Separation, synthesis, and cytotoxicity of a series of mogrol derivatives

Journal of Asian Natural Products Research (2019)

Lei Wang Lianchun Li Yu-Xia Fu Bingchen Li Bing Chen Feng Xu Dianpeng Li

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Abstract:

Four metabolites of mogrol were separated, identified and characterized. Their antitumor activity was evaluated, and the results showed side chain modification would probably enhance the cytotoxicity. Therefore, three types of amines, alcohols and rigid planar derivatives were synthesized. Compounds 20 and 21 containing a tetrahydro-β-carboline structure at the end of the side chain exhibited IC50 values around 2-9 μM against A549 and CNE1 cell comparing with 80-90 μM of mogrol. Structure analysis suggested that the perhydrocyclopentanophenanthrene moiety and the tetrahydro-β-carboline moiety could probably enhance the activity through an intramolecular synergistic effect.[Formula: see text].

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Moiety

Side chain

Structure–activity relationship

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Synthesis and bioactivity of alkaloids

Cancer therapeutics and mechanisms

Phytochemical compounds biological activities

10.1080/10286020.2019.1611785

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Tetrahydropyrrolo[3,2-c]azepin-4-ones as a new class of cytotoxic compounds

Bioorganic & Medicinal Chemistry (2006)

Roberto Martı́nez Javier Ávila Ma. Teresa García Ramírez Araceli Pérez‐Vásquez A.J. Martinez

Lactam

10.1016/j.bmc.2006.02.012

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Scalarane Sesterterpenoids Isolated from the Marine Sponge Hyrtios erectus and their Cytotoxicity

Marine Drugs (2022)

Huynh Nguyen Khanh Tran Min Jin Kim Yeon‐Ju Lee

Eighteen scalarane sesterterpenoids (1–18), including eight new derivatives (1–8), were isolated from the sponge Hyrtios erectus (family Thorectidae), the extract of which showed cytotoxicity against the HeLa and MCF-7 cell lines. Of the new derivatives, six compounds (1–6) were found to contain a γ-hydroxybutenolide moiety capable of reversible stereoinversion at the hydroxylated carbon center. Under the influence of other adjacent functional groups, each derivative exhibited a different stereochemical behavior, which was fully deduced by ROESY experiments. All the isolated compounds were examined for their cytotoxicity by MTS assay using staurosporine as a positive control (IC50 0.18 and 0.13 μΜ against HeLa and MCF-7 cells, respectively), and they were found to show weak growth inhibitory activities against HeLa and MCF-7 cells, with a minimal IC50 value of 20.0 μΜ. The compounds containing a γ-hydroxybutenolide moiety (1–3, 10, 12) showed cytotoxicity, with IC50 values ranging from 24.3 to 29.9 μΜ, and the most potent derivative was heteronemin (16). Although the cytotoxicities of isolated compounds were insufficient to discuss the structure–activity relationship, this research could contribute to expanding the structural diversity of scalaranes and understanding the stereochemical behavior of γ-hydroxybutenolides.

Sponge

10.3390/md20100604

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Citations (6)

Stereoselectivity in the intramolecular Nozaki–Hiyama–Kishi reaction: influence of the substitution pattern and protecting groups in the construction of 10-membered lactones

Tetrahedron Letters (2002)

Ronaldo A. Pilli Maurício M. Victor

Stereocenter

Moiety

Substitution (logic)

10.1016/s0040-4039(02)00347-7

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