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1.
J Ethnopharmacol ; 325: 117830, 2024 May 10.
Artigo em Inglês | MEDLINE | ID: mdl-38301983

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Physalis angulata L., a traditional Chinese medicine called "Kuzhi" in China, was used traditionally to treat liver diseases (eg. icterus, hepatitis) as well as malaria, asthma, and rheumatism. AIM OF THE STUDY: Our study aimed to investigate the withanolides with anti-hepatic fibrosis effect from P. angulate. MATERIALS AND METHODS: Withanolides were obtained from the EtOH extract of P. angulate by bioassay-molecular networking analysis-guided isolation using column chromatography and normal/reversed-phase semipreparative HPLC. The structures of new withanolides were elucidated by combinations of spectroscopic techniques with NMR and ECD calculations. MTT cell viability assay, AO/EB staining method, cell wound healing assay, ELISA and Western blot experiments were employed to evaluate the anti-hepatic fibrosis activity and to uncover related mechanism. Molecular docking analysis and cellular thermal shift assay were used to evaluate and verify the interaction between the active withanolides and their potential targets. RESULTS: Eight unreported withanolides, withagulides A-H (1-8), along with twenty-eight known ones were obtained from P. angulate. Withanolides 6, 9, 10, 24, 27, and 29-32 showed marked anti-hepatic fibrosis effect with COL1A1 expression inhibition above 50 %. Physalin F (9), the main component in the active fraction, significantly decreased the TGF ß1-stimulated expressions of collagen I and α-SMA in LX-2 cells. Mechanism study revealed that physalin F exerted its anti-hepatic fibrosis effect via the PI3K/AKT/mTOR signaling pathway. CONCLUSION: This study suggested that withanolides were an important class of natural products with marked anti-hepatic fibrosis effect. The main withanolide physalin F might be a promising candidate for hepatic fibrosis treatment. The work provided experimental foundation for the use of P. angulate to treat hepatic fibrosis.


Assuntos
Physalis , Vitanolídeos , Vitanolídeos/farmacologia , Vitanolídeos/uso terapêutico , Vitanolídeos/química , Physalis/química , Simulação de Acoplamento Molecular , Fosfatidilinositol 3-Quinases , Cirrose Hepática/induzido quimicamente , Cirrose Hepática/tratamento farmacológico , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Extratos Vegetais/química
2.
J Chem Neuroanat ; 136: 102390, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38228242

RESUMO

Physalis alkekengi L. var. franchetii (Mast.) Makino (PA), a traditional Chinese medicine, is utilised for treating dermatitis, sore throat, dysuria, and cough. This research aimed to identify the main constituents in the four extracted portions from the calyces of PA (PAC) utilising ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The Alzheimer's disease (AD) mice model was induced by D-galactose (D-gal) combined with aluminium chloride (AlCl3). Subsequent investigation into the underlying mechanisms involved behavioural and histopathological observations. The results demonstrated that four extracted portions of PAC (PACE) significantly enhanced memory and learning abilities in the Morris water maze. The concentrations of Aß, tau and p-tau in brain tissue exhibited a significant decrease relative to the model group. Moreover, the four PACE treatment groups increased the glutathione (GSH) and superoxide dismutase (SOD) levels, while concurrently reducing malondialdehyde (MDA), interleukin-1ß (IL-1ß) and interleukin-6 (IL-6), tumour necrosis factor-α (TNF-α) levels. In summary, the current study demonstrates that the four PACE formulations exhibit beneficial anti-AD properties, with the most pronounced efficacy observed in the EA group. Additionally, PAC shows potential in mitigating neuroinflammation and oxidative damage by inhibiting the TLR4/NF-κB signalling pathway. This research lays a theoretical groundwork for the future clinical development and utilisation of PAC in treating AD.


