东风桔化学成分研究

东风桔是芸香科酒饼簕属植物,学名为Atalantia buxifolia (Poir)Oliv,民间用于去瘀去痛,顺气化痰,治跌打肿痛,风湿痛,疟疾。药理试验证明,东风桔叶有明显的抗疟作用。有效成分不明。东风桔化学成分前人有过报道,但国内对东风桔叶化学成分尚末进行过研究。为阐明其有效成分,我们对其化学成分进行了研究,从叶子的石油醚提取部位     

Two novel flavanes from the leaves of Morus alba L.

Two new flavanes, (2R,4S)-2′,4′-dihydroxy-2H-furan-(3″,4″:8,7)-flavan-4-ol (1) and (2S)-2′,4′-dihydroxy-7-methoxyl-8-butyricflavane (2), together with four known flavonoids, were isolated from the leaves of Morus alba L. Their structures were determined on the basis of spectroscopic analysis.     

Three new C-flavonoids from Corallodiscus flabellata

Three new C-glycosylflavones, named 5,7,4′-trihydroxy-6-methoxy-8-C-[β-d-xylopyranosyl- (1 → 2)]-β-d-glucopyranosyl flavonoside (1), 5,7,4′-trihydroxy-8-methoxy-6-C-[β-d-xylopyranosyl-(1 → 2)]-β-d-glucopyranosyl flavonoside (2), and 5,3′,4′-trihydroxy-7,8-dimethoxy-6-C-[β-d-xylopyranosyl-(1 → 2)]-β-d-glucopyranosyl flavonoside (3), along with two known compounds 5,4′-dihydroxy-7-methoxy-6-C-glucopyranosyl-flavonoside (4), 3-methoxy-4-hydroxymethyl benzoate (5) were isolated from 70% acetone extract of Corallodiscus flabellata. Their structures were identified on the basis of spectroscopic techniques and chemical methods.     

Four new isoflavones from Ampelopsis grossedentata

Four new isoflavones have been isolated from the BuOH extract of Ampelopsis grossedentata Hand.-Mazz. Based on spectral and chemical methods, their structures were elucidated as 6,7-dihydroxy-3'-methoxy-4',5'-methylenedioxyisoflavone 1; 6,7-dihydroxy-3'-methoxy-4',5'-methylenedioxyisoflavone 6-O- g - d -glucopyranoside 2; 6,7-dihydroxy-3'-methoxy-4',5'-methylenedioxyisoflavone 6-O- f -L-rhamnopyranoside 3; 6,7-dihydroxy-3'-methoxy-4',5'-methylenedioxyisoflavone 6-O- g -D-xylopyranosyl-(1-6)- g -D-glucopyranoside 4. This is the first report on isolation of isoflavones from this plant.     

Two new bioactive prenylated dihydroflavanoids from the medicinal plant Dolichos tenuicaulis (Baker) Craib

Two new prenylated dihydroflavanoids have been isolated from the medicinal plant of Dolichos tenuicaulis (Baker) Craib. Their structures were elucidated as (2S)-5,2′,6′-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethylpyrano)-3′,4′-(2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (1) and (2S)-5,2′,6′-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (2) on the basis of spectroscopic analysis.     

Novel 19F‐MRS β‐galactosidase reporter molecules incorporated nitrogen mustard analogues

