Advances in studies on structure and pharmacological activities of natural tirucallane-type triterpenoids / 中国中药杂志

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.

Reviews on natural monocyclic sesquiterpenoids and their bioactivities / 中国中药杂志

Sesquiterpenes are a class of terpenoids composed of three isoprene units( 15 carbons). Sesquiterpenoids possess a variety of different structures,including acyclic sesquiterpenes,monocyclic sesquiterpenoids,bicyclic sesquiterpenoids,tricyclic sesquiterpenoids,tetracyclic sesquiterpenoids and macrocyclic sesquiterpenoids. Among them,a large number of monocyclic sesquiterpenoids were isolated and display extensive bioactivities,such as cytotoxic,antioxidant,anti-inflammatory,antibacterial and other activities. In this review,we summarized the progress about the phytochemistry and biological activities of monocyclic sesquiterpenoids( a total of161 compounds) reported from 2014 to 2018( 5 years),including megastigmanes,monocyclofarnesol-type,bisabolane-type,germacrane-type,and other types of monocyclic sesquiterpenoids. Furthermore,several future research perspectives and development of sesquiterpenoids as potential therapeutic agents were discussed as well.

Constituents isolated from n-butanol extract of leaves of Moringa oleifera / 中国中药杂志

Seventeen compounds were isolated from n-butanol extract of the leaves of Moringa oleifera, using column chromatography over macroporous resin HP-20,Sephadex LH-20, and ODS. Their structures were identified as two carboline,tangutorid E(1) and tangutorid F(2); three phenolic glycosides,niazirin(3)，benzaldehyde 4-O-α-L-rhamnopyranoside(4) and 4-O-β-D-glucopyranosidebenzoic acid(5); four chlorogenic acid and derivatives,4-caffeoylquinic acid(6),methyl 4-caffeoylquinate(7),caffeoylquinic acid(8) and methyl caffeoylquinate(9); two nucleosids,uridine(10) and adenosine(11); one flavone,quercetin 3-O-β-D-glucopyranoside(12); five other types of compounds,phthalimidineacetic acid(13),3-pyridinecarboxamide(14),3,4-dihydroxy-benzoic acid(15),5-hydroxymethyl-2-furancarboxylic acid(16) and 5-hydroxymethyl-2-furaldehyde(17) by the spectral data of ¹H, ¹³C-NMR and MS. Among them,compounds 1-2,7,9-10,16 and 17 were isolated from M. oleifera for the first time.

Reviews on natural naphthoquinones and their bioactivities / 中国中药杂志

The naphthaquinones are widely distributed in plants. They are usually in higher plants, but a few of them were also found in microorganisms. There is a lot of research showing that they had multiple pharmaco-activities such as cytotoxic, antioxidant, anti-inflammatory and antibacterial activities, etc. In recent years, they have attracted extensive attention at home and abroad especially in terms of the anti-tumor activity. For further research, 69 new natural naphthoquinones reported in the last five years (2013-2017) were reviewed. They were divided into five major types: simple 1,4-naphthoquinones, furan and pyran naphthoquinones, 1,2-naphthoquinones, naphthohydroquinones and naphthoquinone polymers, which showed cytotoxic, antioxidative, anti-inflammatory and antibacterial biological activities, et al. The research of these compounds in the future was also proposed.

Anti-tumor target prediction and activity verification of Ganoderma lucidum triterpenoids / 中国中药杂志

