Synthesis, DFT analysis and in-vitro anti-cancer study of novel fused bicyclic pyranone isoxazoline derivatives of Goniodiol-diacetate-a natural product derivative

Talimarada, Doddabasappa; Sharma, Akanksha; Wakhradkar, Mahesh G.; Dhuri, Sundar N.; Gunturu, Krishna Chaitanya; Sundaram, Venkata Narayanan Naranammalpuram; Holla, Harish

doi:10.1016/j.fitote.2022.105316

Cited by 3 publications

(2 citation statements)

References 34 publications

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“…The data suggest that the presence of saturated lactones is essential for activity and that changes in the electron-absorbing or electron-donating groups on the aryl rings of all derivatives have little effect on enhancing cytotoxicity. Further molecular biology studies showed compound 38 stalled the cell cycle in the S phase [ 62 ].…”

Section: Biological Effects Of Natural Products Containing the Isoxaz...mentioning

confidence: 99%

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Wang

Tang

et al. 2023

Pharmaceuticals

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Isoxazoles and isoxazolines are five-membered heterocyclic molecules containing nitrogen and oxygen. Isoxazole and isoxazoline are the most popular heterocyclic compounds for developing novel drug candidates. Over 80 molecules with a broad range of bioactivities, including antitumor, antibacterial, anti-inflammatory, antidiabetic, cardiovascular, and other activities, were reviewed. A review of recent studies on the use of isoxazoles and isoxazolines moiety derivative activities for natural products is presented here, focusing on the parameters that affect the bioactivity of these compounds.

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Section: Biological Effects Of Natural Products Containing the Isoxaz...mentioning

confidence: 99%

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Wang

Tang

et al. 2023

Pharmaceuticals

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“…Reports are on the leaf extracts of G. wynaadensis in ethyl acetate and water were cytotoxic to various cancer cell lines and effective against bacteria such as Salmonella typhi, Escherichia coli and Staphylococcus aureus (10). Further purification of the extract using column chromatography yielded the known cytotoxic molecule goniodiol-7-monoacetate, containing α, β-unsaturated δ-lactone (11). The bark juice of G. wynaadensis is used by the tribes of Wayanad as a component of arthritis medications (10,12).…”

Section: Introductionmentioning

confidence: 99%

Epicotyl morphophysiological dormancy and a rare case of epigeal cryptocotylar seed germination in Goniothalamus wynaadensis (Bedd.) Bedd., a tropical threatened endemic tree species of the Western Ghats

Jayan,

Sreekala

2024

Plant Sci. Today

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Goniothalamus wynaadensis (Bedd.) Bedd. is a threatened indigenous tree species found in the Western Ghats and possesses significant medicinal value. This species belongs to the primitive family Annonaceae. However, there is a lack of information regarding seed germination in this species. We conducted experiments on seed germination using various media and found that the species exhibits epicotyl morpho-physiological dormancy (eMPD), marking the first such record in Annonaceae. GA3 at a concentration of 500 ppm and warm stratification at 20 °C for one week proved effective in enhancing embryo growth and radicle emergence. The epicotyl emergence was observed only at 30±2 °C. Because warm stratification promotes both radicle and shoot emergence in G. wynaadensis, the level of eMPD is non-deep and simple. Hence, dormancy in G. wynaadensis can be described as C1b Bb (radicle)- C1b Bb (epicotyl); i.e., the embryo is underdeveloped and grows before radicle emergence and epicotyl emergence under warm temperatures (Bb) and both the radicle and epicotyl have non-deep simple physiological dormancy broken by warm temperatures (C1b). Consequently, G. wynaadensis seed dormancy is phenologically well- adapted to the seasonal climate of Wayanad. Additionally, the species was found to display epigeal cryptocotylar seed germination—a rare occurrence in the development of angiosperm seedlings and this is the first record of such a phenomenon in the genus Goniothalamus.

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Inhibition and kinetic studies of phytochemical constituents of Goniothalamus wynaadensis and their isoxazoline derivatives on α-glucosidase

Bojja,

Kumar,

Palanimuthu

et al. 2024

Natural Product Research

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α-Glucosidase, an enzyme involved in post-prandial hyperglycemia, was used as a target to study the effect of compound(s) isolated from Goniothalamus wynaadensis and its isoxazoline derivatives. Among 13 compounds screened, Compounds 1, 3a, and 3j exhibited significant inhibition with IC50 values of 63.42, 61.36, and 58.89 µg/mL, respectively, outperforming acarbose (71.72 µg/mL). Kinetic studies revealed competitive binding for compound 1 and uncompetitive/non-competitive binding for 3a and 3j. Fluorescence quenching showed a linear relationship between I0/I at different inhibitor concentrations. The binding sites in α-glucosidase were ≤ 1. The binding constants 3a (0.7307) > 3j (0.6563) > 1 (0.5415) displayed strong interactions. Docking study revealed binding affinities; 3j (-8.9) > 3a (-7.7) > 1 (-7), and acarbose, 1, 3a, and 3j had ARG-312, PHE-157 interactions in common to α-glucosidase. The toxicity profile showed compounds fell in class IV and V. Overall; the results indicate that compounds 1, 3a, and 3j are effective against α-glucosidase.

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Synthesis, DFT analysis and in-vitro anti-cancer study of novel fused bicyclic pyranone isoxazoline derivatives of Goniodiol-diacetate-a natural product derivative

Cited by 3 publications

References 34 publications

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Epicotyl morphophysiological dormancy and a rare case of epigeal cryptocotylar seed germination in Goniothalamus wynaadensis (Bedd.) Bedd., a tropical threatened endemic tree species of the Western Ghats

Inhibition and kinetic studies of phytochemical constituents of Goniothalamus wynaadensis and their isoxazoline derivatives on α-glucosidase

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