Chemical constituents of diterpenoids from Boswellia carterii / 中国中药杂志

This paper explored the chemical constituents of Boswellia carterii by column chromatography on silica gel, Sephadex LH-20, ODS column chromatography, and semi-preparative HPLC. The structures of the compounds were identified by physicochemical properties and spectroscopic data such as infrared radiation(IR), ultra violet(UV), mass spectrometry(MS), and nuclear magnetic resonance(NMR). Seven diterpenoids were isolated and purified from n-hexane of B. carterii. The isolates were identified as(1S,3E,7E,11R,12R)-11-hydroxy-1-isopropyl-4,8,12-trimethyl-15-oxabicyclo[10.2.1]pentadeca-3,7-dien-5-one(1),(1R,3S,4R,7E,11E)-4,8,12,15,15-pentamethyl-14-oxabicyclo[11.2.1]hexadeca-7,11-dien-4-ol(2), incensole(3),(-)-(R)-nephthenol(4), euphraticanoid F(5), dilospirane B(6), and dictyotin C(7). Among them, compounds 1 and 2 were new and their absolute configurations were determined by comparison of the calculated and experimental electronic circular dichroisms(ECDs). Compounds 6 and 7 were obtained from B. carterii for the first time.

Quality standard of Lobeliae Chinensis Herba / 中国中药杂志

In light of related methods in Chinese Pharmacopoeia(2020 edition), this study established the quality standard for Lobeliae Chinensis Herba. The TLC identification method was established with silica gel GF_(254) thin layer plate, diosmin standard, linarin standard, and the reference material of Lobeliae Chinensis Herba. The loss on drying, total ash, acid-insoluble ash, and ethanol-soluble extracts of 18 batches of Lobeliae Chinensis Herba samples were determined according to the general principles in Chinese Pharmacopoeia. Then, HPLC was adopted in the establishment of characteristic chromatogram and content determination. The results showed that the established method can achieve good separation for diosmin, linarin, and lobetyolin. Based on the results of detection for 18 batches of Lobeliae Chinensis Herba samples, the draft quality standard was established, which was expected to provide reference for the revision of this medicinal herb in Chinese Pharmacopoeia.

Condensed tannins from roots of Indigofera stachyodes / 中国中药杂志

Eleven condensed tannins were isolated from the roots of Indigofera stachyodes by various column chromatography techniques including silica gel, octadecyl silica(ODS), Sephadex LH-20, and semi-preparative high performance liquid chromatography(HPLC). These compounds were identified on the basis of physicochemical properties, nuclear magnetic resonance(NMR) and mass spectrometry(MS) data as stachyotannin A(1), epicatechin-(2β→O→7,4β→8)-epiafzelechin-(4β→8)-catechin(2), cinnamtannin D1(3), cinnamtannin B1(4), epicatechin-(2β→O→7,4β→8)-epiafzelechin-(4α→8)-epicatechin(5), gambiriin C(6), proanthocyanidin A1(7), proanthocyanidin A2(8), aesculitannin B(9), proanthocyanidin A4(10), and procyanidin B5(11). Compound 1 is a new compound. Compounds 2-11 were isolated from Indigofera for the first time. Furthermore, compounds 1, 2, and 4-11 showed inhibitory effects on thrombin-induced ATP release in platelets.

One new cembranoid diterpene from gum resin of Boswellia carterii / 中国中药杂志

This study aims to study the chemical components from the gum resin of Boswellia carterii. Five cembranoid diterpenes were isolated from the gum resin of B. carterii by various of column chromatographies including silica gel, Sephadex LH-20, and semi-preparative HPLC. Their structures were identified on the basis of physicochemical properties, mass spectrometry(MS), nuclear magnetic resonance(NMR), Ultraviolet(UV) and infrared(IR) spectroscopic data. These compounds were identified as(1S,2E,4R,5S,7E,11E)-4-methoxy-5-hydroxycembrane(1),(1R~*,4R~*,5E,8E,12E,15E)-4-hydroxycembra-5,8,12,15-tetraene(2), cembrene A(3),(3S,4S,7R)-4-hydroxycembrane(4), and pavidolide D(5). Compound 1 was a new compound. Compounds 2, 4, and 5 were obtained from the gum resin of B. carterii for the first time. Compound 2 showed weak inhibition on the human liver cancer cell line HepG2.