In this study, we propose a novel molecular platform‐integrated fluorinated antitumor nitrogen mustards for ¹⁹F‐MRS assay of β‐galactosidase (β‐gal) activity. Following this idea, we have designed, synthesized, and characterized 2‐fluoro‐4‐[bis(2′‐chloroethyl)amino]phenyl β‐D‐galactopyranoside 5 , 2‐fluoro‐4‐{bis[2′‐O‐(β‐D‐galactopyranosyl)ethyl]amino}phenyl β‐D‐galactopyranoside 8 , 2‐fluoro‐4‐{bis[[1″‐(β‐D‐galactopyranosyl)‐1″, 2″, 3″‐triazol‐4″‐yl]methyl] amino}phenyl β‐D‐galactopyranoside 14 and 2‐fluoro‐4‐{bis[[1″‐(β‐D‐glucopyranosyl)‐1″, 2″, 3″‐triazol‐4″‐yl]methyl]amino}phenyl β‐D‐galactopyranoside 15 through glycosylation and click reaction strategies, and their structures were confirmed by NMR and HRMS or elemental analysis data. Among them, 2‐fluoro‐4‐[bis(2′‐chloroethyl)amino]phenyl β‐D‐galacto‐pyranoside 5 was found very sensitive to β‐gal (E801A) in PBS at 37°C with big Δδ_F response. Here, we demonstrated the feasibility of this platform for assessing β‐gal activity in solution, and in vitro with lacZ‐transfected human MCF7 breast and PC3 prostate tumor cells, by the characterization of β‐gal‐responsive ¹⁹F‐chemical shift changes Δδ_F and hydrolytic kinetics.     

Evaluation of the Antioxidant,Hepatoprotective, and Anti-Inflammatory Activities of Bisresorcinol Isolated from the Trunk of Heliciopsis Terminalis

Pharmaceutical Chemistry Journal - A bisresorcinol, (8′Z)-3,5-dihydroxy-1-[16′-(3″,5″-dihydroxyphenyl)-8′-hexadecen-1′-yl]benzene (I), was isolated as an...     

Patent Evaluation: Benzanilide derivatives as 5-HT1D antagonists

Summary

Novelty: Novel benzanilide derivatives are claimed to be 5-HT₁₀ antagonists. They are potentially useful for the treatment of depression, Parkinson's disease and a variety of CNS disorders including anxiety, panic and memory disorders.

Biology: No biological data are disclosed.

Chemistry: A total of forty-six final compounds and fifty-one intermediates are disclosed. Syntheses are given in all cases. Yields, mps and some ¹H nmr data are given. Twenty-five compounds are specifically claimed including 4′-cyano-N4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-2′-methyl-[1,1′-biphenyl]-4-carboxamide.     

Chalcones isolated from <Emphasis Type="Italic">Angelica keiskei</Emphasis> and their inhibition of IL-6 production in TNF-α-stimulated MG-63 cell

Six chalcone compounds, 2′,4′,4-trihydroxy-3′-[2-hydroxy-7-methyl-3-methylene-6-octaenyl]chalcone (1), 2′,4′,4-trihydroxy-3′-geranylchalcone (2), 2′,4′,4-trihydroxy-3′-[6-hydroxy-3,7-dimethyl-2,7-octadienyl]chalcone (3), 2′,4-dihydroxy-4′-methoxy-3′-[2-hydroperoxy-3-methyl-3-butenyl]chalcone (4), 2′,4-dihydroxy-4′-methoxy-3′-geranylchalcone (5), and 2′,4-dihydroxy-4′-methoxy-3′-[3-methyl-3-butenyl]chalcone (6) were isolated from the leaves of Angelica keiskei K (Umbelliferae). The structure of each isolated compound was determined using spectroscopic methods. Among the isolates, compounds 1–3 appeared to have potent inhibitory activity of IL-6 production in TNF-α-stimulated MG-63 cell, while compounds 4–6 did not. The distinct structural difference between compounds 1–3 and 4–6 was the presence of C-4′ hydroxyl group in the chalcone moiety. Our results imply that the inhibitory activity of IL-6 production in TNF-α-stimulated MG-63 cell may be affected by the presence of C-4′ hydroxyl group in the chalcone moiety.     

Polygala molluginifolia A. St.-Hil. and Moq. prevent inflammation in the mouse pleurisy model by inhibiting NF-κB activation

