New phenols and one aminobenzoic acid derivative isolated from the roots of Rhus chinensis Mill.

Four new phenols and one new aminobenzoic acid derivative, with five known phenols were isolated from the roots of Rhus chinensis Mill. Their structures were elucidated by UV, IR, HRESIMS, 1D and 2D NMR spectra, as well as optical rotations. Compound 4 significantly inhibited mouse ear inflammation (inhibitory rate of 44.03%), and significantly extended the time of pain response (extension rate of 48.55%), showing significant anti-inflammatory and analgesic effects in vivo.

Triterpenes from antler-shaped fruiting body of Ganoderma lucidum and their hepatoprotective activities.

Seven previously undescribed triterpenes (1-7), as well as one triterpene (8) previously described as a synthetic product, were isolated from the antler-shaped fruiting body of Ganoderma lucidum. Their structures were established based on comprehensive spectroscopy analysis. At a concentration of 10 µM, (24E)-3-oxo-15α-acetoxy-lanosta-7,9(11),24-trien-26-al (3) and (24R,25S)-3-oxo-lanosta-7,9(11)-dien-25-ethoxyl-24,26-diol (5) provided significant protection against acetaminophen-induced necrosis in human HepG2 liver cancer cells, and the cell survival rates were 69.7 and 76.1% respectively, similar to that of the positive control (glutathione, 72.1%). Based on the present results, these compounds could be potential hepatoprotective agents.

Ten cyclopentanoid monoterpenes from the whole plant of Rehmannia piasezkii maxim.

Ten new cyclopentanoid monoterpenes (1-10) were isolated from the whole plant of Rehmannia piasezkii. The structures of these compounds were elucidated based on spectroscopic data analysis. In in-vitro assays, compounds 3, 7, and 9 exhibited weak hepatoprotective activities against APAP-induced HepG2 cell damage. Compound 9 exhibited protective effect on hapassocin carbon tetrachloride model.

Isolation and characterization of dihydrohomoisoflavonoids from Portulaca oleracea L.

Eight pairs of dihydrohomoisoflavonoids (1-8), including four pairs of enantiomeric aglycones [(R,S)-portulacanones B (1) and C (2) and (R,S)-oleracones C (3) and Q (4)] and four pairs of epimeric glycosides [portulacasides A-D and epiportulacasides A-D (5-8)], were obtained from Portulaca oleracea L. Among them, (R,S)-oleracone Q (4) and four pairs of epimeric glycosides (5-8) were reported for the first time. The 50% EtOH fraction from the 70% EtOH extract prevented HepG2 human liver cancer cell damage induced by N-acetyl-p-aminophenol (APAP), and the cell survival rate was 62.3%. Portulacaside B (6a), which was isolated from the 50% EtOH fraction, exhibited hepatoprotective and anti-inflammatory effects. The compound increased the survival rate of APAP-damaged HepG2 human liver cancer cells from 40.0% to 51.2% and reduced nitric oxide production in RAW 264.7 macrophages, resulting in an inhibitory rate of 46.8%.

Seven new pentasaccharides from the roots of Rehmannia glutinosa.

Seven new pentasaccharides (1-7), rehmaglupentasaccharides A-G, were isolated from the air-dried roots of Rehmannia glutinosa. Their structures were established from the spectroscopic data obtained and by chemical evidence. The known verbascose (8) and stachyose (9) were also obtained in the current investigation, and the structure of stachyose was unequivocally defined using X-ray diffraction data. Compounds 1-9 were tested for their cytotoxicity against five human tumor cell lines, influence on dopamine receptor activation, and proliferation effects against Lactobacillus reuteri.

Two new baccharane triterpenes isolated from Rhus chinensis.

Two new baccharane triterpenes, 17,24-epoxy-23-en-baccharan-3-one (1) and 17,24(S)-epoxy-25-en-21-hydroxy-baccharan-3-one (2) were isolated from Rhus chinensis Mill. The structures were established on the basis of UV, IR, HR-ESI-MS, 1D and 2D NMR spectroscopy and X-ray diffraction analysis.

Four new iridoid glycosides from the roots of Rehmannia glutinosa.

Four new iridoid glycosides (1-4), rehmaglutosides L-O, were isolated from the air-dried roots of Rehmannia glutinosa. Their structures were established from the spectroscopic data obtained and by chemical evidence. The known mellittoside (5) and ajugol (6) were also obtained in the current investigation, and the structure of mellittoside was unequivocally defined using X-ray diffraction data. Compounds 1-6 were tested for their cytotoxicity against five human tumor cell lines and proliferation effects on Lactobacillus Reuteri.