Assuntos
Doença de Alzheimer , Physalis , Camundongos , Animais , Physalis/química , Doença de Alzheimer/induzido quimicamente , Espectrometria de Massas
3.
J Nat Prod ; 87(1): 38-49, 2024 01 26.
Artigo em Inglês | MEDLINE | ID: mdl-38207331

RESUMO

Physalis angulata var. villosa is a plant possessing abundant withanolides, but in-depth research is lacking. In our ongoing study of P. angulata var. villosa, 15 previously undescribed withanolides (1-15), along with 21 known analogs (16-36), were isolated from the whole plant. The structures of the withanolides (1-15) were elucidated based on analysis of their 1D and 2D NMR, HRESIMS, and ECD data. Additionally, the application of γ-gauche effects with the help of ROESY correlations led to the formulation of empirical rules for withanolides with 14-OH/15-OAc to rapidly determine the 14-OH orientations, making it possible to propose configurational revisions of 19 previously reported analogs (1'-19'). Withanolides 1, 4-6, and 10 showed potent cytotoxic activities against three human cancer cell lines (HCT-116, MDA-MB-231, and A549).


Assuntos
Antineoplásicos Fitogênicos , Physalis , Vitanolídeos , Humanos , Vitanolídeos/farmacologia , Vitanolídeos/química , Physalis/química , Extratos Vegetais/química , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Linhagem Celular , Estrutura Molecular
4.
J Ethnopharmacol ; 324: 117736, 2024 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-38242219

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: The genus Physalis L. (Solanaceae) is commonly used in the treatment of dermatitis, leprosy, bronchitis, pneumonia, hepatitis and rheumatism in China and other Asian countries. AIM OF THE REVIEW: This article reviews the resources, cultivation, phytochemistry, pharmacological properties, and applications of Physalis L., and proposes further research strategies to enhance its therapeutic potential in treating various human diseases. MATERIALS AND METHODS: We conducted a systematic search of electronic databases, including CNKI, SciFinder and PubMed, using the term "Physalis L." to collect information on the resources, phytochemistry, pharmacological activities, and applications of Physalis L. in China during the past ten years (2013.1-2023.1). RESULTS: So far, a variety of chemical constituents have been isolated and identified from Physalis L. mainly including steroids, flavonoids, and so on. Various pharmacological activities were evaluated by studying different extracts of Physalis L., these activities include anti-inflammatory, antibacterial, antioxidant, antiviral, antineoplastic, and other aspects. CONCLUSION: Physalis L. occupies an important position in the traditional medical system. It is cost-effective and is a significant plant with therapeutic applications in modern medicine. However, further in-depth studies are needed to determine the medical use of this plant resources and cultivation, chemical composition, pharmacological effects and applications.


Assuntos
Physalis , Humanos , Physalis/química , Medicina Tradicional , Fitoterapia , Medicina Tradicional Chinesa , Anti-Inflamatórios/farmacologia , Anti-Inflamatórios/uso terapêutico , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/uso terapêutico , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Extratos Vegetais/química , Etnofarmacologia
5.
J Nat Prod ; 87(1): 2-13, 2024 01 26.
Artigo em Inglês | MEDLINE | ID: mdl-38117981

RESUMO

The glucose transporter 1 (GLUT1) protein is involved in the basal-level absorption of glucose in tumor cells. Inhibiting GLUT1 decreases tumor cell proliferation and induces tumor cell damage. Natural GLUT1 inhibitors have been studied only to a small extent, and the structures of known natural GLUT1 inhibitors are limited to a few classes of natural products. Therefore, discovering and researching other natural GLUT1 inhibitors with novel scaffolds are essential. Physalis angulata L. var. villosa is a plant known as Mao-Ku-Zhi (MKZ). Withanolides are the main phytochemical components of MKZ. MKZ extracts and the components of MKZ exhibited antitumor activity in recent pharmacological studies. However, the antitumor-active components of MKZ and their molecular mechanisms remain unknown. A cell membrane-biomimetic nanoplatform (CM@Fe3O4/MIL-101) was used for target separation of potential GLUT1 inhibitors from MKZ. A new withanolide, physagulide Y (2), together with six known withanolides (1, 3-7), was identified as a potential GLUT1 inhibitor. Physagulide Y was the most potent GLUT1 inhibitor, and its antitumor activity and possible mechanism of action were explored in MCF-7 human cancer cells. These findings advance the development of technologies for the targeted separation of natural products and identify a new molecular framework for the investigation of natural GLUT1 inhibitors.


