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Arnebinones B, E, and D (1-3) have been found to be sensitive to light, generating complex and diverse proton transfer products when triggered by light. A unique two-step irreversible intramolecular proton transfer of 1 produced five scalemic mixtures, of which four possessed intriguing dual planar chirality. The unprecedented orientation epimerization equilibrium of the intra-annular double bond was first observed and researched in the homologous meroterpenoids by HPLC monitoring and DFT calculations. A "p-benzoquinone-CH2/CH-π" moiety in the structure was the common key feature for the occurrence of this type of photoenolization reaction. The product transformation processes and universality of this photoinduced irreversible proton transfer reaction were analyzed together with the cytotoxic activities of arnebinones B, D, and E, and their photoreaction products.

Eight new arnebinol B-based meroterpenoids ((-)-1, 2, 3, (-)-5, and 7-10) with a constrained 6/10/5 tricyclic backbone were isolated from the roots of Arnebia euchroma. The planar and steric structures of these new compounds were unambiguously elucidated by extensive spectroscopic analyses, X-ray diffraction crystallography, and ECD calculations. The predominant relative orientation between H-7 and the Z double bond with a methyl substituent in the rigid 10-membered carbocycle, along with the planar chirality of the Z double bond was analyzed and discussed for the first time. The illustration of the planar chirality derived from the Z double bond should be paid great importance during the structure elucidation on these homologous meroterpenoids. All the isolated meroterpenoids were screened for their cytotoxicities against the HCT-8, PANC-1, HGC-27, HepG2, and PC9 cell lines, and compounds (+)-5 and (-)-5 exhibited the most potent cytotoxicity.

A series of 4-thiosubstituted flavan derivatives (1-44) were designed and synthesized. The target compounds were assayed for inhibitory activity against α-glucosidase in vitro, and the results indicated that all compounds displayed significant effects in the range of IC

One pair of new amides enantiomers (1a and 1b) and two known amides were isolated from the rhizomes of Polygonum cuspidatum. Their structures were established using UV, IR, HRESIMS, and NMR data. Notably, compound 1 possesses unique C-C connection between feruloyltyramine and resveratrol. Their absolute configurations were determined by the ECD method. All compounds were evaluated for their α-glucosidase inhibitory activity and compounds 2 and 3 showed significant inhibitory activity with IC50 values of 2.82 and 13.06 μmol/L, respectively (positive control acarbose, IC50 385 μmol/L).

Three new monocyclic monoterpenoid containing β-D-apiofuranosyl-(1→2)-O-β-D-glucopyranosyl moieties, together with three other known monocyclic monoterpenoid O-glycosides, were obtained from the roots of Glycyrrhiza uralensis for the first time. Their structures were determined by UV, IR, HRESIMS, and 1D and 2D NMR data.

Phytochemical investigation of the rhizome of Ligusticum chuanxiong Hort led to the isolation and identification of three new compounds, chuanxiongoside A, (2E,4E)-8-(6-O-inositolyl)-8-oxo-2,7-dimethyl-octadienoic acid (2), chuanxiongoside C (3). The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. All the isolated compounds (1-3) were investigated for their inhibitory effects on nitric oxide (NO) production in LPS-induced RAW 264.7 cells. All compounds showed excellent inhibition of NO production stronger than curcumin. [Formula: see text].

Seven new phenolic acids, 7, 8-epiblechnic acid (1), 8-epiblechnic acid 9-ehthyl-9'-methyl ester (2), 9'-ehyl-isolithospermate (3), 9''-methyl-isolithospermate (4), 9'-ethyl-9''-methyl-isolithospermate (5), 9', 9''-dimethyl-isolithospermate (6), sebesteniod E (7), were isolated from the roots of Salvia miltiorrhiza. Their structures were elucidated by detailed spectroscopic means including UV, IR, HRESIMS, and NMR data spectra. The bioactive assays of compounds 1-7 against neuroprotection activities were determined. The results suggested that compound 4 exhibited a moderate glutamate-induced neuroprotective activity and the cell survival rate was 24.0% (10

