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1.
Chem Biodivers ; 21(5): e202400409, 2024 May.
Article in English | MEDLINE | ID: mdl-38459792

ABSTRACT

From Garcinia pedunculata Roxb. fruits, two undescribed aromatic compounds including a benzofuran and a depsidone derivative, and a new natural product, together with four known compounds were isolated. Through the analysis of spectroscopic data, high resolution mass spectrum and calculated nuclear magnetic resonance, their structures were determined. The α-glucosidase inhibitory activity of the isolates was evaluated. And compound 3 exhibited a moderate inhibitory effect on α-glucosidase. The molecular docking of compound 3 was performed to elucidate the interaction with α-glucosidase.


Subject(s)
Fruit , Garcinia , Glycoside Hydrolase Inhibitors , Molecular Docking Simulation , alpha-Glucosidases , Garcinia/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Fruit/chemistry , alpha-Glucosidases/metabolism , Molecular Structure , Structure-Activity Relationship , Depsides/chemistry , Depsides/isolation & purification , Depsides/pharmacology , Benzofurans/chemistry , Benzofurans/isolation & purification , Benzofurans/pharmacology
2.
Phytomedicine ; 128: 155400, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38518641

ABSTRACT

BACKGROUND: The emergence and spread of vancomycin-resistant enterococci (VRE) have posed a significant challenge to clinical treatment, underscoring the need to develop novel strategies. As therapeutic options for VRE are limited, discovering vancomycin enhancer is a feasible way of combating VRE. Gambogic acid (GA) is a natural product derived from the resin of Garcinia hanburyi Hook.f. (Clusiaceae), which possesses antibacterial activity. PURPOSE: This study aimed to investigate the potential of GA as an adjuvant to restore the susceptibility of VRE to vancomycin. METHODS: In vitro antibacterial and synergistic activities were evaluated against vancomycin-susceptible and resistant strains by the broth microdilution method for the Minimal Inhibitory Concentrations (MICs) determination, and checkerboard assay and time-kill curve analysis for synergy evaluation. In vivo study was conducted on a mouse multi-organ infection model. The underlying antibacterial mechanism of GA was also explored. RESULTS: GA showed a potent in vitro activity against all tested strains, with MICs ranging from 2 to 4 µg/ml. The combination of GA and vancomycin exhibited a synergistic effect against 18 out of 23 tested VRE strains, with a median fractional inhibitory concentration index (FICI) of 0.254, and demonstrated a synergistic effect in the time-kill assay. The combination therapy exhibited a significant reduction in tissue bacterial load compared with either compound used alone. GA strongly binds to the ParE subunit of topoisomerase IV, a bacterial type II DNA topoisomerase, and suppresses its activity. CONCLUSIONS: The study suggests that GA has a significant antibacterial activity against enterococci, and sub-MIC concentrations of GA can restore the activity of vancomycin against VRE in vitro and in vivo. These findings indicate that GA has the potential to be a new antibacterial adjuvant to vancomycin in the treatment of infections caused by VRE.


Subject(s)
Anti-Bacterial Agents , Drug Synergism , Microbial Sensitivity Tests , Vancomycin-Resistant Enterococci , Vancomycin , Xanthones , Xanthones/pharmacology , Animals , Vancomycin-Resistant Enterococci/drug effects , Anti-Bacterial Agents/pharmacology , Vancomycin/pharmacology , Mice , Garcinia/chemistry , Female , Gram-Positive Bacterial Infections/drug therapy
3.
Plant Foods Hum Nutr ; 79(1): 12-19, 2024 Mar.
Article in English | MEDLINE | ID: mdl-38191770

ABSTRACT

Native species from the Amazonia are still unknown or underutilized and few information about their chemical and biological properties are available in the literature. Among the underutilized plant species in the Amazonia, Garcinia macrophylla can be seen as a promising source of bioactive compounds with relevant biological properties. The stem bark and leaves were the main investigated plant parts, mainly concerning the antioxidant, antibacterial, cytotoxicity and antidiabetic properties. However, the bioactive compounds and biological properties of the edible fruits were not yet reported. Systematic investigations covering the Amazonia biome, concerning plants and vegetables as strategic resources are of paramount importance for the sustainable development of the forest. Therefore, this review gathered the available information in the literature concerning general aspects, chemical profile and biological properties of G. macrophylla, for the first time, which highlighted that systematic and robust in vitro and in vivo research, are still needed to elucidate the phytochemical profiles and associated relevant biological properties.


