Comparison of Chromone Components and Their Contents between Bolting and Non-bolting Saposhnikoviae Radix / 中国药学杂志

OBJECTIVE: To establish a high performance liquid chromatography(HPLC) method for determining chromone components in Saposhnikoviae Radix, and compare the similarities and differences between bolting and non-bolting samples. METHODS: Agilent Ecilpse Plus C18 column(4.6 mm×250 mm,5 μm) was used for chromatographic analysis, water and methanol were used as mobile phase for gradient elution at a flow rate of 1 mL•min-1. Detection was conducted at 254 nm. The column temperature was maitained at 35 ℃ and the injection volume was 10 μL. RESULTS: There were 10 common peaks in the HPLC fingerprints of 8 batches of Saposhnikoviae Radix,with similarity above 0.94 in six batches of bolting and non-bolting samples and below 0.90 in two batches of second-stubble samples.The HPLC assay had good linearity for the four chromone components. The average recoveries for prim-O-glucosylcimifugin,cimicifugin, 5-O-methylvisamidol glycoside and sec-O-glu cosylhamaudol were 95.05%, 98.62%, 98.3% and 99.02%,and the RSDs of repeatability test were 1.60%, 1.77%, 1.24% and 3.09%, respectively. When comparing the bolting and non-bolting Saposhnikoviae Radix, the content of cimicifugin increased after bolting, the other three components and the total amount of the four chromone components did not have significant variation. CONCLUSION: The establishment of HPLC fingerprint combined with simultaneous determination of four chromone components provides a more comprehensive reference for the quality control and quality evaluation of Saposhnikoviae Radix. There are no obvious differences in chromone components between bolting and non-bolting Saposhnikoviae Radix, but there is significant difference between second-stubble and first-stubble Saposhnikoviae Radix.

Based on appearance and index components to study on standards of commodity classes of Saposhnikovia Radix / 中草药

Objective: A new table of standards of commodity classes of Saposhnikovia Radix is formed through literature market and local area survey. To explore the scientific nature and practicability of new standards of commodity classes of Saposhnikovia Radix, according to the appearance and index components related to quality of Saposhnikovia Radix, through statistical analysis and comparison of characteristic spectrum. Methods: Samples of different specifications and grades were collected from Northeast China, Inner Mongolia, Hebei, and the other main production areas, mainstream medicine market. Measuring samples appearance, extractum, characteristic spectrum of four chromones and analyzing data and discussing the relationship between standards of commodity classes and the appearance and index components to provide datas and theoretical support for the new table. Results: According to appearance character, the standards of commodity classes of Saposhnikovia Radix divided into three specifications of wild, imitates wild, cultivated were science based. At the same time, it is suggested to increase the content of the cimifugin as the index to distinguish between wild and cultivated Saposhnikovia Radix. Conclusion: There were significant differences in appearance and index components between different standards of Saposhnikovia Radix. Whether different classes of Saposhnikovia Radix only depend on size remains to be discussed.

Mechanism of anti-fatigue of Epimedii Folium based on network pharmacology / 中草药

Objective: To study the anti-fatigue mechanism of Epimedii Folium by network pharmacology. Methods: The main active ingredients of Epimedii Folium and the targets of active ingredients were obtained by TCMSP. The GeneCards was used to predict and screen the anti-fatigue targets. The Cytoscape 3.6.1 software was used to construct the active ingredient-disease-target network. The protein interactions network was constructed using the String database. The GO enrichment and KEGG pathways of the targets were analyzed by using DAVID database. Results: Nine active ingredients were screened from Epimedii Folium, including chrysoeriol, kaempferol, anhydroicaritin, C-homoerythrinan,1,6-didehydro-3,15,16-trimethoxy-,(3.beta.)-, 8-(3-methylbut-2-enyl)-2-phenyl- chromone, luteolin, magnograndiolide, quercetin, 8-isopentenyl-kaempferol, which acted on 31 fatigue targets such as PPARG, GABRA1, CASP3, ICAM1, etc. Biological function analysis showed that the targets of Epimedii Folium included cellular response to hypoxia, regulation of apoptotic, positive regulation of nitric oxide biosynthetic, cellular response to hydrogen peroxide, cellular response to hyperoxia, and negative regulation of lipid storage. Signaling pathway analysis showed that Epimedii Folium exerted the anti-fatigue effect by regulating PI3K-Akt, P53, HIF-1, TNF, FoxO, ErbB, MAPK, and other pathways. Conclusion: This study reflects the characteristics of multi-component, multi-target, and multi-pathway of Epimedii Folium, which provides reference for further research on the mechanism of anti-fatigue effects of Epimedii Folium.

