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Aphanapolystachones A–C (1 – 3), three undescribed sesquiterpene-diterpene heterodimers, were obtained from the fruits of Aphanamixis polystachya. Their structures and absolute configurations were identified by extensive analysis of HR-ESI-MS, NMR, experimental and TD-DFT calculated ECD spectra. The biosynthetic pathway of them was also proposed, which is produced by key intermolecular Diels-Alder [4 + 2]-cycloaddition reaction between a guaiane sesquiterpene and an acyclic diterpene. Compounds 1 – 3 inhibited NO production in LPS activated RAW 264.7 cells with the IC 50 values of 1.7 ± 0.2, 3.0 ± 0.3, 5.3 ± 0.3 μM, respectively, lower than that of the positive control L-NMMA (31.5 ± 2.6 μM). In addition, compounds 1 – 3 significantly reduced IL-6 secretion at diluted concentration of 0.4 μM. Three undescribed sesquiterpene-diterpene heterodimers, aphanapolystachones A–C (1 – 3), were obtained from the fruits of Aphanamixis polystachya. These compounds were proposed to biosynthesize by key intermolecular Diels-Alder [4 + 2]-cycloaddition reaction between a guaiane sesquiterpene and an acyclic diterpene. Compounds 1 – 3 inhibited NO production and IL-6 secretion in LPS activated RAW264.7 cells. [Display omitted] • Three undescribed compounds were isolated from Aphanamixis polystachya. • Their structures were determined by HRESIMS, NMR, and ECD spectra. • Sesquiterpene-diterpene heterodimer is an undescribed backbone in vascular plants. • Aphanapolystachones A–C inhibited NO production and IL-6 secretion. [ABSTRACT FROM AUTHOR]

Seven undescribed neovibsane-type diterpenoids (1 – 7) were isolated from the leaves of Viburnum odoratissimum. Their planar structures and relative configurations were elucidated based on a combination of 1D and 2D NMR analysis. The absolute configurations were confirmed by Rh 2 (OCOCF 3) 4 -induced ECD analysis and comparison of experimental and TDDFT-calculated ECD spectrum. Based on the empirical results of the ECD of in situ formed Rh-complexes, rapid determination of the absolute configuration of C-14 within vibsane-type diterpenoids was proposed. In addition, 3 exhibited a high neuroblastoma cell protective effect of 81.8 % at 50 μM (the control group showed a neuroblastoma cell protective effect of 56.2 % at 50 μM). Seven undescribed neovibsane-type diterpenoids were isolated from the leaves of Viburnum odoratissimum , and their neuroblastoma cell protective effects were tested. [Display omitted] • Seven undescribed neovibsane diterpenoid were isolated from Viburnum odoratissimum. • The Rh 2 (OCOCF 3) 4 -induced ECD of the vibsane-type diterpenoids was described. • (8 E)-7 R ,14 R -Neovibsanin T showed a significant neuroblastoma cell protective effect. [ABSTRACT FROM AUTHOR]

Investigation on the chemical constituents of Artemisia scoparia resulted in the isolation of sixteen compounds, including undescribed six pairs of diprenylated phenolic enantiomers (±)-scopacoumaricin A-F, and two pairs of cis-trans isomers cis / trans -scopacoumaricin G and cis/trans -artepillin A. Trans -artepillin A was obtained from this plant for the first time. The structures of the isolates were proposed by analysis of their 1D, 2D-NMR and HRESIMS spectroscopic data. Their absolute configurations were determined by comparison of their experimental and calculated electronic circular dichroism spectra. Evaluations of the anti-inflammatory activity revealed that (−)-scopacoumaricin D, (+)-scopacoumaricin F and cis -scopacoumaricin G showed moderate anti-inflammatory activity on lipopolysaccharide-induced nitric oxide production in RAW264.7 cell. Sixteen compounds, including six pairs of diprenylated phenolic enantiomers and two pairs of cis - trans isomers, were isolated and identified from Artemisia scoparia. 1a/1b-6a/6b , 7 – 9 were previously undescribed, and 10 was obtained from A. scoparia for the first time. Anti-inflammatory activity and cytotoxicity of the isolates were studied. [Display omitted] • Fifteen undescribed diprenylated phenolic isomers were identified from A. Scoparia. • Structures were determined by extensive spectroscopic analyses. • Anti-Inflammatory and cytotoxicity of the isolates were tested. [ABSTRACT FROM AUTHOR]

Ten lignans, including six previously undescribed phenolic ester glycosyl lignans (1 – 6), were isolated from a well-known traditional Chinese medicine, Qin-Jiao, which is the dry root of Gentiana macrophylla Pall. (Gentianaceae). Their structures were determined by spectroscopic and chemical methods, especially 2D NMR techniques. Quantum chemical calculations of theoretical ECD spectra allowed the determination of their absolute configurations. Refer to its traditional applications for the treatment of rheumatic arthralgia and hepatopathy, these compounds were evaluated on a TNF-α induced MH7A human synoviocyte inflammation model and a D-GalN induced AML12 hepatocyte injury model. Compounds 1 , 2 , 5 , and 6 significantly reduced the release of proinflammatory cytokine IL-1β in MH7A cells at 15 μM and they also could strongly protect AML12 cells against D-GalN injury at 30 μM. Flow cytometry and Western blot analysis showed that compound 5 ameliorated D-GalN induced AML12 cell apoptosis by upregulating the expression of anti-apoptotic Bcl-2 protein and down-regulating the expression of pro-apoptotic Bax protein. Six undescribed phenolic ester glycosyl lignans were discovered from the well-known traditional Chinese medicine Gentiana macrophylla. Compound 5 ameliorates D-GalN induced AML12 cell apoptosis by up-regulating Bcl-2 and down-regulating Bax proteins. [Display omitted] • Six undescribed glycosyl lignans were discovered from Gentiana macrophylla. • The absolute configurations were determined by quantum chemical calculations. • Some lignans exhibited promising anti-arthritis and hepatoprotection activities. • Compound 5 ameliorates AML12 cell apoptosis by regulating Bcl-2 and Bax protein expression. [ABSTRACT FROM AUTHOR]