Chemical investigation of the Kappaphycus alvarezii-derived endophytic fungus Aspergillus micronesiensis lead to the isolation of three novel dibenzospiroketals, aspermicrones A-C (1-3). Their ...chemical structures were determined by extensive analysis of HR-ESI-MS and NMR spectral data. The absolute configurations of them were determined by experimental and TD-DFT theoretical calculated circular dichroism spectra. Compound 2 exhibited selective cytotoxic effect toward HepG2 cell line (IC
= 9.9 µM). Additionally, both of compounds 2 and 3 displayed anti-microbial activity against Staphylococcus aureus (MIC = 123.2 µM for each compound). Compound 1 was inactivity in both cytotoxic and anti-microbial assays.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
Five new dibenzocyclooctadiene lignans, named kadsuindutains A–E (1–5), and three known ones schizanrin F (6), schizanrin O (7), and schisantherin J (8) were isolated from the stems of Kadsura induta .... Their structures were determined by analyses of HR-ESI-MS, NMR, and ECD spectra. Compounds 1–5 contain a 2′,4′-dioxygenated-2′,3′-dimethylbutyryl moiety which is rarely reported for dibenzocyclooctadiene lignans. Molecular docking predicted that compounds 1–8 displayed good binding affinity to the active site of iNOS and TNF-α proteins but unstable binding to the active site of COX-2 protein. Additionally, in vitro experiments showed that compounds 1–8 inhibited NO production in LPS-activated RAW264.7 cells with IC 50 values from 10.7 μM to 34.0 μM, compared to the positive control L-NMMA (IC 50 = 31.2 μM).
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IJS, KILJ, NUK, UL, UM, UPUK
Five new secondary metabolites, modiolides D-G (1-4) and 1-(2,5-dihydroxyphenyl)-3-methoxy-butan-1-one (8), one new natural product, 1-(2,5-dihydroxyphenyl)-3-hydroxybutan-1-one (7), along with three ...known compounds, modiolides A (5) and B (6), and 1-(2,5-dihydroxyphenyl)-2-buten-1-one (9) were isolated from a fermentation culture of the marine endophytic fungus Paraconiothyrium sp. VK-13. Their chemical structures were elucidated by the NMR and MS spectroscopic analysis as well as the modified Mosher's method. Compounds 7 and 9 inhibited the overproduction of proinflammatory mediators NO and PGE
in LPS-stimulated RAW264.7 cells, with IC
values ranging from 3.9 to 12.5 µM. The inhibitory effects of 7 and 9 on the release of NO and PGE
were correlated with their significant suppression of iNOS and COX-2 protein expression, respectively. Furthermore, both compounds 7 and 9 inhibited the mRNA expression of proinflammatory cytokines, including TNF-α, IL-1β, IL-6, and IL-12, with IC
values in a range of 2.4-12.5 µM.
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EMUNI, FIS, FZAB, GEOZS, GIS, IJS, IMTLJ, KILJ, KISLJ, MFDPS, NLZOH, NUK, OILJ, PNG, SAZU, SBCE, SBJE, SBMB, SBNM, UKNU, UL, UM, UPUK, VKSCE, ZAGLJ
A new sesquiterpene (1) and a new norsesquiterpene (2) belonging guaiane-type skeletone together with six known compounds (3-8) were isolated from the rhizomes of Alisma plantago-aquatica. Their ...structures were determined by HR-ESI-MS, 1D and 2D NMR spectroscopic methods. Absolute configurations of new compounds were established by experimental and TD-DFT computational ECD spectra. Compounds 1-8 exhibited xanthine oxidase inhibitory activity with their IC50 values in range of 9.4-66.7 µM. The sesquiterpenoids 1-5 displayed the inhibitory activity and hence they could be potential xanthine oxidase inhibitors from A. plantago-aquatica.
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BFBNIB, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
A chemical study of the methanol extract of the aerial parts of Achyranthes aspera led to the isolation of four new flavonoid C‐glycosides (1–4) along with eight known analogs (5–12). Their ...structures were elucidated by a combination of spectroscopic data analysis, HR‐ESI‐MS, 1D and 2D NMR spectra. All the isolates were evaluated their NO production inhibitory activity in LPS‐activated RAW264.7 cells. Compounds 2, 4, and 8–11 showed significant inhibition with IC50 values ranging from 25.06 to 45.25 μM, compared to that of the positive control compound, L‐NMMA, IC50 value of 32.24 μM, whereas the remaining compounds were weak inhibitory activity with IC50 values over 100 μM. This is the first report of 7 from Amaranthaceae family, and 11 from the genus Achyranthes.
