Quercetin analogs with high fetal hemoglobin-inducing activity

Pabuprapap, Wachirachai; Wassanatip, Yanisa; Khetkam, Pichit; Chaichompoo, Waraluck; Kunkaewom, Sukanya; Senabud, Pongpan; Hata, Janejira; Chokchaisiri, Ratchanaporn; Svasti, Saovaros; Suksamrarn, Apichart

doi:10.1007/s00044-019-02412-7

Cited by 13 publications

(5 citation statements)

References 40 publications

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“…Fraction 4 was chromatographed eluting with CH 2 Cl 2 -EtOAc (65:35) to yield 3,5,7,4′-tetrahydroxy-2′-methoxyflavone (5 mg) as a white powder. The NMR spectroscopic data of the two isolated compounds were consistent with the reported values (Gonda et al, 2000;Pabuprapap et al, 2019). The pulverized, dried heartwood of M. cochinchinensis (1.0 kg) was extracted successively with n-hexane, EtOAc and MeOH in the same manner to that of A. luzonensis to give the hexane (1.24 g), EtOAc (159.2 g) and MeOH (101.8 g) extracts.…”

Section: Isolation Of Flavonoids From Plantssupporting

confidence: 82%

Model yeast as a versatile tool to examine the antioxidant and anti-ageing potential of flavonoids, extracted from medicinal plants

et al. 2022

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The demand for the production of herbal extracts for cosmetics, food, and health supplements, known as plant-based medicine, is rising globally. Incorporating herbal extracts could help to create higher value products due to the functional properties of bioactive compounds. Because the phytochemical composition could vary depending on the processing methods, a simple bioassay of herbal bioactive compounds is an important screening method for the purposes of functional characterization and quality assurance. As a simplified eukaryotic model, yeast serves as a versatile tool to examine functional property of bioactive compounds and to gain better understanding of fundamental cellular processes, because they share similarities with the processes in humans. In fact, aging is a well-conserved phenomenon between yeast and humans, making yeast a powerful genetic tool to examine functional properties of key compounds obtained from plant extracts. This study aimed to apply a well-established model yeast, Saccharomyces cerevisiae, to examine the antioxidant and anti-aging potential of flavonoids, extracted from medicinal plants, and to gain insight into yeast cell adaptation to oxidative stress. Some natural quercetin analogs, including morin, kaempferol, aromadendrin, and steppogenin, protected yeast cells against oxidative stress induced by acetic acid, as shown by decreased cell sensitivity. There was also a reduction in intracellular reactive oxygen species following acetic acid treatment. Using the chronological aging assay, quercetin, morin, and steppogenin could extend the lifespan of wild-type S. cerevisiae by 15%–25%. Consistent with the fact that oxidative stress is a key factor to aging, acetic acid resistance was associated with increased gene expression of TOR1, which encodes a key growth signaling kinase, and MSN2 and MSN4, which encode stress-responsive transcription factors. The addition of the antioxidant morin could counteract this increased expression, suggesting a possible modulatory role in cell signaling and the stress response of yeast. Therefore, yeast represents a versatile model organism and rapid screening tool to discover potentially rejuvenescent molecules with anti-aging and anti-oxidant potential from natural resources and to advance knowledge in the molecular study of stress and aging.

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Section: Isolation Of Flavonoids From Plantssupporting

confidence: 82%

Model yeast as a versatile tool to examine the antioxidant and anti-ageing potential of flavonoids, extracted from medicinal plants

et al. 2022

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“…The structures were characterized by the analysis of their spectroscopic data, including the single-crystal X-ray diffraction analysis of compound 1 . The known compounds ent -3β,19-dihydroxykaur-16-ene ( 7 ), 23 24 ent -3β-hydroxykaur-16-en-19-oic acid ( 8 ), 25 ent -16β,17-dihydroxykauran-19-oic acid ( 9 ), 25 ent -3β,16α,17-trihydroxykaurane ( 10 ), 26 16β,17-dihydroxykaurane ( 11 ), 27 ent -3β-hydroxykaur-16-ene ( 12 ), 28 quercetin-3-rhamnose-4,7-dimethyl ether ( 13 ), 29 3,7,4′-tri- O -methylkaempferol ( 14 ), 30 3,7,3′,4′-tetra- O -methyl quercetin ( 15 ), 31 ayanin ( 16 ), 32 stigmasterol ( 17 ), 33 the pinane-type monoterpenoids 2-hydroxy-2-(hydroxymethyl)-6,6-dimethylbicyclo[3.1.1]heptan-3-one ( 18 ), 34 and p -hydroxyphenylethyl ferute ( 19 ) 35 were identified by comparison of their spectroscopic data ( Figures S49–S145, Supporting Information ) to those reported in the literature.…”