Subject(s)
Garcinia , Plant Extracts , Plant Extracts/pharmacology , Plant Extracts/chemistry , Garcinia/chemistry , Brazil , Anti-Bacterial Agents/chemistry , Plant Leaves , Phytochemicals/pharmacology , Phytochemicals/chemistry
4.
Nat Prod Res ; 38(10): 1687-1694, 2024 May.
Article in English | MEDLINE | ID: mdl-37234037

ABSTRACT

Bioassay-guided isolation of the stems of Garcinia paucinervis led to one new adamantane-type polycyclic polyprenylated acylphloroglucinols (PPAPs), (-)-garpauvinin A (1), and four known analogues (2-5). The structure and absolute configuration of 1 was established via spectroscopic techniques and ECD method. All the isolates displayed moderate antiproliferative activity against HL-60, PC-3 and Caco-2 human cancer cell lines with IC50 values ranging from 0.81 to 19.92 µM, and exhibited low toxicity on WPMY-1 normal human cells, showing selectivity between normal and malignant prostate cells. The biosynthetic pathways of the isolated PPAPs were proposed.


Subject(s)
Garcinia , Hypericum , Humans , Molecular Structure , Caco-2 Cells , Garcinia/chemistry , HL-60 Cells , Phloroglucinol , Hypericum/chemistry
5.
Phytochemistry ; 217: 113898, 2024 Jan.
Article in English | MEDLINE | ID: mdl-37875167

ABSTRACT

Eight previously undescribed and seven known xanthones were isolated from the fruits of Garcinia pedunculata Roxb. The structures were identified by a variety of spectroscopic methods as well as by comparison with the literature. The isolates showed appreciable cytotoxicity against three human tumor cell lines (HepG2, A549, and MCF-7). Pedunculaxanthone G exhibited inhibitory activities with IC50 values of 12.41, 16.51, and 15.45 µM against the cancer cell lines and induced cell apoptosis in HepG2 cells.


Subject(s)
Antineoplastic Agents, Phytogenic , Antineoplastic Agents , Garcinia , Thoracica , Xanthones , Animals , Humans , Garcinia/chemistry , Xanthones/pharmacology , Xanthones/chemistry , Fruit , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Cell Line, Tumor , Molecular Structure
6.
Fitoterapia ; 172: 105779, 2024 Jan.
Article in English | MEDLINE | ID: mdl-38104910

ABSTRACT

Six new compounds, including two depsidones garciculendepsidones A and B (1 and 2), one prenylated xanthone garciculenxanthone (3) and three dimeric xanthones bigarciculenxanthones A-C (4-6), were isolated from the twigs and leaves of Garcinia esculenta Y. H. Li. Their structures were elucidated based on comprehensive analyses of spectral data, including HRESIMS, 1D and 2D NMR, and ECD calculation. All the isolates were tested for their cytotoxicity against five human cancer cell lines (myeloid leukemia HL-60, lung cancer A-549 cells, hepatocellular carcinoma SMMC-7721, breast cancer MDA-MB-231 and colon cancer SW480), among them, compounds 3-5 displayed cytotoxic potential, especially garciculenxanthone (3) had the lowest IC50 value of 8.2 µm for lung cancer A-549 cells.