Assuntos
Antineoplásicos Fitogênicos , Physalis , Vitanolídeos , Humanos , Physalis/química , Transportador de Glucose Tipo 1 , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/química , Proteínas Facilitadoras de Transporte de Glucose , Extratos Vegetais/química , Vitanolídeos/farmacologia , Vitanolídeos/química , Proteínas de Membrana Transportadoras , Estrutura Molecular
6.
J Agric Food Chem ; 71(44): 16581-16592, 2023 Nov 08.
Artigo em Inglês | MEDLINE | ID: mdl-37897427

RESUMO

Physalis angulata Linn. is an exotic Amazonian fruit that is commonly recognized as wild tomato, winter cherry, and gooseberry. While its fruit is known to contain many nutrients, such as minerals, fibers, and vitamins, few papers have investigated withanolide derivatives from its fruits. UPLC-Q-Orbitrap-MS/MS, which produces fragmentation spectra, was applied for the first time to guide the isolation of bioactive withanolide derivatives from P. angulata fruits. As a result, twenty-six withanolide derivatives, including two novel 1,10-secowithanolides (1 and 2) and a new derivative (3), were obtained. Compounds 1 and 2 are rare rearranged 1,10-secowithanolides with a tetracyclic 7/6/6/5 ring system. All structures were assigned through various spectroscopic data and quantum chemical calculations. Nine withanolide derivatives exhibited significant inhibitory effects on three tumor cell lines with IC50 values of 0.51-13.79 µM. Moreover, three new compounds (1-3) exhibited potential nitric oxide inhibitory effects in lipopolysaccharide-stimulated RAW264.7 cells (IC50: 7.51-61.8 µM). This investigation indicated that fruits of P. angulata could be applied to treat and prevent cancer and inflammatory-related diseases due to their potent active withanolide derivatives.


Assuntos
Physalis , Vitanolídeos , Physalis/química , Relação Estrutura-Atividade , Vitanolídeos/farmacologia , Vitanolídeos/química , Frutas , Espectrometria de Massas em Tandem , Extratos Vegetais/farmacologia , Extratos Vegetais/química
7.
Biomed Chromatogr ; 37(10): e5701, 2023 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-37406673

RESUMO

Physalis Calyx seu Fructus (PCF) is a herb widely used in China for its function of clearing heat and detoxifying, benefitting the pharynx and reducing phlegm, both in health care and in tea drinking. However, the quality of its fruit and calyx is uneven and the storage period is short. Therefore, it is crucial to develop other parts of PCF with longer storage periods and obvious medicinal effects. Firstly, high-performance liquid chromatography was used to develop the fingerprint of different parts of PCF, and various chemometric analyses were conducted to screen out chemical markers. The calyxes of PCF were found to cluster together, distinct from the fruits, roots, stems and leaves. The active components of PCF were concentrated in the persistent calyxes, and flavonoids were mainly found in the persistent calyxes and leaves. Secondly, the extraction of persistent calyxes showed the strongest scavenging ability of DPPH and ABTS. Finally, the important chemical markers were verified by network pharmacological analysis and molecular docking. It provides a reference for the clinical application of PCF, and the obtained chemical markers offer a scientific basis for quality evaluation.


