Flavonoid aglycones from Centaurea maroccana

Journal of Biobased Materials and Bioenergy, 2022

Nowadays, plants bioactive compounds are considered as a new source of therapy, especially for the elaboration process of more effective drugs. 80% of the actual drug substances are purely natural and originate from plants, representing a new hope, especially for the treatment of chronic illnesses. The aim of this study is to characterize the phytochemical composition of C. tougourensis via gas chromatography-mass spectrometry (GC-MS) approach. This method allowed the identification of 45 compounds in the n-butanol extract (n- BuOH), in which 12 compounds were in majority, namely; 2H-Furo [2,3-b] indole, 3,3a,8,8atetrahydro- 2,3-dimethyl- (16.12%), Benz [c] pyran-1,3-dione, 4,4-dimethyl- (14.87%), Octadecanoic acid,9-oxo-, methyl ester (9.69%), Hydromorphone (7.94%), Acetamide, N-[3-[2-(2,3-dihydro-3- hydroxy-2-oxo-3-indolyl)-1-oxoethyl]p (6.14%), 2,6-Di-n-propyl-4-(2-furyl)pyridine (6.11%), Norhydrocodone (5.98%), Anthracene, 1,2,3,4,5,6,7,8-octahydro- (4.72%), 2,4,6-Trimethylbenzonitrile, N-oxide (4.47%), 3-O-Methyl-d-glucose (2.94%), 3,5-Diethyl-4-(2-furyl) pyridine (2.75%) and 3H-Pyrrolo [3,2-f] quinoline, 5-methoxy-1,2,7,9-tetramethyl- (2.30%). Concerning the ethyl acetate (EA) extract; 23 compounds were identified, in which 13 compounds were in majority, namely; [Bi-1,4-cyclohexadien-1-yl]-3,3',6,6'-tetrone, 4,4'-dihydroxy-2,2',5,5'-tetramethyl- (27.31%), Thiosulfuric acid, S-(2-aminoethyl) ester (15.07%), 2-Pentadecanone, 6,10,14-trimethyl- (8.91%), 3-Methyl-4-(phenylthio)-2-prop-2-enyl-2,5-dihydrothiophene 1,1-dioxide (7.12%), Tetrapentacontane, 1,54-dibromo- (5.74%), Heptacos-1-ene (5.03%), Propionic acid, 3-iodo-, tetradecyl ester (4.92%), 2-Methyl-E-7-octadecene (4.68%), 7,8-Epoxylanostan-11-ol, 3-acetoxy- (3.65%), 4-Fluoro-1-methyl-5-carboxylic acid, ethyl(ester) (3.15%), Tetrapentacontane, 1,54-dibromo- (2.79%), Undec-10-ynoic acid, tetradecyl ester (2.77%), 3,7,11,15-Tetramethyl-2-hexadecen-1-ol (2.72%).

Chemistry of Natural Compounds

The large genus Centaurea consists of more than 700 species [1], from which 75 species are found in Iran. They are widespread around the country. In Iran their common name is Gole-gandom. Centaurea behen (Gole-Gandome-Talaei in Persian) is a perennial plant 60-200 cm tall that is traditionally used as a tonic for jaundice, cystic fibrosis, and impotence. It is an Irano-Turanian plant grows on stony hillsides, meadows, and along the roadsides [2]. Several sesquiterpene lactones of the guaianolide type (cynaripicrin, arguerin B, deacylcynaropicrine, grosshemin, and 4β,15-dihydro-3-dehydrosolstitialin A) [3, 4], two methoxylated flavone (crisimaritin and jeceosidin) [4, 5], and a flavonoid aglycone (luteolin) [6] were isolated from the leaves of Centaurea behen. In this study, fractionation of the petroleum ether and chloroform extracts of Centaurea behen L. resulted in the isolation of two methoxylated flavones, two triterpenes, and sterols. All compounds were isolated from C. behen for the first time. The structures of the isolated compounds 1-5 were elucidated by spectroscopic methods (MS, 1 H NMR and 13 C NMR) and by comparison with literature data. They were elucidated as ψ-taraxasterol (1) [7], β-sitosterol (2) [8], daucosterol [β-sitosterol-β-D-glucopyranoside] (3) [9], oleanolic acid (4) [10], salvigenin (5) [11, 12], and pectolinarigenin (6) [13]. The compounds were identified for the first time from Centaurea behen. To the best of our knowledge this is the first time of ψ-taraxasterol (1) was found in Centaurea genus. General. The NMR spectra were recorded on a Bruker Avance AV-400 (1 H) and AV-100 (13 C) using CDCl 3 , pyridine-d 5 , and DMSO-d 6 as solvent. Two-dimensional (2D) experiments (HSQC, HMBC) were set up, performed, and processed with the standard Bruker protocol. EI-MS spectra were measured on a 7890 GC/7200 Q-TOF MS system.TLC was carried out on precoated aluminum foil silica gel 60 F254 (Merck, Germany). Column chromatography (CC) was performed with silica gel 60 (Merck, Germany) and Sephadex LH-20 (Pharmacia, Piscataway, NJ, USA). For vacuum liquid chromatography (VLC), silica gel 60 G (15 μm, Merck, Germany) and polyamide (Sigma-Aldrich, St Louis, MO, USA) were applied. Thin-layer chromatography detection was achieved by spraying the silica gel plates with anisaldehyde-sulfuric acid reagent (AS) and natural products-polyethylene glycol reagent (NP/PEG).