It has reported that Ganoderma lucidum triterpenoids had anti-tumor activity. However, the anti-tumor target is still unclear. The present study was designed to investigate the anti-tumor activity of G. lucidum triterpenoids on different tumor cells, and predict their potential targets by virtual screening. In this experiment, molecular docking was used to simulate the interactions of 26 triterpenoids isolated from G. lucidum and 11 target proteins by LibDock module of Discovery Studio2016 software, then the anti-tumor targets of triterpenoids were predicted. In addition, the in vitro anti-tumor effects of triterpenoids were evaluated by MTT assay by determining the inhibition of proliferation in 5 tumor cell lines. The docking results showed that the poses were greater than five, and Libdock Scores higher than 100, which can be used to determine whether compounds were activity. Eight triterpenoids might have anti-tumor activity as a result of good docking, five of which had multiple targets. MTT experiments demonstrated that the ganoderic acid Y had a certain inhibitory activity on lung cancer cell H460, with IC₅₀ of 22.4 μmol•L ⁻¹, followed by 7-oxo-ganoderic acid Z2, with IC₅₀ of 43.1 μmol•L ⁻¹. However, the other triterpenoids had no anti-tumor activity in the detected tumor cell lines. Taking together, molecular docking approach established here can be used for preliminary screening of anti-tumor activity of G.lucidum ingredients. Through this screening method, combined with the MTT assay, we can conclude that ganoderic acid Y had antitumor activity, especially anti-lung cancer, and 7-oxo-ganoderic acid Z2 as well as ganoderon B, to a certain extent, had anti-tumor activity. These findings can provide basis for the development of anti-tumor drugs. However, the anti-tumor mechanisms need to be further studied.

Research on certified reference material of emodin in rhubarb and its alcohol extract, water extract / 中国中药杂志

The certified reference materials (CRMs) of emodin in rhubarb and its alcohol extract, water extract were developed by using quantity transfer technology from single chemical composition to the complex systems. The CRM of emodin was used for quantity transfer, and high performance liquid chromatography (HPLC) method was used to determine the contents of emodin in different matrix composition. By establishing mathematical model and calculating the parts of uncertainty, the uncertainty values were finally gotten. CRMs of emodin in rhubarb, alcohol extract and water extract were accomplished. The content values of emodin were 0.40% ±0.03%, 1.15%±0.18%, 0.16%±0.08% (k=2,P=0.95), respectively. The established method for quantity transfer has successfully solved the technical problems that the value of active ingredient of traditional Chinese medicine can't be traced to SI units. The series of CRMs are assigned as grade primary reference materials, which are useful for quality control of the emodin content, also provide the accurate and reliable CRM, materials standard and standard methods.

Triterpenoids from Ganoderma theaecolum / 中国中药杂志

Fifteenlanostane triterpenoids were isolated from the ethanol extract of Ganoderma theaecolum by means of preparative HPLC,column chromatography over silica gel,ODS and were identified as lucidone C(1),lucidone D(2),7-oxo-ganoderic acid Z2(3),7-oxo-ganoderic acid Z(4),ganoderenicacid H(5),ganoderenic acid B(6),3β,7β-dihydroyl-11,15,23-trioxo-lanost-8,16-dien-26-oic acid(7),3β,7β-dihydroyl-11,15,23-trioxo-lanost-8,16-dien-26-oic acid methyl ester(8),ganolucidic acid B(9),ganolucidate F(10),methyl ganoderate C2(11),ganoderic acid ζ(12),ganoderic acid AP3(13),methyl ganoderate B(14),and ganoderol B(15). Compounds 1-15 were isolated from this specie for the first time.

Flavonol glycosides from Lysimachia clethroides / 中国中药杂志

Eleven flavonol glycosides were isolated from the ethanol extract of Lysimachia clethroides by a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified as astragalin (1), isoquercitrin (2), isorhamnetin-3-O-β-D-glucopyranoside (3), quercetin-3-O-β-D-6"-acetylglucopyranoside (4), quercetin-7-O-β-D-glucopyranoside (5), prunin (6), 2-hydroxynaringin-5-O-β-D-glucopyranoside (7), kaempferol-3-O-rutinonoside (8), kaempferol-3-O-robinobioside (9), rutin (10) and kaempferol-3,7-di-O-β-D-glucopyranoside (11). Among them, compounds 4, 7 and 11 were obtained from the Lysimachia genus for the first time, while compounds 3, 5 and 9 were firstly reported from this plant. In the preliminary assays, compounds 2, 6 and 8 possessed significant inhibition against aldose reduc- tase, with IC50 values of 2.69, 1.00, 1.80 μmol · L(-1), respectively; none of compounds 1-11 exhibited obvious cytotoxic activity (IC50 > 10 μmol · L(-1)).