Subject(s)
Antineoplastic Agents, Phytogenic , Antineoplastic Agents , Depsides , Garcinia , Lactones , Lung Neoplasms , Xanthones , Humans , Molecular Structure , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Garcinia/chemistry , Xanthones/pharmacology , Xanthones/chemistry , Lung Neoplasms/drug therapy
7.
Drug Des Devel Ther ; 17: 3625-3660, 2023.
Article in English | MEDLINE | ID: mdl-38076632

ABSTRACT

The previous phytochemical analyses of Garcinia hanburyi revealed that the main structural characteristic associated with its biological activity is the caged polyprenylated xanthones with a unique 4-oxatricyclo [4.3.1.03,7] dec-2-one scaffold, which contains a highly substituted tetrahydrofuran ring with three quaternary carbons. Based on the progress in research of the chemical constituents, pharmacological effects and modification methods of the caged polyprenylated xanthones, this paper presents a preliminary predictive analysis of their drug-like properties based on the absorption, distribution, metabolism, excretion and toxicity (ADME/T) properties. It was found out that these compounds have very similar pharmacokinetic properties because they possess the same caged xanthone structure, the 9,10-double bond in a,b-unsaturated ketones are critical for the antitumor activity. The author believes that there is an urgent need to seek new breakthroughs in the study of these caged polyprenylated xanthones. Thus, the research on the route of administration, therapeutic effect, structural modification and development of such active ingredients is of great interest. It is hoped that this paper will provide ideas for researchers to develop and utilize the active ingredients derived from natural products.


Subject(s)
Biological Products , Garcinia , Xanthones , Molecular Structure , Garcinia/chemistry , Xanthones/pharmacology , Xanthones/chemistry
8.
Zhongguo Zhong Yao Za Zhi ; 48(21): 5817-5821, 2023 Nov.
Article in Chinese | MEDLINE | ID: mdl-38114177

ABSTRACT

Eight compounds were isolated from ethyl acetate fraction of 80% ethanol extract of the hulls of Garcinia mangostana by silica gel, Sephadex LH-20 column chromatography, as well as prep-HPLC methods. By HR-ESI-MS, MS, 1D and 2D NMR spectral analyses, the structures of the eight compounds were identified as 16-en mangostenone E(1), α-mangostin(2), 1,7-dihydroxy-2-(3-methy-lbut-2-enyl)-3-methoxyxanthone(3), cratoxyxanthone(4), 2,6-dimethoxy-para-benzoquinone(5), methyl orselinate(6), ficusol(7), and 4-(4-carboxy-2-methoxyphenoxy)-3,5-dimethoxybenzoic acid(8). Compound 1 was a new xanthone, and compound 4 was a xanthone dimer, compound 5 was a naphthoquinone. All compounds were isolated from this plant for the first time except compounds 2 and 3. Cytotoxic bioassay suggested that compounds 1, 2 and 4 possessed moderate cytotoxicity, suppressing HeLa cell line with IC_(50) va-lues of 24.3, 35.5 and 17.1 µmol·L~(-1), respectively. Compound 4 also could suppress K562 cells with an IC_(50) value of 39.8 µmol·L~(-1).


Subject(s)
Antineoplastic Agents , Garcinia mangostana , Garcinia , Xanthones , Humans , Garcinia mangostana/chemistry , HeLa Cells , Magnetic Resonance Spectroscopy , Xanthones/pharmacology , Garcinia/chemistry , Plant Extracts/chemistry , Molecular Structure
9.
CuidArte, Enferm ; 17(2): 197-203, jul.-dez. 2023. graf, ilus
Article in Portuguese | BDENF - Nursing | ID: biblio-1552910