To further reveal the active ingredients of Danshen, we systematically studied its chemical components and obtained two new lithospermic acid derivatives (compounds 1 and 2) together with five known phenylpropionic acids (compounds 3-7) from the dried rhizomes of Salvia miltiorrhiza. The structures of the two new compounds were determined by multiple spectral analyses (UV, IR, HR-ESI-MS, NMR, and ECD). In addition, the absolute configurations were established by chiral analysis and calculated and experimental circular dichroism spectra. Biological research indicated that compound 1 could significantly inhibit the proliferation of isoproterenol (ISO)-treated cardiac fibroblasts (AC16 cells), and MMP9 was found to be the most likely target of compound 1. The protein expression and mRNA levels of MMP9 were increased in ISO-induced AC16 cells, which could be reversed by treatment with compound 1. Furthermore, this treatment could alleviate the migration and activation of ISO-induced cardiac fibroblasts.

Two new lignans, wikstronoside B (1) and forsysesquinorlignan (2), were isolated from the fruits of Forsythia suspensa, along with two known sesquineolignans, hedyotol A and hedyotol C (3 and 4). The structures of new compounds were established via extensive spectroscopy techniques, including UV, IR, HRESIMS, NMR, and ECD. Compounds 3 and 4 were isolated from this plant for the first time. Their anti-inflammatory effects were evaluated via a detection model with LPS-induced murine macrophage RAW264.7 cells, and compound 3 showed a moderate activity.

Eight new triterpenoid saponins (1-8), were isolated from the roots of Glycyrrhiza uralensis Fisch., together with 10 known triterpenoid saponins (9-18). Their structures were determined by analysis of their spectroscopic data and comparison with the reference. All of the compounds were evaluated for their antioxidant effects in the in vitro assay. Compounds 2 and 8 showed significant antioxidant activities against Fe2+/cysteine-induced liver microsomal lipid peroxidation at 0.1 μM.

Radix Clematidis (RC) is the roots and rhizomes of Clematis chinensis Osbeck, which has potent effects for expelling wind and dispelling dampness. Processing RC with yellow wine is a traditional processing method. This study aimed to investigate thermal and yellow wine processing influences on potential effective components of RC and its anti-rheumatoid arthritis enhancement mechanisms. Different thermal and wine processing were adopted to get different RC samples. Scanning electron microscope and mercury intrusion porosimetry were used to measure fractal parameters of pore structure. Based on ultra performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-QTOF/MS), main constituents were identified and quantified. Besides, the correlation between fractal parameters and main constituents was investigated. The anti-rheumatoid arthritis effect was researched in adjuvant-induced arthritis (AIA) rats. The levels of inflammatory cytokine were determined with ELISA kits. Non-targeted serum metabolomics was performed with UPLC-QTOF/MS. 35 compounds were identified in RC, mainly triterpenoid saponins, also including organic acids and lignanoids. The extraction yield of four active triterpenoid saponins significantly increased because looser tissue and wider pore size distribution. Fractal dimension and total surface area significantly increased while total porosity and total volume decreased. In AIA rats, thermal and wine processed RC could markedly inhibit inflammatory cytokines IL-6, IL-1β, TNF-α, and VEGF. Besides, tryptophan and lipid metabolism disorders were ameliorated. Thermal and yellow wine treatments engendered complex pore structure to increase the contents of four active triterpenoid saponins of RC, leading to greater anti-rheumatoid arthritis efficacy.

Neuroinflammation is emerging as a crucial reason of major neurodegenerative diseases in recent years. Increasingly evidences have supported that bioactive natural products from traditional Chinese medicines have efficiency for neuroinflammation. Forsythia suspensa, a typical medicinal herb, showed potential neuroprotective and anti-inflammatory properties in previous pharmacological studies. In our research to obtain neuroprotective and anti-inflammatory natural products, three unprecedented C6–C7′/C6–C16′ linked phenylethanoid glycoside dimers (1–3), three new phenylethanoid glycosides (4–6), and six known compounds (7–12) were isolated from the fruits of Forsythia suspensa. Their structures were determined by comprehensive spectroscopic data and comparison to the literature data. All isolated compounds were evaluated their neuroprotective and anti-inflammatory activities. Compounds 1 and 10 exhibited significant neuroprotective activities with the cell viability values of 75.24 ± 8.05% and 93.65 ± 10.17%, respectively, for the serum-deprivation and rotenone induced pheochromocytoma (PC12) cell injury. Meanwhile, compound 1 exhibited excellent anti-inflammatory activity against tumor necrosis factor (TNF)-α expression in LPS induced RAW264.7 cells with the IC50 value of 1.30 μM. This study revealed that the bioactive phenylethanoid glycosides may attenuate neuroinflammation through their neuroprotective and anti-inflammatory activities.