Chemical constituents from Morus notabilis and their cytotoxic effect / 药学学报

Une new flavonoids named as notabilisin K (1), together with four known compounds, morusin (2), mulberrofuran A (3), neocyclomorusin (4) and mornigrol F (5) are separated from 95% ethanol extracts of the twigs of Morus notabilis. Compounds 2-5 are separated from this plant for the first time. Notabilisin I, notabilisin J exhibits certain effect against cells of HCT-116, HepG2 and A2780 with IC50 values ranging from 1.47 μmol x L(-1) to 5.46 μmol x L(-1). Morusin exhibits strong effect against five kinds of human cancer cells (BGC823, A2780, HCT-116, HepG2 and NCI-H1650) with IC50 values ranging from 0.74 μmol x L(-1) to 1.58 μmol x L(-1).

Neuroprotective effects of the effective components group of xiaoshuantongluo against oxygen-glucose deprivation in primary cultured rat cortical neurons / 药学学报

This study is to investigate the effect of the effective components group of Xiaoshuantongluo (XECG) on neuronal injury induced by oxygen-glucose deprivation (OGD) in primary cortical cultures isolated from SD rat cortex at day 3 and the possible mechanism. Cells were divided into control group, OGD model group and XECG group (1, 3 and 10 mg x L(-1)). The cell viability was assessed with MTT assay and the LDH release rate was measured by enzyme label kit. The cell apoptosis was analyzed using Hoechst staining. RT-PCR was applied to detect the mRNA levels of JAK2 and STAT3. Western blotting was used to detect the expressions of Bcl-2, Bax, p-JAK2 and p-STAT3 proteins. Results showed that XECG resulted in an obvious resistance to oxygen-glucose deprivation-induced cell apoptosis and decrement of cell viability, decrease the cell LDH release rate. XECG could adjust the expression of Bcl-2 and Bax proteins and increase Bcl-2/Bax ratio, up-regulate the expression of p-JAK2 and p-STAT3. In conclusion, XECG could protect against the neuronal injury cells exposed to OGD, which may be relevant to the promotion of JAK2/STAT3 signaling pathway, and impact the expression of Bax and Bcl-2.

Chemical constituents of Poria cocos / 中国中药杂志

The chemical constituents of Poria cocos were studied by means of silica gel, ODS column chromatography, Sephadex LH-20 and preparative HPLC. Thirteen compounds were isolated from this plant. By analysis of the ESI-MS and NMR data, the structures of these compounds were determined as tumulosic acid (1), dehydrotumulosic acid (2), 3beta, 5alpha-dihydroxy-ergosta-7, 22-dien-6-one (3), 3beta, 5alpha, 9alpha-trihydroxy-ergosta-7, 22-diene -6-one (4), ergosta-7, 22-diene-3-one (5), 6, 9-epoxy-ergosta-7,22-diene-3-ol (6), ergosta-4,22-diene-3-one (7), 3beta, 5alpha, 6beta-trihydroxyl-ergosta-7,22-diene (8), ergosta-5, 6-epoxy-7,22-dien-3-ol (9), beta-sitosterol (10), ribitol (11), mannitol (12), and oleanic acid 3-O-acetate (13), respectively. Compounds 3-13 were isolated from the P. cocos for the first time.

Chemical constituents from Chenopodium ambrosioides / 中国中药杂志

Twelve compounds were isolated from the herb of Chenopodium ambrosioides, and their structures were identified by spectroscopic methods as kaempferol-7-O-alpha-L-rhamnopyranoside (1), kaempferol-3,7-di-O-alpha-L-rhamnopyranoside (2), patuletin (3), quercetin-7-O-alpha-L-rhamnopyranoside (4), grasshopper ketone (5), 4-hydroxy-4-methyl-2-cyclohexen-1-one (6), syringaresinol (7), benzyl beta-D-glucopyranoside (8), dendranthemoside B (9), N-trans-feruloyl tyramine (10), N-trans-feruloyl 4'-O-methyldopamine (11), and 4-hydroxy-N-[2-(4-hydroxyphenyl) ethyl] benzamide (12). Among them,compounds 3, 6-8,10, and 12 were isolated from the genus Chenopodium for the first time, and compounds 2-12 were isolated from this plant for the first time.