Bioactive Natural Products, 2019

Aglaia is the largest genus in the Meliaceae family (also known as Mahagoni in Indonesia), consisting of over 150 species, of which 65 are indigenous to Indonesia. These species spread through the tropical regions, especially Southeast Asia as well as the Nothern part of Australia, and have been used in traditional medicine for the treatment of several diseases. However, preliminary chemical researches commenced in 1965, where dammarane-type triterpenoids, aglaiol was isolated, and the structure was determined by chemical reaction and spectroscopic methods. Several studies have been carried out on the stembark, bark, leaves, seeds and leaves in the last fifty five years, and about 291 metabolites have been isolated from the sesquiterpenoid, diterpenoid, triterpenoid, limonoid, steroid, lignan, and alkaloid groups, as well as flavagline, which known to be the largest. This specifically amounts to 34% of Aglaia species, reported to show cytotoxic and insecticidal potentials, and also the tendency for use as chemical markers for this species. The extracts and compounds obtained from Aglaia species are evaluated for potential biological activities, including cytotoxicity, insecticidal, anti-inflammatory, antifungal, molluscicidal, antituberculosis and antiviral effects. In addition, flavagline (rocaglamide) derivatives have been confirmed to exhibit exceptional cytotoxicity, and are, thus, considered lead compounds for further development. Therefore, the results support the concept of utilizing Aglaia species as a potential source for the production of biologically active compounds.

Biochemical Systematics and Ecology, 2004

Crystals, 2022

Bioinformatics as a newly emerging discipline is considered nowadays a reference to characterize the physicochemical and pharmacological properties of the actual biocompounds contained in plants, which has helped the pharmaceutical industry a lot in the drug development process. In this study, a bioinformatics approach known as in silico was performed to predict, for the first time, the physicochemical properties, ADMET profile, pharmacological capacities, cytotoxicity, and nervous system macromolecular targets, as well as the gene expression profiles, of four compounds recently identified from Centaurea tougourensis via the gas chromatography– mass spectrometry (GC–MS) approach. Thus, four compounds were tested from the n-butanol (n-BuOH) extract of this plant, named, respectively, Acridin-9-amine, 1,2,3,4-tetrahydro-5,7-dimethyl- (compound 1), 3-[2,3-Dihydro-2,2-dimethylbenzofuran-7-yl]-5-methoxy-1,3,4-oxadiazol-2(3H)-one (compound 2), 9,9-Dimethoxybicyclo[3.3.1]nona-2,4-dione (compound 3), and 3-[3-Bromophenyl]-7- chloro-3,4-dihydro-10-hydroxy-1,9(2H,10H)-acridinedione (compound 4). The insilico investigation revealed that the four tested compounds could be a good candidate to regulate the expression of key genes and may also exert significant cytotoxic effects against several tumor celllines. In addition, these compounds could also be effective in the treatment of some diseases related to diabetes, skin pathologies, cardiovascular, and central nervous system disorders. The bioactive compounds of plant remain the best alternative in the context of the drug discovery and development process.

