Phytochemistry and biological activities of algerian Centaurea and related genera

Ayad, Radia; Akkal, Salah

doi:10.1016/b978-0-12-817901-7.00012-5

Cited by 28 publications

(28 citation statements)

References 43 publications

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“…However, eupatorin and jaceosidin besides the above mentioned species have been found together in aerial parts of C. grisebatchii (Nyman) Heldr (Djeddi et al 2008a ). Nepetin and protocatechuic acid from C. calcitrapa leaves have been previously detected in the related species C. melitensis L. (Ayad et al 2012 ; Khammar and Djeddi 2012 ). Chlorogenic acid together with protocatechuic acid, kaempferol 3- O -glucoside and quercetin 3- O -glucoside has been obtained from C. isaurica Hub.-Mor extracts (Flamini et al 2004 ).…”

Section: Discussionmentioning

confidence: 88%

New perspectives of purple starthistle (Centaurea calcitrapa) leaf extracts: phytochemical analysis, cytotoxicity and antimicrobial activity

et al. 2020

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Ethnobotanical and ethnopharmacological studies of many Centaurea species indicated their potential in folk medicine so far. However, investigations of different Centaurea calcitrapa L. extracts in terms of cytotoxicity and antimicrobial activity against phytopathogens are generally scarce. The phenolic profile and broad antimicrobial activity (especially towards bacterial phytopathogens) of methanol (MeOH), 70% ethanol (EtOH), ethyl-acetate (EtOAc), 50% acetone (Me2CO) and dichloromethane: methanol (DCM: MeOH, 1: 1) extracts of C. calcitrapa leaves and their potential toxicity on MRC-5 cell line were investigated for the first time. A total of 55 phenolic compounds were identified: 30 phenolic acids and their derivatives, 25 flavonoid glycosides and aglycones. This is also the first report of the presence of centaureidin, jaceidin, kaempferide, nepetin, flavonoid glycosides, phenolic acids and their esters in C. calcitrapa extracts. The best results were obtained with EtOAc extract with lowest MIC values expressed in µg/mL ranging from 13 to 25, while methicillin resistant Staphylococcus aureus was the most susceptible strain. The most susceptible phytopathogens were Pseudomonas syringae pv. syringae, Xanthomonas campestris pv. campestris and Agrobacterium tumefaciens. The highest cytotoxicity was recorded for EtOAc and Me2CO extracts with the lowest relative and absolute IC50 values between 88 and 102 µg/mL, while EtOH extract was the least toxic with predicted relative IC50 value of 1578 µg/mL. Our results indicate that all tested extracts at concentration considered as non-toxic can be one of great importance in combat towards phytopathogenic and human pathogenic strains, as well as natural sources of antimicrobials.

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Section: Discussionmentioning

confidence: 88%

New perspectives of purple starthistle (Centaurea calcitrapa) leaf extracts: phytochemical analysis, cytotoxicity and antimicrobial activity

et al. 2020

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“…There are also review articles that describe sesquiterpene lactones isolated from specific Centaurea species, including 20 guaianolides isolated from C. acaulis , C. omphalotricha , and C. musimomum ; 11 germacranolides and 12 elemanolides from C. acaulis , C. melitensis , C. calictrapa , C. foucauldiana , C. lippii , C. parviflora , C. tougourensis , C. sulphurea , C. papposa , C. sicula , and C.pullata; and 8 eudesmanolides from C. acaulis , C . papposa , C. granata , C. pullata and C. maroccana [ 43 ]. In addition, guaianolides and elemanolides have been isolated from Centaurea, including four guaianolides and cynaratriol from C. musimomum [ 44 ]; centaurpensin and 13-acetyl solstitian A from C. solstitialis [ 45 ]; cebellin M from C. bella [ 46 ]; the elemanolideshierapolitanins A, B, C, and D isolated from C. hierapolitana [ 22 ]; and 13- N -proline melitensin and 13- N -proline-6α, 8α, 15-trihydroxy elema-1,3-diene-oic acid from C. polyclada [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