Two new phenylpropanoid amide glycosides from whole plants of Corydalis racemosa / 中国中药杂志

Two new phenylpropanoid amide glycosides and ten analogues were isolated from the CH_2Cl_2 layer of 95% ethanol extract of the whole plants of Corydalis racemosa by using various chromatographic techniques, including silica gel, Sephadex LH-20, ODS column chromatographies, and semi-preparative HPLC. Their structures were identified on the basis of physicochemical properties, MS, NMR, and IR spectroscopic data as N-cis-sinapoyltyramine-4'-O-β-glucoside(1), N-cis-sinapoyl-3-methoxytyramine-4'-O-β-glucoside(2), N-cis-sinapoyltyramine(3), N-cis-feruloyltyramine(4), N-trans-cinnamoyltyramine(5), N-trans-feruloylphenethylamine(6), N-trans-p-methoxycinnamoyl-3-hydoxyoctopamine(7), N-cis-feruloyl-3-methoxytyramine(8), N-trans-feruloyltyramine(9), N-trans-feruloyl-3-methoxytyramine(10), N-trans-sinapoyltyramine(11), and N-trans-p-coumaroyltyramine(12). Compounds 1 and 2 are new compounds. Compounds 3-7 are obtained from the plants of Papaveraceae for the first time, and compounds 8-12 are firstly isolated from C. racemosa.

Anti-tumor activity of HIS-4,a biflavonoid from Resina draconis,on human hepatoma HepG2 and SK-HEP-1 cells / 中国中药杂志

The research of anti-hepatocellular carcinoma(HCC) drug has attracted more and more attention. Natural products are the important source of active compounds for cancer treatment. A biflavonoid HIS-4 was isolated from Resina draconis in our previous study. MTT assay, hoechst staining, and flow cytometry analysis were used to investigate the effects of HIS-4 on the proliferation and apoptosis of human hepatoma HepG2 and SK-HEP-1 cells. Moreover, the effects of HIS-4 on the migration and invasion ability of HepG2 and SK-HEP-1 cells were evaluated by wound healing assay and Transwell assay. In addition, MTT assay, flow cytometry analyses, Hoechst staining, wound healing assay, Transwell assay, and tube formation assay were used to explore the anti-angiogenic activity of HIS-4 in human umbilical vein endothelial cells(HUVECs). Mechanistically, the HIS-4 regulatory of signal pathways in H9 epG2 and SK-HEP-1 cells were analyzed by Western blot. This results showed that HIS-4 suppressed the proliferation of human hepatoma HepG2 and SK-HEP-1 cells. Moreover HIS-4 induced their apoptosis of HepG2 and SK-HEP-1 cells. HIS-4 inhibited the migration and invasion of HepG2 and SK-HEP-1 cells. Additionally, HIS-4 exhibited angiogenesis effects. Mechanistically, up-regulation of MAPK signaling pathway and down-regulation of mTOR signaling pathway may be responsible for anti-hepatoma activity of HIS-4. Therefore, HIS-4 may be a promising candidate drug for HCC treatment.

Rapid chemical profiling of Artemisiae Scopariae Herba using reversed phase liquid chromatography-hydrophilic interaction liquid chromatography-predictive multiple reaction monitoring / 中国中药杂志

Chemical profiling of a given herbal medicine( HM) is the prerequisite for clarifying the effective material basis and therapeutic mechanisms,and it is an important integral part of traditional Chinese medicine chemical biology( TCMCB). In current study,we aimed to propose a new strategy for fast chemical characterization of HM by using reversed phase liquid chromatography-hydrophilic interaction chromatography-predictive multiple reaction monitoring( RPLC-HILIC-p MRM),and Artemisiae Scopariae Herba was employed in this study to illustrate the entire strategy. In response to wide polarity spanning of the diverse chemical clusters in Artemisiae Scopariae Herba,RPLC and HILIC were coupled in series to retain and separate hydrophilic and hydrophobic components simultaneously by identifying the characteristics of chromatographic separation. Most of the chemical constituents in traditional Chinese medicine can be predicted by summarizing the results of chemical constituents of the same genera and introducing primary metabolites and possible substitution reaction types. Therefore,we constructed predictive ion pairs to rapidly identify the chemical constituents of Artemisiae Scopariae Herba. After comparison with control products,discussion on fragmentation pattern,and access to relevant information from literature and databases,a total of 139 components were detected and structurally annotated by matching the obtained spectral data with the information of authentic compounds. Above all,RPLC-HILIC-p MRM could be used as an eligible analytical tool for the chemical profiling of HMs.