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BFBNIB, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
Three new isomalabaricanes (1-3), a new α-pyrone derivative (4), together with four known isomalabaricane analogs rhabdastrellin G (5), isogeoditin A (6), stelliferin A (7), and (13
)-isogeoditin A ...(8) were isolated from the marine sponge
. Their chemical structures were determined by HR-ESI-MS, 1D and 2D-NMR spectroscopic data analysis. The absolute configurations were identified by Mo
(OAc)
induced ECD spectra and TD-DFT theoretical calculated ECD spectra. Compound 6 exhibited weak cytotoxic effects against HepG2 and SKMel2 cell lines with the IC
values of 7.53 ± 0.70 and 9.93 ± 0.95 μM, respectively.
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Phytochemical investigation of methanol extract from Elaeocarpus hainanensis Oliv. leaves and twigs led to the isolation and structural determination of three 16,23-epoxycucurbitacin-type ...triterpenoids, including a new hydroperoxide, 16α,23α-epoxy-3β,20β-dihydroxy-24α-hydroperoxy-10αH,23βH-cucurbit-5,25-dien-11-one (elahainencin A, 1), and two known analogs (2 and 3). Their chemical structures were determined by the spectroscopic analyses, including 1 D-, 2 D NMR and HR ESI MS spectra. Compound 1 represents a cucurbitacin derivative incorporating a hydroperoxide. In addition, these isolated compounds have been found to be noncytotoxic when tested in vitro against five human cancer cell lines (A549, T24, 8505, Huh-7 and SNU-1) by using the SRB method.
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One new octulosonic acid derivative, chrysannol A (1), along with 17 known compounds (2-18), were isolated from Chrysanthemum indicum flowers. Their structures were determined from 1D NMR, 2D NMR, ...HR-ESI-MS spectral data, and comparisons with previous reports. The effects of these compounds on lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor alpha (TNF-α) production by RAW 264.7 cells were investigated. Compound 8 showed the highest inhibition of NO production of 46.09% at a concentration of 10.0μM. Compounds 7, 10, 11, and 16 inhibited TNF-α secretion at all concentration tested (0.4, 2.0, and 10.0μM), with inhibition values ranging from 22.27% to 33.13%. In addition, compound 8 and 9 decrease COX-2 and iNOS protein on Western blot analysis in dose dependent manner.
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GEOZS, IJS, IMTLJ, KILJ, KISLJ, NUK, OILJ, PNG, SAZU, SBCE, SBJE, UL, UM, UPCLJ, UPUK
Phytochemical investigation on the aerial parts of Elsholtzia blanda Benth. afforded four new oleuropeic acid derivatives (1–4), named as elsholblanosides A−D, respectively, together with 11 known ...compounds (5–15). Their structures were determined based on extensive analyses of HR‐ESI‐MS, 1D and 2D NMR, and ECD spectra. Compounds 1–4 and 14 showed moderate NO production inhibition in LPS‐activated RAW264.7 cells with their IC50 values ranging from 23.2 to 86.33 μM, compared to that of the positive control compound, dexamethasone, IC50 value of 16.9 μM.
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BFBNIB, FZAB, GIS, IJS, KILJ, NLZOH, NUK, OILJ, SAZU, SBCE, SBMB, UL, UM, UPUK
Two new phenolic glycosides, 4-(3-hydroxypropyl)-2,6-dimethoxyphenol β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1), trans-cinnamyl alcohol 9-O-(6′-O-β-D-apiofuranosyl)-β-D-glucopyranoside (2), ...together with nine known phenolic glycosides (3-11) were isolated from the roots of Pandanus tonkinensis. Their structures were determined by extensive analysis of HRESIMS and NMR spectral data, as well as by comparison of their spectral data (including CD spectra) with those reported in the literature. Compounds 1-4 and 6-11 inhibited NO production in LPS-activated RAW264.7 cells with IC
50
values in the range from 0.80 ± 0.06 µM to 43.38 ± 3.92 µM, whereas compound 5 was inactive. The NO production inhibitory activities of compounds 1, 4, 8, and 10 with IC
50
values of 10.16 ± 1.05, 0.80 ± 0.06, 1.10 ± 0.13, and 2.79 ± 0.21 µM, respectively, are as potent as that of the positive control of N
G
-monomethyl-L-arginine acetate (L-NMMA) with an IC
50
value of 9.80 ± 0.78 µM.
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