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Isolation, structural elucidation, and cytotoxic activity investigation of novel styryl-lactone derivatives from Goniothalamus elegans: in vitro and in silico studies.

ABSTRACT: Two styryl-lactone derivatives (1 and 2) were isolated from the aerial parts of Goniothalamus elegans. Compound 1 is a newly discovered natural product, and compound 2 is reported in this plant for the first time. The absolute configuration of 1 was determined based on the ECD spectrum. The two styryl-lactone derivatives were tested for cytotoxicity activity against five cancer cell lines and human embryonic kidney cells. The newly discovered compound demonstrated potent cytotoxicity, with IC₅₀ values ranging from 2.05 to 3.96 μM. Computational methods were also applied to investigate the mechanism of the cytotoxic activity of the two compounds. Density functional theory and molecular mechanisms were used to assess the interaction between protein targets to compound 1 and 2, respectively, through the EGF/EGFR signaling pathway. The results indicated that 1 showed a strong binding affinity for two proteins EGFR and HER-2. Finally, ADMET predictions were used to validate the pharmacokinetics and toxicity of these compounds. The results showed that both compounds are likely to be absorbed in the gastrointestinal tract and penetrate the blood-brain barrier. Based on our findings, these compounds may have potential for further studies to be developed into active ingredients for cancer treatment.

SUBMITTER: Nguyen TK

PROVIDER: S-EPMC10258602 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Isolation, structural elucidation, and cytotoxic activity investigation of novel styryl-lactone derivatives from Goniothalamus elegans: in vitro and in silico studies.

Nguyen Tan Khanh TK Thi Tran Linh Thuy LT Truong Tan Trung T Pham Phu Tran Vinh PTV Nguyen Linh Thuy Khanh LTK Nguyen Hoai Thi HT Ho Duc Viet DV Tran Manh Hung MH Tran Manh Hung MH

RSC advances 20230612 26

Two styryl-lactone derivatives (1 and 2) were isolated from the aerial parts of Goniothalamus elegans. Compound 1 is a newly discovered natural product, and compound 2 is reported in this plant for the first time. The absolute configuration of 1 was determined based on the ECD spectrum. The two styryl-lactone derivatives were tested for cytotoxicity activity against five cancer cell lines and human embryonic kidney cells. The newly discovered compound demonstrated potent cytotoxicity, wit ...[more]

PMID: 37312988

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Project description:Styryl quinolines are biologically active compounds with properties largely depending on the substituents on the styryl and quinoline rings. The supramolecular aspects of this class of compounds are rarely explored. In this study, two new series of styryl quinoline derivatives, bearing -OH and -NO2 groups at the eighthposition of the quinoline ring and -SCH3, -OCH3, and -Br groups on the styryl ring, have been developed, and their structural, supramolecular, and cytotoxic properties have been analyzed. Crystallographic analyses revealed the exciting substituent-dependent structural and supramolecular features of these compounds. In general, the 8 -OH substituted derivatives (SA series) exhibited a non-planar molecular geometry having larger dihedral angles (5.75-59.3°) between the planes of the aromatic rings. At the same time, the 8 -NO2 substituted derivatives (SB series) exhibited a more or less planar molecular geometry, as revealed by the smaller dihedral angles (1.32-3.45°) between the aromatic rings. Multiple O-H···O, C-H···O, O-H···N, and π-π stacking interactions among the molecules lead to fascinating supramolecular architectures such as hydrogen-bonded triple helices, zig-zag 1D chains, π-π stacked infinite chains, and so forth in their crystal lattice. Hirshfeld surface analyses confirmed the existence of strong π-π stacking and other weak bonding interactions in these compounds. The preliminary cytotoxic properties of SA and SB series compounds were evaluated against the human cervical cancer cell lines (HeLa cells), which further highlighted the roles of functional substituents on the aromatic rings. The SA series compounds with the -OH substituent on the quinoline ring exhibited better cytotoxicity than the SB series compounds with a -NO2 substituent. Similarly, the electron-withdrawing group -Br on the styryl ring enhanced the cytotoxicity in both series. The IC50 values were 2.52-4.69 and 2.897-10.37 μM, respectively, for the SA and SB series compounds. Compound S3A having -OH and -Br groups on the quinoline and styryl ring, respectively, exhibited the best IC50 value of 2.52 μM among all the compounds tested. These findings confirm the relevance of the hydroxyl group in the eighth position of quinoline. In short, the present study attempts to provide a systematic analysis of the effects of aromatic ring substituents on the structural, supramolecular, and cytotoxic properties of styryl quinolines for the first time.

Dataset Information

Isolation, structural elucidation, and cytotoxic activity investigation of novel styryl-lactone derivatives from Goniothalamus elegans: in vitro and in silico studies.

Publications

Isolation, structural elucidation, and cytotoxic activity investigation of novel styryl-lactone derivatives from <i>Goniothalamus elegans</i>: <i>in vitro</i> and <i>in silico</i> studies.

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