Flavonoids from the seeds of Alpinia galanga Willd / 药学学报

Ten flavonoids were isolated from the 95% ethanol extract of the seeds of Alpinia galanga Willd. with a combination of various chromatographic techniques, including silica gel, Sephadex LH-20 and preparative HPLC. On the basis of spectroscopic data analysis, they were elucidated as (2R, 3S)-pinobaksin-3-cinnamate (1), (2R, 3R)-pinobaksin-3-cinnamate (2), pinocembrin (3), pinobaksin (4), 3-O-acetylpinobaksin (5), galangin (6), galangin-3-methylether (7), kumatakenin (8), 3-methylkaempferol (9) and (2R, 3R)-3, 5-dihydroxy-7-methoxyflavanone (10). Among them, compound 1 is a new compound, compounds 2, 5 and 10 were isolated from the genus Alpinia for the first time, and others were isolated from this plant for the first time.

Studies on chemical constituents from fruits of Morus alba L / 药学学报

Chemical investigation of fruits of Mours alba L. lead to the isolation of fifteen compounds by various chromatographies such as silica gel, Sephadex LH-20, RP-C18 column chromatography. Their structures were determined to be: 1-[5-(2-formlfuryl) methyl] dihydrogen 2-hydroxypropane-1, 2, 3-tricarboxylate 2, 3-diethyl ester (1), 1-[2-(furan-2-yl)-2-oxoethyl] pyrrolidin-2-one (2), divaricataester A (3), methyl 1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylate (4), 1-[2-(furan-2-yl)-2-oxoethyl]-5-oxopyrrolidine-2-carboxylic acid (5), L-pyroglutamic acid (6), L-pyroglutamic acid ethyl ester (7), 3-O-caffeoylquinic acid methyl ester (8), 3-O-caffeoylquinic acid ethyl ester (9), 5-O-caffeoylquinic acid methyl ester (10), 5-O-caffeoylquinic acid ethyl ester (11), 4-O-caffeoylquinic acid methyl ester (12), 4-O-caffeoylquinic acid methyl ester (13), 4-O-caffeoylquinic acid (14), 3-O-caffeoylquinic acid (15), respectively, based on the spectral analysis such as NMR, MS etc. Compounds 1-14 were isolated from this genus for the first time, among which 1 was a new compound.

Advances of chemical constituents and pharmacological activities of schefflera genus / 中国中药杂志

The genus Schefflera (Araliaceae) consists of 1100 species, 35 of which can be found in China. Some species of the genus have been used in traditional medicine to treat rheumatalgia, trauma, fracture, headache, and so on. Phytochemical studies of the genus have demonstrated the presence of large number of triterpenoids and their saponins, along with some long-chain compounds, steroids and sesquiterpenes. Furthermore, many pharmacological activities of the genus such as anti-inflammatory, anticancer and antiviral activities have been reported. In this article, new development of constituents and biological activities of Schefflera genus is reviewed and summarized for its further development and utilization.

Chemical constituents of Camellia sinensis var. assamica / 中国中药杂志

To study the chemical constituents of Camellia sinensis var. assamica. The compounds were isolated by NKA Macroporous resin silica gel, Sephadex LH-20, RP-C18 column chromatographies and semi-preparative HPLC,and their structures were elucidated by physicochemical properties and spectral analysis. Thirteen compounds were isolated and identified as caffeine (1), theobromine (2), gallic acid (3), (+)-catechin (4), ampelopsin (5), (-)-epicatechin (6), (-)-epiafzelechin (7), (-)-epicatechin-3-O-gallate (8), (-)-epiafzelechin-3-O-gallate (9) , (+)-catechin-3-O-gallate (10) , (+)-afzelechin-3-O-gallate (11), quemefin-3-O-alpha-L-arabinopyranosid (12), and (-)-epicatechin-3-O-p-hydroxybenzoate (13). Compounds 2, 5, 10-13 were isolated from this plant for the first time, and compound 11 is a new natural product.

