A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves (2017)

Nyandoro, S. S., Munissi, J. J. E., Gruhonjic, A., Duffy, S., Pan, F., Puttreddy, R., Holleran, J. P., Fitzpatrick, P. A., Pelletier, J., Avery, V. M., Rissanen, K., & Erdélyi, M. (2017). Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves. Journal of Natural Products, 80(1), 114-125. https://doi.org/10.1021/acs.jnatprod.6b00759

JYU-tekijät tai -toimittajat

Pan, Fangfang
Puttreddy, Rakesh
Rissanen, Kari

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Nyandoro, Stephen S.; Munissi, Joan J. E.; Gruhonjic, Amra; Duffy, Sandra; Pan, Fangfang; Puttreddy, Rakesh; Holleran, John P.; Fitzpatrick, Paul A.; Pelletier, Jerry; Avery, Vicky M.; et al.

Lehti tai sarja: Journal of Natural Products

ISSN: 0163-3864

eISSN: 1520-6025

Julkaisuvuosi: 2017

Volyymi: 80

Lehden numero: 1

Artikkelin sivunumerot: 114-125

Kustantaja: American Chemical Society and American Society of Pharmacognosy

Julkaisumaa: Yhdysvallat (USA)

Julkaisun kieli: englanti

DOI: https://doi.org/10.1021/acs.jnatprod.6b00759

Julkaisun avoin saatavuus: Ei avoin

Julkaisukanavan avoin saatavuus:

Tiivistelmä

Thirteen new metabolites, including the polyoxygenated cyclohexene derivatives cleistodiendiol (1), cleistodienol B (3), cleistenechlorohydrins A (4) and B (5), cleistenediols A–F (6–11), cleistenonal (12), and the butenolide cleistanolate (13), 2,5-dihydroxybenzyl benzoate (cleistophenolide, 14), and eight known compounds (2, 15–21) were isolated from a MeOH extract of the leaves of Cleistochlamys kirkii. The purified metabolites were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of compounds 1, 17, and 19 were established by single-crystal X-ray diffraction. The configuration of the exocyclic double bond of compound 2 was revised based on comparison of its NMR spectroscopic features and optical rotation to those of 1, for which the configuration was determined by X-ray diffraction. Observation of the co-occurrence of cyclohexenoids and heptenolides in C. kirkii is of biogenetic and chemotaxonomic significance. Some of the isolated compounds showed activity against Plasmodium falciparum (3D7, Dd2), with IC50 values of 0.2–40 μM, and against HEK293 mammalian cells (IC50 2.7–3.6 μM). While the crude extract was inactive at 100 μg/mL against the MDA-MB-231 triple-negative breast cancer cell line, some of its isolated constituents demonstrated cytotoxic activity with IC50 values ranging from 0.03–8.2 μM. Compound 1 showed the most potent antiplasmodial (IC50 0.2 μM) and cytotoxic (IC50 0.03 μM, MDA-MB-231 cell line) activities. None of the compounds investigated exhibited translational inhibitory activity in vitro at 20 μM.

Vapaat asiasanat: metabolites; spectrometric analyses

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