A phytochemistry of the whole plant of Agrimonia pilosa led to the discovery of two new nortriterpenoids, agrimonorterpenes A and B (1 and 2), together with one known triterpenoid fupenzic acid (3) and seven known sesquiterpenoids (4-10). The new structures were determined as 19α-hydroxy-2-oxo-nor-A (3)-urs-11,12-dien-28-oic acid (1) and 2, 19β-dihydroxy-3-oxo-23-noroleana-1, 4, 12-trien-28-oic acid (2) by the spectroscopic data of UV, IR, HR-ESI-MS, and NMR. Notably, the structure of 1 possessed a rare five-membered A- ring. And this is the first time to discover the sesquiterpenoids (4-10) from A. pilosa. Compound 3 displayed the selective cytotoxicity against HCT116, BGC823, and HepG2 cell lines with the IC

Four new compounds including two new phenylpropanoid esters of sucrose, polygonusucroside A (1) and B (2); two new anthraquinones, 8-O-β- d -(6′-galloyl)-glucopyranoside (3) and polyanthraquinoside A (4), together with six known compounds were isolated from Polygonum cuspidatum. Their structures were established using UV, IR, HRESIMS, and NMR data. All compounds were evaluated for their α-glucosidase inhibitory activities and neuroprotective effects. Compounds 5, 7 and 9 showed significant α-glucosidase inhibitory activities with IC50 values of 27.30, 5.51, and 1.09 μmol/L, respectively (acarbose as positive control, IC50 = 6.17 μmol/L). In addition, the assessment of neuroprotective effect showed that compound 3 exhibited remarkable effect against PC12 cells injured by serum-deprivation and compounds 2, 7, and 9 exhibited moderate effects against PC12 cells injured by rotenone.

Ligusticum chuanxiong Hort is a famous health promoting plant cultivated in China, and widely consumed due to its various curative effects. To study the potential bioactive constituents from the rhizome of L. chuanxiong, a chemical investigation was thus performed. In present study, we report the isolation and identification of ten new compounds, including two coumarins (1-2), four lignans (3-6), and four phenols (7-10), along with five known compounds (11-15) from the rhizome of L. chuanxiong. The structures of these compounds were unambiguously established by HR-ESI-MS, UV, IR, CD, NMR spectral data and comparison to reported data. Meanwhile, the anti-inflammation and hepatoprotective activities of all these compounds were evaluated. The results show that compounds 5, 6 and 7 showed excellent inhibition of NO production in LPS-induced RAW 264.7 cells stronger than curcumin, and compounds 5, 7 and 9 exhibited greater hepatoprotective effect than that of bicyclol.

Three new compounds named tanshinoic acid A (1), tanshinoic acid B (2), and tanshinoic acid C (3) were isolated from the rhizomes of Salvia miltiorrhiza, together with two known compounds methyl salvianolate A (4) and methyl salvianolate C (5). Their structures were determined on the basis of spectroscopic data (UV, IR, HRESIMS, 1 D and 2 D NMR). The in vitro assay indicated that 4 and 5 could improve the survived rate of cells on oxygen glucose deprivation (OGD) induced neurons damage model and glutamate-induced neurons damage model at a concentration of 10 μM.

Two new benzoic acid derivatives, sophophenoside A (1) and sophophenoside B (2), were isolated from Sophora flavescens. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. Compounds 1 and 2 were assayed for their hepatoprotective activity on the cytotoxic effect of D-galactosamine on HL-7702 cells, and compound 1 exhibited a moderate hepatoprotective activity at a concentration of 10 μM.

Two new quinochalcone glycosides, hydroxysafflor yellow A-4'-O-β-D-glucopyranoside (1) and 3'-hydroxyhydroxysafflor yellow A (2), were isolated from the safflower yellow pigments of Carthamus tinctorius. The structures of new compounds were elucidated by a detailed spectroscopic analysis (UV, IR, HR-ESI-MS, 1D and 2D NMR, ECD). The in vitro assay indicated that compound 1 could improve the survived rate of primary mouse cortical neurons on glutamate-induced neurons damage model at a concentration of 10 μM.