Four sesquiterpenes isolated from Taraxacum mongolicum.

One new sesquiterpene, (6S,7R,11S)-13-carboxy-1(10)-en-dihydroartemisinic acid (1), together with three known sesquiterpenes, ainsliaea acid B (2), mongolicumin B (3), and 11ß,13-dihydroxydeacetylmatricarin (4) were isolated from Taraxacum mongolicum Hand.-Mazz. The structures were established on the basis of UV, IR, HR-ESI-MS, 1D and 2D NMR spectroscopy, ECD spectroscopy, and X-ray diffraction analysis. Compound 1 was found to have potential anti-inflammatory activity and could reduce LPS-induced NO levels in murine macrophage, with inhibitory rate of 37%.

Derivatives of sesquiterpenes, 2-furaldehyde, phenols, and alkaloids isolated from Taraxacum mongolicum.

Four new compounds (1-4), together with 23 known compounds (5-27), were isolated from the whole plant of Taraxacum mongolicum. Among them, one racemic mixture (4) was separated with a chiral HPLC column. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of compounds 1, 3, and 4 were determined via comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 3 showed an inhibitory effect against aldose reductase with a 59.1% inhibition. Two known compounds (13 and 27) showed α-glucosidase inhibition of 51.5% and 56.0%, respectively.

Nine geranylgeranylated derivatives isolated from the roots of Rhus chinensis Mill.

Nine undescribed geranylgeranylated derivatives (chinensens A-G), including malic acid derivative (A) and phenolic derivatives (B-E), as well as two pairs of enantiomers, [(R), (S)]-chinensens F and [(R), (S)]-chinensens G, were isolated from the roots of Rhus chinensis Mill. Their structures were elucidated by UV, IR, HRESIMS, 1D and 2D NMR spectra, as well as optical rotations. The 95% EtOH extract (95% EXT, 500 mg/kg, p. o.) of the roots of Rhus chinensis and the 95% EtOH fraction (95% FRA, 500 mg/kg, p. o.) from the microporous resin column significantly alleviated indomethacin-induced or water immersion-restraint stress-induced damage in rat gastric mucosa with inhibitory rates from 53% to 89%. The racemic mixture (chinensen G) and its enantiomers [(R), (S)]-chinensens G showed weak activities against H+,K+-ATPase (20%-24%) at a concentration of 0.1 mM, respectively.

MicroRNAs in the regulation of Th17/Treg homeostasis and their potential role in uveitis.

Th17 and regulatory T cells (Tregs) play crucial roles in the pathogenesis of autoimmune diseases. Th17/Treg homeostasis is critically involved in maintaining the immune balance. Disturbed Th17/Treg homeostasis contributes to the progression of autoimmune diseases. MicroRNAs (miRNAs) have emerged as a new vital factor in the regulation of disturbed Th17/Treg homeostasis. To better understand the epigenetic mechanisms of miRNAs in regulating Treg/Th17 homeostasis, we included and evaluated 97 articles about autoimmune diseases and found that miRNAs were involved in the regulation of Treg/Th17 homeostasis from several aspects positively or negatively, including Treg differentiation and development, Treg induction, Treg stability, Th17 differentiation, and Treg function. Uveitis is one of the ocular autoimmune diseases, which is also characterized with Th17/Treg imbalance. However, our understanding of the miRNAs in the pathogenesis of uveitis is elusive and not well-studied. In this review, we further summarized miRNAs found to be involved in autoimmune uveitis and their potential role in the regulation of Th17/Treg homeostasis.

Three new pyridine alkaloids and one new iridoid analogue from the leaves of Rehmannia glutinosa.

As part of an ongoing project on Rehmannia species, three new pyridine alkaloides (glutinosines A - C), and one new iridoid analogue (rehmaglutin E), were isolated from the leaves of Rehmannia glutinosa. The structures of the new compounds were established by extensive spectroscopic analysis and electronic circular dichroism calculations.

Cyclopentanoid monoterpenes from the whole plant of Rehmannia piasezkii maxim.

Twelve undescribed cyclopentanoid monoterpenes, Jiopiasins A-K and 6-epi-rehmaglutin A, and 19 known compounds were isolated from the whole plant of Rehmannia piasezkii Maxim. The structures of these compounds, especially their absolute stereochemistry, were established by extensive spectroscopic analysis, various quantum chemical calculations, and/or X-ray diffraction analyses. Furthermore, in vitro assays, some compounds exhibited moderate hepatoprotective activities against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage.

Four ionones and ionone glycosides from the whole plant of Rehmannia piasezkii.