Assuntos
Frutas , Physalis , Antioxidantes/farmacologia , Physalis/química , Simulação de Acoplamento Molecular , Quimiometria , Farmacologia em Rede
8.
Chem Biodivers ; 20(9): e202301075, 2023 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-37505462

RESUMO

Physalis alkekengi L. var. franchetii (Mast.) Makino (PA) is a natural plant which is utilised as a traditional herbal medicine. It has properties that make it effective against inflammation and free radical damage. In the present study, the major constituents of four extraction parts of the fruits of PA (PAF) were investigated by combining ultra-performance liquid chromatography with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS). The mice model of Alzheimer's disease (AD) induced by aluminum chloride (AlCl3 ) combined with D-galactose (D-gal) was established to comprehend the mechanism behind PAF's anti-AD activity from both behavioural and pathological perspectives. The results showed that four extraction parts of PAF (PAFE) had favorable anti-AD effects and the ethyl acetate (EA) group showed the best activity. UPLC-Q-TOF-MS analysis identified Physalin B, Nobiletin and Caffeic acid as the main anti-AD active constituents in EA extract. This study reveals that PAF can reduce neuroinflammatory damage by inhibiting p38 mitogen-activated protein kinase (p38 MAPK) signaling pathway, which is the theoretical basis for clinical development and utilization of PAF in AD therapy.


Assuntos
Doença de Alzheimer , Physalis , Camundongos , Animais , Frutas , Physalis/química , Doença de Alzheimer/induzido quimicamente , Doença de Alzheimer/tratamento farmacológico , Extratos Vegetais/química
9.
Biosci Biotechnol Biochem ; 87(9): 972-980, 2023 Aug 23.
Artigo em Inglês | MEDLINE | ID: mdl-37279446

RESUMO

Inflammation, characterized by the overexpression of IL-6 in various tissues, has been reported as a symptom of coronavirus disease 2019. In this study, we established an experimental system for overexpression of IL-6 in HeLa cells stimulated by TNF-α and IL-17, along with identification of anti-inflammatory materials and components from local agricultural, forestry, and fishery resources. We constructed a library of extracts from natural sources, of which 111 samples were evaluated for their anti-inflammatory activities. The MeOH extract of Golden Berry (Physalis peruviana L) leaf was found to exhibit strong anti-inflammatory properties (IC50 = 4.97 µg/mL). Preparative chromatography identified two active constituents, 4ß-hydroxywithanolide E (4ß-HWE) (IC50 = 183 nM) and withanolide E (WE) (IC50 = 65.1 nM). Withanolides are known anti-inflammatory ingredients of Withania somnifera, an Ayurvedic herbal medicine. P. peruviana leaves containing 4ß-HWE and WE should be considered as useful natural resources for anti-inflammatory products.


Assuntos
COVID-19 , Physalis , Extratos Vegetais , Folhas de Planta , Vitanolídeos , Humanos , Células HeLa , Interleucina-17 , Interleucina-6/genética , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Fator de Necrose Tumoral alfa , Vitanolídeos/farmacologia , Vitanolídeos/análise , Vitanolídeos/química , Physalis/química , Folhas de Planta/química
10.
Biomed Pharmacother ; 162: 114622, 2023 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-37003035

RESUMO

Atopic dermatitis (AD) is a common, chronic, and recurring inflammatory skin disease. Physalis alkekengi L. var. franchetii (Mast) Makino (PAF), a traditional Chinese medicine, is primarily used for the clinical treatment of AD. In this study, a 2,4-dinitrochlorobenzene-induced AD BALB/c mouse model was established, and a comprehensive pharmacological method was used to determine the pharmacological effects and molecular mechanisms of PAF in the treatment of AD. The results indicated that both PAF gel (PAFG) and PAFG+MF (mometasone furoate) attenuated the severity of AD and reduced the infiltration of eosinophils and mast cells in the skin. Serum metabolomics showed that PAFG combined with MF administration exerted a synergistic effect by remodeling metabolic disorders in mice. In addition, PAFG also alleviated the side effects of thymic atrophy and growth inhibition induced by MF. Network pharmacology predicted that the active ingredients of PAF were flavonoids and exerted therapeutic effects through anti-inflammatory effects. Finally, immunohistochemical analysis confirmed that PAFG inhibited the inflammatory response through the ERß/HIF-1α/VEGF signaling pathway. Our results revealed that PAF can be used as a natural-source drug with good development prospects for the clinical treatment of AD.