In our ongoing investigation of the bioactive compounds from the extract of the roots of Sophora flavescens, two novel prenylated flavanones, named sophoflavanones A (1) and B (2), each with an unusual pyran ring were isolated. Their structures, as well as their absolute configurations, were elucidated based on spectroscopic data including a comparison of their experimental and calculated electronic circular dichroism (ECD) spectra. Additionally, compounds 1 and 2 showed moderate antioxidant activities against Fe2+/cysteine-induced toxicity at a concentration of 0.1 µM (inhibition values of 71.65% and 72.49%, respectively, using vitamin C as a positive control (87.83%)).

An efficient 1H NMR spectroscopic approach for determining the relative configurations of lignans with a 7,9′:7′,9-diepoxy moiety has been established. Using the chemical shift differences of H2-9 and H2-9′ (ΔδH-9 and ΔδH-9′), the configurations of 8-H and 8-OH furofuran lignans can be rapidly and conveniently determined. The rule is applicable for data acquired in DMSO-d6, methanol-d4, or CDCl3. Notably, the rule should be applied carefully when the C-2 or C-6 substituent of the aromatic rings may alter the dominant conformers of the furofuran moiety.

Four new ferulic acid derivatives ligusticumacid A-C (1-3) and ligusticumaldehyde A (4), one new dimer ligusticumacid D (5), and two novel 8-8' lignans ligusticumacid E-F (6-7) were isolated from the rhizome of Ligusticum chuanxiong Hort. In particular, compounds 1-2, 5 were rarely phenylpropanoid phenolic acid dimers through different polymerization action in natural products. Their structures were established using UV, IR, HRESIMS, NMR data. The absolute configurations of 3 was determined by quantum ECD calculation and 4, 6-7 were determined by the ECD exciton chirality method. In addition, all compounds were evaluated for their neuroprotective effects on human neuroblastoma SH-SY5Y cell injury induced by H2O2. Compound 2 had a moderate neuroprotective activity and 7 had a weak neuroprotective activity on human neuroblastoma SH-SY5Y cell injury induced by H2O2 respectively.

Five new dimeric phloroglucinol derivatives, agrimones A − E (1–5), were isolated from the whole plant of Agrimonia pilosa. Their structures including absolute configurations were determined by a series of spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR), complemented with the comparison of the experimental and calculated ECD spectra, and gauge-independent atomic orbital (GIAO) NMR calculations. Notably, compounds 1 and 2 represent a highly oxidized 6/6/6 tricyclic ring skeleton based on the cis-fused paraquinone and chroman. Compounds 1a, 4, and 5 exhibited moderate hepatoprotective activities against APAP-induced HepG2 cell injury at 10 μM.

Six new phenylethanoid glycosides possessing dioxane moieties, named forsyoxasides A−F ( 1–6 ), together with four known such compounds ( 7–10 ) were isolated from the fruits of Forsythia suspensa . These structures were illustrated by extensive NMR spectroscopic techniques and by comparing their NMR data with the related literatures. Notably, forsyoxaside A ( 1 ) is a novel dioxane phenylethanoid glycoside with an axial aromatic ring, which is rare in the natural sources. Compounds 1 , 4 , 7 and 8 showed remarkable bioactivities against rotenone induced PC12 cell damage. Furthermore, 1 and 7 displayed strong activities against serum deprivation induced damage on the same cells.

Five new heterocyclic compounds, 5-α-d-fructofuranosylmethyl-furfural (1), 5-β-d-fructofuranosylmethyl-furfural (2), 5-β-d-fructopyranosylmethyl-furfural (3), 4-(2-((2S-2,3-dihydroxypropoxy)methyl)-5-formyl-1H-pyrrol-1-yl)butanoic acid (4), and 3S,4S-4,5,8-trihydroxy-3-(prop-1-en-2-yl)isochroman-1-one (5), were obtained from the root of Ranunculus ternatus Thunb., which is a traditional Chinese anti-tuberculosis medicine. Their structures were elucidated by UV, IR, HRESIMS, NMR data, and the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Notably, compounds 1-3 are rarely occurring furfural fructosides in natural sources. These heterocyclic compounds could be further studied for the synthetic chemists and pharmacologists due to the source and structural properties.

