A dihydro-β-agarofuran sesquiterpene from <i>Maytenus boaria</i>

Paz, Cristian; Dossow, Daniela Von; Tiznado, Victor; Suárez, Sebastián; Cukiernik, Fabio Daniel; Baggio, Ricardo

doi:10.1107/s2053229617006817

Cited by 8 publications

(12 citation statements)

References 23 publications

(21 reference statements)

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“…As shown above, the inner skeleton in (II), (III) and (IV) is identical to that in (I) and, as already shown in Paz et al (2017), to the 19 remaining molecular skeletons in the literature therein compared, is indicative of the robustness of the group, irrespective of the substituents present.…”

Section: Discussionsupporting

confidence: 78%

“…The use of Mo K radiation rendered the discrimination of the absolute structure impossible (the heaviest atom is O), for which the assignment was made by matching it with the reported configuration of all the related structures analyzed in Paz et al (2017).…”

Section: Refinementmentioning

confidence: 99%

“…As part of recent structural work, we have made a literature survey of sesquiterpenes with a reported crystal structure, to which we refer the interested reader (Paz et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

“…A preliminary successful result of this study was the recently reported structure of a new sesquiterpene, i.e. (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9,10-trihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin-5-yl furan-3-carboxylate [hereinafter (I)] (Paz et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

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Three new dihydro-β-agarofuran sesquiterpenes from the seeds ofMaytenus boaria

et al. 2018

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As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new β-agarofuran sesquiterpenes, namely (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9-dihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepine-5,10-diyl bis(furan-3-carboxylate), CHO, (II), (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepine-5,10-diyl bis(furan-3-carboxylate), CHO, (III), and (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-10-(benzoyloxy)-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin-5-yl furan-3-carboxylate, CHO, (IV), obtained from the seeds of Maytenus boaria and closely associated with a recently published relative [Paz et al. (2017). Acta Cryst. C73, 451-457]. In the (isomorphic) structures of (II) and (III), the central decalin system is esterified with an acetate group at site 1 and furoate groups at sites 6 and 9, and differ at site 8, with an OH group in (II) and no substituent in (III). This position is also unsubstituted in (IV), with site 6 being occupied by a benzoate group. The chirality of the skeletons is described as 1S,4S,5S,6R,7R,8R,9R,10S in (II) and 1S,4S,5S,6R,7R,9S,10S in (III) and (IV), matching the chirality suggested by NMR studies. This difference in the chirality sequence among the title structures (in spite of the fact that the three skeletons are absolutely isostructural) is due to the differences in the environment of site 8, i.e. OH in (II) and H in (III) and (IV). This diversity in substitution, in turn, is responsible for the differences in the hydrogen-bonding schemes, which is discussed.

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Section: Discussionsupporting

confidence: 78%

Section: Refinementmentioning

confidence: 99%

“…As part of recent structural work, we have made a literature survey of sesquiterpenes with a reported crystal structure, to which we refer the interested reader (Paz et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Three new dihydro-β-agarofuran sesquiterpenes from the seeds ofMaytenus boaria

et al. 2018

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“…Looking for natural anticancer agents, we previously studied the Chilean native tree Maytenus boaria, isolating four dihydro-β-agarofurans sesquiterpenoids from organic extracts of its seeds [27,28]. However, these compounds were not active in cancer cells models, specifically against MCF-7, PC9, and C4-2B cells (data not shown).…”

Section: Resultsmentioning

confidence: 99%

Maytenus disticha Extract and an Isolated β-Dihydroagarofuran Induce Mitochondrial Depolarization and Apoptosis in Human Cancer Cells by Increasing Mitochondrial Reactive Oxygen Species

et al. 2020

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Maytenus disticha (Hook F.), belonging to the Celastraceae family, is an evergreen shrub, native of the central southern mountains of Chile. Previous studies demonstrated that the total extract of M. disticha (MD) has an acetylcholinesterase inhibitory activity along with growth regulatory and insecticidal activities. β-Dihydroagarofurans sesquiterpenes are the most active components in the plant. However, its activity in cancer has not been analyzed yet. Here, we demonstrate that MD has a cytotoxic activity on breast (MCF-7), lung (PC9), and prostate (C4-2B) human cancer cells with an IC50 (µg/mL) of 40, 4.7, and 5 µg/mL, respectively, an increasing Bax/Bcl2 ratio, and inducing a mitochondrial membrane depolarization. The β-dihydroagarofuran-type sesquiterpene (MD-6), dihydromyricetin (MD-9), and dihydromyricetin-3-O-β-glucoside (MD-10) were isolated as the major compounds from MD extracts. From these compounds, only MD-6 showed cytotoxic activity on MCF-7, PC9, and C4-2B with an IC50 of 31.02, 17.58, and 42.19 µM, respectively. Furthermore, the MD-6 increases cell ROS generation, and MD and MD-6 induce a mitochondrial superoxide generation and apoptosis on MCF-7, PC9, and C4-2B, which suggests that the cytotoxic effect of MD is mediated in part by the β-dihydroagarofuran-type that induces apoptosis by a mitochondrial dysfunction.

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