ABSTRACT

Introdução: A Garcinia gardneriana é utilizada na medicina tradicional brasileira para o tratamento de tumores, inflamações e alívio de dores, mas as informações científicas são ainda limitadas. Objetivos: Diante do uso popular e o anseio por efeitos colaterais mínimos, o objetivo geral deste estudo foi avaliar as propriedades anti-inflamatórias da G. gardneriana em modelo de peritonite induzido por lipopolissacarideo (LPS). Métodos: Ratos Wistar foram divididos aleatoriamente em 3 grupos (n= 5/ grupo): controle, induzido à peritonite e não tratado e induzido à peritonite e tratado com extrato de folhas alcoólico de G. gardneriana a 4%. A peritonite foi induzida por única injeção intraperitoneal de LPS (1 mg/kg). O tratamento com o extrato foi realizado por gavagem (1 ml), administrado antes e 12h após a injeção do LPS. Os ratos foram eutanasiados após 24h da indução de peritonite. Amostras de sangue foram coletadas para análise plasmática de histamina, o lavado intraperitoneal para quantificação de neutrófilos e o intestino delgado para processamento histológico, quantificação de mastócitos e imuno-histoquímica da expressão da proteína Anexina A1 (AnxA1). Resultados: As análises quantitativas indicaram os efeitos anti-inflamatórios do extrato, pela redução do recrutamento de neutrófilos para a cavidade peritoneal e a diminuição da quantidade de mastócitos na lâmina própria do intestino delgado, comparadas aos animais não tratados. Não houve diferença estatística dos níveis de histamina. A imuno-histoquímica indicou diminuição acentuada da expressão da AnxA1 na mucosa intestinal dos animais tratados. Conclusão: Nossos dados demonstraram que o extrato alcoólico de G. gardneriana tem forte ação anti-inflamatória e potencial terapêutico para o desenvolvimento de fitoterápicos com propriedades anti-inflamatórias


Introduction: Garcinia gardneriana is used in traditional Brazilian medicine for the treatment of tumors, inflammation and relief of pain, but scientific information is still limited. Objective: In the face of popular use and the desire for minimal side effects, the general objective of this study was to evaluate the anti-inflammatory properties of G. gardneriana in a model of lipopolysaccharide-induced peritonitis (LPS). Methods: Wistar rats were randomly divided into 3 groups (n = 5 / group): control, induced to peritonitis and untreated and induced to peritonitis and treated with 4% alcoholic extract of G. gardneriana leaves. Peritonitis was induced by single intraperitoneal injection of LPS (1 mg/kg). Treatment with the extract was performed by gavage (1 ml), given before and 12h after LPS injection. The rats were euthanized 24h after the peritonitis induction. Blood samples were collected for plasma analysis of histamine, intraperitoneal lavage for quantification of neutrophils and the small intestine for histological processing for quantification of mast cells, and immunohistochemical analysis of the expression of Annexin A1 (AnxA1) protein. Results: Quantification analyses indicated the anti-inflammatory effects of the extract by reducing the recruitment of neutrophils into the peritoneal cavity and reducing the amount of mast cells in the lamina propria of the small intestine compared to the untreated animals. There was no statistical difference in the levels of histamine. Immunohistochemical studies indicated a marked decrease of the AnxA1 expression in the intestinal mucosa of the treated animals. Conclusion: Our data demonstrated that the alcoholic extract of G. gardneriana has a strong anti-inflammatory action and therapeutic potential for the development of herbal products with anti-inflammatory properties


Introducción: Garcinia gardneriana se utiliza en la medicina tradicional brasileña para el tratamiento de tumores, inflamaciones y alivio del dolor, pero la información científica aún es limitada. Objetivo: Frente al uso popular y la búsqueda de efectos secundarios mínimos, lo objetivo general de este estudio fue evaluar las propiedades antiinflamatorias de G. gardneriana en un modelo de peritonitis inducido por lipopolisacárido (LPS). Métodos: Se dividieron aleatoriamente ratas Wistar en 3 grupos (n= 5/grupo): control, inducido a peritonitis y no tratado, e inducido a peritonitis y tratado con extracto alcohólico de hojas de G. gardneriana al 4%. La peritonitis fue inducida por una única inyección intraperitoneal de LPS (1 mg/kg). El tratamiento con el extracto se realizó por gavaje (1 ml), administrado antes y 12 horas después de la inyección de LPS. Las ratas fueron sacrificadas después de 24 horas de la inducción de peritonitis. Se recopilaron muestras de sangre para el análisis plasmático de histamina, el lavado intraperitoneal para la cuantificación de neutrófilos y el intestino delgado para el procesamiento histológico, la cuantificación de mastocitos y la inmunohistoquímica de la expresión de la proteína Anexina A1 (AnxA1). Resultados: Los análisis cuantitativos indicaron los efectos antiinflamatorios del extracto, mediante la reducción del reclutamiento de neutrófilos en la cavidad peritoneal y la disminución de la cantidad de mastocitos en la lámina propia del intestino delgado, en comparación con los animales no tratados. No hubo diferencia estadística en los niveles de histamina. La inmunohistoquímica indicó una disminución pronunciada de la expresión de AnxA1 en la mucosa intestinal de los animales tratados. Conclusión: Nuestros datos demostraron que el extracto alcohólico de G. gardneriana tiene una fuerte acción antiinflamatoria y potencial terapéutico para el desarrollo de fitoterapéuticos con propiedades antiinflamatorias.


