187 results match your criteria triterpenes friedelin


Molecular Docking and Molecular Dynamics Simulation Studies of Triterpenes from with the Cannabinoid Type 1 Receptor.

Int J Mol Sci 2021 Mar 30;22(7). Epub 2021 Mar 30.

Natural Products Research Laboratory, Strathclyde Institute of Pharmacy and Biomedical Sciences, University of Strathclyde, Glasgow G4 0RE, UK.

A molecular docking approach was employed to evaluate the binding affinity of six triterpenes, namely epifriedelanol, friedelin, α-amyrin, α-amyrin acetate, β-amyrin acetate, and bauerenyl acetate, towards the cannabinoid type 1 receptor (CB1). Molecular docking studies showed that friedelin, α-amyrin, and epifriedelanol had the strongest binding affinity towards CB1. Molecular dynamics simulation studies revealed that friedelin and α-amyrin engaged in stable non-bonding interactions by binding to a pocket close to the active site on the surface of the CB1 target protein. Read More

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Two Triterpene Synthases from Imperata cylindrica Catalyzing the Formation of a Pair of Diastereoisomers through Boat or Chair Cyclization.

Chembiochem 2021 Mar 4. Epub 2021 Mar 4.

School of Agriculture, Meiji University, 1-1-1 Higashimita, Tama-ku, Kawasaki, Kanagawa, 214-8571, Japan.

Imperata cylindrica is known to produce a pair of triterpenes, isoarborinol and fernenol, that exhibit identical planar structures but possess opposite stereochemistry at six of the nine chiral centers. These differences arise from a boat or a chair cyclization of the B-ring of the substrate. Herein, we report the characterization of three OSC genes from I. Read More

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Friedelin exhibits antidiabetic effect in diabetic rats via modulation of glucose metabolism in liver and muscle.

J Ethnopharmacol 2021 Mar 1;268:113659. Epub 2020 Dec 1.

Division of Ethnopharmacology, Entomology Research Institute, Loyola College, Chennai, 600034, India.

Ethnopharmacological Relevance: Demand for plant-based medications and therapeutics is increasing worldwide as of its potential effects and no toxic. Traditionally, so many medicinal plants are used to treat diabetes. Subsequently, investigation on medicinal plants was enduring to discover potential antidiabetic drugs. Read More

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Phytochemical, metabolic profiling and antiparasitic potential from leaves (Fabaceae).

Nat Prod Res 2020 Sep 9:1-6. Epub 2020 Sep 9.

Department of Organic Chemistry, Institute of Chemistry, Nucleus of Bioassays, Biosynthesis and Ecophysiology of Natural Products (NuBBE), São Paulo State University UNESP, Araraquara, Sao Paulo, Brazil.

Natural Products phytochemical provide a rich source for therapeutic discovery and has led to the development of many drugs. Thus, the aim of this study was to obtaining a metabolic profiling from ethanol extract of leaves (EEIS) selected by bioassay antimalarial and nematostatic and identify metabolites in mixture by co-injection experiments and NMR spectroscopy. The chemical composition of this species indicated a wide variety of aromatic acids (vanillic acid, 3,4,5-trimethoxy benzoic acid, gallic acid, , -coumaric acid and ferulic acid), flavonoids (quercetin, myricetin-3- rhamnoside and myricetin-3- -(2"-O-)--rhamnopyranoside), triterpenes (lupeol, -amyrin, friedelin and oleanolic acid) and the 2-hydroxyethyl-dodecanoate. Read More

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September 2020

Friedelin inhibits the growth and metastasis of human leukemia cells via modulation of MEK/ERK and PI3K/AKT signalling pathways.

J BUON 2020 May-Jun;25(3):1594-1599

Department of Hematology , CR&WISCO General Hospital Affiliated to Wuhan University of Science and Technology,Wuhan,Hubei, 430080, China.

Purpose: Leukemia constitutes just 3% of all malignancies but because of its high incidence and mortality in children and persons below 40 years of age, it is considered one of the devastating malignant conditions. This study was undertaken to evaluate the anticancer effects of Friedelin triterpenoid against the human AML-196leukemia cells.

Methods: CCK-8 assay was used to determine cell viability. Read More

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February 2021

Oxidosqualene cyclases involved in the biosynthesis of triterpenoids in Quercus suber cork.

Sci Rep 2020 05 15;10(1):8011. Epub 2020 May 15.

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z4, Canada.

