Bioassay-Guided Isolation, Identification of Compounds from Sterculia diversifolia and Investigation of Their Anti-Glycation and Antioxidant Activities

Rabbi, Fazle; Zada, Amir; Nisar, Amna; Sohail, Muhammad; Khalil, Saifullah Khan; Shah, Waheed Ali

doi:10.1007/s11094-020-02137-7

Cited by 13 publications

(6 citation statements)

References 19 publications

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“…Starting from p ‐coumaric acid ( 1 , 307 mg) gave 11 as a white solid (272.34 mg, 81.3%), C 10 H 10 O 3 , mp 135–137°C; 1 H NMR (500 MHz, CDCl 3 ): δ = 7.62 (d, J = 16.9 Hz, 1H), 7.42 (d, J = 8.2 Hz, 2H), 6.82 (d, J = 8.1 Hz, 2H), 6.28 (d, J = 16.3 Hz, 1H), 3.78 (s, 3H); 13 C NMR (126 MHz, CDCl 3 ): δ = 168.15, 157.96, 144.87, 130.21, 116.10, 115.54, 51.90. The NMR data were consistent with those of literature (Rabbi et al, 2020).…”

Section: Methodssupporting

confidence: 91%

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Methyl benzoate and cinnamate analogs as modulators of DNA methylation in hepatocellular carcinoma

et al. 2022

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Phenolic acids represent a large collection of phytochemical molecules present in the plant kingdom; they have an important role as epigenetic regulators, particularly as inhibitors of DNA methylation. In the present study, 14 methyl benzoate and cinnamate analogs were synthesized (11–24). Their cytotoxic activity on hepatocellular carcinoma cells (Hep3B) and immortalized human hepatocyte cells was then evaluated. In addition, its effect on the inhibition of global DNA methylation in Hep3B was also determined. Our results showed that the cinnamic derivatives 11–14 and 20–22 were more potent than the free caffeic acid (IC50 109.7–364.2 µM), being methyl 3,4‐dihydroxycinammate (12) the most active with an IC50 = 109.7 ± 0.8 µM. Furthermore, 11–14, 20–23 compounds decreased overall DNA methylation levels by 63% to 97%. The analogs methyl 4‐hydroxycinnamate (11), methyl 3,4,5‐trimethoxycinnamate (14), methyl 4‐methoxycinnamate (21), and methyl 3,4‐dimethoxycinnamate (22) showed relevant activities of both cytotoxicity and global DNA methylation inhibition. The molecular docking of 21 and 14 suggested that they partly bind to the SAH‐binding pocket of DNA methyltransferase 1. These results emphasize the importance of natural products and their analogs as potential sources of DNA methylation modulating agents.

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Section: Methodssupporting

confidence: 91%

“…15, 157.96, 144.87, 130.21, 116.10, 115.54, 51.90. The NMR data were consistent with those of literature (Rabbi et al, 2020).…”

Section: Synthesis Of Methyl Esters (11-20)supporting

confidence: 91%

Methyl benzoate and cinnamate analogs as modulators of DNA methylation in hepatocellular carcinoma

et al. 2022

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“…A number of NMR data was found in literature. In general, our spectra's profiles reproduced the results of previous researches, and signal were assigned correctly [23][24][25]. The absence of the majority signals associated with hydrogen atoms in hydroxyl functional groups can be explained by hydrogen-deuterium exchange between solvent and flavonoid.…”

Section: Discussioinsupporting

confidence: 87%

Analysis of <i>cis</i>-isomer-enriched dihydroquercetin sample by 1D and 2D NMR spectroscopy

