytokines and increasing the production of IL-10. Overall, results suggest that the regulatory effect on PADF towards macrophages might contribute to the therapeutic activity observed in the murine model of inflammatory bowel disease.
| S-EPMC7168001 | biostudies-literature
Project description:Withanolides are steroidal lactones widespread in Nightshade plants with often potent antiproliferative activities. Additionally, the structural diversity of this compound class holds much potential for the discovery of novel biological activity. Here, we report two newly characterised withanolides, named irinans, from Physalis peruviana with highly unusual truncated backbones that resemble mammalian androstane sex hormones. Based on biomimetic chemical reactions, we propose a model that links these compounds to withanolide biosynthesis. Irinans have potent antiproliferative activities, that are however lower than those of 4ß-hydroxywithanolide E. Our work establishes androwithanolides as a new subclass of withanolides.
| S-EPMC6720484 | biostudies-literature
Project description:Physalis angulata is a renowned traditional Chinese medicine for the treatment of various conditions. Physalin is the major type of bioactive constituents conferring medicinal properties of P. angulata. Despite the medicinal importance, the pathways leading to physalin are largely unknown. In this study, we employed a transcriptomic approach to identify a Pa24ISO gene from P. angulata. Through heterologous expression in yeast, Pa24ISO was revealed to catalyze an isomerization reaction in converting 24-methylenecholesterol to 24-methyldesmosterol. Real-time PCR analysis showed that the abundance of Pa24ISO transcripts correlated with the accumulation pattern of physalin B in different tissues of P. angulata. A direct role of Pa24ISO in channeling of 24-methylenecholesterol for physalin B biosynthesis was illustrated by suppressing the gene in P. angulata via the VIGS approach. Down-regulation of Pa24ISO led to reduced levels of 24-methyldesmosterol and physalin B, accompanied with an increase of campesterol content in P. angulata. The results supported that 24ISO is involved in physalin biosynthesis in plants.
| S-EPMC8931419 | biostudies-literature