Anti-inflammatory Chromones from Agarwood Produced Via Whole-Tree Agarwood-Inducing Technique of Aquilaria sinensis / 中国药学杂志

OBJECTIVE: To investigate the chromones and anti-inflammation effect of agarwood produced via whole-tree agarwood-inducing technique (Agar-Wit) from A. sinensis. METHODS: The constituents were isolated and purified by chromatographic technique and semi-preparation HPLC. RAW264.7 cell model induced by lipopolysaccharide was used to evaluate the anti-inflammatory activity of some compounds, and the secretion level of TNF-α was detected by ELISA. RESULTS: A new 2-(2-phenylethyl) chromone, (7'R)-2-[2-(7'-hydroxyphenyl)ethyl] chromone (1), along with nine analogues (2-10) were isolated from the agarwood produced by Agar-Wit, their structures were identified on the basis of physicochemical characteristics and spectroscopic data analysis as 6,7-dimethoxy-2-[2-(7'-hydroxyphenyl)ethyl] chromone (2), 6-hydroxy-2-[2-(7'-hydroxyphenyl)ethyl] chromone (3), 8-chloro-6-hydroxy-2-(2-phenylethyl)chromen-4-one (4), 8-chloro-6-hydroxy-2-[2-(4'-methoxyphenyl)ethyl] chromone (5), 8-chloro-6-hydroxy-2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl] chromone (6), 7-hydroxy-6-methoxy-2-(2-phenylethyl) chromone (7), 6-hydroxy-7-dimethoxy-2-[2-(4'-hydroxyethyl)] chromone (8), 6-hydroxy-2-[2-(3'-methoxy-4'-hydroxy)ethyl] chromone (9), 6-hydroxy-2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl] chromone (10). The results showed that compounds 1, 4, 6, 9 significantly inhibited the release of TNF-α inflammatory factors in RAW264.7 cells induced by LPS, with IC50 values of 13.30, 8.53, 7.72, and 10.87 μg•mL-1, respectively. CONCLUSION: Compound 1 is a new compound. The crystal structure of compound 4 is reported for the first time. Compounds 1, 4, 6, 9 show significant anti-inflammation activities.

One new 2-(2-phenylethyl) chromone derivative from agarwood of Aquilaria crassna in Cambodia / 中草药

Objective: To study the chemical constituents of agarwood originating from Aquilaria crassna in Cambodia. Methods: The compounds were isolated and purified by silica gel column chromatography and semi-preparetive HPLC and so on. Their structures were identified by spectroscopic data. All compounds were tested for cytotoxic activities against two human cancer cell lines by MTT method. Results: Four compounds were isolated and elucidated as 6-methoxy-8-hydroxy-2-(2-phenylethyl) chromone (1), 6-methoxy-7-hydroxy-2-[2-(4-methoxyphenyl) ethyl] chromone (2), 7β,8β-epoxy-6α-hydroxy-5α-methoxy-5,6,7,8-tetrahydro-2-[2-(4- methoxyphenyl) ethyl] chromone (3), and rel-(1aR,2R,3R,7bS)-5,6-epoxy-7,8-dihydroxy-5,6,7,8-tetrahydro-2-[2-(4-methoxyphenyl) ethyl] chromone (4). Conclusion: Compound 1 is a new compound, while compounds 2-4 are isolated from this agarwood for the first time. Among them, compound 4 showed inhibitory activities against SGC-7901 and A549 cells.

Chemical constituents of Cassia siamea / 中国中药杂志

A total of ten compounds were isolated from the 90% Et OH extract of Cassia siamea by using various chormatographic techniques,and their structures were established as( 2' S)-2-( propan-2'-ol)-5,7-dihydroxy-benzopyran-4-one( 1),chrobisiamone( 2), 2-( 2'-hydroxypropyl)-5-methyl-7-hydroxychromone( 3), 2,5-dimethyl-7-hydroxychromone( 4), 2-methyl-5-acetonyl-7-hydroxychromone( 5),3-O-methylquercetin( 6),3,5,7,3',4'-pentahydroxyflavonone( 7),luteolin-5,3'-dimethylether( 8),4-( trans)-acetul-3,6,8-trihydroxy-3-methyl-dihydronapht halenone( 9) and 6-hydroxymellein( 10) based on the spectroscopic data.Compound 1 was a new compound,and 3,4,6,8 were isolated from this plant for the first time.