Cork is a water-impermeable, suberin-based material harboring lignin, (hemi)cellulose, and extractable small molecules (primarily triterpenoids). Extractables strongly influence the properties of suberin-based materials. Though these previous findings suggest a key role for triterpenoids in cork material quality, directly testing this idea is hindered in part because it is not known which genes control cork triterpenoid biosynthesis. Read More

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Integrating pathway elucidation with yeast engineering to produce polpunonic acid the precursor of the anti-obesity agent celastrol.

Microb Cell Fact 2020 Jan 28;19(1):15. Epub 2020 Jan 28.

Plant Biochemistry Section, Department of Plant and Environmental Sciences, University of Copenhagen, Thorvaldsensvej 40, 1871, Frederiksberg C, Denmark.

Background: Celastrol is a promising anti-obesity agent that acts as a sensitizer of the protein hormone leptin. Despite its potent activity, a sustainable source of celastrol and celastrol derivatives for further pharmacological studies is lacking.

Results: To elucidate the celastrol biosynthetic pathway and reconstruct it in Saccharomyces cerevisiae, we mined a root-transcriptome of Tripterygium wilfordii and identified four oxidosqualene cyclases and 49 cytochrome P450s as candidates to be involved in the early steps of celastrol biosynthesis. Read More

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January 2020

Anti-inflammatory and cytotoxic activities of the extracts, fractions, and chemical constituents isolated from Luehea ochrophylla Mart.

BMC Complement Altern Med 2019 Oct 28;19(1):284. Epub 2019 Oct 28.

Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil.

Background: Stem bark of Luehea ochrophylla (L. ochrophylla) is used by the traditional Brazilian medicine for treatment of rheumatic diseases and tumors. This study aimed to investigate inhibition of acute and chronic inflammations and cytotoxic activity of extracts, fractions, and isolated compounds from L. Read More

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October 2019

Rapid simultaneous determination of pentacyclic triterpenoids by mixed-mode liquid chromatography-tandem mass spectrometry.

J Chromatogr A 2020 Jan 14;1609:460458. Epub 2019 Aug 14.

Core Facility Center "Arktika", Northern (Arctic) Federal University, nab. Severnoy Dviny 17, Arkhangelsk 163002, Russia.

Pentacyclic triterpenoids (PCTs) possess high biological activity, including antitumor, anti-inflammatory, antiviral and hepatoprotective properties and are widespread in a plant biomass. Due to significant differences in polarity and other physicochemical properties, the simultaneous determination of different classes of PCTs by the methods of reversed phase liquid chromatography is difficult. In the present study, we proposed a new approach to chromatographic separation of such compounds based on the use of a stationary phase with a mixed retention mechanism combining hydrophobic, weak anion exchange and hydrophilic interactions. Read More

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January 2020

In evaluation of apoptogenic potential and toxicological profile of triterpenoids.

Indian J Pharmacol 2019 May-Jun;51(3):181-207

Department of Pharmacology, Maliba Pharmacy College, Tarsadi, Gujarat, India.

Aim: Caspases-3 and 8 are key mediators of intrinsic and extrinsic pathway of apoptosis, respectively. Triterpenoids of natural and synthetic origin reported as anticancer agents with apoptotic potential and hence may prove to be good candidates for testing against caspases-3 and 8.

Materials And Methods: Various naturally-occurring and synthetic triterpenoids were subjected to activity prediction using PASS Online software, and among them, 67 compounds were selected for further processing. Read More

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January 2020

CYP712K4 Catalyzes the C-29 Oxidation of Friedelin in the Maytenus ilicifolia Quinone Methide Triterpenoid Biosynthesis Pathway.

Plant Cell Physiol 2019 Nov;60(11):2510-2522

Department of Plant Biotechnology and Bioinformatics, Ghent University, Ghent, Belgium.

The native Brazilian plant Maytenus ilicifolia accumulates a set of quinone methide triterpenoids with important pharmacological properties, of which maytenin, pristimerin and celastrol accumulate exclusively in the root bark of this medicinal plant. The first committed step in the quinone methide triterpenoid biosynthesis is the cyclization of 2,3-oxidosqualene to friedelin, catalyzed by the oxidosqualene cyclase friedelin synthase (FRS). In this study, we produced heterologous friedelin by the expression of M. Read More

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November 2019

A new demethyl abietane diterpenoid from the roots of .

Nat Prod Res 2020 Nov 24;34(21):3094-3100. Epub 2019 Jun 24.

Fujian Key Laboratory of Natural Medicine Pharmacology, School of Pharmacy, Fujian Medical University, Fuzhou, P. R. China.

A new demethyl abietane diterpenoid, Triptotin K () together with three known compounds, friedelin (), canophyllal (), and triptonoterpene () were isolated from the roots of Hook. f. by silica gel column and preparative high performance liquid chromatography. Read More

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November 2020

Friedelane-type triterpene cyclase in celastrol biosynthesis from Tripterygium wilfordii and its application for triterpenes biosynthesis in yeast.