Terekhov,

Taldaev,

Bocharov

et al. 2024

Razrabotka i registraciâ lekarstvennyh sredstv

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Introduction. The structure of dihydroquercetin (DHQ) is characterized by two chiral centers at positions 2 and 3 of the benzopyran cycle, resulting in possible diastereomers: trans- and cis-isomers. Therefore, the development of methods for qualitative and quantitative control of DHQ diastereomers in analyzed samples is essential for patient safety management. Nuclear magnetic resonance (NMR) spectroscopy is one of the physicochemical methods that can be used for this purpose.Aim. The study objective was to accumulate the analytical and structural characteristics of cis-DHQ by NMR spectroscopy of the spheroidal form of this flavonoid (DHQs).Materials and Methods. 1D 1H, 1H,1H-COSY, 1H,1H-NOESY, and 1H,13C-HSQC NMR spectra were acquired at 298 K on an 800 MHz NMR spectrometer equipped with a TXI triple resonance probe. The number of scans was 32. The mixing time in the NOESY experiment was 400 ms. The 1H and 13C were analyzed using CcpNmr software. The dihedral angles were calculated by applying the Karplus equation.Results and discussion. In trans-DHQ, the chemical shift values for H2 and H3 are 4.93 ppm and 4.52 ppm, respectively, and in cis-DHQ they are 5.31 ppm and 4.20 ppm, respectively. The spin-spin coupling constants between H2 and H3 of trans- and cis-DHQ are 12.00 Hz and 2.40 Hz, respectively. Thus, the dihedral angles for the trans- and cis-isomers are 154° and 64°, respectively. We found that DHQs contains 12.5 % of the cis-isomer.Conclusion. Our experiments confirmed that NMR spectroscopy can discriminate between trans- and cis-DHQ based on the chemical shift values for the cross-peaks of H2 and H3. The second major finding was that this method can be considered as a more selective quantitative analysis than HPLC with UV detection without reference. One of the most important results of this study for drug development is the updated information on the structural parameters of DHQ diastereomers in the liquid phase.

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“…After maceration, filtration was conducted with Whatman grade-1 filter paper. Then under reduced pressure crude extracts were concentrated at 40 o C using rotary evaporator (Rabbi et al, 2020b). Methanolic extract stem bark and leaves were obtained in 950 g and 1.2 kg quantity, respectively.…”

Section: Preparation Of Extractmentioning

confidence: 99%

“…Peshawar (Jamshed et al, 2014). Medicinally, the plant bears immunomodulatory, cytotoxic, anti-glycation, larvicidal, anthelmintic, leishmanicidal, insecticidal and antioxidant activity (Rabbi et al, 2017, Rabbi et al, 2020b, Rabbi et al, 2020c. In earlier studies, few fatty acid constituents were isolated from Sterculia diversifolia (Salem et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of in-Vivo Biological Activities of Sterculia Diversifolia (G. Don) in Relevance to the Isolated Secondary Metabolites

2020

THE JAPS

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Genus Sterculia possess various types of compounds which have therapeutic potential. This study was aimed to explore the anticonvulsant, CNS depressant, analgesic, anti-inflammatory and anti-pyretic activities of Sterculia diversifolia stem bark and leaves extracts in mice. The secondary metabolites in MESD (methanolic extract of Sterculia diversifolia) was characterized by UV, IR, 1 H-NMR, 13 C NMR and 2D-NMR spectra in combination with EI-MS spectrometric techniques. Anticonvulsant and CNS depressant effect of MESD was assessed using strychnine-induced convulsion and phenobarbitone-induced hypnotic protocol. Analgesic activity was performed by acetic acid induced writhing and hot plate test while anti-inflammatory and anti-pyretic activities were assessed by carrageenan induced right hind paw edema and brewer's yeast induced pyrexia. The isolation of compounds with different elucidation techniques (1 H-NMR, 13 C NMR and 2D-NMR spectra in combination with EI-MS spectrometric techniques) led to luteolin, isoquercitrin and ursolic acid. The current study results showed that crude MESD significantly (p < 0.05) delayed the onset, shortened the duration and offered protection against strychnine-induced convulsion. Crude MESD significantly (p < 0.05) prolonged the time of phenobarbitone-induced hypnosis. The analgesic response of crude MESD stem bark was more significant as compare to crude MESD leaves, while crude MESD also showed significant anti-inflammatory and antipyretic activity through dose dependent phenomenon. These significant results might be due to flavonoids (luteolin, isoquercitrin) and triterpenoids (ursolic acid) presence, though the involvement of other biologically active secondary metabolites cannot be overlooked.

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Bioassay-Guided Isolation, Identification of Compounds from Sterculia diversifolia and Investigation of Their Anti-Glycation and Antioxidant Activities

Cited by 13 publications

References 19 publications

Methyl benzoate and cinnamate analogs as modulators of DNA methylation in hepatocellular carcinoma

Methyl benzoate and cinnamate analogs as modulators of DNA methylation in hepatocellular carcinoma

Analysis of <i>cis</i>-isomer-enriched dihydroquercetin sample by 1D and 2D NMR spectroscopy

Evaluation of in-Vivo Biological Activities of Sterculia Diversifolia (G. Don) in Relevance to the Isolated Secondary Metabolites

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