Four new and rare iridoid glucosides, cornusfuroside A-D (1-4), containing the furan ring were identified from water extract of the fruit of Cornus officinalis. These new chemical structures were determined through extensive spectroscopic analysis, including 1D and 2D NMR, IR, HRESIMS, experimental and calculated electronic circular dichroism (ECD). Notably, this study is the first report on the isolation of four iridoid glucoside structures with acetal functions in the sugar moiety. The neuroprotective effects of these compounds were also evaluated in vitro.

Three new caffeoylquinic acid derivatives, chrysanthemorimic acids A-C (1-3), and 11 known compounds (4-14) were isolated and characterized from the flowers of Chrysanthemum morifolium. Their structures were confirmed by spectroscopic data as well as by comparison of the experimental and calculated electronic circular dichroism spectra. Chrysanthemorimic acids A-C possess a rare 8-oxa-bicyclo[3.2.1]oct-3-en-2-one ring that is formed through a [5+2] cycloaddition of caffeoylquinic acid with a d-glucose derivative. Compounds 1-3, 6-8, 12, and 13 displayed significant effects against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells at 10 μM.

The Chrysanthemum morifolium flower is widely used in China and Japan as a food, beverage, and medicine for many diseases. In our work, two new caffeoylquinic acid derivatives (1, 2), a new flavanone glycoside (3), and six reported flavanones (4&ndash, 9) were isolated and identified from the flowers of C. morifolium. The chemical structures of all isolates were elucidated by the analysis of comprehensive spectroscopic data as well as by comparison with previously reported data. The isolated constituents 1&ndash, 8 were evaluated for their neuroprotective activity, and compounds 3 and 4 displayed neuroprotective effects against hydrogen peroxide-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.

One new epoxydon ester (1) and a new benzolactone derivative (2), along with four known compounds (3−6), were isolated from the insect-associated fungus Phoma sp. Their structures were confirmed by extensive MS and NMR spectroscopic analysis and their absolute configurations were determined by a combination of modified Mosher method and Mo2(OCOCH3)4-induced electronic circular dichroism (ECD) experiments. Compounds 1 and 5 were revealed to have potent antioxidant activities, which were approximate to the potency of the positive control trolox. In addition, 1 also exhibited moderate cytotoxic effect against human MGC-803 tumor cell line.

Two new isobenzofuranone derivatives, polyphthaliside A (1) and polyphthaliside B (2), and a new isocoumarin derivative, polyisocoumarin (3), were isolated from Polygonum cuspidatum. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. The cytotoxicity activity and PTP1B inhibitory activity of compounds 1–3 were estimated and none of them exhibited activities at a concentration of 10 μM.

In the course of studying the components from the roots of Sophora flavescens, eight new unusual biflavonoids consisting of a flavanone fused with a dihydrochalcone skeleton were isolated. These new chemical structures were elucidated by means of UV, IR, HRESIMS, NMR and ECD spectroscopic data and a comparison of experimental ECD spectra with calculated ECD spectra. Some compounds were subjected to an antidiabetic bioassay on human recombinant PTP1B inhibition, and showed strong inhibitory activity.

An ongoing phytochemical investigation of the rhizomes of Atractylodes lancea resulted in the isolation of four new C10-type polyacetylene glycosides (1-4). Their structures were elucidated on the basis of extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). The absolute configurations of compounds 2-4 were determined by comparing the specific rotations of their aglycones. Notably, compounds 2 and 3 exhibited significant hepatoprotective activities against APAP-induced HepG2 cell injury at a concentration of 10 μM. Compounds 2 and 3 showed weak anti-inflammatory effects on LPS-induced NO production in microglia BV2 cells at a concentration of 10 μM.

Lyciumsterols A-K (1-11), 11 new octahydroxylated C21 steroids, were isolated from the root bark of Lycium chinense, along with 15 known compounds. Characterization of these C21 steroids showed the presence of eight hydroxy groups on the C21 steroid skeleton with a (2E,4E)-5-phenyl-2,4-pentadienoate group at C-12 or C-20 and various 2,6-deoxy sugar residues at C-3. The structures of these compounds were elucidated using spectroscopic data interpretation. Compounds 2, 3, and 7 exhibited dose-dependent protective effects on pancreatic islet cells and may help to improve cell viability. In addition, it was found that compounds 7, 8, 9, and 11 exhibited autophagy activation.