Advance in study on chemical constituents of Saposhnikovia divaricate and their pharmacological effects / 中草药

Saposhnikovia divaricate, a kind of traditional medicinal herbs, is widely used in China. The chemical composition of S. divaricate is very complicated, whose main active substances are ketone, coumarin, volatile oil and other ingredients. The pharmacological activities of S. divaricate are mainly concentrated in the antipyretic, analgesic, anti-inflammatory, and other aspects. In this paper, the literatures on the chemical composition and pharmacological effects of S. divaricate at home and abroad are summarized, and some suggestions are put forward for future research. The aim is to provide theoretical reference for the development and utilization and in-depth study of S. divaricate.

Quality Analysis of Eaglewood Induced by New Stimulation Technology / 广州中医药大学学报

Objective To evaluate the quality of different parts of agarwood formed by stimulation with biological induction method, thus to provide evidence for agarwood quality control. Methods The identification of agarwood and the determination of alcohol extracts from agarwood were achieved by the methods of Chinese Pharmacopeia. The determination of total chromones from agarwood was achieved by ultraviolet spectrophotometry(UVS), with aquilarone E as reference substance and 760 nm as the detective wavelength. Results The UVS method was stable within 5 h and the recovery rate was 95.71%(sR=2.09%). The average alcohol extract content of the outside part of the xylem of Aquilaria sinensis(Lour.) Gilg(part B) was 109.4 mg/g,which was higher than that (100 mg/g) of the Chinese Pharmacopoeia standard. The average content of total chromones was 15.73 mg/g. The rest identification results were accorded with the requirements of Chinese Pharmacopeia. The average alcohol extract content of the inside part of the xylem(part Z) was 47.6 mg/g, and the average content of total chromones was 2.66 mg/g. The rest identification results did not reach the requirements of Chinese Pharmacopeia. Conclusion The obtained part B of the agarwood meets the requirements of Chinese Pharmacopeia, while part Z has color changed and its quality has not yet reached the requirements. The results indicated that the biological induction method impacts Aquilaria sinensis xylem from outside to inside, and then the xylem grows into agarwood gradually.

A new 2-(2-phenylethyl) chromone from Chinese eaglewood / 中草药

Objective: To study the chemical constituents of Chinese eaglewood. Methods: The column chromatography on silica gel, Sephadex LH-20, and semi-preparative HPLC were used to separate and purify the compounds, their structures were elucidated by NMR and MS analyses. Results: Four compounds were isolated from the petroleum ether of Chinese eaglewood and identified as 6-methoxy-7-hydroxy-2-(2-phenylethyl) chromone (1), 6,7-dimethoxy-2-(2-phenylethyl) chromone (2), 6,7-dimethoxy-2-[2-(4'- methoxyphenyl) ethyl] chromone (3), and 6-methoxy-2-[2-(3'-methoxy-4'-hydroxyphenyl) ethyl] chromone (4). Conclusion: Compound 1 is a new compound named as Aquilarone J, and compound 4 is isolated from Chinese eaglewood for the first time.

Cucumin S, a new phenylethyl chromone from Cucumis melo var. reticulatus seeds

ABSTRACTA new phenylethyl chromenone, cucumin S [(R)-5,7-dihydroxy-2-[1-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]chromone] (1), along with five known compounds: 5,7-dihydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (2), 5,7-dihydroxy-2-[2-(3,4-dihydroxyphenyl)ethyl]chromone (3), luteolin (4), quercetin (5), and 7-glucosyloxy-5-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (6) were isolated from the EtOAc fraction of Cucumis melo var. reticulatus Ser., Cucurbitaceae, seeds. Their structures were determined by spectroscopic means (1D and 2D NMR), as well as HRESIMS, optical rotation measurement, and comparison with literature data. The isolated compounds 1–6 were assessed for their antioxidant activity using DPPH assay. Compounds 3, 4, and 5 showed potent activities compared to propyl gallate at concentration 100 µM.