Assuntos
Dermatite Atópica , Physalis , Camundongos , Animais , Physalis/química , Extratos Vegetais/farmacologia , Flavonoides , Hormônios
11.
Rocz Panstw Zakl Hig ; 74(1): 49-57, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-37010381

RESUMO

Background: Physalis peruviana L. fruit contains nutritional and bioactive compounds of immense importance to public health and represents a potential ingredient for the development of functional foods and beverages. Objective: This study aimed to determine the chemical and nutritional composition as well as the antioxidant capacity of the P. peruviana L. fruit grown in Peru in three areas of the Central Andean region. Material and methods: Proximal and physicochemical analyses and estimation of mineral content, vitamin C, total carotenoids, total polyphenols, and antioxidant capacity (2, 2-diphenyl-1-picrylhydrazyl [DPPH] and 2, 2'-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) [ABTS] assays) were performed using standardized methods. Results: The fruits were collected from three regions of the Peruvian Andes (Ancash, Cajamarca, and Cusco). The results showed that the content of potassium (306.54-327.60 mg/100 g) and iron (12.93-14.47 mg/kg) was prominent. The Physalis fruit had high levels of vitamin C (47.20-52.20 mg/100 g), total polyphenols (68.17-83.40 mg equivalents of gallic acid/100 g), and carotenoids (1.12-1.73 mg ß-carotene/100 g). Higher values for antioxidant capacity were obtained with the ABTS method (896-1003.33 µmol Trolox/100 g) than with the DPPH method (290-309 µmol Trolox/100 g). Conclusions: This study confirms that the P. peruviana fruit has properties that could provide important health benefits and that it could be used for the development of functional foods and food supplement.


Assuntos
Antioxidantes , Physalis , Humanos , Antioxidantes/análise , Frutas/química , Physalis/química , Peru , Ácido Ascórbico/análise , Carotenoides/análise , Polifenóis/análise , Extratos Vegetais/química , Vitaminas
12.
Chem Biodivers ; 20(4): e202300195, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-36932465

RESUMO

Six new withanolides, angulasteroidins A-F (1-6), along with twelve known analogs (7-18) were isolated from the whole plants of Physalis angulata. Their structures were elucidated by analysis of 1D and 2D NMR, ECD and IR spectra, HR-ESI-MS data, and ECD calculation. Compounds 1 and 6 were rare 1-10 seco withanolides. Compounds 2-4, 7-9, and 15 exhibited significant inhibitory activity on the production of nitric oxide in the LPS-activated RAW 264.7 mouse macrophage cell lines with IC50 values ranging from 0.23 to 9.06 µM.


Assuntos
Physalis , Vitanolídeos , Animais , Camundongos , Relação Estrutura-Atividade , Vitanolídeos/farmacologia , Vitanolídeos/química , Óxido Nítrico , Células RAW 264.7 , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Physalis/química , Physalis/metabolismo , Estrutura Molecular
13.
BMC Complement Med Ther ; 23(1): 21, 2023 Jan 27.
Artigo em Inglês | MEDLINE | ID: mdl-36707799

RESUMO

BACKGROUND: Cadmium is an environmentally toxic metal that has deleterious effects on both animals and humans due to its accumulation in different body tissues. Physalis peruviana L. fruit and calyx contain many active constituents which are used traditionally for their different biological activities. Based on the traditional uses of P. peruviana L. calyx, we aimed to evaluate the nephroprotective effect of their 80% aqueous methanol extract (AME) and n-butanol fraction (Bu.F.) against cadmium chloride-induced nephrotoxicity in rats and to correlate this activity with phytoconstituents isolated using molecular docking studies. METHODS: The n-butanol fraction of P. peruviana L. calyx was fractionated using various chromatographic techniques and the isolated compounds were identified based on their chemical and spectroscopic data. The nephroprotective activity was assessed using cadmium chloride-induced nephrotoxicity in the rat model, by measuring some important parameters such as body weight, kidney weight, serum urea, and creatinine levels, oxidative stress markers, inflammatory markers, and histopathological examinations of kidney tissue. Molecular docking studies of the isolated compounds were performed. RESULTS: Three withanolides named 4 ß-hydroxywithanolide E (1), Physalin B (2) and 3α, 14ß-dihydroxywithaphysalin N (3) were isolated and identified from the n-butanol fraction of P. peruviana L calyx extract. The extract and its butanol fraction significantly improved the serum kidney function markers and tissue oxidative status including malondialdehyde (MDA), reduced glutathione (GSH) and catalase (CAT). Additionally, the extracts significantly decreased the levels of tumor necrosis factor-alpha (TNF-α) and nuclear factor kappaB (NF-κß). Moreover, the histological changes were ameliorated by the extracts. The molecular docking study showed that the isolated compounds displayed a remarkable inhibitory activity against IκB kinase. CONCLUSION: The AME and its butanol fraction of P. peruviana L calyx showed potential nephroprotective activity against cadmium chloride-induced nephrotoxicity which is correlated at least in part to its considerable withanolides content.


