Novel diastereoselective trans 2, 3-dihydrobenzofuran derivatives: Tandem synthesis, crystal structure, antioxidant and anticancer activity

Nousheen, Anshra; Chandrakanth, Munugala; Sagar, Banoth Karuna; Somarapu, Vijaya Laxmi

doi:10.1016/j.molstruc.2022.132899

Cited by 10 publications

(2 citation statements)

References 42 publications

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“…Some previous studies showed that these phenolic compounds mentioned exhibited antimicrobial, antiosteoporotic, and control of human tumors [32][33][34]. Our findings also found benzaldehyde, 2-hydroxy-4-methyl, and 2,3-dihydro-benzofuran in the R.A. Poir leaf extract, which exhibited strong antioxidant capacity and anticancer [35,36]. As can be concluded from the results, the identified compounds could be responsible for the ABTS radical scavenging activity of the extract obtained by the UAE method.…”

Section: Optimization and Comparison Of Uae Withsupporting

confidence: 77%

Optimization Conditions of Ultrasound-Assisted Extraction for Phenolic Compounds and Antioxidant Activity from Rubus alceifolius Poir Leaves

Tran,

Nghiem,

Dinh

et al. 2023

International Journal of Food Science

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Rubus alceifolius Poir (R.A. Poir) leaves are rich in phenolic compounds, offering many health benefits due to their incredible antioxidant potential. In this study, conditions for the ultrasound-assisted extraction (UAE) of phenolic compounds and antioxidant activity from R.A. Poir leaves were optimized using response surface methodology (RSM). This methodology assessed the effects of ultrasound power ( X 1 : 100-500 W), extraction temperature ( X 2 : 30-60°C), and extraction time ( X 3 : 5-55 min). The optimized UAE conditions were then compared with conventional extraction methods (Soxhlet extraction: SE and maceration extraction: ME) for extracting total phenolics. A phenolic profile using GC-MS and antioxidant activity (ABTS) was also compared. According to the RSM, the best conditions for UAE to extract the highest total polyphenol content and ABTS radical scavenging activity were 320 W ultrasound power, 40°C extraction temperature, and 35.5 min sonication duration. Under these optimal conditions, the TPC and antioxidant activity reached 16.68 mg GAE/g dm and 21.9 mg TE/g, respectively, closely aligning with the predicted values. The UAE extraction technique proved to be more efficient in extracting phenolics and antioxidant capacity (ABTS (2,2 ′ -azino-bis(3-ethylbenzthiazoline-6-sulphonic acid)) radical scavenging activity, and enzyme inhibition) compared to the conventional extraction methods (SE and ME). A GC-MS analysis identified 12 components, including 5 phenolics and 3 flavonoids, which likely contribute to the antioxidant activity. Consequently, the UAE method improved extraction efficiency within a shorter time frame, suggesting that UAE is a promising, efficient, and ecofriendly technology for extracting bioactive compounds from R.A. Poir leaves.

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Section: Optimization and Comparison Of Uae Withsupporting

confidence: 77%

Optimization Conditions of Ultrasound-Assisted Extraction for Phenolic Compounds and Antioxidant Activity from Rubus alceifolius Poir Leaves

Tran,

Nghiem,

Dinh

et al. 2023

International Journal of Food Science

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“…This may suggest that the cytotoxic activity observed in the extract is associated with the effect of this compound; selectivity against cancer cells was also observed. The selectivity index is commonly reported in the literature as a ratio of IC 50 values calculated for healthy cells and cancer cells [30,88], with values greater than 1 indicating desirable selectivity against cancer cells. The selectivity index of 2,3-dihydrobenzofuran (7) was 5.17, 1.53, 1.54, 1.65, and 1.15 for HeLa, PC-3, Huh-7, HepG2, and MCF-7 cells, respectively.…”

Section: Cytotoxic Effect Of the Compound 23-dihydrobenzofuranmentioning

confidence: 99%

Cytotoxic Activity of Wild Plant and Callus Extracts of Ageratina pichinchensis and 2,3-Dihydrobenzofuran Isolated from a Callus Culture

Sánchez-Ramos,

Encarnación-García,

Marquina-Bahena

et al. 2023

Pharmaceuticals

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Ageratina pichinchensis (Kunth) R.M. King & H. Rob. belongs to the Asteraceae family and is a plant native to Mexico to which several biological properties are attributed. In this study, the cytotoxic effect of four extracts from the wild plants and two extracts from A. pichinchensis callus culture were evaluated against carcinogenic cell lines including prostate carcinoma, cervical cancer, hepatocellular carcinoma, hepatoma human, lung cancer, and cellular keratinocytes. The extracts were obtained with ethyl acetate and methanol using both leaves and stems or the callus. Only the ethyl acetate extract of the callus culture influenced the cervical cancer cell line (HeLa) with an IC50 of 94.79 ± 2.0 µg/mL. From the ethyl acetate callus extract, 2,3-dihydrobenzofuran was isolated and purified and also evaluated against cancer cells. The cytotoxic evaluation of this compound showed a significant effect against the HeLa cell line with an IC50 of 23.86 ± 2.5 µg/mL. Our results contribute to the development of biotechnological alternatives and extraction processes to produce compounds with possible potential against certain types of human cancer.

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Transition Metal‐Free Diastereoselective Synthesis of β‐Carboline Tethered Dihydrofurocoumarin Derivatives

Banyal,

Malakar,

Kumar

et al. 2024

Asian J Org Chem

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One‐pot procedure has been developed for the synthesis of novel β‐carboline tethered trans 2,3‐furocoumarins via assembling 1‐formyl‐β‐carbolines, 4‐hydroxycoumarins, and phenacyl bromides in pyridine under transition metal‐free conditions. The strategy was also found applicable to gram scale synthesis and a library of 40 molecules has been developed. The significant features of this operationally facile approach includes high efficiency, short reaction time, excellent yields, multicomponent character of the reaction, metal‐free mild reaction conditions, and a column chromatography free purification procedure.

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Novel diastereoselective trans 2, 3-dihydrobenzofuran derivatives: Tandem synthesis, crystal structure, antioxidant and anticancer activity

Cited by 10 publications

References 42 publications

Optimization Conditions of Ultrasound-Assisted Extraction for Phenolic Compounds and Antioxidant Activity from Rubus alceifolius Poir Leaves

Optimization Conditions of Ultrasound-Assisted Extraction for Phenolic Compounds and Antioxidant Activity from Rubus alceifolius Poir Leaves

Cytotoxic Activity of Wild Plant and Callus Extracts of Ageratina pichinchensis and 2,3-Dihydrobenzofuran Isolated from a Callus Culture

Transition Metal‐Free Diastereoselective Synthesis of β‐Carboline Tethered Dihydrofurocoumarin Derivatives

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