Section: Results and Discussionmentioning

confidence: 99%

Crotofolane Diterpenoids and Other Constituents Isolated from Croton kilwae

Colores

Miah

et al. 2023

J. Nat. Prod.

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Six new crotofolane diterpenoids ( 1 – 6 ) and 13 known compounds ( 7 – 19 ) were isolated from the MeOH–CH 2 Cl 2 (1:1, v/v) extracts of the leaves and stem bark of Croton kilwae . The structures of the new compounds were elucidated by extensive analysis of spectroscopic and mass spectrometric data. The structure of crotokilwaepoxide A ( 1 ) was confirmed by single-crystal X-ray diffraction, allowing for the determination of its absolute configuration. The crude extracts and the isolated compounds were investigated for antiviral activity against respiratory syncytial virus (RSV) and human rhinovirus type-2 (HRV-2) in HEp-2 and HeLa cells, respectively, for antibacterial activity against the Gram-positive Bacillus subtilis and the Gram-negative Escherichia coli , and for antimalarial activity against the Plasmodium falciparum Dd2 strain. ent -3β,19-Dihydroxykaur-16-ene ( 7 ) and ayanin ( 16 ) displayed anti-RSV activities with IC 50 values of 10.2 and 6.1 μM, respectively, while exhibiting only modest cytotoxic effects on HEp-2 cells that resulted in selectivity indices of 4.9 and 16.4. Compounds 2 and 5 exhibited modest anti-HRV-2 activity (IC 50 of 44.6 μM for both compounds), while compound 16 inhibited HRV-2 with an IC 50 value of 1.8 μM. Compounds 1 – 3 showed promising antiplasmodial activities (80–100% inhibition) at a 50 μM concentration.

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“…1). The known compounds were identified as dihydrooroxylin A (7) [12], 7-hydroxy-6-methoxyflavanone (8) [13], 4′,5,7-trihydroxy-6-methylflavanone (9) [14], 4′-O-methylquercetin (10) [15], 3,3′-di-Omethylquercetin (11) [16], kaempferol-3-methyl ether (12) [17], jaceidin (13) [18], 7-hydroxy-6-methoxyflavone (14) [19], 6,8-dimethylchrysin (15) [20], strobochrysin (16) [21], 3,5,7-trihydroxy-6-methylflavanone (17) [21], 3,5,7-trihydroxy-6-methoxyflavanone (18) [22], and 3,7-dihydroxy-6-methoxyflavanone (19) [23].…”

Section: Resultsmentioning

confidence: 99%

Inhibition of Proinflammatory Cytokine Release by Flavones and Flavanones from the Leaves of Dracaena steudneri Engl.

et al. 2020

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The leaves of Dracaena steudneri yielded 6 new flavonoids–3,5,7-trihydroxy-6-methyl-3′,4′-methylenedioxyflavone (1), 5,7-dihydroxy-3-methoxy-6-methyl-3′,4′-methylenedioxyflavone (2), 3,5,7-trihydroxy-6-methoxy-3′,4′-methylenedioxyflavone (3), (2S,3S)-3,7-dihydroxy-6-methoxy-3′,4′-methylenedioxyflavanone (4), 4′,5,7-trihydroxy-3,3′,8-trimethoxy-6-methylflavone (5), (2R) 7-hydroxy-2′,8-dimethoxyflavanone (6)–together with 13 known congeners. Their structures were established using spectroscopic and spectrometric methods including NMR, CD, and HRMSn measurements. The compounds were evaluated for their anti-inflammatory potential through measurement of the levels of cytokines IL-1β, IL-2, GM-CSF, and TNF-α in the supernatant of human peripheral blood mononuclear cells stimulated by lipopolysaccharide. Flavones derivatives 1–4 with a C-3′/4′ methylenedioxy substituent led to a substantial increase in the production of IL-1β and GM-CSF out of 4 pro-inflammatory cytokines relative to LPS control. Quercetin derivatives 5, 11, and 13 with a hydroxyl group at C-4′ inhibited the production of IL-2, GM-CSF, and TNF-α. The presence of a C-2/C-3 double bond in 14 was pivotal to the significantly stronger (0.4 to 27.5% of LPS control) inhibitory effect compared to its dihydro derivative 8 (36.2 to 262.7% of LPS control) against all tested cytokines. It is important to note that the inhibitory activity of 14 was substantially higher than that of the standard drug used, ibuprofen.

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Quercetin analogs with high fetal hemoglobin-inducing activity

Cited by 13 publications

References 40 publications

Model yeast as a versatile tool to examine the antioxidant and anti-ageing potential of flavonoids, extracted from medicinal plants

Model yeast as a versatile tool to examine the antioxidant and anti-ageing potential of flavonoids, extracted from medicinal plants

Crotofolane Diterpenoids and Other Constituents Isolated from Croton kilwae

Inhibition of Proinflammatory Cytokine Release by Flavones and Flavanones from the Leaves of Dracaena steudneri Engl.

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