Four new ionones and ionone glycosides (1-4) were isolated from the whole plant of Rehmannia piasezkii Maxim. Their planar structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. Compounds 1-4 were tested for their cytotoxicity against five human tumor cell lines and ability to inhibit LPS-activated NO production in the BV2 cell line.

Benzobicyclic ketones, cycloheptenone oxide derivatives, guaiane-type sesquiterpenes, and alkaloids isolated from Taraxacum mongolicum Hand.-Mazz.

Ten previously undescribed compounds, including two benzobicyclic ketones, one cycloheptenone oxide derivative, three guaiane-type sesquiterpenes, and four alkaloids, along with one known cycloheptenone oxide derivative, were isolated from the whole plants of Taraxacum mongolicum Hand.-Mazz. Their structures were elucidated by UV, IR, HR-ESI-MS, 1D and 2D NMR spectroscopy, ECD spectroscopy, or X-ray diffraction analysis. Notably, benzobicyclic ketones have never been isolated from nature before. The 70% EtOH-H2O extract of T. mongolicum displayed a significant inhibitory activity (33%) against croton oil-induced mouse ear edema. The two cycloheptenone oxide derivatives exhibited anti-inflammatory activities at 10 µM and significantly reduced the nitric oxide (NO) and interleukin-6 (IL-6) levels in RAW 264.7 macrophages induced by lipopolysaccharide (LPS), with inhibitory rates of 26.4-64.4%.

Two new sesquiterpene dimers isolated from the roots of Saussurea lappa (Yunmuxiang).

Two new sesquiterpene dimers, lappadimers A and B, were isolated from the roots of Saussurea lappa (Yunmuxiang). Their structures were established on the basis of spectroscopic methods. They were found to have potential anti-inflammatory activity at 10 µM and could reduce LPS-induced NO levels in murine macrophage, with inhibitory rates of 67% and 47%, respectively.

New quinones, a sesquiterpene and phenol compounds with cytotoxic activity from the aerial parts of Morinda umbellata L.

Eight previously undescribed compounds, two quinones (1-2), one sesquiterpene (3), and five phenol compounds (4-8), including three enantiomers (6a, 7a, and 8a), along with three corresponding known enantiomers (6b-8b) were isolated from the aerial parts of Morinda umbellata L. Their structures were elucidated by 1D and 2D NMR spectroscopy, X-ray diffraction, and experimental and calculated ECD spectra, respectively. Compound 5 was found to have weak cytotoxity, which inhibited the growth of seven human cancer cell lines (A2780, HeLa, MCF-7, BGC-823, H7420, Ketr3 and SW 1990) with IC50 values from 13.3 to 15.1 µM.

Water-soluble alkaloids isolated from Portulaca oleracea L.

Fifteen new water-soluble alkaloids were obtained from the fresh herbs of Portulaca oleracea L. The structures of 15 alkaloids 1-15 were established according to spectroscopic data, and the stereoconfigurations were determined based on experimental and calculated electronic circular dichroism (ECD) data and single crystal X-ray diffraction. Alkaloids 1-15 were found to display good anti-inflammatory activity at 10 µM and could significantly reduce the interleukin-6 (IL-6) and nitric oxide (NO) levels induced by lipopolysaccharide (LPS) in RAW 264.7 macrophages.

The racemic trimeric quinone and polycyclic quinones isolated from the aerial parts of Morinda umbellata L.

Four undescribed racemic quinones, umbellatas Q-T, were isolated from the aerial parts of Morinda umbellata L. All enantiomers were separated on a chiral HPLC column, and their structures were elucidated by UV spectroscopy, IR spectroscopy, HR-ESI-MS, 1D and 2D NMR spectroscopy, DP4+ NMR calculations, ECD spectroscopy, and X-ray diffraction. Three of the racemes are polycyclic anthraquinones, and one is a rare racemic trimer of naphthoquinone-bisnaphthohydroquinones. (+)-Umbellata S exhibited potent cytotoxicity (IC50: 6.2-9.3 µM) against the A2780, HeLa, H7420, Ketr3 and SW 1990 human cancer cell lines.

[Advances in studies on structure and pharmacological activities of natural tirucallane-type triterpenoids].

The tirucallane-type triterpenoids, composed of six isoprene units, belong to a group of tetracyclic triterpenoids. Although the naturally-derived tirucallane-type triterpenoids were found in a small amount, the kind of compounds showed various structures, which consist of apo-type, linear said-chain-type and cyclolike said-chain-type and broad bioactivities, such as cytotoxicity, anti-inflammation, antioxidation and anti-plasmin, etc. This paper summarized origins, structures and bioactivities of tirucallane-type triterpenoids in recent ten years. The future research and exploration of tirucallane-type triterpenoids were discussed and prospected.