Chemical constituents of Gleditsiae Spina and their antitumor activity / 中草药

Objective: To investigate the chemical constituents from Gleditsiae Spina (the thorns of Gleditsia sinensis) and their antitumor activitives. Methods: The chemical constituents were isolated and purified by the chromatography on repeated silica gel, Sephadex LH-20 column, semi-preparative HPLC, etc. Their structures were elucidated by NMR and MS spectroscopic data analyses; The cytotoxicity of compounds 1-4 and 6 was evaluated against human liver cancer SK-HEP-1 cells by MTT assay. Results: Twelve compounds were isolated from Gleditsiae Spina, and identified as 2-aminoimidazole (1), 2,3-dihydro-5-(2-formylvinyl)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-benzofuranmethanol (2), E-cinnamic acid (3), 3-O-trans-feruloylquinic acid (4), trans-caffeic acid (5), 4-hydroxy-3-methoxybenzamide (6), threo-guaiacylglycerol-β-coniferyl aldehyde ether (7), 5,7-dihydroxy-chromone (8), vanillic acid (9), protocatechuic acid (10), 3-O-caffeoylquinic acid methyl ester (11), and 3-O-caffeoylquinic acid ethyl ester (12); Compound 1 exhibited the potent cytotoxicity against SK-HEP-1 cells with IC50 value of 34.47 μg/mL. Conclusion: All the compounds except compound 5 are isolated from the plants of Gleditsia L. for the first time; Compound 1 shows significant cytotoxic activity against SK-HEP-1 cells.

A new chromone glycoside from Dryopteris fragrans (II) / 中草药

Objective: To study the chemical constituents from the whole plants of Dryopteris fragrans. Methods: The chemical constituents were isolated by various column chromatographic methods. The structures of the compounds were elucidated on the basis of physiochemical properties and spectral analyses. Results: Three compounds named 2-isopropyl-5, 7-dihydroxy-1'-O-β-D-glucopyranosyl chromone (1), (6R, 9R)-3-oxo-α-ionol-9-O-β-D-glucopyranoside (2), and taxicatin (3) were isolated and identified. Conclusion: Compound 1 is a new compound named frachromone B, compounds 2 and 3 are reported for the first time from family Dryopteridaceae.

A new chromone glycoside from Dryopteris fragrans / 中草药

Objective: To study the chemical constituents from the whole plants of Dryopteris fragrans. Methods: The chemical constituents were isolated by various column chromatographic methods. The structures of the compounds were elucidated on the basis of physiochemical properties and spectral analysis. Results: Four compounds named 2-ethyl-5, 7-dihydroxy-1'-O-β-Dglucopyranosyl chromone (1), vitexin (2), isoquercitrin (3), and divarin-3-O-β-glucopyranoside (3-hydroxy-5-propylphenyl-O-β-Dglucopyranoside, 4) were isolated and identified. Conclusion: Compound 1 is a new compound named as frachromone A, compound 2 is obtained from this plant for the first time, and compound 4 is reported for the first time from the plants of family Dryopteridaceae.

Synthesis of novel 3-(substituted phenyl) chromone derivatives and their anti-tumor activities / 第二军医大学学报

Objective: To search for new isoflavones with more potent antitumor activities from the target compounds synthesized by inserting a double bond or an acetylene bond between chromone and its 3-substituted phenyl, ester and hydroxymethyl groups, or by formation of an amide of 3′ or 4′-amino group of isoflavones with norcantharidin. Methods: The key intermediate 3-iodo-7-methoxyl-4H-chromen-4-one (5) was prepared with 2-hydroxyl-4-methoxyl- acetophenone and ethyl formate. The target compounds with 3-substituted double bond or acetylene groups were synthesized by Heck coupling and Sonogashira coupling reaction; the amide compounds were synthesized by Suzuki coupling reaction and amide formation of 3′ or 4′-amino group of isoflavones with norcantharidin. All of the target compounds were confirmed by 1HNMR, MS and IR spectra. The IC50 values of target compounds were determined by the standard method using two kinds of human tumor cell lines, colon cancer cell line HCT116 and liver cancer cell line SMMC 7721 to study their anti-tumor activities. Results: All the 17 target compounds obtained had certain anti-tumor effect in vitro, with compounds 7h and 7e showing better anti-tumor effects, which were similar to that of control curcumin and more potent than that of genistein in vitro. Conclusion: The insertion of a double bond or an acetylene bond between chromone and its 3-substituted phenyl, ester and hydroxymethyl groups may promote the anti-tumor activities of isoflavone analogues. It seems that the formation of an amide of 3′- or 4′-amino group of isoflavones with norcantharidin has no noticeable promotion effect on the anti-tumor activities.