Assuntos
Physalis , Vitanolídeos , Humanos , Ratos , Animais , Cloreto de Cádmio , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Physalis/química , Vitanolídeos/farmacologia , Simulação de Acoplamento Molecular , Cloretos , 1-Butanol
14.
J Asian Nat Prod Res ; 25(4): 349-356, 2023 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35796599

RESUMO

Two new withaphysalin-type withanolides (18-O-ethylwithaphysalin R and 5-O-ethylphysaminimin C, 1 and 2), along with twelve known withanolides (3-14), were purified and identified from Physalis peruviana L. The chemical structures of these new isolates were elucidated through analyzing spectroscopic and HRESIMS data. All the obtained metabolites were appraised for their potential antiproliferative activity against the human breast cancer cell line MCF-7. Compound 7 was discovered to exhibit potent activity with an IC50 value of 3.51 µM and compounds 2, 6 and 14 showed weak cytotoxic effect.


Assuntos
Antineoplásicos , Physalis , Vitanolídeos , Humanos , Physalis/química , Vitanolídeos/química , Extratos Vegetais/química
15.
Food Res Int ; 161: 111903, 2022 11.
Artigo em Inglês | MEDLINE | ID: mdl-36192919

RESUMO

In this work, metabolic profiling of the different parts of ground cherry (P. pruinosa) including fruits, calyces, leaves, stems and roots using UPLC-MS/MS analysis combined to chemometric analysis was attempted. A total of 82 chromatographic peaks belonging to different metabolite classes were identified including terpenes, flavonoids genin and glycosides, withanolides, physalins, sucrose esters, fatty acids and other miscellaneous compounds with withanolides being the most predominant class. Roots extracts possessed the highest relative content of the identified 5ß,6ß-epoxy withanolides and intermediate withanolides, while sucrose esters and flavonoidal glycosides were found in a great abundance in calyces extracts. Moreover, physalins were found in all extracts except for roots extracts. Studying the coefficients plots revealed that terpenes and physalins (physanicantriol, loliolide, physalisitin C) were responsible for discrimination of fruits extracts. Calyces, leaves and stems extracts were found to possess antioxidant activity and higher inhibition of α-glucosidase activity. In an attempt to identify the compounds responsible for the hypoglycemic activity using both α-amylase and α-glucosidase inhibition assays, OPLS models coefficient plots were constructed which indicated that physangulide B, physaperuvin G, neophysalin A, and acylsucroses were positively correlated to α-glucosidase inhibition, while guaiacyl-primeveroside, phyperunolide C, physalactone, physalolactone C and perulactone, were positively correlated to α-amylase inhibitory activity.