New Phytol 2019 07 19;223(2):722-735. Epub 2019 Apr 19.

School of Traditional Chinese Medicine, Capital Medical University, Beijing, 100069, China.

Celastrol is a promising bioactive compound isolated from Tripterygium wilfordii and has been shown to possess many encouraging preclinical applications. However, the celastrol biosynthetic pathway is poorly understood, especially the key oxidosqualene cyclase (OSC) enzyme responsible for cyclisation of the main scaffold. Here, we report on the isolation and characterisation of three OSCs from T. Read More

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Chemical constituents from leaves and trunk bark of (Violaceae).

Nat Prod Res 2020 Jul 20;34(14):2014-2021. Epub 2019 Feb 20.

Department of Organic Chemistry, Faculty of Science, University of Yaounde I, Yaounde, Cameroon.

Two new coruleoellagic acid derivatives, 3,4',5,5',-tetramethylcoruleoellagic acid ; 3',4,4',5,5'-pentamethylcoruleoellagic acid and a new friedelane-type triterpene derivative rinol , were isolated from leaves and trunk bark of (Violaceae) along with seven known compounds including 3,3',4,4',5'-pentamethylcoruleoellagic acid , hexamethylcoruleoellagic acid 28-hydroxyfriedelin friedelin friedelan-3-ol scopoletin and β-sitosterol-3--β-D-glucopyranoside Their structures were elucidated by means of spectroscopic methods including IR, 1D and 2D NMR in conjunction with mass spectrometry. Crude extracts of leaves and trunk bark as well as compounds were evaluated for their antibacterial activities against 7 pathogenic bacterial strains ( ATCC49619, ATCC 43300, ATCC 700603, ATCC 49247, ATCC 25922, HM601, BAA 977). Compound displayed noteworthy activity against with MIC value of 9. Read More

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Functional characterization of an oxidosqualene cyclase (PdFRS) encoding a monofunctional friedelin synthase in Populus davidiana.

Planta 2019 Jan 25;249(1):95-111. Epub 2018 Aug 25.

Department of Forest Resources, College of Forest and Environmental Sciences, Kangwon National University, Chuncheon, 200-701, Republic of Korea.

Main Conclusion: An oxidosqualene cyclase (PdFRS) from Populus davidiana was characterized as a monofunctional friedelin synthase by its heterologous expression in yeast and overexpression in plants. Triterpenes are one of the largest classes of plant chemical compounds composed of three terpene units, which form the basic skeleton of all sterols and saponins. Friedelin (friedelan-3-one), a pentacyclic triterpene, occurs in many plant families and is particularly present in rich amounts in cork tissues from trees. Read More

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January 2019

In vitro inhibitory effects of Friedelin on human liver cytochrome P450 enzymes.

Pharm Biol 2018 Dec;56(1):363-367

a Department of Public Health , Yidu Central Hospital of Weifang , Weifang , Shandong , China.

Context: Friedelin is a triterpenoid with several biological activities. However, the affects of Friedelin on the activity of human liver cytochrome P450 (CYP) enzymes remains unclear.

Objective: This study investigates the inhibitory effects of Friedelin on the major human liver CYP isoforms (CYP3A4, 1A2, 2A6, 2E1, 2D6, 2C9, 2C19 and 2C8). Read More

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December 2018

Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols.

J Ethnopharmacol 2018 Dec 4;227:82-96. Epub 2018 May 4.

Faculty of Pharmacy, Division of Pharmaceutical Biosciences, Viikki Biocenter, University of Helsinki, P.O. Box 56, FIN-00014, Finland. Electronic address:

Ethnopharmacological Relevance: Terminalia laxiflora Engl. & Diels, (Sudanese Arabic name: Darout الدروت) and Terminalia brownii Fresen (Sudanese Arabic name: Alshaf ألشاف) (Combretaceae) are used in Sudanese traditional folk medicine and in other African countries for treatment of infectious diseases, TB and its symptoms, such as cough, bronchitis and chest pain.

Aim Of Study: Because of the frequent use of T. Read More

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December 2018

Screening of 2A peptides for polycistronic gene expression in yeast.

FEMS Yeast Res 2018 08;18(5)

Department of Biology and Biological Engineering, Chalmers University of Technology, Kemivägen 10, Gothenburg 41296, Sweden.

