Natural product coumarins: biological and pharmacological perspectives

Hussain, M. Iftikhar; Syed, Qamar Abbas; Khattak, Muhammad Nasir Khan; Hafez, Baraa; Reigosa, Manuel J.; El‐Keblawy, Ali

doi:10.2478/s11756-019-00242-x

Cited by 74 publications

(50 citation statements)

References 307 publications

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“…The much great diversity of identified allelopathic compounds in nature implies a high variability in their mode of action. Works found in literature show that allelochemicals interfere with several and diverse metabolic processes in plants [ 38 , 39 , 40 ]. Application of cinnamic acid (100 μM) caused significant reduction in photosynthetic rate but there was no effect on efficiency and quantum yield of ΦPSII [ 41 ].…”

Section: Discussionmentioning

confidence: 99%

Secondary Metabolites, Ferulic Acid and p-Hydroxybenzoic Acid Induced Toxic Effects on Photosynthetic Process in Rumex acetosa L.

Hussain

Reigosa

2021

Biomolecules

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The elimination of broadleaf weeds from agricultural fields has become an urgent task in plant and environment protection. Allelopathic control is considered a potential approach because of its exclusive and ecological safety measures. Plant secondary metabolites also called allelochemicals are released from plant leaves, roots, stem, bark, flowers and play significant roles in soil rhizosphere signaling, chemical ecology, and plant defense. The present study was carried out to evaluate the impact of two allelochemicals; ferulic acid (FA) and p-hydroxybenzoic acid (pHBA) on photosynthetic characteristics; Fv/Fm: efficiency of photosystem II photochemistry in the dark-adapted state; ΦPSII: photosynthetic quantum yield; NPQ, non-photochemical quenching; qP, photochemical quenching, and photon energy dissipation (1−qP)/NPQ in Rumex acetosa following 6 days exposure. R. acetosa seedlings were grown in perlite culture, irrigated with Hoagland solution and treated with allelopathic compounds FA and pHBA and were evaluated against the photosynthetic attributes. Both compounds behaved as potent inhibitors of photosynthetic traits such as Fv/Fm, ΦPSII, qP, and NPQ in R. acetosa. Photon energy dissipation (1−qP)/NPQ increased significantly from days 3 to 6. Higher dissipation of absorbed energy indicates the inactivation state of reaction centers and their inability to effectively use the absorbed energy in photosynthesis. These results indicated the potential allelopathic application of FA and pHBA for control of broadleaf weed, Rumex acetosa.

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Section: Discussionmentioning

confidence: 99%

Secondary Metabolites, Ferulic Acid and p-Hydroxybenzoic Acid Induced Toxic Effects on Photosynthetic Process in Rumex acetosa L.

Hussain

Reigosa

2021

Biomolecules

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“…Protocatechuic acid was demonstrated to possess chemopreventive activity against several different types of cancers in animal and cell studies ( 24 , 25 ). Coumarins are another group of phenolic compounds that possess various biological and therapeutic properties such as anti-oxidant, anti-microbial, anti-viral, anti-diabetic, anti-coagulant, estrogenic, vasodilator, anti-convulsant, anti-inflammatory, anti-hypertensive, and anti-cancer activities ( 26 ). In blueberry fillings, the amount of 6-methoxy-7,8-dihydroxycoumarin increased remarkably by 13 times after stir-frying, and by 34 times by the end of thermal processing.…”

Section: Resultsmentioning

confidence: 99%

Widely Targeted UHPLC-MS/MS Metabolomic Analysis on the Chemical Variation in Blueberry-Filled Pastries During Processing

et al. 2020

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“…The absolute configuration was determined by X-ray analysis. It should be noted that 6-arylmethylidenebenzo[d] [1,3]dioxol-5(6H)-ones are stable, while their precursors are not. Allene ketones were then allowed to react with o-quinone methides (Scheme 22) [36].…”

Section: Cycloaddition Of Ortho-quinone Methidesmentioning

confidence: 99%

“…Chiral chromanes are a class of privileged structural motif present in a plethora of natural products and synthetic analogs, displaying a wide range of biological activities and used as drugs [1,2]. Moreover, the chromane structure is the core nucleus of the natural class of compounds named flavonoids.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Organocatalyzed Asymmetric Synthesis of Benzopyran and Benzodihydropyran (Chromane) Nuclei