An efficient method for the synthesis of (Z)-3-ylidenephthalides is reported in moderate to high yield with AlCl3 as catalyst. Different substrates of the 2-acylbenzoic acids are well performed in the Z/E selectivity. This method is highlighted by the gram-scale synthesis of the natural product (Z)-3-butylidene-5-hydroxyphthalide with anti-inflammatory activity.

Seven new butylphthalide derivatives, ligusticumolide A-G (1–7), together with two known butylphthalide derivatives (8–9) were isolated from an ethanol extract of Ligusticum chuanxiong Hort. The structures of these derivatives were elucidated from analysis of 1D/2D NMR, UV, IR and HRESIMS data. The absolute configurations of these derivatives were determined by electronic circular dichroism (ECD) calculations and Mosher′s method. Ligusticumolide A (1) and ligusticumolide B (2) are enantiomers that were obtained by chiral separation. Ligusticumolide C (3) and ligusticumolide D (4) are diastereomers. All of the compounds were evaluated for their hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury. Compounds 4, 5, and 7–9 showed more significant hepatoprotective activity than that of the positive control drug (bicyclol) at a concentration of 10 μM (p

Flower of Chrysanthemum morifolium is widely used in China and Japan as a folk medicine in treatment of many diseases. However, its active compounds remain largely unknown. In the present work, we have isolated, purified and characterized six new compounds (1-6), including two new arylnaphthalene lignans and four new phenolic glycosides, together with eight known compounds (7-14), from the flower of C. morifolium. Their structures and absolute configurations were elucidated in detail using 1D and 2D NMR, UV, IR, ORD, HRESIMS and ECD spectrometric data. In addition, compounds 1-3 possessed the significant neuroprotective activity against hydrogen peroxide-induced neurotoxicity in human neuroblastoma SH-SY5Y cells.

Phytochemical investigation on the rhizomes of Atractylodes lancea led to the isolation of two new thiophene polyacetylene glycosides (1 and 2) and six known compounds (3-8). Their structures were elucidated based on the extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). The absolute configurations of new compounds were established by calculated and experimental circular dichroism. All the compounds were assessed on the lipopolysaccharide-induced NO production in BV2 cells and compounds 3, 7, and 8 showed moderate inhibitory activities.

Forsythoneosides A-D (1-4), four unusual adducts of a flavonoid unit fused to a phenylethanoid glycoside through a pyran ring or carbon-carbon bond, and four new phenylethanoid glycosides (5-8) were isolated from the fruits of Forsythia suspensa, together with nine known compounds. The structures of 1-8, including their absolute configurations, were elucidated by spectroscopic data as well as experimental and calculated electronic circular dichroism analysis. Compounds 2 and 4 inhibited PC12 cell damage induced by rotenone, and increased cell viability from 53.9 ± 7.1% to 70.1 ± 4.0% and 67.9 ± 5.2% at 0.1 μM, respectively.

In recent years, certain "new" naturally occurring compounds (1-28) with 3,5-dioxygenated aromatic rings have been reported. A comparison of the NMR data of these compounds with the data of four model compounds (A-D) indicated that the structures of these "new" compounds were erroneous. The reason for the incorrect elucidation of the structures of 1-28 was attributed to "deceptively simple" (1)H NMR spectra, which displayed two broad singlets with integrations of 1:2 for H-2 and H-5, H-6, respectively. To expose the misleading results from the spectra, serial (1)H NMR experiments on compounds A-D were performed using various deuterated solvents and temperatures. The results revealed separated proton signals for the ABX system in certain deuterated solvents. Additionally, the characteristic differences between 3,4- and 3,5-dioxygenated aromatic rings in their (13)C NMR spectra are summarized based on our experiment and data reported. This approach is useful for analyzing the patterns of dioxygenated aromatic rings in natural products, especially when "deceptively simple" (1)H NMR spectra are displayed.