LC-MS guided isolation of two anti-inflammatory cyclic dihydrochalcane trimers from Chinese dragon's blood / 中国中药杂志

As an important integral part of traditional Chinese medicine chemical biology( TCMCB),it is of great importance to rapid isolate,and reliably identify the chemical components in herbal medicines. Phytochemical studies on the anti-inflammatory active part of Chinese dragon's blood,the red resin of Dracaena cochinchinensis,resulted in the isolation of two compounds,nordracophane( 1) and dracophane( 2),using LC-MS and chromatographic techniques( Silica gel,ODS and preparative HPLC). The structures,cyclic dihydrochalcane trimers,were elucidated on the basis of 1 D and 2 D NMR,MS,IR and UV spectral analysis. Compound 1 is a new compound,and 2 is isolated from D. cochinchinensis for the first time. Both compounds exhibited significant inhibition of nitric oxide production in lipopolysaccharides( LPS)-stimulated RAW264. 7 cells with IC50 values of( 14. 9±4. 50) and( 9. 0±0. 7) μmol·L-1.

Inhibitory effect of BF523 from Ilex hainanensis on ox LDL-induced foam cells formation / 中国中药杂志

Cardio-cerebral vascular disease induced by atherosclerosis is a serious cause of human health. The pathogenesis of AS is very complex,and the oxidized low-density lipoprotein( ox LDL) induced foam cells formation is considered to be the most important cytological change in AS. Based on the definition of " TCM chemical biology",we clarified the chemical composition of Ilex hainanensis,the effective substances of I. hainanensis on the activity of anti-AS were screened. Then we found that saponin BF523 had the good inhibitory effect on foam cell formation. In this research,we studied the BF523 as the research object to clarify the molecular target of the active compound of I. hainanensis by foam cell formation model. The results showed that BF523 significantly inhibited the oxidation of ox LDL-induced macrophage foaming and decreased the lipid content in macrophages. BF523 had inhibited the phagocytosis of ox LDL in macrophages by reducing the mRNA and protein levels of scavenger receptor CD36,thereby inhibiting the occurrence and development of AS. These findings not only clarified the mechanism of the inhibition of foam cell formation by saponin BF523,but also provided a useful exploration for the enrichment of the theory of " TCM chemical biology".

Phenylpropanoid amides from whole plants of Corydalis edulis / 中国中药杂志

Ten phenylpropanoid amides were isolated from the whole plants of Corydalis edulis Maxim. by various of column chromatographies including silica gel, Sephadex LH-20, and ODS. Their structures were identified on the basis of physicochemical properties, MS, NMR, and IR spectroscopic data. These compounds were identified as N-trans-sinapoyl-3-methoxytyramine-4'-O-β-glucoside(1), N-trans-sinapoyl-3-methoxytyramine(2), N-trans-sinapoyltyramine(3), N-trans-p-coumaroyltyramine(4), N-trans-sinapoyl-7-hydroxytyramine(5), N-cis-feruloyltyramine(6), N-cis-p-coumaroyltyramine(7), N-trans-feruloyltyramine(8), N-trans-feruloyl-3-methoxytyramine(9), and N-trans-feruloyl-7-hydroxytyramine(10). Compound 1 is a new compound. Compounds 2-7 are obtained from the plants of Papaveraceae for the first time, while compounds 8-10 are firstly isolated from C. edulis.