Subject(s)
Animals , Female , Rats , Peritonitis/chemically induced , Peritonitis/drug therapy , Plant Extracts/therapeutic use , Garcinia/chemistry , Lipopolysaccharides , Rats, Wistar
10.
Bioorg Chem ; 138: 106651, 2023 09.
Article in English | MEDLINE | ID: mdl-37300961

ABSTRACT

Eight previously undescribed polycyclic polyprenylated acylphloroglucinols (PPAPs) were isolated from the fruits of Garcinia bracteata and named garcibractinols A-H. Garcibractinols A-F (compounds 1-6) were bicyclic polyprenylated acylphloroglucinols (BPAPs) sharing a rare bicyclo[4.3.1]decane core. On the other hand, garcibractinols G and H (compounds 7 and 8) shared an unprecedented BPAP skeleton bearing a 9-oxabicyclo[6.2.1]undecane core. The structures andabsolute configurations of compounds 1-8 were determined by spectroscopic analysis,single-crystal X-ray diffraction analysis, and quantum chemical calculation. The breakage of the C-3/C-4 linkage through the retro-Claisen reaction was a key step in the biosynthesis of compounds 7 and 8. The antihyperglycemic effects of the eight compounds were evaluated in insulin-resistant HepG2 cells. At a concentration of 10 µM, compounds 2 and 5-8 significantly increased the glucose consumption in the HepG2 cells. Furthermore, compound 7 was more effective than metformin (which was used as a positive control) in promoting glucose consumption in the cells. The findings of this study suggest that compounds 2 and 5-8 have anti-diabetic effects.


Subject(s)
Garcinia , Garcinia/chemistry , Molecular Structure , Fruit , Phloroglucinol/pharmacology , Phloroglucinol/chemistry , Hypoglycemic Agents/pharmacology
11.
J Pharm Pharmacol ; 75(8): 1058-1065, 2023 Aug 01.
Article in English | MEDLINE | ID: mdl-37307431

ABSTRACT

OBJECTIVES: We investigate the anticancer activity and human stimulator of interferon genes pathway activation by a new hydrated-prenylated tetraoxygenated xanthone, garcicowanone I (1) and two known xanthones (2 and 3) that were isolated from the root bark of Garcinia cowa Roxb. ex Choisy. METHODS: The anticancer activity of each compound was evaluated by sulforhodamine B assay in immortalized cancer cell lines. Stimulator of interferon genes pathway activation was assessed by western blot analysis using human THP-1-derived macrophages. The production of pro-inflammatory cytokines from these macrophages was also evaluated via enzyme-linked immunosorbent assay. KEY FINDINGS: Both compounds 1 and 3 displayed moderate inhibitory effects on the cancer cells, including a cisplatin-resistant cell line, with IC50 values in the range of 10-20 µM. All three xanthones activated the stimulator of interferon genes, as evidenced by phosphorylation of tank-binding kinase 1, the stimulator of interferon genes protein and interferon regulatory factor 3. Furthermore, treatment of these macrophages with compounds 1-3 led to the production of pro-inflammatory cytokines, including interleukin 6, tumour necrosis factor α and interleukin 1ß. CONCLUSIONS: In conclusion, the isolated xanthones, including the novel garcicowanone I, displayed promising anticancer and immunomodulatory activity that warrants further research.