Dalpozzo

Mancuso

2019

Symmetry

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Benzopyran and benzodihydropyran (chromane) nuclei are the core structure of many natural products, in particular flavonoids. Many compounds possessing this structure are nutraceuticals, pharmaceutical nutrients. Therefore, benzopyran and chromane scaffolds are important building blocks in organic synthesis and many efforts have been made to set up efficient methods for their synthesis. In particular, asymmetric methods are of great importance, being natural products, and generally chiral substances. This review aims to cover literature in the range 2017-first half of 2019.It should be noted that the oxa-Michael-Henry reaction between two molecules of nitrostyrene was not observed. Symmetry 2020, 12, x FOR PEER REVIEW 4 of 33 Scheme 2. Heterogeneous enantioselective synthesis of chromanes.Xia, Xu and co-workers performed an enantioselective, organocatalytic oxa-Michael-nitro-Michael reaction, but in this case, too, 2-hydroxynitrostyrenes reacted only with β-nitroolefins different from themselves [10]. The reaction afforded chiral chromane derivatives bearing three contiguous stereogenic centers (Scheme 3). The all-S stereochemistry was assigned by X-ray analysis. Subsequently, Andrés, Pedrosa and co-workers extended the reaction to polymer-supported squaramides [11]. Initially, they tested some 4-vinylphenyl-substituted squaramides and found that Squa2 (see Scheme 1, 5 mol%, rt, 12-72 h in dichloromethane) gave the best results (65-88% yields, 63:27 to >99:1 dr, 70-> 99% ee, 13 examples). The absolute configuration was once more (2S,3S,4S) and was established by X-ray analysis. The configuration of the minor isomer was instead established as (2S,3R,4S) by comparison of the 1 H-NMR coupling constants of the two diastereomers. Then Squa2 was co-polymerized with styrene and divinylbenzene and the experiments were repeated (65-86% yields, 58:42 to >99:1 dr, 56-74% ee). The polymer-supported catalyst was also recovered and recycled five times without affecting yields and selectivity. Finally, the enantiomers were obtained from a squaramide derived from (1R,2R)-1,2-cyclohexanediamine instead of Squa2 derived from α-amino acid. The authors attributed the opposite stereochemistry to a different assembly of the ternary complex formed by catalyst, nitroalkene and 2-hydroxynitrostyrene in the two cases. S O HN HO HO OHC Symmetry 2019, 11, 1510 5 of 31 Symmetry 2020, 12, x FOR PEER REVIEW 5 of 33 Scheme 3. Organocatalytic oxa-Michael nitro-Michael domino reaction.Another domino Michael/hemiacetalization (see also Scheme 2, eq 3) was carried out between aliphatic aldehydes and (E)-2-(2-nitrovinyl)phenols under modularly designed organocatalysts (Scheme 4) [12]. Cis-3,4-disubstituted chroman-2-ones were obtained after oxidation of the hemiacetal intermediate or chromanes after dehydroxylation. The reaction was scaled up to 0.5 mmol scale, without significant modification of yield and selectivity. The absolute stereochemistry was determined by the optical rotation of known compounds. Scheme 4. Domino reaction catalyzed by MDO o...

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Natural product coumarins: biological and pharmacological perspectives

Cited by 74 publications

References 307 publications

Secondary Metabolites, Ferulic Acid and p-Hydroxybenzoic Acid Induced Toxic Effects on Photosynthetic Process in Rumex acetosa L.

Secondary Metabolites, Ferulic Acid and p-Hydroxybenzoic Acid Induced Toxic Effects on Photosynthetic Process in Rumex acetosa L.

Widely Targeted UHPLC-MS/MS Metabolomic Analysis on the Chemical Variation in Blueberry-Filled Pastries During Processing

Recent Advances in Organocatalyzed Asymmetric Synthesis of Benzopyran and Benzodihydropyran (Chromane) Nuclei

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