Anti-inflammatory and antiproliferative compounds from Sphaeranthus africanus

Tran, Huyen Thi Thanh; Gao, X.; Kretschmer, Nadine; Pferschy‐Wenzig, Eva‐Maria; Raab, P; Pirker, Teresa; Temml, Veronika; Schuster, Daniela; Kunert, Olaf; Huynh, Loi; Bauer, R.

doi:10.1016/j.phymed.2019.152951

Cited by 16 publications

(25 citation statements)

References 34 publications

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“…The iNOS inhibitory activity of the isolated compounds and respective cytotoxicity was determined using a previously described protocol [40]. Briefly, BV-2 mouse microglial (25,000 cells/well) and RAW 264.7 mouse macrophage (100,000 cells/well) cell lines were seeded into 96-well plates in high glucose Dulbecco's Modified Eagle's Medium (DMEM, Gibco) containing 4 mM L-glutamine, 10% FBS, 2% HEPES, 1% penicillin/streptomycin, and 0.5% amphotericin B.…”

Section: No Production Inhibition Assaymentioning

confidence: 99%

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

et al. 2021

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Garcinia picrorhiza, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC50 values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC50 values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.

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Section: No Production Inhibition Assaymentioning

confidence: 99%

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

et al. 2021

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“…All detailed phytochemical and general experimental procedures on S. africanus L., such as isolations and structure identifications of the compounds 1-7 (Figure 1) are described in previously published research [21,22]…”

Section: Phytochemical Proceduresmentioning

confidence: 99%

“…After partitioning this crude extract with n-hexane, dichloromethane, ethyl acetate, and butanol, the following four sub-extracts were obtained: SA-Hex (6.0 g), SA-DCM (4.0 g), SA-Et (7.5 g), and SA-Bu (10 g), respectively. Sub-extracts were analyzed for phytochemical properties by using TLC, HPLC, and LC-MS. Carvotacetones 1-7 ( Figure 1) were isolated from SA-DCM extract as described before [21,22]. A detailed description of the isolation procedure together with spectroscopic data used for the identification of structures 1-7 is presented in the reported literature [20,21].…”

Section: Extractions and Isolationsmentioning

confidence: 99%

“…In some essential oils of Pluchea and Vernonia species, carvotacetone was identified as the dominating constituent. Furthermore, carvotacetones could be detected in several other Sphaeranthus species showing anti-proliferative [21], anti-inflammatory [22], and anti-parasitic in vitro activities [23], as well as significant inhibitory effects on the ubiquitin-proteasome pathway [24].…”

Section: Introductionmentioning

confidence: 99%

“…Compounds 1-7 ( Figure 1) have been previously isolated from Sphaeranthus africanus L. and have shown anti-proliferative and anti-inflammatory activities in cellular models [21,22].…”

Section: Introductionmentioning

confidence: 99%

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Antimicrobial and Efflux Pump Inhibitory Activity of Carvotacetones from Sphaeranthus africanus Against Mycobacteria

et al. 2020

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Carvotacetones (1–7) isolated from Sphaeranthus africanus were screened for their antimycobacterial and efflux pump (EP) inhibitory potential against the mycobacterial model strains Mycobacterium smegmatis mc2 155, Mycobacterium aurum ATCC 23366, and Mycobacterium bovis BCG ATCC 35734. The minimum inhibitory concentrations (MICs) of the carvotacetones were detected through high-throughput spot culture growth inhibition (HT-SPOTi) and microbroth dilution assays. In order to assess the potential of the compounds 1 and 6 to accumulate ethidium bromide (EtBr) in M. smegmatis and M. aurum, a microtiter plate-based fluorometric assay was used to determine efflux activity. Compounds 1 and 6 were analyzed for their modulating effects on the MIC of EtBr and the antibiotic rifampicin (RIF) against M. smegmatis. Carvotacetones 1 and 6 had potent antibacterial effects on M. aurum and M. bovis BCG (MIC ≤ 31.25 mg/L) and could successfully enhance EtBr activity against M. smegmatis. Compound 1 appeared as the most efficient agent for impairing the efflux mechanism in M. smegmatis. Both compounds 1 and 6 were highly effective against M. aurum and M. bovis BCG. In particular, compound 1 was identified as a valuable candidate for inhibiting mycobacterial efflux mechanisms and as a promising adjuvant in the therapy of tuberculosis or other non-tubercular mycobacterial infections.

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A New Carvotacetone Derivative from the Aerial Part of Sphaeranthus africanus

Duong

Nguyen

et al. 2023

Chemistry & Biodiversity

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Sphaeranthus africanus L. is native in Vietnam. Little is known about α‐glucosidase inhibition of Sphaeranthus africanus and its isolated compounds. A bioactive‐guided isolation was applied to the Vietnamese Sphaeranthus africanus to find α‐glucosidase inhibitory components. Eight compounds were detected and structurally elucidated. They are 3‐angeloyloxy‐5‐[2′′,3′′‐epoxy‐2′′‐methylbutanoyloxy]‐7‐hydroxycarvotacetone, 3‐angeloyloxy‐5‐[3′′‐chloro‐2′′‐hydroxy‐2′′‐methylbutanoyloxy]‐7‐hydroxycarvotacetone, 3‐angeloyloxy‐5‐[2′′R,3′′R‐dihydroxy‐2′′‐methyl‐butanoyloxy]‐7‐hydroxycarvotacetone, 3‐angeloyloxy‐5‐[2′′S,3′′R‐dihydroxy‐2′′‐methylbutanoyloxy]‐7‐hydroxycarvotacetone, 3‐angeloyloxy‐5‐[2′′S,3′′S‐dihydroxy‐2′′‐methylbutanoyloxy]‐7‐hydroxycarvotacetone, 5‐angeloyloxy‐7‐hydroxy‐3‐tigloyloxycarvotacetone, 3‐O‐methylquercetin, and chrysosplenol D. Their chemical structures were elucidated by extensive 1D and 2D NMR analysis and high‐resolution mass spectroscopy as well as comparisons in literature. 3‐Angeloyloxy‐5‐[2′′S,3′′S‐dihydroxy‐2′′‐methylbutanoyloxy]‐7‐hydroxycarvotacetone is a new compound. Isolated compounds were evaluated for the α‐glucosidase inhibition. Isolated compounds showed moderate activity with IC50 values ranging from 128.9–274.3 μM while others are weak. A molecular docking study was conducted, indicating that isolated compounds are potent α‐glucosidase inhibitory compounds.

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Anti-inflammatory and antiproliferative compounds from Sphaeranthus africanus

Cited by 16 publications

References 34 publications

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Antimicrobial and Efflux Pump Inhibitory Activity of Carvotacetones from Sphaeranthus africanus Against Mycobacteria

A New Carvotacetone Derivative from the Aerial Part of Sphaeranthus africanus

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