This study was conducted to investigate the anti-inflammatory activity of Polygala molluginifolia (Polygalaceae) on the mouse pleurisy model induced by carrageenan. P. molluginifolia is a plant native to southern Brazil that is popularly called “canfora”. The Polygala genus is used to treat different pathologies, including inflammatory diseases, in traditional medicine.Material and methodsThe whole P. molluginifolia plant material was extracted by maceration with 96% ethanol. The crude hydroalcoholic extract (CE) was subjected to chromatographic procedures to produce various derivate fractions, including its aqueous (Aq), ethyl acetate (EtOAc), and hexane (Hex) fractions. Compound 1 (5,3′,4′-trihydroxy-6″,6″-dimethylpyrano [2″,3″:7,6] isoflavone) (Iso), which was isolated from the EtOAc fraction, and Compound 2 (rutin) (Rut), which was isolated from the Aq fraction, were identified using ¹H and ¹³C NMR spectroscopy and quantified using an HPLC apparatus.ResultsThe CE, the Aq, EtOAc, and Hex fractions, and the isolated compounds Iso and Rut were able to reduce cell migration and exudation. Furthermore, the plant material also decreased the myeloperoxidase (MPO) and adenosine-deaminase (ADA) activities and the nitric oxide (NO_x), tumor necrosis factor-alpha (TNF-α), and interleukin-1 beta (IL-1β) levels. In addition, Iso and Rut reduced the TNF-α and IL-1β mRNA expression levels and significantly decreased NF-κB p65 phosphorylation.ConclusionThe results show that P. molluginifolia has a significant anti-inflammatory action and that this effect is due, at least in part, to the presence of Iso and Rut in large amounts. Moreover, this effect was found to be closely related to the inhibitory effects of the isolated compounds on the NF-κB pathway.     

Isoflavanones from Desmodium oxyphyllum and their cytotoxicity

Two new isoflavanones, (3R)-7-hydroxy-4′-methoxy-5-methoxycarbonyl-isoflavanone (1) and (3R)-8-hydroxy-4′-methoxy-7-methoxycarbonyl-isoflavanone (2), together with seven known isoflavanones (3–9) were isolated from Desmodium oxyphyllum of the Leguminosae family. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compound 1 showed good cytotoxicity against NB4 and SHSY5Y cell lines with IC₅₀ values of 3.1 and 2.5 μM; compound 2 exhibited cytotoxicity against PC3 cell lines with a IC₅₀ value of 3.6 μM; compound 4 showed cytotoxicity against A549 and SHSY5Y cell lines with IC₅₀ values of 3.6 and 2.8 μM; and compound 5 displayed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC₅₀ values of 2.6, 3.8, and 2.8 μM, respectively. Other compounds also showed moderate cytotoxicity for some tested cell lines with IC₅₀ values between 5.4 and 8.8 μM.     

Two new selaginellin derivatives from Selaginella tamariscina (Beauv.) Spring

Two new selaginellin derivatives, selaginellins K (1) and L (2), were isolated from Selaginella tamariscina (Beauv.) Spring and characterized as 2-formyl-4,4′-dihydroxy-3-[(4-hydroxyphenyl)ethynyl]biphene and 4,4′-dihydroxy-2-methyl-3-[(4-hydroxyphenyl)ethynyl]biphene on the basis of their spectroscopic data including UV, IR, 1D, and 2D NMR as well as HR-ESI-MS spectroscopic analysis.     

Development and Validation of Liquid Chromatography Method for Quantification of the Active Markers of Hintonia standleyana. and Hintonia latiflora. Crude Drugs

Abstract

The infusions prepared from the stem-bark of Hintonia latiflora. (Sesse et Mociño ex DC) Bullock or Hintonia standleyana. Bullock (Rubiaceae) are indistinctly used in Mexican traditional medicine for the treatment of non–insulin-dependent diabetes mellitus and malaria fevers. Suitable high-performance liquid chromatography (HPLC)-UV methods for quantitative determination of 5-O.-[β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranosyl]-7-methoxy-3′,4′-dihydroxy-4-phenylcoumarin (1) and 5-O.-[β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranosyl]-7-methoxy-3′,4′-dihydroxy-4-phenylcoumarin (2) in the infusions of H. standleyana. and H.. latiflora., respectively, were established. Coumarins 1 and 2 are the major antihyperglycemic compounds found in the infusions prepared from stem-bark of H. standleyana. and H.. latiflora., respectively, and are proposed as the active markers. The methods were found to be reliable, reproducible, and accurate.     

