Cytotoxic polyoxygenated cyclohexene derivatives from the aerial parts of Uvaria cherrevensis

Jaipetch, Thaworn; Hongthong, Sakchai; Kuhakarn, Chutima; Pailee, Phanruethai; Piyachaturawat, Pawinee; Suksen, Kanoknetr; Kongsaeree, Palangpon; Prabpai, Samran; Nuntasaen, Narong; Reutrakul, Vichai

doi:10.1016/j.fitote.2019.104182

Cited by 11 publications

(7 citation statements)

References 27 publications

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“…Based on this evidence and in comparison with the published data, compound 7 was identified as (-)-6-acetylzeylenol [26]. is compound has been shown to exhibit cytotoxic activity [27].…”

Section: Determination and Elucidation Of Isolated Compoundsmentioning

confidence: 78%

“…e CD spectrum of 8 exhibited a positive Cotton effect (∆ε 242 + 11.56), indicating that the 6-position was shown to have an S-configuration. e absolute configuration at the 9-position was elucidated to be S when comparing with the 1 H, 13 C NMR, and the positive optical rotation value [27]. e 1D and 2D NMR spectra indicated this compound had megastigmane skeleton and identified as cucumegastigmane I in comparison with the literature [28].…”

Section: Determination and Elucidation Of Isolated Compoundsmentioning

confidence: 81%

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Anti-Inflammatory Compounds from Vietnamese Piper bavinum

Hoang

Nguyen

Doan

et al. 2020

Journal of Chemistry

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This study reports the anti-inflammatory activity-guided fractionation of the aerial part of Piper bavinum C. CD. (Piperaceae) that led to the isolation of eight secondary metabolites (1–8). The chemical structures of 1–8 were established mainly by NMR and mass spectra. Compound 5 was isolated from P. bavinum for the first time. All the isolated compounds were evaluated against LPS-induced NO production in macrophage RAW 264.7 cells in vitro. Among them, compound 4 showed the most potent inhibitory activity against the LPS-induced NO production with an IC50 value of 5.2 μM followed by compound 5 that inhibited NO production with an IC50 value of 13.5 μM. In the protein levels, compound 4 suppressed LPS-induced COX-2 and iNOS expressions in a dose-dependent manner. The results suggested that P. bavinum and its constituents might exert anti-inflammatory effects.

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“…Based on this evidence and in comparison with the published data, compound 7 was identified as (-)-6-acetylzeylenol [26]. is compound has been shown to exhibit cytotoxic activity [27].…”

Section: Determination and Elucidation Of Isolated Compoundsmentioning

confidence: 78%

Section: Determination and Elucidation Of Isolated Compoundsmentioning

confidence: 81%

Anti-Inflammatory Compounds from Vietnamese Piper bavinum

Hoang

Nguyen

Doan

et al. 2020

Journal of Chemistry

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“…The NMR data of 3 consisted of signals corresponding to a tetra-oxygenated cyclohexene skeleton (δ H/C 5.72 (H-1)/132.8, 5.71 (H-2)/128.2, 4.02 (H-3)/71.2, 3.65 (H-5)/74.4, 4.18 (H-6)/71.7; C-4 (76.4)), a benzoyloxy unit (δ H/C 8.02 (H-2″/6″)/130.5, 7.60 (H-4″)/132.8, 7.48 (H-3″/5″)/129.6, C-1 (134.2), C-7″ (169.4)), and an oxymethylene unit (δ H/C 3.82 (H-1′)/66.2). Contrary to 1 and 2 and to most polyoxygenated cyclohexenyl derivatives, − ,− ,− compound 3 lacked an HMBC cross-peak (Figure S21, Supporting Information) from the oxymethylene protons (CH 2 -1′; δ H 3.82, δ C 66.2) to a carbonyl carbon, indicating that the oxymethylene unit is not connected to the benzoyloxy moiety. Thus, the HMBC correlations of CH 2 -1′ (δ H 3.82) to C-3 (δ C 71.2), C-4 (δ C 76.4), and C-5 (δ C 74.3) supported the placement of the oxymethylene functionality at C-4.…”