Assuntos
Physalis , Vitanolídeos , Antioxidantes/química , Quimiometria , Cromatografia Líquida , Ésteres , Ácidos Graxos , Flavonoides , Glicosídeos , Hipoglicemiantes , Metabolômica/métodos , Physalis/química , Extratos Vegetais/química , Sacarose , Espectrometria de Massas em Tandem , Terpenos , Vitanolídeos/química , Vitanolídeos/farmacologia , alfa-Amilases , alfa-Glucosidases
16.
Fitoterapia ; 163: 105340, 2022 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-36283569

RESUMO

From the extracts of stems and leaves as well as of calyxes of Physalis grisea were isolated four withalactols, the new griselactols A (3) and B (6) and the known physapubescin (1) and peruvianolide E (2). Other four known compounds were also isolated, kaempferol 3-O-ß-sophoroside (5) and three sterols. The structures of compounds were elucidated by extensive spectroscopic data analyses, chemical and physical-chemical methods, including electronic circular dichroism (ECD), and by comparison with data described in the literature. The antihyperglycemic activity of the extracts and of the three more abundant metabolites (1, 3, and 5) was evaluated in the α-glucosidase inhibition assay.


Assuntos
Physalis , Physalis/química , Extratos Vegetais/química , Estrutura Molecular , Folhas de Planta , Flores
17.
Molecules ; 27(18)2022 Sep 07.
Artigo em Inglês | MEDLINE | ID: mdl-36144521

RESUMO

In recent years there has been an extensive search for nature-based products with functional potential. All structural parts of Physalis alkekengi (bladder cherry), including fruits, pulp, and less-explored parts, such as seeds and peel, can be considered sources of functional macro- and micronutrients, bioactive compounds, such as vitamins, minerals, polyphenols, and polyunsaturated fatty acids, and dietetic fiber. The chemical composition of all fruit structural parts (seeds, peel, and pulp) of two phenotypes of P. alkekengi were studied. The seeds were found to be a rich source of oil, yielding 14-17%, with abundant amounts of unsaturated fatty acids (over 88%) and tocopherols, or vitamin E (up to 5378 mg/kg dw; dry weight). The predominant fatty acid in the seed oils was linoleic acid, followed by oleic acid. The seeds contained most of the fruit's protein (16-19% dw) and fiber (6-8% dw). The peel oil differed significantly from the seed oil in fatty acid and tocopherol composition. Seed cakes, the waste after oil extraction, contained arginine and aspartic acid as the main amino acids; valine, phenylalanine, threonine, and isoleucine were present in slightly higher amounts than the other essential amino acids. They were also rich in key minerals, such as K, Mg, Fe, and Zn. From the peel and pulp fractions were extracted fruit concretes, aromatic products with specific fragrance profiles, of which volatile compositions (GC-MS) were identified. The major volatiles in peel and pulp concretes were ß-linalool, α-pinene, and γ-terpinene. The results from the investigation substantiated the potential of all the studied fruit structures as new sources of bioactive compounds that could be used as prospective sources in human and animal nutrition, while the aroma-active compounds in the concretes supported the plant's potential in perfumery and cosmetics.


Assuntos
Frutas , Physalis , Arginina/análise , Ácido Aspártico/análise , Ácidos Graxos/análise , Ácidos Graxos Insaturados/análise , Frutas/química , Humanos , Isoleucina , Ácido Linoleico/análise , Ácido Oleico/análise , Fenilalanina/análise , Physalis/química , Óleos de Plantas/química , Estudos Prospectivos , Sementes/química , Treonina , Tocoferóis/análise , Valina/análise , Vitaminas/análise
18.
Phytochemistry ; 202: 113301, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35780926

RESUMO

Eight undescribed and two known withanolides were obtained from the aerial parts of Physalis minima. The structures of these compounds were defined by spectroscopic methods including 1D and 2D NMR, HRESIMS, and electronic circular dichroism (ECD) data analysis. Physminin E was elucidated to be a rare 13,14-seco-withanolide. Inhibitory effects of these compounds on nitric oxide (NO) production were evaluated by using LPS-activated RAW264.7 macrophages, and physminin C was shown to be the most active with an IC50 value of 3.5 µM. The further mechanistic analysis of NO inhibition was performed by molecular docking and Western blotting.