Effect of Longxuetongluo capsule in protecting vascular endothelial cells against oxygen-glucose deprivation/reoxygenation-induced apoptosis / 中国中药杂志

Focal cerebral ischemia reperfusion is an essential process during ischemic stroke. The apoptosis of vascular endothelial cells induced by ischemia/reperfusion (I/R) injury is an important cause for brain injury after focal cerebral ischemia. Longxuetongluo capsule (LTC) has been used for the treatment of ischemic stroke in clinic. However, its underlying action mechanism is still unclear. This study aimed to verify the protective effect and mechanisms of LTC on HUVEC cells against oxygen-glucose deprivation/reoxygenation (OGD/R) injury through MTT, LDH, flow cytometry, AO/EB staining and western blot assays. As a result, OGD/R significantly decreased the viability of HUVEC cells, which was significantly improved by LTC. LDH release assay showed that OGD/R significantly increased the lactate dehydrogenase (LDH) release, and LTC dramatically reduced the OGD/R-induced LDH release. Further mechanism study indicated that LTC dose-dependently inhibited the cleavage of PARP, caspase 3, and caspase 9 induced by OGD/R, suggesting that LTC could inhibit the activation of caspase 3/9 apoptosis pathway in the OGD/R-induced apoptosis of HUVEC cells. In conclusion, LTC could protect HUVEC cells against OGD/R injury by inhibiting the activation of mitochondria-related caspase 3/9 apoptosis pathway.

Transformation pathways in methanol of echinacoside, a principal effective ingredient of Cistanches Herba / 中国中药杂志

Echinacoside (ECH) is one of the active ingredients in Cistanche Herba and the principal effective component of Memoregain© as well. Moreover, a new agent namely Naoqing Zhiming tablet, derived from ECH has been licensed for clinical trials. However, the knowledge regarding the stability of is limited, till now, initiating a significant barrier for its further development along with the clinical trials. Herein, we aim to in depth characterize the transformation pattern of ECH in methanol. When ECH was stored in methanol, two primary products (P1 and P2) could be observed in HPLC chromatogram. A home-made automated fraction collector was configured via employing two 2-phase/6-port electronic valves to prepare P1 and P2. Following ¹H-NMR and LC-MS/MS assays, P1 and P2 were unambiguously identified as acteoside and cistanoside A, respectively. Moreover, the existences of cis-ECH, cis-acteoside, and cis-cistanoside A were claimed after careful analysis of the ¹H-NMR spectra of ECH, P1 and P2. Above all, the primary transformation pathways of ECH in methanol included methylation as well as hydrolysis, and mild transformation could also be initiated by cis/trans- configuration transferring for the caffeoyl group. The findings obtained in current study are envisioned to provide useful insight for the further development of ECH and the impurity detection of Naoqing Zhiming tablet. Moreover, the automated fraction collector configured in current study is able to serve as a versatile tool for the collection of signals-of-interest within phytochemical evaluations and impurity isolation.

Efficacy and mechanism of puerin Ⅰ in improving disorder of glycolipid metabolism in ApoE-/-mice / 中国中药杂志

Pu-erh tea is a unique post-fermented tea processed from tender leaves of Camellia assamica. Characteristic component puerins were produced during the microbial fermentation process.This study focuses on the therapeutic effect and mechanism of puerinⅠ(P1) in Pu-erh tea on ApoE-/- mice with dyslipidemia and diabetes. It was found that P1 could significantly decreased total cholesterol (TC), triglyceride (TG) and fast blood glucose (FBG), and markedly improved impaired glucose tolerance (IPGTT) and insulin sensitivity (ITT) in hyperlipidemic and hyperglycemic ApoE-/- mice. Further experiments proved that P1 reduced FBG and plasma TG levels by inhibiting intestinal α-glycosidase enzymes activity and by activating low-density lipoprotein receptor respectively. This study confirmed the therapeutic effect and mechanism of P1 on ApoE-/- mice with diabetes and hyperlipidemia. Based on the good efficacy of this compound, P1 could be used as a new drug to treat the disorder of glycolipid metabolism.