Antioxidant and α-amylase inhibitory activities of extract and isolates from Zygogynum pancheri subsp. arrhantum

One new sesquiterpenoid (5R^*,8R^*,9R^*,10R^*)-cinnamolide (8), and seven known compounds, 5-hydroxy-7-methoxyflavonone (1), 8-hydroxy-3-(4′-hydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (2), 8-hydroxy-3-(3′,4′-dihydroxyphenyl)-6,7-(2″,2″-dimethylchromene)-tetralone (3), 1β-E-O-p-methoxycinnamoyl-bemadienolide (4), 1β-O-(E-cinnamoyl)-6α-hydroxy-9-epi-polygodial (5), 1β-O-(E-cinnamoyl)-6α-hydroxypolygodial (6), and 1β-O-E-cinnamoylpolygodial (7) were isolated from the ethyl acetate extract of barks of Zygogynum pancheri subsp. arrhantum (Winteraceae). The structures of these molecules were assigned predominantly based on spectral data. The structure of compound 8 was confirmed by X-ray crystallographic analysis. Compounds 2 and 3 exhibited significant antioxidant activity, whereas compounds 1 and 4–7 showed significant α-amylase inhibitory activity.     

A new cytotoxic homoisoflavonoid from Dracaena cambodiana

A new homoisoflavonoid, named cambodianol (1), together with the two known flavanes, (2S)-7,3′-dihydroxy-4′-methoxy-8-methylflavane (2) and (2R)-7,4′-dihydroxy-8-methylflavane (3), were isolated from the stems of Dracaena cambodiana. Their structures were determined based on HR-ESI-MS and spectroscopic techniques (UV, IR, 1D-, and 2D-NMR). Compound 1 exhibited significant cytotoxic activities against K562 and SGC-7901 with the IC₅₀ values of 1.4 and 2.9 μg/ml, respectively.     

New synthesis of 6″-[18F]fluoromaltotriose for positron emission tomography imaging of bacterial infection

6″-[¹⁸F]fluoromaltotriose is a positron emission tomography tracer that can differentiate between bacterial infection and inflammation in vivo. Bacteria-specific uptake of 6″-[¹⁸F]fluoromaltotriose is attributed to the targeting of maltodextrin transporter in bacteria that is absent in mammalian cells. Herein, we report a new synthesis of 6″-[¹⁸F]fluoromaltotriose as a key step for its clinical translation. In comparison with the previously reported synthesis, the new synthesis features unambiguous assignment of the fluorine-18 position on the maltotriose unit. The new method utilizes direct fluorination of 2″,3″,4″-tri-O-acetyl-6″-O-trifyl-α-D -glucopyranosyl-(1-4)-O-2′,3′,6′-tri-O-acetyl-α-D-glucopyranosyl-(1-4)-1,2,3,6-tetra-O-acetyl-D-glucopyranose followed by basic hydrolysis. Radiolabeling of the new maltotriose triflate precursor proceeds using a single HPLC purification step, which results in shorter reaction time in comparison with the previously reported synthesis. Successful synthesis of 6″-[¹⁸F]fluoromaltotriose has been achieved in 3.5 ± 0.3% radiochemical yield (decay corrected, n = 7) and radiochemical purity above 95%. The efficient radiosynthesis of 6″-[¹⁸F]fluoromaltotriose would be critical in advancing this positron emission tomography tracer into clinical trials for imaging bacterial infections.     

Two new stilbenoids from Pleione bulbocodioides

Two new stilbenoids, 9-(4′-hydroxy-3′-methoxyphenyl)-10-(hydroxymethyl)-11-methoxy-5,6,9,10-tetrahydrophenanthro[2,3-b]furan-3-ol (1) and 2-(4″-hydroxybenzyl)-3-(3′-hydroxyphenethyl)-5-methoxy-cyclohexa-2,5-diene-1,4-dione (2), together with the three known stilbenoids were isolated from the tubers of Pleione bulbocodioides (Franch.) Rolfe. Their structures were elucidated by spectroscopic methods.     