A complexity of pathway expression in yeast compared to prokaryotes is the need for separate promoters and terminators for each gene expressed. Single transcript expression and separated protein production is possible via the use of 2A viral peptides, but detailed characterization to assess their suitability and applications is needed. The present work aimed to characterize multiple 2A peptide sequences to determine suitability for metabolic engineering applications in Saccharomyces cerevisiae. Read More

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Friedelin in Maytenus ilicifolia Is Produced by Friedelin Synthase Isoforms.

Molecules 2018 Mar 20;23(3). Epub 2018 Mar 20.

Instituto de Química, Univ. Estadual Paulista-UNESP, Rua Prof. Francisco Degni, 55, Quitandinha, Araraquara, SP 14800-060, Brazil.

Triterpenes are interesting compounds because they play an important role in cell homeostasis and a wide variety exhibiting defense functions is produced by plant secondary metabolism. Those same plant secondary metabolites also exhibit biological properties with promising therapeutic potential as anti-inflammatory and antitumor agents. Friedelin is a triterpene ketone with anti-inflammatory and gastroprotective activities and it is a precursor of relevant antitumor quinonemethides. Read More

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Astertarone A Synthase from Chinese Cabbage Does Not Produce the C4-Epimer: Mechanistic Insights.

Org Lett 2018 04 20;20(7):1802-1805. Epub 2018 Mar 20.

The Brassica rapa oxidosqualene cyclase Bra032185 makes 60% astertarone A (1) and 20 minor triterpenes (0.1-11%). Mechanistic analysis indicates the absence of an enol intermediate to generate the 4 S epimer of 1, unless workup involves saponification. Read More

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A new coumarin from stem bark of Calophyllum wallichianum.

Nat Prod Res 2018 Nov 22;32(21):2565-2570. Epub 2018 Jan 22.

a Faculty of Science, Department of Chemistry , Universiti Putra Malaysia , Serdang , Malaysia.

A phytochemical study carried out on the plant, Calophyllum wallichianum has led to the isolation of a new coumarin, wallimarin T (1) and a known coumarin, calanolide E (2) along with two common triterpenes, friedelin (3) and stigmasterol (4). The structures of these compounds were elucidated with the aid of spectroscopic analyses such as FT-IR, GC-MS, and NMR. MIC assay against the Bacillus bacteria were conducted on the extracts and this gave MIC values ranging from 0. Read More

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November 2018

Effects of friedelin on the intestinal permeability and bioavailability of apigenin.

Pharmacol Rep 2017 Oct 23;69(5):1044-1048. Epub 2017 Apr 23.

Research Group of Nutraceuticals for Metabolic Syndrome, Korea Food Research Institute, Anyangpangyoro, Seongnam, Gyeonggi, Republic of Korea. Electronic address:

Background: Although apigenin possesses diverse pharmacological activities, its utilization as a bioactive substance is limited by poor oral bioavailability. The aim of this study was to improve the bioavailability of apigenin by co-administration of friedelin.

Methods: To achieve this, the intestinal permeability of apigenin in the absence or presence of friedelin was investigated in both Caco-2 cells and single-pass rat intestinal perfusion models. Read More

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October 2017

A new sesquiterpene from Kalimeris integrifolia.

Nat Prod Res 2018 May 19;32(9):1004-1009. Epub 2017 Sep 19.

a Anhui Key Laboratory of Modern Chinese Materia Medica, School of Pharmacy , Anhui University of Chinese Medicine , Hefei , China.

A new sesquiterpene kalinturoside A (1), and 17 known compounds friedelan-3-ol (2), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (3), friedelin (4), syringaresinol (5), α-spinasterol (6), ciwujiatone (7), syringic acid (8), scopoletin (9), apocynin (10), 1-(3-hydroxy-4, 5-dimethoxyphenyl)ethan-1-one (11), apigenin (12), 5-hydroxymethylfurfural (13), stigmasterol-3-O-β-d-glucopy-ranoside (14), bidenoside C (15), citrusin (16), irioresinol A (17) and syringaresinol-4-O-β-d-glucopyranoside (18) were isolated from the herbs of Kalimeris integrifolia. The structures of these compounds were elucidated using spectroscopic techniques such as NMR and MS. All of the compounds were isolated from this genus for the first time. Read More

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In vitro cytotoxic potential of friedelin in human MCF-7 breast cancer cell: Regulate early expression of Cdkn2a and pRb1, neutralize mdm2-p53 amalgamation and functional stabilization of p53.

Exp Toxicol Pathol 2017 Oct 12;69(8):630-636. Epub 2017 Jun 12.