In our study to investigate components with hepatoprotective activities, eight new phenylethanoid glycoside derivatives (1-8) were isolated from the 75% EtOH-H2O extract of the fruits of Forsythia suspensa along with six known compounds (9-14). These new structures were elucidated through HRESIMS and extensive NMR spectroscopic techniques. The absolute configurations of their sugars were determined by GC analysis. The pharmacological assay showed that compounds 2, 3, and 9-11 displayed remarkable hepatoprotective activities against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage at the concentration of 10μM (Bicyclol as positive contrast).

Five new phenylpropanoid glycosides, susaroysides A–E (1–5) were isolated from the fruits of Forsythia suspensa. Their structures were elucidated by comprehensive spectroscopic data analysis. The absolute configurations of their sugars were determined by GC analysis. Notably, susaroysides A–D possessed a sugar with an unsubstituted anomeric carbon, which is relatively rare in natural sources. Compound 1 exhibited significant anti-inflammatory activity against the lipopolysaccharide (LPS)-induced tumor necrosis factor (TNF)-α expression in macrophage cells with the IC50 value of 1.053 μM.

Twelve new dibenzoyl derivatives sophodibenzoside A-L (1-12) and five new isoflavone glycosides (13-17) have been isolated from the roots of Sophora flavescens together with eight known compounds (18-25). Notably, the use of acetic acid-d4 was required to enable identification of the dibenzoyl glycoside structures. Compounds 1, 2, 13, 14, and 19 exhibited weak inhibition of the cytotoxic effect of d-galactosamine on the human hepatic cell line HL-7702.

Hydroxysafflor yellow A (HSYA), a representative component of Carthamus tinctorius, has attracted much attention because of its remarkable cardiovascular activities. Its structure was originally reported in 1993 and has been widely cited to date. In our experiments, its solution structure was studied using NMR techniques in different solvents, including DMSO-d(6), pyridine-d(5), and CD(3)OH. The results indicate that the structure of HSYA is different than the previously described 1b, with 3-enol-1,7-diketo form. The structure has two keto-enol tautomers (2a and 2b), and 2a, with the 1-enol-3,7-diketo form, is the preferred tautomer. On the basis of this finding, other published quinochalcone C-glycoside structures were revised. Furthermore, a trend in the (13)C NMR data of the (E)-olefinic carbons of quinochalcone C-glycosides is summarized, and a hypothesis is proposed for the relationship between the features of the molecular structure and the preferred keto-enol tautomer.

Two new phenolic glycosides with a rare β- d -glucopyranosyl-(1 → 3)-α- l -rhamnopyranosyl moiety ( 1 , 2 ), one new dihydrobenzofuran derivative ( 3 ), one new pyrazine derivative ( 4 ), two new furofuran lignan glycosides ( 5 , 6 ), and six known compounds ( 7 – 12 ) were isolated from the rhizomes of Atractylodes lancea . The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh 2 (OCOCF 3 ) 4 -induced circular dichroism for configurational assignments. Notably, compounds 1 – 3 showed significant hepatoprotective activities against N -acetyl- p -aminophenol-induced HepG2 cell injury. This study is also the first Letter on the isolation of furofuran lignans and pyrazine derivatives ( 4 – 7 ) from the genus Atractylodes .

Phytochemical and pharmacological study on the rhizomes of Atractylodes lancea led to the identification of twenty-one compounds: six new eudesmane-type sesquiterpenoids ( 1 – 6 ), two new eremophilane-type sesquiterpenoids ( 7 , 8 ), and thirteen known compounds ( 9 – 21 ). These new compounds were elucidated using extensive spectroscopic analyses with experimental and calculated electronic circular dichroism (ECD) for the configurational assignments. Notably, this study was the first report on the isolation of two eremophilane-type sesquiterpenoids ( 7 , 8 ) from the genus Atractylodes . Compounds 5 , 7 , and 16 showed potent hepatoprotective activities against N -acetyl- p -aminophenol (APAP)-induced HepG2 cell injury at a concentration of 10 μM (bicyclol as the positive drug).