Subject(s)
Garcinia , Xanthones , Humans , Garcinia/chemistry , Xanthones/pharmacology , Xanthones/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Cell Line , Interferons , Molecular Structure
12.
Phytochemistry ; 211: 113701, 2023 Jul.
Article in English | MEDLINE | ID: mdl-37127017

ABSTRACT

Ten undescribed benzophenones, schomburginones A-J, together with 14 known analogs were isolated from the leaves of Garcinia schomburgkiana, an edible plant native to the Indochina region. The structures of the undescribed compounds were elucidated by NMR combined with HRMS spectroscopy, while their absolute configurations were determined using ECD and single-crystal X-ray diffraction analysis. The isolated metabolites represent benzophenone derivatives containing a modified monoterpene unit, including tri- and tetracyclic skeletons, which are rarely found in genus Garcinia. The cytotoxic evaluation on three cancerous cell lines demonstrated that schomburginone G, schomburginone H, and 3-geranyl-2,4,6-trihydroxybenzophenone were active against HeLa cells with IC50 values in the range of 12.2-15.7 µM, respectively, and selective compared to the non-cancerous L929 cells (SI > 3.5). In addition, the three cytotoxic compounds together with clusiacyclol A showed significant NO inhibitory activity in RAW 264.7 macrophage cells over 85% inhibition without obvious cytotoxicity at a final concentration of 100 µM. The promising activities of these compounds in cytotoxic and anti-inflammatory assays make them attractive for further study in the development of anticancer drugs.


Subject(s)
Antineoplastic Agents, Phytogenic , Antineoplastic Agents , Garcinia , Xanthones , Humans , HeLa Cells , Molecular Structure , Garcinia/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Benzophenones/pharmacology , Benzophenones/chemistry , Xanthones/chemistry
13.
Nutrients ; 15(6)2023 Mar 07.
Article in English | MEDLINE | ID: mdl-36986038

ABSTRACT

The study of medicinal plants, such as the genus Garcinia (Clusiaceae), in the treatment of non-communicable chronic diseases has aroused the interest of researchers. However, there are no studies in the literature that have investigated the effects of Garcinia gardneriana in experimental models of obesity for possible metabolic alterations. Swiss mice receiving a high-fat diet were supplemented with aqueous or ethanolic extract of G. gardneriana at doses of 200 or 400 mg/kg/day. It was found that there was a reduction in food consumption in experimental groups compared with the control groups, and the group supplemented with aqueous extract at a dose of 200 mg/kg/daydisplayed a reduction in weight. The results showed an increase in the values of high density lipoprotein (HDL-c), total cholesterol, triglycerides and fasting blood glucose. G. gardneriana did not protect against insulin resistance, and caused in an increase in monocyte chemoattractant protein-1 (MCP-1) concentrations and a reduction in interleukin 10 (IL-10). In addition, hepatic steatosis and microvesicular steatosis were indicated. It was revealed that, under the experimental conditions in the study, G. gardneriana did not prevent weight gain or comorbidities; that is, a different behavior was obtained from that described in the literature with regard to the medicinal potential of the Garcinia species, which is probably related to the phytochemical properties.


Subject(s)
Fatty Liver , Garcinia , Plants, Medicinal , Mice , Animals , Garcinia/chemistry , Plant Extracts/pharmacology , Ethanol , Water , Diet, High-Fat/adverse effects
14.
Biofactors ; 49(3): 584-599, 2023.
Article in English | MEDLINE | ID: mdl-36785888

ABSTRACT

Garcinia gummi-gutta, also known as Garcinia cambogia, is a member of the Guttiferae family. Garcinia is a polygamous genus consisting 200 species of trees and shrubs. It is found in different zones of the planet including Asia's tropical regions. In India alone, around 30 species have been discovered. They are widely used as a flavoring agent to garnish fish curry in southern India, particularly in Kerala and Karnataka. The fruit rind of G. gummi-gutta has traditionally been used to treat gastrointestinal problems, diarrhea, and ulcers. South Indian people have been utilizing it traditionally as evidenced by its ethnobotanical properties. In vivo and in vitro effects of the crude fruit extract showed anti-inflammatory, anti-cancer, anthelmintic, anti-microbial, and antioxidant activities. G. gummi-gutta fruit rind is medicinally significant and is frequently used in ayurvedic and traditional medicine for many diseases. Various secondary metabolites such as organic acids-hydroxycitric acid (HCA), flavonoids, terpenes, polysaccharides and polyisoprenylated benzophenones-garcinol, xanthochymol, guttiferone, benzophenone, xanthone, biflavonoids, alkaloids, tannins, phenols, and saponins isolated from the G. gummi-gutta have diverse pharmacological activities. This review provides a summary of G. gummi-gutta, including its biological activities, phytochemistry, and ethnobotanical applications.