International Journal of Innovative Research and Development

Introduction Medicinal plants have been the mainstay of traditional herbal medicine amongst rural dwellers worldwide since time immemorial. The therapeutic use of plants certainly goes back to the Sumerian and the Akkadian civilizations in about the third millennium BC (Mandal et al. 2005). One of the ancient authors, who described medicinal natural products of plant and animal origins, listed approximately 400 different plant species for medicinal purposes. Medicinal plants have always been considered as a source for healthy life for people. Therapeutic properties of medicinal plants are very useful in healing various diseases and the advantages of these medicinal plants are natural (Kalemba and Kunicka, 2003). Over the years they have assumed a very central stage in modern civilization as natural source of chemotherapy as well as amongst scientist in search for alternative sources of drugs. About 3.4 billion people in the developing world depend on plant-based traditional medicines. This represents about 88 per cent of the world's inhabitants, who rely mainly on traditional medicine for their primary health care. According to the World Health Organization, a medicinal plant is any plant which, in one or more of its organs, contains substances that can be used for therapeutic purposes, or which are precursors for chemo-pharmaceutical semi synthesis. Such a plant will have its parts including leaves, roots, rhizomes, stems, barks, flowers, fruits, grains or seeds, employed in the control or treatment of a disease condition and therefore contains chemical components that are medically active. These non-nutrient's plant chemical compounds or bioactive components are often referred to as phytochemicals (phyto in Greek translation meaning 'plant') or phyto constituents are responsible for protecting the plant against microbial infections or infestations by pests (Doughariet al., 2009). The study of natural products on the other hand is called phytochemistry. Phytochemicals have been isolated and characterized from fruits such as grapes and apples, vegetables such as broccoli and onion, spices such as turmeric, beverages such as green tea and red wine, as well as many other sources (Doughari, 2009). The science of application of these indigenous or local medicinal remedies including plants for treatment of diseases is currently called ethno pharmacology but the practice dates back since antiquity. A plant in which one or more of its organs contains substances that can be used for therapeutic purposes on which are precursors for the synthesis of useful drugs are called medicinal plants. Medicinal plants contain biologically active chemical substances (phytochemicals) such as saponins, tannins, essential oils, flavonoids, alkaloids and other chemical compounds, which have preventive and curative properties. These complex chemical substances of different compositions are found as secondary plant metabolites in one or more of these plants and are useful for humanity (Okigbo, 2000). In view of many diseases defiling drugs, health practices are now changing from curative to preventive medicine. Phytochemicals popular in preventive medicine are flavonoids, polyphenols, saponins, lignoids and vitamins. Also, a knowledge of the chemical constituents of plants is desirable, not only for the discovery of therapeutic agents, but also because such information may be of value in disclosing new sources of such economic materials as tannins, oils, gums, which are precursors for the synthesis of complex chemical substances, etc. In addition, the knowledge of the chemical

Journal of Pharmacy and Bioallied Sciences, 2020

Preparation of medicinal plants for experimental purposes is an initial step and key in achieving quality research outcome. It involves extraction and determination of quality and quantity of bioactive constituents before proceeding with the intended biological testing. The primary objective of this study was to evaluate various methods used in the preparation and screening of medicinal plants in our daily research. Although the extracts, bioactive fractions, or compounds obtained from medicinal plants are used for different purposes, the techniques involved in producing them are generally the same irrespective of the intended biological testing. The major stages included in acquiring quality bioactive molecule are the selection of an appropriate solvent, extraction methods, phytochemical screening procedures, fractionation methods, and identication techniques. The nitty-gritty of these methods and the exact road map followed solely depends on the research design. Solvents commonly used in extraction of medicinal plants are polar solvent (e.g., water, alcohols), intermediate polar (e.g., acetone, dichloromethane), and nonpolar (e.g., n-hexane, ether, chloroform). In general, extraction procedures include maceration, digestion, decoction, infusion, percolation, Soxhlet extraction, supercial extraction, ultrasound-assisted, and microwaveassisted extractions. Fractionation and purication of phytochemical substances are achieved through application of various chromatographic techniques such as paper chromatography, thin-layer chromatography, gas chromatography, and high-performance liquid chromatography. Finally, compounds obtained are characterized using diverse identication techniques such as mass spectroscopy, infrared spectroscopy, ultraviolet spectroscopy, and nuclear magnetic resonance spectroscopy. Subsequently, different methods described above can be grouped and discussed according to the intended biological testing to guide young researchers and make them more focused.

Natural product communications

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Gas Chromatography-Mass Spectrometry (GC chromatography of the ethyl acetate extract of Ficus sycomorus Linn. root two compounds. The mass spectral data shows that all the compounds have molecular ion peak and base peak with M/Z 468 and 218 respectively. The tentative identification was achieved by comparing their mass spectra with the data sys compounds are suggested to be pentacyclic triterpenoid isomers, and this include; 12 yl, acetate (3.alpha) and Urs-12-en sycomorus suggests that the plant conforms to other members of the genus Ficus. The result of this study shows that pentacyclic triterpenoid isomers can be useful in the chemotaxonomy of the Moraceae Family if the investigation is extended to other genera and species. Furth should be carried out to isolate the compounds in their pure forms and detail spectroscopic studies should also be carried out to fully elucidate their structures.