Nine new sesquiterpenoids (1–9), five new polyacetylenes (10–14), and six known compounds were isolated from the rhizomes of Atractylodes lancea. These new chemical structures were established using NMR, MS, and ECD data. Notably, compounds 3–5, the aglycone of which possesses two stereogenic centers (C-5 and C-7), exhibited similar ECD spectra to compounds 1 and 2, the aglycone of which possesses one stereogenic center (C-7). Such a difference was supported by the experimental and calculated ECD data and single-crystallographic analyses of 3a. In addition, compound 3 inhibited lipopolysaccharide-induced NO production in BV2 cells with an IC50 value of 11.39 μM (positive control curcumin, IC50 = 4.77 μM); compound 4 showed better hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury than the positive drug (bicyclol) at a concentration of 10 μM (p < 0.001).

Phytochemical investigation of the extract of Arctii Fructus led to the isolation and characterization of two new compounds, named arctiisesquineolignan B (1) and arctiiphenolglycoside A (2). Their structures were elucidated by means of spectroscopic methods (UV, IR, HR-ESI-MS, 1D and 2D NMR) and chemical evidence, as well as by comparison with known analogs in the literature. Compound 2 exhibited stronger antioxidant activity than the positive control ascorbic acid at a concentration of 10 μM.

A series of novel 1,3,4-thiadiazine derivatives were synthesized via chemical optimization on phthiobuzone. Their anti-herpes simplex virus (HSV) activities in vitro were also tested. Several compounds exhibited more highly potent anti-HSV activity and much higher selectivity index (SI) values than those of phthiobuzone. The most potent anti-HSV compound was 4f, which showed marked inhibition against HSV-1 (IC₅₀=77.04 µg/ml) and HSV-2 (IC₅₀=30.00 µg/ml). Meanwhile it had low cytotoxicity (CC₅₀=1000.00 µg/ml), resulting in high (SI(HSV-1)=12.98, SI(HSV-2)=33.33, respectively). Furthermore, a computational study for prediction of absorption, distribution, metabolism, excretion (ADME) properties of compound 4f was performed by determination of topological polar surface area, absorption and Lipinski parameters.

Three new glucaric acids, namely 2-feruloyl-4-syringoyl or 5-feruloyl-3-syringoyl glucaric acid (1), 2-syringoyl-4-feruloyl or 5-syringoyl-3-feruloyl glucaric acid (2), and 3-feruloyl-4-syringoyl or 4-feruloyl-3-syringoyl glucaric acid (3), were isolated from Leonurus japonicus Houtt. Their structures were elucidated by detailed spectroscopic means including UV, IR, HR-ESI-MS, 1D and 2D NMR data spectra. The bioactive assays of compounds 1-3 against hepatoprotection activity were determined. The result suggested that compound 2 exhibited a moderate hepatoprotection activity and the cell survival rate was 74% (10(-5)mol/L), using bicyclol (survival rate: 66%, 10(-5)mol/L) as a positive control. Furthermore, compounds 1-3 were evaluated cytotoxic activities in vitro using HCT-8, Bel-7402, BGC-823, A-549, and A2780 model and the results exhibited no obvious cytotoxicity activity.

Eleven new acyl quinic acid derivatives, 4-O-caffeoyl-3-O-syringoylquinic acid methyl ester (1), 4-O-caffeoyl-3-O-vanilloylquinic acid (2), 4-O-caffeoyl-3-O-vanilloylquinic acid methyl ester (3), 5-O-caffeoyl-3-O-vanilloylquinic acid (4), 5-O-caffeoyl-3-O-vanilloylquinic acid methyl ester (5), 5-O-caffeoyl-3-O-sinapoylquinic acid (6), 5-O-caffeoyl-4-O-vanilloylquinic acid (7), 4-O-(7‴S, 8‴R)-glycosmisoyl-5-O-caffeoylquinic acid methyl ester (8), 4-O-(7‴S, 8‴R)-glycosmisoyl-5-O-caffeoylquinic acid (9), 3-O-(7‴S, 8‴R)-glycosmisoyl-4-O-caffeoylquinic acid (10), and 3-O-(7‴S, 8‴R)-glycosmisoyl-4-O-caffeoylquinic acid methyl ester (11), have been isolated from the stems of Erycibe obtusifolia together with eight known compounds (12-19). Their structures were elucidated on the basis of spectroscopic data analysis (UV, IR, HRESIMS, CD, and 1D and 2D NMR) and chemical evidence. In in vitro assay, compounds 7 and 16-18 exhibited significant neuroprotective effects against rotenone induced PC12 cell damage at 10 μM.