Subject(s)
Garcinia , Animals , Garcinia/chemistry , India , Garcinia cambogia/chemistry , Antioxidants/pharmacology , Plant Extracts/pharmacology , Plant Extracts/chemistry , Phytochemicals/pharmacology
15.
Fitoterapia ; 166: 105435, 2023 Apr.
Article in English | MEDLINE | ID: mdl-36731607

ABSTRACT

In order to find potential agents for treating cancer disease in naturally occurring compounds, we conducted a systematic phytochemical investigation on the endemic species of Garcinia nujiangensis. Three new biphenyl derivatives (1-3) and one new polycyclic polyprenylated benzophenone (4), together with four known benzophenone analogues (5-8), have been isolated from the CH2Cl2 extract of the twigs and leaves of G. nujiangensis. Their structures were determined by detailed spectroscopic analyses and comparison with structurally related known analogues. Experimental and calculated ECD method was used to determine the absolute configuration of 1 and 4. Moreover, compounds 5-7 were isolated for the first time from this species. The cytotoxicities of the new compounds were evaluated using HL-60, HepG2, and A549 human cancer cell lines. Compound 4 showed more significant antiproliferative effects against HepG2 cells with an IC50 value of 11.38 ± 0.79 µM than that of three biphenyl derivatives. The morphological features of apoptosis were evaluated in 4-treated HepG2 cells. Compound 4 effectively prevented the cell cycle progression of HepG2 cells in G2 phase. Additionally, western blot analysis indicated that treatment of 4 on HepG2 cells led to decreased expression of anti-apoptotic Bcl-2 and pro-Caspase-3, and increased protein expression of both pro-apoptotic Bax and cleaved PARP with reference to ß-actin. Overall, our results suggested that the active polycyclic polyprenylated benzophenone derivatives in the twigs and leaves of G. nujiangensis can be used as a valuable source of bioactive compounds for the pharmaceutical industry.


Subject(s)
Antineoplastic Agents, Phytogenic , Garcinia , Humans , Phenols/pharmacology , Cell Line, Tumor , Molecular Structure , Garcinia/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Apoptosis , Benzophenones/pharmacology
16.
Phytochemistry ; 209: 113622, 2023 May.
Article in English | MEDLINE | ID: mdl-36849096

ABSTRACT

Ten undescribed polyprenylated benzoylphloroglucinol derivatives named garcowacinols A‒J (1-10) and four known analogues (11-14) were isolated from the twigs of Garcinia cowa. Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and their absolute configurations were established based on NOESY and ECD data. All isolated compounds were evaluated for their cytotoxicity against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29) as well as Vero cells by MTT colorimetric assay. Garcowacinol C was significantly active against all the five cancer cells with IC50 values in the range of 0.61-9.50 µM. Selective proliferative inhibitions were observed on garcowacinol F and 7-epiclusianone against KB cells, and guttiferone Q toward MCF-7 cells with IC50 values less than 10 µM.


Subject(s)
Antineoplastic Agents, Phytogenic , Antineoplastic Agents , Garcinia , Xanthones , Animals , Chlorocebus aethiops , Humans , Garcinia/chemistry , Molecular Structure , Vero Cells , Antineoplastic Agents, Phytogenic/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Xanthones/chemistry
17.
Fitoterapia ; 165: 105427, 2023 Mar.
Article in English | MEDLINE | ID: mdl-36621652

ABSTRACT

Our continuous study of the dry fruits of Garcinia xanthochymus led to the isolation and structural characterization of four new prenylated acylphloroglucinols, xanthochymusones J-M (1-4), together with the known polycyclic polyprenylated acylphloroglucinols, garciniagifolone A (5) and garcinialiptone A (6). Their structures were elucidated by interpretation of NMR and MS spectroscopic data. Compound 1 bearing a similar core to that of hulupinic acid should be derived via oxidization and ring contraction of prenylated acylphloroglucinol. The inhibitory activities of all the compounds against three human hepatocellular carcinoma cell lines Huh-7, Hep 3B, and Hep G2 were evaluated, and compounds 4 and 5/6 exhibited moderate cytotoxic activities against Hep G2 cells with IC50 values10.4 and 8.8 µM.