Assuntos
Physalis , Vitanolídeos , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Simulação de Acoplamento Molecular , Estrutura Molecular , Óxido Nítrico , Physalis/química , Componentes Aéreos da Planta , Vitanolídeos/química , Vitanolídeos/farmacologia
19.
Molecules ; 27(13)2022 Jun 30.
Artigo em Inglês | MEDLINE | ID: mdl-35807484

RESUMO

There is increasing interest in research of secondary metabolites from Physalis peruviana (Cape gooseberry) because of their potential bioactivities. In this study, the profile of compounds found in fruits and husks from Costa Rica was determined through ultra-performance liquid chromatography coupled with high-resolution mass spectrometry using a quadrupole time-of-flight analyzer (UPLC-ESI-QTOF MS) on extracts (n = 10) obtained through pressurized liquid extraction (PLE) conditions. In total, 66 different compounds were identified, comprising 34 withanolides, 23 sucrose ester derivatives and 9 flavonoids. UPLC-DAD analysis was performed to determine the ß-carotene in fruits and to quantify the flavonoids in all 10 samples, with the results showing higher contents in samples from the Dota region (58.6−60.1 µg/g of dry material versus 1.6−2.8 mg/g of dry material). The Folin−Ciocalteau total polyphenolic content (FC) and antioxidant activity using the DPPH method showed better results for the husk extracts, with the ones from the Dota region holding the best values (4.3−5.1 mg GAE/g of dry material versus IC50 = 1.6−2.3 mg of dry material/mL). In addition, a significant negative correlation was found between the RU, FC and DPPH values (r = −0.902, p < 0.05), aligning with previous reports on the role of polyphenols in antioxidant activity. Principal correlation analysis (PCoA) and hierarchical clustering (HC) analysis were performed on HRMS results, and they indicated that the D1 and D2 fruit samples from the Dota region were clustered with husks related to a higher presence of the analyzed metabolites. In turn, principal component analysis (PCA) performed on the flavonoid content and antioxidant activity yielded results indicating that the D1 and D2 husks and fruit samples from the Dota region stood out significantly, showing the highest antioxidant activity. In summation, our findings suggest that P. peruviana husks and fruits from Costa Rica constitute a substrate of interest for further studies on their potential health benefits.


Assuntos
Physalis , Ribes , Antioxidantes/química , Costa Rica , Flavonoides/química , Frutas/química , Physalis/química , Extratos Vegetais/química
20.
J Nat Prod ; 85(6): 1522-1539, 2022 06 24.
Artigo em Inglês | MEDLINE | ID: mdl-35608269

RESUMO

The inherent structural instability of some physalins has hampered the isolation and identification of these compounds for approximately 50 years, and an effective method to overcome these challenges remains unavailable. In the present study, the unprecedented tautomerization mechanism of unstable physalins was elucidated by performing isotopic labeling experiments and DFT calculations, which led to the successful separation of tautomers and isolation of highly pure products for the first time. As a result, 15 new physalins, physaminins A-O (1-15), as well as 17 known analogues (16-32), were isolated from the whole plants of Physalis minima L. The chemical structures of the new compounds were established by performing a comprehensive analysis of spectroscopic data, and their absolute configurations were confirmed by using computational ECD calculations and/or single-crystal X-ray diffraction analyses. All obtained isolates were evaluated for their antiproliferative effects against four human cancer cell lines (A549, HepG2, MCF-7, and SCG-7901) and two noncancerous cell lines (RAW 264.7 and human normal hepatocytes L02), as well as their anti-inflammatory activities by measuring their abilities to inhibit NO production in LPS-stimulated murine RAW 264.7 cells in vitro. Compounds 1-5, 13, 16, 18, 19, 23, and 30 exerted significant antiproliferative effects on the four human cancer lines, with IC50 values ranging from 0.2(0) to 24.7(2) µM, and these compounds were not toxic to the two noncancerous cell lines at a concentration of 10 µM. Moreover, compounds 7, 10, 11, 12, 14, 17, 22, and 27 significantly inhibited NO production, with IC50 values ranging from 2.9(1) to 9.5(2) µM.


Assuntos
Physalis , Animais , Anti-Inflamatórios/farmacologia , Humanos , Camundongos , Estrutura Molecular , Physalis/química , Células RAW 264.7
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