Guaianolide Sesquiterpene Lactones from Centaurothamnus maximus

et al. 2021

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Centaurothamnus maximus (family Asteraceae), is a leafy shrub indigenous to the southwestern Arabian Peninsula. With a paucity of phytochemical data on this species, we set out to chemically characterize the plant. From the aerial parts, two newly identified guaianolides were isolated: 3β-hydroxy-4α(acetoxy)-4β(hydroxymethyl)-8α-(4-hydroxy methacrylate)-1αH,5αH, 6αH-gual-10(14),11(13)-dien-6,12-olide (1) and 15-descarboxy picrolide A (2). Seven previously reported compounds were also isolated: 3β, 4α, 8α-trihydroxy-4-(hydroxymethyl)-lαH, 5αH, 6βH, 7αH-guai-10(14),11(13)-dien-6,12-olide (3), chlorohyssopifolin B (4), cynaropikrin (5), hydroxyjanerin (6), chlorojanerin (7), isorhamnetin (8), and quercetagetin-3,6-dimethyl ether-4’-O-β-d-pyranoglucoside (9). Chemical structures were elucidated using spectroscopic techniques, including High Resolution Fast Atom Bombardment Mass Spectrometry (HR-FAB-MS), 1D NMR; 1H, 13C NMR, Distortionless Enhancement by Polarization Transfer (DEPT), and 2D NMR (1H-1H COSY, HMQC, HMBC) analyses. In addition, a biosynthetic pathway for compounds 1–9 is proposed. The chemotaxonomic significance of the reported sesquiterpenoids and flavonoids considering reports from other Centaurea species is examined.

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“…Currently, the family has 32,913 recognized species divided into 1911 genera in 13 subfamilies [ 3 ]. Plants of this family are widespread throughout the world; many have proven therapeutic potential and contain a wide range of biologically active compounds [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

“…The biological activity of extracts and essential oils of different types of Centaurea L. has been established, and includes antitumor, antidiabetic, anti-inflammatory, analgesic, antidepressant, antiplasmoid, antirheumatic, antioxidant, antimicrobial, and enzymatic properties [ 1 , 2 , 4 , 5 , 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

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Comparative Assessment of the Phytochemical Composition and Biological Activity of Extracts of Flowering Plants of Centaurea cyanus L., Centaurea jacea L. and Centaurea scabiosa L.

Sharonova

Nikitin

Terenzhev

et al. 2021

Plants

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The data on the phytochemical composition and biological activity for flowering plant extracts of the genus Centaurea (Knapweed)—cornflower (Centaurea cyanus L.), brown knapweed (Centaurea jacea L.), and greater knapweed (Centaurea scabiosa L.), which are typical representatives of the flora in the middle belt of the Russian Federation, were obtained. For the first time, biologically active substances such as pyranone, coumaran (2,3-dihydrobenzofuran), and 5-hydroxymethylfurfural were identified in ethanol and methanol extracts of Centaurea scabiosa L. by gas chromatography–mass spectrometry. Catechol and α-amyrin were the major components of the ethanol extract from Centaurea cyanus L., and flavone was the major component of Centaurea jacea L. flower extract. The greatest antimicrobial activity against phytopathogens was detected in Centaurea scabiosa L. when extracting freshly harvested flower biomass with methyl tert-butyl ether at room temperature: the minimum inhibitory concentrations were 60–120 µg/mL, the minimum fungicidal concentration was 120 µg/mL, and the minimum bactericidal concentration was 250 µg/mL. The low antioxidant activity of the studied plant extracts was established using the maximum values of Centaurea jacea L. Ethanol extract of Centaurea cyanus L. flowers had low antimicrobial and antioxidant activity. The extracts showed no phytotoxicity to garden cress germination but inhibited the growth of juvenile plants, especially roots. The greatest phytotoxic effect was revealed with methyl tert-butyl ether, where the depression of growth indicators was 35% or more.

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Phytochemistry and biological activities of algerian Centaurea and related genera

Cited by 28 publications

References 43 publications

New perspectives of purple starthistle (Centaurea calcitrapa) leaf extracts: phytochemical analysis, cytotoxicity and antimicrobial activity

New perspectives of purple starthistle (Centaurea calcitrapa) leaf extracts: phytochemical analysis, cytotoxicity and antimicrobial activity

Guaianolide Sesquiterpene Lactones from Centaurothamnus maximus

Comparative Assessment of the Phytochemical Composition and Biological Activity of Extracts of Flowering Plants of Centaurea cyanus L., Centaurea jacea L. and Centaurea scabiosa L.

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