A new terpenoid from Ganoderma lucidum / 药学学报

A new terpenoid, lucidone D (1), has been isolated from Ganoderma lucidum. Its structure was determined to be 7beta, 15alpha-dihydroxy-4, 4, 14alpha-trimethyl-3, 11, 20-trioxo-5alpha-pregn-8-en on the basis of 1D and 2D-NMR spectral analysis.

Determination of nine triterpenoid acids from Ganoderma lucidum of different producting areas by HPLC / 中国中药杂志

<p><b>OBJECTIVE</b>To establish an HPLC method for determining nine triterpenes contained in Ganoderma lucidum.</p><p><b>METHOD</b>Chromatography conditions: Alltima C18 (4.6 mm x 150 mm, 5 microm) was adopted as the chromatographic column, with acetonitrile-0.04% formic acid solution as the mobile phase. The detective wavelength was set at 254 nm, and the column temperature was 15 degrees C.</p><p><b>RESULT</b>The linearities of ganoderic acid C2, ganoderic acid G, ganoderenic acid B, ganoderic acid B, ganoderenic acid A, ganoderic acid A, lucideric acid A, ganoderenic acid D, and ganoderic acid C1 ranged between 6.81-40.88, 6.38-38.25, 6.75-40.50, 6.38-38.25, 5.95-35.65, 5.90-35.25, 7.00-42.00, 6.20-37.15 and 6.05-36.4 mg x L(-1) (r = 0.999 4, 0.999 2, 0.999 4, 0.999 2, 0.999 2, 0.994 5, 0.999 0, 0.999 2 and 0.998 4). Their recoveries were 102.1%, 102.3%, 100.6%, 103.3%, 104.1%, 103.2%, 96.42%, 102.5% and 101.5%, with RSD being 1.5%, 0.96%, 1.9%, 1.3%, 1.7%, 2.5%, 0.62%, 2.9% and 1.3%. The content of triterpenes contained in G. lucidum samples from 31 different areas and under different cultivation conditions.</p><p><b>CONCLUSION</b>The method is so feasible and highly reproducible that it can be used for quantitatie determination of the content of triterpenoid acid contained in G. lucidum.</p>

Chemical constituents from Salvia przewalskii Maxim / 药学学报

The investigation on Salvia przewalskii Maxim was carried out to find the relationship of the constituents and their pharmacological activities. The isolation and purification were performed by various chromatographies such as silica gel, Sephadex LH-20, RP-C18 column chromatography, etc. Further investigation on the fraction of the 95% ethanol extract of Salvia przewalskii Maxim yielded przewalskin Y-1 (1), anhydride of tanshinone-II A (2), sugiol (3), epicryptoacetalide (4), cryptoacetalide (5), arucadiol (6), 1-dehydromiltirone (7), miltirone (8), cryptotanshinone (9), tanshinone II A (10) and isotanshinone-I (11). Their structures were elucidated by the spectral analysis such as NMR (Nuclear Magnetic Resonance) and MS (Mass Spectrometry). Compound 1 is a new compound. Compounds 4 and 5 are mirror isomers (1 : 3). Compounds 4, 5, 6, 8, 11 were isolated from Salvia przewalskii Maxim for the first time.

A quantitation method for andrographolide and dehydroandrographolide by X-ray powder diffraction Fourier fingerprint pattern technique / 药学学报

The powder X-ray diffraction Fourier fingerprint pattern technique was used to develop a new quantitation method for the analysis of andrographolide and dehydroandrographolide. And the high performance liquid chromatography method was used to evaluate the quantity of andrographolide and dehydroandrographolide. The relationship of diffraction peak intensity and content of andrographolide and dehydroandrographolide was investigated. The powder X-ray diffraction Fourier fingerprint pattern analysis technique can be used to evaluate the quantity of andrographolide and dehydroandrographolide in the herb simultaneously.