Section: Resultsmentioning

confidence: 99%

“…Members of the genus Uvaria host a vast number of secondary metabolites with varied chemical structures and biological activities . The phytochemical constituents of the genus Uvaria include flavonoids and oxygenated cyclohexene derivatives, with the latter being restricted to the genus and its closely related genera within the Uvariae tribe, − albeit with very few plant families other than Annonaceae. − Thus, oxygenated cyclohexene derivatives have so far been reported from about 20 species of Uvaria ,− ,,− and other genera of the Uvariae tribe such as Monanthotaxis , ,, Ellipeiopsis , , Dasymaschalon , Cleistochlamys , , and Artabotrys . , These compounds exhibit diverse bioactivities including antiproliferative, ,,, antimalarial, ,, antibacterial, and cytotoxic ,, activities.…”

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confidence: 99%

Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis

Maeda

Gilissen²,

Rudenko

et al. 2021

J. Nat. Prod.

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Five new cyclohexene derivatives, dipandensin A and B ( 1 and 2 ) and pandensenols A–C ( 3 – 5 ), and 16 known secondary metabolites ( 6 – 21 ) were isolated from the methanol-soluble extracts of the stem and root barks of Uvaria pandensis . The structures were characterized by NMR spectroscopic and mass spectrometric analyses, and that of 6-methoxyzeylenol ( 6 ) was further confirmed by single-crystal X-ray crystallography, which also established its absolute configuration. The isolated metabolites were evaluated for antibacterial activity against the Gram-positive bacteria Bacillus subtilis and Staphylococcus epidermidis and the Gram-negative bacteria Enterococcus raffinosus , Escherichia coli , Paraburkholderia caledonica , Pectobacterium carotovorum , and Pseudomonas putida , as well as for cytotoxicity against the MCF-7 human breast cancer cell line. A mixture of uvaretin ( 20 ) and isouvaretin ( 21 ) exhibited significant antibacterial activity against B. subtilis (EC 50 8.7 μM) and S. epidermidis (IC 50 7.9 μM). (8′α,9′β-Dihydroxy)-3-farnesylindole ( 12 ) showed strong inhibitory activity (EC 50 9.8 μM) against B. subtilis , comparable to the clinical reference ampicillin (EC 50 17.9 μM). None of the compounds showed relevant cytotoxicity against the MCF-7 human breast cancer cell line.

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“…For example, the ethanolic extract of the roots of U. chamae was used as an antidiabetic agent and for the treatment of infections [3]. The decoction of the roots of U. cherrevensis was used for treatment of urinary disorders and being used as tonic for blood system and kidney [4].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and antimicrobial alkaloids isolated from twigs of Uvaria grandiflora Roxb.

Kongkum¹,

Thanasansurapong²,

Surapanich³

et al. 2021

ScienceAsia

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Phytochemical investigation of the MeOH-EtOAc (1:1 v/v) soluble fraction partitioned from the MeOH extract of twigs of Uvaria grandiflora Roxb. led to the isolation of six known compounds including aristolactam AII (1), aristolactam BI (2), velutinam (3), griffithinam (4), isoursuline (5), and sinactine (6). Their structures were determined on the basis of spectroscopic analysis and comparison with the literature data. Described in this work is the first report of isoursuline (5), an azafluorene derivative, and sinactine (6), a tetrahydroepiberberine, being isolated from plants in the Uvaria genus. Antioxidant and antimicrobial activities of some isolated compounds were evaluated. Among screened compounds, velutinam (3) showed antioxidant activity in the DPPH radical scavenging assay.

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Cytotoxic polyoxygenated cyclohexene derivatives from the aerial parts of Uvaria cherrevensis

Cited by 11 publications

References 27 publications

Anti-Inflammatory Compounds from Vietnamese Piper bavinum

Anti-Inflammatory Compounds from Vietnamese Piper bavinum

Oxygenated Cyclohexene Derivatives from the Stem and Root Barks of Uvaria pandensis

Antioxidant and antimicrobial alkaloids isolated from twigs of Uvaria grandiflora Roxb.

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