Cancer Molecular Biology Research Lab, Department of Food Science and Nutrition, College of Food and Agricultural Sciences, King Saud University, Riyadh 11451, Saudi Arabia. Electronic address:

We aimed to explore the cytotoxic and apoptotic effect of friedelin on breast cancer MCF-7 cells. Cytotoxic effect of friedelin on MCF-7 cells was analyzed using MTT, cell and nuclear morphology. The apoptosis mechanism of friedelin on MCF-7 cells was analyzed using real-time PCR. Read More

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October 2017

A new biflavonoid and a new triterpene from the leaves of Garcinia paucinervis and their biological activities.

J Nat Med 2017 Oct 26;71(4):642-649. Epub 2017 May 26.

Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, People's Republic of China.

A new biflavonoid, paucinervin K (1) and a new triterpene, 23-hydroxy-friedelin (2), together with eleven known compounds 3-13 were isolated from the leaves of Garcinia paucinervis. Their structures, including stereochemistry, were determined by spectroscopic analysis of NMR, MS, IR and ECD calculation and the octant rule. Some of the isolated compounds were tested for antiproliferative, α-glucosidase inhibitory and antioxidant activities in vitro. Read More

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October 2017

Triterpenes from Pouteria ramiflora (Mart.) Radlk. Leaves (Sapotaceae).

Food Chem Toxicol 2017 Nov 19;109(Pt 2):1063-1068. Epub 2017 May 19.

Faculdade de Ciências da Saúde, Universidade de Brasília - UnB, DF, Brazil. Electronic address:

Pouteria ramiflora (Mart.) Radlk. (Sapotaceae) is a species used by inhabitants from the Cerrado for its edible fruits and medicinal value. Read More

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November 2017

BIOLOGICAL AND PHYTOCHEMICAL INVESTIGATIONS OF EXTRACTS FROM POIR (FABACEAE) ROOT BARKS.

Afr J Tradit Complement Altern Med 2017 23;14(1):187-195. Epub 2016 Nov 23.

Département de médecine-pharmacopée traditionnelle/pharmacie (IRSS/CNRST) 03 BP 7192 Ouagadougou 03, Burkina Faso.

Background: Poir. belonging to Fabacae familly is used as medicinal plant in Burkina Faso's folk medicine. Roots of are used to treat ulcer, stomach ache and inflammatory diseases. Read More

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Constituents from stem barks of Luehea ochrophylla Mart and evaluation of their antiparasitic, antimicrobial, and antioxidant activities.

Nat Prod Res 2017 Aug 14;31(16):1948-1953. Epub 2016 Dec 14.

a Departamento de Química , Instituto de Ciências Exatas, Universidade Federal de Minas Gerais , Belo Horizonte , Brazil.

Luehea species are found in almost all Central and South American countries. The present work describes the phytochemical study, isolation, and structural characterisation of friedelin, β-friedelinol, lupeol, pseudotaraxasterol, β-sitosterol, betulinic acid, taraxasterol, (-)-epicatechin, β-sitosterol-3-O-β-d-glucopyranoside, and (+)-epicatechin-(4β→8)-epicatechin from stem barks of Luehea ochrophylla Mart. The structural identification of the isolated compounds was mainly performed by NMR analyses and comparison with the data from literature. Read More

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Friedelin Synthase from Maytenus ilicifolia: Leucine 482 Plays an Essential Role in the Production of the Most Rearranged Pentacyclic Triterpene.

Sci Rep 2016 11 22;6:36858. Epub 2016 Nov 22.

Faculdade de Ciências Farmacêuticas, Univ. Estadual Paulista-UNESP, Rod. Araraquara-Jaú km 1, Araraquara, SP 14801-902, Brazil.

Among the biologically active triterpenes, friedelin has the most-rearranged structure produced by the oxidosqualene cyclases and is the only one containing a cetonic group. In this study, we cloned and functionally characterized friedelin synthase and one cycloartenol synthase from Maytenus ilicifolia (Celastraceae). The complete coding sequences of these 2 genes were cloned from leaf mRNA, and their functions were characterized by heterologous expression in yeast. Read More

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November 2016

Seasonal variation of gastroprotective terpenoids in Maytenus robusta (Celastraceae) quantified by gas chromatography-flame ionization detection (GC-FID).

Z Naturforsch C J Biosci 2016 Nov;71(11-12):369-373

The triterpenes friedelin (1), β-friedelinol (2) and 3,15-dioxo-21α-hydroxyfriedelane (3) in the aerial parts of Maytenus robusta, a Brazilian medicinal plant with antiulcer potential, were seasonally quantified by gas chromatography flame-ionization detection (GC-FID) using an external standard. The method was found to be linear, precise and sensitive. Compounds 1 and 2 were found in M. Read More

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November 2016