Subject(s)
Antineoplastic Agents, Phytogenic , Antineoplastic Agents , Garcinia , Humans , Molecular Structure , Garcinia/chemistry , Fruit/chemistry , Cell Line , Phloroglucinol
18.
Chem Biodivers ; 20(2): e202200910, 2023 Feb.
Article in English | MEDLINE | ID: mdl-36628555

ABSTRACT

Garcinia cowa of the Clusiaceae family, native to South-East Asia used in traditional medicine. It has antipyretic, antimicrobial, and many other biological activities. In this review, a thorough study of this plant's chemical constituents and pharmacological and therapeutic effects was conducted from the research articles from PubMed, Science Direct, Google Scholar, and Scopus from 1977 to 2022. Reported secondary metabolites are enriched with xanthones, phloroglucinols, depsidones, steroids, etc. α-mangostin, ß-mangostin, cowaxanthone, rubraxanthone, cowanin, norcowanin, etc. represent the major xanthones. This article discusses the relationship between the different functional groups in xanthone compounds and their bioactivity against cancer, diabetes, bacteria, leishmania, malaria, and inflammation. This review is a comprehensive compendium of major bioactive molecules and its implication for human disease.


Subject(s)
Garcinia , Xanthones , Humans , Garcinia/chemistry , Phytochemicals , Plant Extracts/chemistry , Xanthones/chemistry
19.
Nat Prod Res ; 37(5): 750-758, 2023 Mar.
Article in English | MEDLINE | ID: mdl-35727176

ABSTRACT

Nine compounds including a new one, garcichaudiic acid (1), were isolated from the bark of G. gaudichaudii and their structures were characterized mainly by 1 D and 2 D NMR experiments. The antioxidant capacity of the isolated compounds was determined using DPPH radical scavenging assay and the anti-hyperglycemic activity was assessed by measuring the inhibitory effect against α-glucosidase. Among them, compound 4 showed higher antioxidant activity than the positive control, ascorbic acid, while both compounds 1 and 7 exhibited more significant α-glucosidase inhibitory activity than the reference drug acarbose. Molecular docking analysis of the bioactive compounds was also performed to examine the binding modes and key interactions with the catalytic site.


Subject(s)
Antioxidants , Garcinia , Antioxidants/chemistry , alpha-Glucosidases/metabolism , Glycoside Hydrolase Inhibitors/chemistry , Molecular Docking Simulation , Garcinia/chemistry
20.
Nat Prod Res ; 37(2): 188-196, 2023 Jan.
Article in English | MEDLINE | ID: mdl-34498967

ABSTRACT

Two new polyisoprenylated benzophenones, planchoniones A (1) and B (2), together with two known benzophenones (3, 4) and six known xanthones (5-10), were isolated from an ethyl acetate extract of the pericarp of Garcinia planchonii Pierre. Their structures were established using spectroscopic methods, mainly 1D and 2D NMR. The four benzophenones were evaluated for their cytotoxicity against MCF-7 human breast cancer cells, and showed almost no activity. Meanwhile, compounds 5-10 were investigated for their inhibitory effects towards α-glucosidase, and γ-mangostin (5) exhibited the most remarkable effect with IC50 value of 15.3 ± 0.9 µM (compared with acarbose, IC50 = 224.9 ± 3.6 µM).


Subject(s)
Garcinia , Xanthones , Humans , Garcinia/chemistry , Benzophenones/pharmacology , Benzophenones/chemistry , Xanthones/pharmacology , Xanthones/chemistry , Magnetic Resonance Spectroscopy , alpha-Glucosidases/metabolism , Molecular Structure
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