Cytotoxic activity of coumarins from Micromelum minutum

The crude petroleum ether and chloroform extracts of Micromelum minutum (G. Frost.) Wright & Arn (Rutaceae) showed strong cytotoxic activity when tested against a T-lymphoblastic leukemia cell line. Further fractionation of the extracts resulted in the isolation of five new coumarins 3″,4″-dihydrocapnolactone, 2′,3′-epoxyisocapnolactone, 8-hydroxyisocapnolactone-29,39-diol, 8-hydroxy-3″,4″-dihydrocapnolactone-29,39-diol and 8,4″-dihydroxy-3″,4″-dihydrocapnolactone-29,39-diol, and two triterpenes. Some of these compounds were strongly active against T-lymphoblastic leukemia (CEM-SS), promyeolocytic leukemia (HL60), cervical cancer (HeLa) and liver cancer (HepG2) cell lines. 8-Hydroxyisocapnolactone-29,39-diol was found to be the most active with IC₅₀ values of 2.9, 2.5, 6.9, and 5.9 μg/ml, respectively. This was followed by 2′,3′-epoxyisocapnolactone. When evaluated against the normal mouse fibroblast (3T3) cell line, 8-hydroxyisocapnolactone-29,39-diol was found to be inactive, hence it could serve as a valuable lead for further design and synthesis of more active analogues.     

New anthraquinone dimer from the root bark of Cassia artemisioides (Gaudich. Ex. DC) Randell

The phytochemical investigation of the root bark of Cassia artemisioides (Gaudich. Ex. DC) Randell resulted in the isolation of one new anthraquinone 1,1′-dihydroxy-3,3′-dimethyl-8,8′-dimethoxy-6,6′-O-bianthraquinone (1) along with four known anthraquinones 1,6-dihydroxy-8-methoxy-3-methylanthraquinone (2), 1-hydroxy-8-methoxy-3-methylanthraquinone (3), 1,8-dihydroxy-6-methoxy-3-methylanthraquinone (4), and 1,6,8-trihydroxy-3-methylanthraquinone (5). The structures of the compounds were elucidated using spectroscopic techniques including 1D and 2D NMR. The compounds were evaluated for antioxidant activity. 1,6,8-Trihydroxy-3-methyl anthraquinone (5) showed good activity among the tested compounds.     

Cytotoxic C-Methylated Chalcones from Syzygium samarangense.

Abstract

The flavonoids 2′-hydroxy-4′,6′-dimethoxy-3′-methylchalcone (1), 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone (2), 2′,4′-dihydroxy-6′-methoxy-3′-methylchalcone (3), 2′,4′-dihydroxy-6′-methoxy-3′-methyldihydrochalcone (4) and 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethyldihydrochalcone (5), isolated from Syzygium samarangense. (Blume) Merr. & L.M. Perry (Myrtaceae), were subjected to cytotoxicity testing using the dimethylthiazoldiphenyl tetrazolium (MTT) assay. The cell lines used were the Chinese hamster ovarian (CHO-AA8) and the human mammary adenocarcinoma, (MCF-7 and SKBR-3). Among the test compounds, 2 exhibited significant differential cytotoxicity against the MCF-7 cell line with an IC₅₀ of 0.0015 ± 0.0001 nM. It was also cytotoxic against the SKBR-3 cell line with an IC₅₀ of 0.0128 ± 0.0006 nM. Doxorubicin, the positive control, had an IC₅₀ of 2.60 ± 0.28 × 10^?4 nM against the MCF-7 cell line and an IC₅₀ of 2.76 ± 0.52 × 10^?5 nM against the SKBR-3 cell line. When tested in a mechanism-based yeast bioassay for detecting DNA-damaging agents using genetically engineered Saccharomyces cerevisiae. RS322Y (RAD52) mutant strain and (LF15/11) (RAD+) wild-type strain, 2 showed significant selective cytotoxicity against the RAD52 yeast mutant strain. It had an IC₁₂ of 0.1482 nM, as compared with the positive control, streptonigrin, which had an IC₁₂ of 0.0134 nM. Hence, 2 is a cytotoxic natural product with potential anticancer application.