D-奎尼酸: 一个多用途的手性合成子

综述了D-奎尼酸在各种环状和链状生物活性化合物合成中的应用。奎尼酸分子中特有的顺式γ-羟基羧酸的结构单元提供了区别分子中各种羟基,以及进行其它区域选择性和立体选择性控制的方便途径。奎尼酸的结构特征以及其价廉、易得的优点,使之成为一个有用的而且重要的手性合成子。     

New Quinic Acid Derivatives from Hepatoprotective Inula crithmoides Root Extract

Fractionation directed by hepatoprotective activity of Inula crithmoides L. root resulted in the isolation of two new quinic acid derivatives, 3,5‐di‐O‐caffeoylquinic acid 1‐methyl ether ( I ; caffeoyl=(E)‐3‐(3,4‐dihydroxyphenyl)prop‐2‐enoyl; quinic acid=1,3,4,5‐tetrahydroxycyclohexanecarboxylic acid) and 4,5‐di‐O‐caffeoylquinic acid 1‐methyl ether ( II ), in addition to the well‐known hepatoprotective compound, 1,5‐di‐O‐caffeoylquinic acid ( III ). The hepatoprotective effect was indicated by the significant decrease in the level of four measured serum biochemical parameters (SGOT, SGPT, ALP, and bilirubin) in experimental rats. The structures of the isolated compounds were determined by analyses of 1D‐ and 2D‐NMR spectroscopic data.     

A new coruleoellagic acid derivative from stems of Rhodamnia dumetorum

A new coruleoellagic acid derivative, 3,3′,4,4′,5′-pentamethylcoruleoellagic acid (1) together with nine known compounds, hexamethylcoruleoellagic acid (2), 3,4,3′-tri-O-methylellagic acid (3), heptaphylline (4), 7-methoxymukonal (5), dentatin (6), sinapaldehyde (7), gallic acid (8), 2,6-dimethoxy-4H-pyran-4-one (9) and β-sitosterol (10) were isolated from the stems of Rhodamnia dumetorum. Their structures were identified by physical and spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds 1, 2 and 7-10 were tested for antibacterial activity against six pathogenic bacterial strains (Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica serovar Typhimurium, Staphylococcus aureus, and Methicillin resistant S. aureus (MRSA)).     

A new ellagic acid derivative from Polygonum runcinatum

A new ellagic acid derivative, 3,3′-dimethylellagic acid-4′-O-(6″-galloyl)-β-d-glucoside, named runcinatside (5), together with four known compounds 3,3′-dimethylellagic acid (1), 3,3′,4′-trimethylellagic acid (2), 3,3′-dimethylellagic acid-4′-O-β-d-glucoside (3) and 3-methylellagic acid-4′-O-α-l-rhamno-pyranoside (4), was isolated from the roots of Polygonum runcinatum Buch.-Ham. ex D.Don Var. sinense Hemsl and the structures of these compounds were established by spectroscopic methods and comparison with previously reported data. All compounds showed antioxidant activities in vitro and compound 5 possessed the highest activity.     

cis-decalins from quinic acid: toward a synthesis of branimycin

[reaction: see text] Starting from (-)-quinic acid an efficient synthesis of highly functionalized cis-alpha,beta-unsaturated ketone 3, an advanced precursor of branimycin, has been accomplished via two key step reactions: a ring closing metathesis reaction to prepare the cis-decalin system, and a highly stereoselective epoxidation reaction.     

A new flavane acid from the fruits of Illicium verum

A new compound, illiciumflavane acid (1), along with 13 known compounds (2–14), were isolated from the fruits of Illicium verum Hook. F. Their structures were elucidated through various spectroscopic methods, including 1D NMR (¹H NMR, ¹³C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centres was determined using CD spectrum as well as analyses of coupling constants and optical rotation data. Cytotoxicity evaluation of four compounds showed that illiciumflavane acid and (E)-1,2-bis(4-methoxyphenyl)ethene exhibited potential against A549 activities with IC₅₀ values of 4.63 μM and 9.17 μM, respectively.     

A new chromanone acid from the stem bark of Calophyllum teysmannii

A new chromanone acid, namely caloteysmannic acid (1), along with three known compounds, calolongic acid (2), isocalolongic acid (3) and stigmasterol (4) were isolated from the stem bark of Calophyllum teysmannii. All these compounds were evaluated for their cytotoxic and antioxidant activities in the MTT and DPPH assays, respectively. The structure of compound 1 was determined by means of spectroscopic methods including 1D and 2D NMR experiments as well as HR-EIMS spectrometry. The stereochemical assignment of compound 1 was done based on the NMR results and X-ray crystallographic analysis. The preliminary assay results revealed that all the test compounds displayed potent inhibitory activity against HeLa cancer cell line, in particular with compound 1 which exhibited the highest cytotoxic activity comparable to the positive control used, cisplatin. However, no significant antioxidant activity was observed for all the test compounds in the DPPH radical scavenging capacity assay.     

(−)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties

Syntheses of three novel analogues of the Streptomyces metabolite COTC are described, using the versatile chiral pool starting material, (−)-quinic acid. The results of bioassays of the target compounds against two lung cancer cell lines, A549 and H460, are presented.     