Chemome comparison between cultivated and wild Cistanche tubulosa using ¹H-NMR spectroscopy / 中国中药杂志

As a famous tonic medicine, Cistanche tubulosa has been honored as "ginseng of the deserts" for centuries. Aiming to address the resource shortage as well as the wild resource protection towards this herbal medicine, wide cultivation has been achieved in the southern Xinjiang. Herein, in-depth chemome comparison was conducted between cultivated and wild plants using ¹H-NMR spectroscopy that is capable of comprehensively providing qualitative and quantitative information of given complicated matrices. Multivariate statistical analysis was employed to process the dataset as well as to consolidate that the cultivated plants are comparable to those wild ones in term of chemome. ¹H-NMR spectra of both wild and cultivated plants were acquired in parallel after extraction. Following direct overlaying, great similarity occurred between these two groups. A total of 28 compounds were tentatively identified by referring to authentic compounds together with those available databases, such as HMDB and BMRB. Following principal component analysis, none significant difference was observed between wild and cultivated groups. Above all, from the viewpoint of chemical profile, the cultivated plants were almost equal to the wild plants; therefore, the cultivated plants are able to take the load of wild plants in clinical usage. Moreover, ¹H-NMR spectroscopy is a promising tool for chemical profiling traditional Chinese medicines because of the potential towards simultaneously exhibiting both quantitative and qualitative information for complicated matrices.

Chemical characterization for flowers and lignified stems of Cistanche deserticola / 中国中药杂志

As a holoparasitic plant, Cistanche deserticola is one of the two original sources of Cistanches Herba that is one of the most famous tonic medicines, in Chinese Pharmacopoeia. The succulent stems are used for medicinal usage, whereas those lignified stems as well as flowers of less pharmacological importance are usually deserted, suggesting extensive resource waste. Herein, chemical characterization of the flowers along with lignified stems was conducted using HPLC-IT-TOF-MS aiming to explore the medicinal valu of those non-medicinal parts. Following ultrasonication-assisted extraction with 50% aqueous methanol, either flower or lignified stem extract was subjected onto LC-IT-TOF-MS equipped with a Capcell core ADME column to acquire both MS¹ and MSº spectra, and gradient elution was carried out with combinatory 0.1% aqueous formic acid and acetonitrile. Both positive and negative ionization polarities were deployed, resulting in the observation of 62 components, in total. Thirty-nine signals were structurally annotated, including phenylethanoid glycosides, iridoids, lignans and saccharides according to matching with authentic components and literature information, as well as applying the proposed mass fragmentation rules. A total of 62 ones were putatively identified. Above all, lignified stems and flowers should not the qualified substitutes for the succulent stems attributing to the significant differences between the medicinal portion and those parts with less medicinal values.

Two new polypeptides from extract of deer bone extract / 中国中药杂志

Two new polypeptides were isolated and purified from the extract of deer bone (constitutive part of Cucumis and Cervus polypeptide injection) by various column chromatography including C₄ 300Å and Sephadex G-50, as well as semipreparative HPLC. Their N-terminal amino acid sequences were identified by De Novo sequencing on the basis of MALDI-TOF-MS data and Explorer™ software. The N-terminal amino acid sequences of polypeptides were identified as NH₂-Gly-Pro-Val-Gly-Pro-Thr-Gly-Pro-Val-Gly-Ala-Ala-Gly-Pro-Ser-Gly-Pro-Asp (Mei18 peptide, 1) and NH₂-Ala-Gly-Pro-Ala-Gly-Pro-Leu-Gly-Pro-Leu-Gly-Pro-Leu-Gly-Pro-Leu-Gly-Pro-Pro-Asp-Ser-Try-Asp (Mei23 peptide, 2), respectively. Mei18 and Mei 23 peptides are new polypeptides.

Progress in research for pharmacological effects of Pu-erh tea / 中国中药杂志

Pu-erh tea has gradually aroused general concern with social development and people's enhanced awareness of health. Pu-erh tea is rich in multiple active constitute such as flavonoids, catechins, phenolic acids, flavanols polymer, purine alkaloids, and hydrolysable tannin as a microbial-fermented tea.It is reported that Pu-erh tea have a variety of pharmacologically activities, such as anti-hyperlipidemic, anti-diabetic, anti-oxidative, anti-tumor, anti-bacterial, anti-inflammatory, and anti-viral effects. In this paper, the main pharmacological effects of Pu-erh tea are reviewed. We wish this work will provide some references and clues for further research of Pu-erh tea.

Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their biological activities in vitro / 中国中药杂志

Chemical constituents from the fruits of Vitex negundo var. cannabifolia and their nitric oxide (NO) inhibitory and cytotoxic activities were investigated. The compounds were isolated and purified by various column chromatography, and their structures were identified by physiochemical properties and spectroscopic data. Thirteen lignans and six phenolic compounds were isolated from the CH2Cl2 extract of the fruits of V. negundo var. cannabifolia, respectively. Their structures were elucidated as 6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-7-methoxy-3,4-dihydro-2-naphthaldehyde (1), vitedoin A (2), vitexdoin F (3), detetrahydroconidendrin (4), vitexdoin E (5), 4-oxosesamin (6), L-sesamin (7), (+)-beechenol (8), ligballinol (9), 2-(4-hydroxyphenyl)-6-(3-methoxy-4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (10), (-)-pinoresinol (11), balanophonin (12), thero-guaiacylglycerol-β-coniferyl aldehyde ether (13), trans-p-coumaryl aldehyde (14), coniferyl aldehyde (15), 5,7-dihydroxychromone (16), trans-3,5-dimethoxy-4-hydroxy-cinnamic aldehyde (17), frambinone (18), and alternariol 4-methyl ether (19). Compounds 8-10,14,18,19 were firstly isolated from Verbenaceae family, compound 13 was obtained from Vitex species, and 6,7,12,15-17 from V. negundo var. cannabifolia for the first time, respectively. The isolated compounds were evaluated for their anti-inflammatory and cytotoxic effects in vitro. Eight compounds (3,5,7,10,11,14,15,17) showed inhibition against NO production in LPS-stimulated RAW 267.4 cells (IC₅₀ in the range of 7.8-81.1 μmol•L⁻¹) and four compounds (1-4) showed cytotoxicity on HepG-2 cells (IC₅₀ in the range of 5.2-24.2 μmol•L⁻¹).

Inhibitory effect of ilexpernoside C from Ilex pernyi on aggregated LDL-induced foam cells formation / 中国中药杂志

The aggregation of macrophage-derived foam cells on vascular wall is considered to be a main cause of atherosclerosis. In the present study, we evaluated the inhibitory effect of the compound ilexpernoside C (IC1) extracted from Ilex pernyi (Aquifoliaceae) on foam cell formation in THP-1 macrophages cells which were induced by low density lipoproteins aggregates (LDL aggregates). Results showed that IC1 could significantly inhibit the formation of foam cells. The analysis on related receptors of foam cells indicated that IC1 could significantly decrease the expression of low density lipoprotein-related receptor 1(LRP1). Therefore, these findings indicated that IC1 inhibited the formation of foam cells by inhibiting endocytosis of macrophages, thus it may act as a potential anti-atherosclerotic agent.

Flavonoids from whole plants of Lagopsis supina / 中国中药杂志

The flavonoids were investigated from the whole plants of Lagopsis supina. The compounds were isolated and purified by various column chromatography, and their structures were identified by physiochemical properties and spectroscopic data. Two flavones were isolated from the CH2Cl2 layer of Lagopsis supina extract and identified as genkwanin (1) and 5-hydroxy-7,4'-dimethoxyflavone (2), respectively. Ten flavonoid glycosides were isolated from the water layer of Lagopsis supina and elucidated as kaempferol-3-O-6" (3-hydroxy-3-methylglutaryl) -β-D-glucoside (3), quercetin-3-O-6"-(3-hydroxy-3-methylglutaryl) -β-D-glucoside (4), quercetin-3-O-β-D-glucoside(5), kaempferol-3-Of3-D-glucoside ( 6), isorhamnetin-3-O-/-D-glycopyranoside (7), apigenin-7-O-6-D-glucoside (8), luteolin-7-O-β-D-glucoside (9), chrysoeriol-7-O-β-D-glucoside (10), rutin (11 ), and kaempferol-3-β-(6"-p-coumaroyl) -β-D-glucoside (tiliroside, 12). Compounds 3 and 4 were firstly isolated from Lamiaceae family, and compounds 1-12 were isolated from the plants of Lagopsis genus for the first time.