The chemical constituents of Rhododendron ovatum Planch / 药学学报

Aim To study the chemical constituents of Rhododendron ovatum Planch. Methods The chemical constituents were isolated and purified by silica gel column chromatography and identified on the basis of their physiochemical and spectral data. Results Seven compounds were isolated and identified. Their structures were established as 3,5,7-trihydroxylchromone 3-O-β-D-xylopyranoside (I), taraxerol (II), β-sitosterol (III), betulinic acid (IV), quercetin (V), quercetin-3-O-α-L-rhamnopyranoside (VI), and D-glucose (VII). Conclusion Compound I is a new compound. Compounds II-VII were isolated from this plant for the first time.

Chromones from Angelica morri Hayata / 中国药科大学学报

AIM:Bioactive constituents were expected to be obtained from the roots of Angelica morri Hayata. METHOD:They were extracted with 95% alcohol and isolated by using column chromatography and recrystallization methods. The structures were elucidated by means of physico-chemical data and UV,IR,1HNMR, 13CNMR,and EIMS. The inhibitory effect on the constriction of rat aortic rings was induced by K+ or Ca2+. RESULT:3′S-(-)-hamaudol,3′S-(-)-Ο-acetylhamaudol,3′R-(+)-hamaudol,and (±)-hamaudol were isolated from the pieces of Radix Angelica Morri. The inhibitory rate of 3′S-(-)-Ο-acetylhamaudol and (±)-hamaudol on the above pharmacologic model appears the relation of quantity response. CONCLUSION:All the above compounds were found in this species for the first time,and(±)-hamaudol is a new. One of effect mechanisms of 3′S-(-)-Ο-acetylhamaudol and (±)-hamaudol diluted aorta could contribute to be inhibiting Ca2+ influx of vascular smooth muscle.

Chemical constituents of Lignum Aquilariae Resinatum(Ⅱ) / 中草药

Objective To study the chemical constituents of Lignum Aquilariae Resinatum.MethodsThe compounds were isolated and purified by silica chromatography and their structures were identified on the basis of physicochemical constant and spectral analysis.Results The compounds were determined as 6-hydroxy-2-[2-(3'-methoxy-4'-hydroxy phenylethyl)] chromone(Ⅰ)and a triterpene,hederagenin(Ⅱ).Conclusion Compound I is a new compound and compound Ⅱ is found in this plant for the first time.

Induction of chromones in excised lateral roots culture of Aquilaria sinensis / 中草药

Objective To study the biosynthesis of the second metabolites in Aquilaria sinensis.Methods Chromones of agarwood were elicited by tissue culture and the inducer contents were determined by HPLC.Results 2-(2-Phenylethyl) chromones could be elicited in excised lateral roots suspension culture of A.sinensis.Conclusion Fungal extracts of Menanotus flavolives could induce the production of characteristic components of agarwood in A.sinensis.

Search for the substances causing allergic contact dermatitis by chrysanthemums on the growers / 日本農村医学会雑誌

Since 1976, allergic contact dermatitis caused by <I>Chrysanthemum morifolium</I> Ramalk (commercial name: Kinriki) occured on the grower in Tokushima Prefecture. Consequently, a systematic study aimed at the isolation of the allergen of the chrysanthemum was udertaken.<BR>The allergens were contained in the fresh juice of the leaves of chrysanthemum and they were of two types: one was water-soluble and the other was fat-soluble, judging from the results of application test of the skin reaction for sensitized guinea pigs.<BR>The fresh juice of the chrysanthemums was fractionated with ammonioum sulfate saturation method and the active precipitates were chromatographed on Sephacryl S-300 and DEAE-cellulose column, successively. The most active fractions contained sugar and protein, suggesting that the water-soluble principles are high molecular glyco-protein. The other hand fat-soluble fraction was obtained from ethyl acetate extract of the supernatant of 65% ammonium sulfate saturation. The extract was chromatographed on silica gel column and on the thin layer to yield 5, 7-dihydroxychromone (I) and sesquiterpens (II-VI). Unfortunately, at that time the sensitization of ginea pigs was unsuccessfuly. Therefore their compounds could not be tested for the allergenic reaction.<BR>When the precipitates of ammonium sulfate were extrcted with ethyl acetate, the allergenic activeity of the precipitates decreased. However, re-addition of the ethyl acetate extracts to the extracted precipitates recovered the activity. Cross reaction between the juice of leaves and sesquiterpene lactone, alantolactone, failed on skin reaction of sensitized ginea pigs.