Towards understanding antimicrobial activity, cytotoxicity and the mode of action of dichapetalins A and M using in silico and in vitro studies

Chama, Mary Anti; Módos, Dezső; Mervin, Lewis; Owusu, Kofi Baffour-Awuah; Ayine-Tora, Daniel Moscoh; Egyir, Beverly; Paemka, Lily; Yankson, George; Ohashi, Mitsuko; Afzal, Avid M.

doi:10.1016/j.toxicon.2021.01.002

Cited by 5 publications

(9 citation statements)

References 36 publications

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“…Dichapelonin Q (17), colorless crystals, exhibited a (−)-HRMS (ESI) ion at m/z 703.3476 [M + HCO 2 ] − , corresponding to the molecular formula of C 40 H 50 O 8 , as supported by its 13 C NMR data. The 1 H and 13 C NMR data (Table 7) of 17 resembled those of 16, with major differences 7, CCDC 2204502, absolute structure parameter: 0.16 (7)].…”

Section: ■ Results and Discussionmentioning

confidence: 91%

“…The 1 H and 13 C NMR data (Table 7) of 16 and 7hydroxydichapetalin P were closely comparable, suggesting that they share the same planar structure. However, the relative and absolute configurations of 7-hydroxydichapetalin P in ref 7, CCDC 2204502, absolute structure parameter: 0.16 (7)].…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Crystallographic data of 17. C 40 H 50 O 8 , M = 658.80 g/mol, orthorhombic, space group P2 1 2 1 2 1 , a = 6.4649(4) Å, b = 10.3991 (7) Å, c = 49.975(3) Å, α = β = γ = 90°, V = 3359.8(4) Å 3 , Z = 4, T = 170.0 K, μ(Gu Kα) = 0.722 mm −1 , D calcd = 1.302 g/cm 3 , A total of 39 005 reflections were measured in the range 7.076°≤ 2θ ≤ 155.164°, containing 7045 independent reflections (R int = 0.0600, R sigma = 0.0457). The final R 1 was 0.0676 (I > 2σ(I)), and wR 2 was 0.2161 (all data).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The goodness of fit on F 2 was 1.040. The absolute configuration was determined by the Flack parameter = 0.16 (7).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Dichapetalins represent a small class of hybrid molecules featuring a 13,30-cyclodammarane scaffold conjugated with a C6–C2 unit, which have been found only in plants of the genera Dichapetalum and Phyllanthus . , Typical dichapetalins possess a common 2-phenylpyran moiety that is fused to the A ring of a 13,30-cyclodammarane with diverse C-17 side chains, comprising lactone, spirolactone, methyl ester, acetal, or furan moieties . Recently, a number of structurally intriguing dichapetalins with potent cytotoxic and immunosuppressive activities have been identified, which have attracted considerable interest from the research community. ,− …”

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confidence: 99%

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Dichapetalins from the Twigs of Dichapetalum longipetalum with Cytotoxic Activities

et al. 2022

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Continued efforts to expand the structural diversity of dichapetalins and explore further the cytotoxic structure–activity relationships have led to the isolation of 17 undescribed analogues, dichapelonins A–Q (1–17), and three known compounds (18–20) from the twigs of Dichapetalum longipetalum. Compounds 1–17 comprise five compound classes as classified by varied C6–C2 conjugates at the A ring of the 13,30-cyclodammarane skeleton, and their structures were determined by spectroscopic data analysis, experimental electronic circular dichroism measurements, and X-ray crystallography. Biological tests revealed compounds 1–7 with a phenyl-butadiene appendage to be the most potent cytotoxic compound type of those evaluated.

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Section: ■ Results and Discussionmentioning

confidence: 91%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The goodness of fit on F 2 was 1.040. The absolute configuration was determined by the Flack parameter = 0.16 (7).…”

Section: ■ Results and Discussionmentioning

confidence: 99%