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A new megastigmane glycoside, (3S,4R,7E)-megastigma-5,7-diene-9-one-3,4-diol 3-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside (1) and a new cyanogenic glycosyl derivative, (S)-2-(6′-O-R-rosmarinoyl-β-D-glucopyranosyloxy)-phenylacetonitrile (2) were isolated from the methanol extract of the Elsholtzia ciliata together with twelve known compounds, 1-O-β-D-glucopyranosyl-2-hydroxy-4-allylbenzene (3), citrusin C (4), 1,2-di-O-β-D-glucopyranosyl-4-allylbenzene (5), manglieside B (6), 4-allyl-2-hydroxyphenyl 1-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (7), (-)-isolariciresinol 3α-β-D-glucopyranoside (8), 7R,8R-threo-4,7,9-trihydroxy-3,3′-dimethoxy-8-O-4′-neolignan-9′-O-β-D-glucopyranoside (9), 7R,8R-threo-4,7,9,9′-tetrahydroxy-3-methoxy-8-O-4′-neolignan-9′-O-β-D-glucopyranoside (10), cedrusin-4-O-β-D-glucopyranoside (11), icariside E3 (12), everlastoside L (13) and rosmarinic acid (14). Their chemical structures were elucidated on the basic of extensive 1D and 2D-NMR experiments, as well as their mass spectroscopic data. The absolute configurations of the compounds 1 and 2 were successfully indicated by both theoretical and calculated CD spectra. Compounds 3–7, 9 and 10 potential inhibited NO production in LPS-activated RAW264.7 cells with IC50 values of 6.71, 8.97, 12.38, 14.27, 16.13, 13.54, 16.27 µM, respectively, compared to that of the positive control of NG-monomethyl-L-arginine acetate (L-NMMA), IC50 = 32.51 µM. [ABSTRACT FROM AUTHOR]

Objectives: Elsholtzia blanda Benth. is a Vietnamese medicinal plant, used to treat inflammation, cough, and flu. Therefore, this current study focused on the isolation of the active ingredients from this plant and their NO production inhibitory activity. Methods: E. blanda aerial parts were dried, minced, and ultrasonically extracted with methanol and further separated by various chromatographic methods. The chemical structures of isolates were revealed by nuclear magnetic resonance, high resolution lectrospray ionization mass spectrometry, and circular dichroism spectra. The nitric oxide inhibition effects were evaluated in lipopolysaccharide-activated RAW264.7 cells. Results: Ten phenolic components [1 new (1) and 9 known (2-10)] were isolated and their chemical structures determined. Compound 5 (innovanoside, IC50 = 19.23 ± 1.43 µM) and 6 (maltol- O - β -D-glucopyranoside, IC50 = 21.73 ± 1.27 µM) showed the highest activity, and 2 - 4 showed moderate inhibition (IC50 = 47.36 ∼ 57.29 µM). The other compounds were inactive with IC50 values >100 µM. Conclusions: One previously undescribed and 9 known phenolic components isolated from E. blanda have been screened for their nitric oxide inhibitory activity. Compounds 2 - 6 showed moderate to significant inhibition with IC50 values of 19.23∼57.29 µM. [ABSTRACT FROM AUTHOR]

[Display omitted] • Three tetracyclic and pentacyclic terpenoids isolated from Rhabdastrella globostellata. • Their structures were established by HR-ESI-MS, NMR, and ECD spectra. • 6/6/5/5-tetracyclic core is unprecedented feature of isomalabaricane terpenoid. • 6/6/5/5-tetracyclic core might be important for cytotoxic activity. Three unprecedented tetracyclic and pentacyclic isomalabaricanes, named rhabdaglostelones A-C (1 – 3), were isolated from the marine sponge Rhabdastrella globostellata. Their chemical structures were determined by extensive analyses of HR-ESI-MS, 1D- and 2D-NMR spectra. Absolute configurations of them were identified by experimental and TD-DFT theoretical calculated ECD spectra. The tetracyclic and pentacyclic backbone are predicted biological generation from isomalabaricane triterpenoid, a unique compound class in the Rhabdastrella species. Compounds 1 and 2 exhibited cytotoxic activities toward LU1, HepG2, MCF7, and SKMel2 cell lines with their IC 50 values ranging from 15.91 ± 1.21 to 23.21 ± 1.89 µM, while compound 3 was inactivity on these cancerous cell lines. [ABSTRACT FROM AUTHOR]

Phytochemical study on the methanol extract of Aglaia odorata leaves resulted in the isolation of four previously undescribed compounds, including three 2,9-deoxyflavonoids and one flavonol-diamide [3 + 2] adduct, and 13 known compounds. The chemical structures of the four undescribed compounds were elucidated on the basis of their IR, HR-ESI-MS, 1D and 2D NMR, and ECD spectra. The results revealed an unprecedented 2,9-deoxyflavonoid framework, which was confirmed by TD-DFT, ECD, and GIAO 13C-NMR calculations using sorted training set methods. The 17 compounds were examined for their ability to inhibit NO production activity in cultured lipopolysaccharide-activated RAW264.7 cells with aglaodoratas A-C, odorine, and epi-odorine inhibiting NO production, with IC 50 values in the range of 16.2–24.3 μM. The other investigated compounds had either weak or no activity. Four undescribed (three 2,9-deoxyflavonoids and one flavonol-diamide [3 + 2] adduct) and thirteen known compounds were isolated from the leaves of Aglaia odorata Lour. The 2,9-deoxyflavonoid structure is an unprecedented carbon framework. Five isolated compounds inhibited NO production, with IC 50 values in the range 16.2–24.3 μM. [Display omitted] • Four undescribed compounds were isolated from Aglaia odorata. • Structures were established by experimental and theoretical spectroscopic methods. • 2,9-deoxyflavonoid is an unprecedented carbon framework. • Five isolated compounds inhibited NO production better than positive control. [ABSTRACT FROM AUTHOR]