4-Alkyl- and 4-phenylcoumarins from Mesua ferrea as promising multidrug resistant antibacterials

Verotta, Luisellá; Lovaglio, Erminio; Vidari, Giovanni; Finzi, Paola Vita; Neri, Maria Grazia; Raimondi, Alessandro; Parapini, Silvia; Taramelli, Donatella; Riva, Antonella; Bombardelli, Ezio

doi:10.1016/j.phytochem.2004.07.001

Cited by 122 publications

(83 citation statements)

References 15 publications

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“…In particular, 4-aryl derivatives constitute a subgroup of flavonoids that have received considerable attention, as they exhibit important biological activities such as anti-HIV, [1] antimalarial, [2,3] antibacterial, [4] and cytotoxic properties. [5] Several natural and synthetic polyoxygenated 4-arylcoumarins have been evaluated as the nonisomerizable analogues of combretastatin A-4, which is an important antitubulin agent that interacts with the binding site of colchicine.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Promoted, One‐Pot, Solvent‐Free Synthesis of 4‐Arylcoumarins from 2‐Hydroxybenzophenones

Crecente‐Campo¹,

Vázquez-Tato²,

Seijas³

2010

Eur J Org Chem

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Section: Introductionmentioning

confidence: 99%

Microwave‐Promoted, One‐Pot, Solvent‐Free Synthesis of 4‐Arylcoumarins from 2‐Hydroxybenzophenones

Crecente‐Campo¹,

Vázquez-Tato²,

Seijas³

2010

Eur J Org Chem

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“…Previous phytochemical investigations on the genus show the existence of xanthones (Bandaranayak et al 1975;Walia & Mukerjee 1984;Ee et al 2005b), coumarins (Bandaranayak, Selliah et al 1975;Morel, Guilet et al 1999;Awang, Chan et al 2010), terpenoids (Ee et al 2005a) and essential oils (Bala & Seshadri 1971). These secondary metabolites have been extensively reported for their biological activities; for instance antifungal (Pinto et al 1994), anticancer (Ee et al 2005a), antibacterial (Mazumder, Dastidar et al 2004;Verotta, Lovaglio et al 2004), and anti-HIV-1(Huerta- Reyes et al 2004). However, pharmacognosy and preliminary phytochemical analysis on this species have not been reported before.…”

Section: S1 Commentmentioning

confidence: 96%

“…For the biological activity of Congestiflora species, see : Pinto et al (1994); Ee et al (2005a); Mazumder et al (2004); Verotta et al (2004); Huerta-Reyes et al (2004). For related structures, see: Hua et al (2008); Liu et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

rac-[3-Hydroxy-6,9-dimethyl-6-(4-methylpent-3-en-1-yl)-6a,7,8,9,10,10a-hexahydro-6H-1,9-epoxybenzo[c]chromen-4-yl](phenyl)methanone

Teh

Kwong

et al. 2012

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 150 K; mean (C-C) = 0.003 Å; R factor = 0.046; wR factor = 0.117; data-to-parameter ratio = 15.0.The title compound congestiflorone, C 28 H 32 O 4 , which was isolated from the stem bark of Mesua congestiflora, consists of a benzophenone skeleton with two attached pyran rings to which a cyclohexane ring and a C6 side chain are bonded. The benzene ring is significantly distorted from planarity (r.m.s. deviation = 0.0007 Å ) due to the constraints imposed by junctions with the two pyran rings. The cyclohexane ring is in a chair conformation, one pyran ring is in a boat conformation, while the other is a distorted chair. The phenyl and benzene rings make a dihedral angle of 55.85 (9) . An intramolecular O-HÁ Á ÁO hydrogen bond is observed. In the crystal, molecules are linked via C-HÁ Á ÁO interactions. Related literature

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“…When the concentrations inhibiting 90% of the strains (MIC 90%) were compared, some of the Mesua derivatives exhibited the best activity. There was a weak inhibitory activity against P. falciparum (Verotta et al, 2004).…”

Section: Anti-microbial Activitymentioning

confidence: 96%

Mesua ferrea L.: A review of the medical evidence for its phytochemistry and pharmacological actions

Chahar¹,

Kumar²,

Geetha³

et al. 2013

Afr. J. Pharm. Pharmacol.

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The plant kingdom provides many plants with properties which are conducive to health and to secure the best results from the use of the plants as remedial agencies. Mesua ferrea Linn (Nagakesar) is a rare plant which is traditionally being used for its antiseptic, anti-inflammatory, blood purifier, anthelmintic, cardiotonic, diuretic, expectorant, antipyretic, purgative, antiasthmatic, antiallergic and several other effects. The scientific screening of the plant confirms its antioxidant, hepatoprotective, antiinflammatory, central nervous system (CNS) depressant, analgesic, antimicrobial, antispasmodic, antineoplastic, antivenom and immunostimulant activity. The phytochemical screening confirms the presence of phenyl coumarins, xanthones, triterpenoids, fats and flavanoids as main constituents responsible for its biological activity. It is a substitute for petroleum gasoline. It is also used in cosmetics, as fire wood and the polymer obtained from seed oil is used in the preparation of resins. The present review summarizes the phyto-pharmacological role of this valuable medicinal plant.

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4-Alkyl- and 4-phenylcoumarins from Mesua ferrea as promising multidrug resistant antibacterials

Cited by 122 publications

References 15 publications

Microwave‐Promoted, One‐Pot, Solvent‐Free Synthesis of 4‐Arylcoumarins from 2‐Hydroxybenzophenones

Microwave‐Promoted, One‐Pot, Solvent‐Free Synthesis of 4‐Arylcoumarins from 2‐Hydroxybenzophenones

rac-[3-Hydroxy-6,9-dimethyl-6-(4-methylpent-3-en-1-yl)-6a,7,8,9,10,10a-hexahydro-6H-1,9-epoxybenzo[c]chromen-4-yl](phenyl)methanone

Mesua ferrea L.: A review of the medical evidence for its phytochemistry and pharmacological actions

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