A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase

The phytochemical study of the aerial parts of Aster scaber Thunb. (Asteraceae) yielded a new caffeoyl quinic acid, (-) 3,5-dicaffeoyl-muco-quinic acid (2) and three known compounds, (-) 3,5-dicaffeoyl quinic acid (1), (-) 4,5-dicaffeoyl quinic acid (3), (-) 5-caffeoyl quinic acid (4). The structures were established by high resolution spectroscopic methods. The antiviral effects against HIV-1 integrase of the compounds was evaluated. (-) 3,5-Dicaffeoyl-muco-quinic acid (2) exhibited potent antiviral activity with an IC50 value of 7.0 +/- 1.3 microg/ml.     

A new hydroxybenzoic acid glycosides from the plant of Trifolium lupinaster

<正>A new 5-O-(β-D-glucopyranosyl)-6'-O-benzoyl-2,5-dihydroxybenzoic acid was isolated from the ethyl acetate extract from the whole plants of Trifolium lupinaster L.Its structure was determined and deduced on the basis of their spectral data.     

A novel alkenoic acid ester and a new benzophenone from Ranunculus ternatus

A novel alkenoic acid ester,(E)-4-hydroxy-dodec-2-enedioic acid-12-O-methyl ester and a new benzophenone,ethyl (S)-3-[2- (3,4-dihydroxybenzoyl)-4,5-dihydroxyphenyl]-2-hydroxypropanoate,together with a known compound,(E)-4-hydroxy-dodec-2- enedioic acids were isolated from the roots of Ranunculus ternatus.Their structures were elucidated by spectroscopic methods.     

A new caffeic acid tetramer from the Dracocephalum moldavica L.

A new caffeic acid tetramer compound, named (+) methyl rabdosiin (4), together with seven known caffeic acid multimers (1–3, 5–8) and one caffeic acid monomer (9), were isolated from the aerial parts of Dracocephalum moldavica L. The structures of these compounds were assigned on the basis of 1D and 2D NMR spectroscopic and mass spectrometry analyses. The protective effects of compounds 2–4 against hydrogen peroxide (H₂O₂)-induced apoptosis were evaluated in primary cardiomyocytes of SD neonatal rats in vitro by the MTT method. Three compounds exhibited potent protective activities at 12.5 μg/mL.     

A new ureido-substituted amino acid from the tubers of Gymnadenia conopsea

A new ureido-substituted amino acid, conopsamide A (1), has been isolated from an ethanolic extract of the tubers of Gymnadenia conopsea. Its structure was elucidated by extensive spectroscopic analysis, and the absolute configuration was assigned by Marfey's method. The new compound was evaluated for in vitro assay for HDAC1 (Histone Deacetylase 1) inhibitory activity.     

A new cinnamic acid glycoside from roots of Heracleum dissectum

From the roots of Heracleum dissectum Lebb., one new cinnamic acid glycoside derivative named dissectumoside (1), together with eight known compounds including three phenolics, three phenolic glycosides and two phenylpropanoic glycoside were isolated using various chromatographic methods. Among them compound 2–9 was isolated from the plant for the first time. Their structures were elucidated and identified on the basis of their physicochemical properties and by extensive analyses of NMR spectroscopy and high-resolution mass spectrometry. The results of triglyceride accumulation screening in 3T3-L1 cells showed that compounds 1, 5 and 9 exhibited significantly accelerating activities of adipogenesis in adipocytes.     

A new caffeoylgluconic acid derivative from the nearly ripe fruits of Evodia rutaecarpa

A new caffeoylgluconic acid derivative, trans-caffeoyl-6-O-d-gluconic acid methyl ester (1), together with two known compounds named trans-caffeoyl-6-O-d-glucono-γ-lactone (2) and trans-caffeoyl-6-O-d-gluconic acid (3), was isolated from the nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth.. These compounds were isolated by various separation methods associated with the UPLC-Q-TOF-MS technique. Their structures were elucidated on the basis of extensive spectroscopic methods.     

A new fatty acid ester from an edible mushroom Rhizopogon luteolus

Phytochemical investigation of the Rhizopogon luteolus Fr. led to the isolation of one new fatty acid ester, 3-hydroxy-2,4-dimethylheptacosyl acetate (1) together with two known compounds tetracosanoic acid (2) and ergosterol (3). 1D and 2D NMR, and MS techniques were used for structural elucidation. Phenolic and fatty acid compositions were identified using HPLC–DAD and GC–MSD, respectively. Fumaric acid was the major phenolic acid, whereas linoleic, stearic and oleic acids were the most abundant fatty acids. Antioxidant and anticholinesterase activities of the extracts and compounds (1–3) were tested spectrophotometrically. Among the extracts, hexane extract showed the highest activity in all tests, particularly in β-carotene-linoleic acid assay (IC₅₀: 16.65 ± 1.12 μg/mL). Furthermore, compound 3 exhibited higher antioxidant and anticholinesterase activities. The study indicates that R. luteolus can be used in food, cosmetic and pharmaceutical industries.     

Five new nervogenic acid derivatives from Liparis nervosa

Five new nervogenic acid derivatives(1-5) have been isolated from Liparis nervosa(Thunb.ex A.Murray) Lindl.Their structures were elucidated on the basis of extensive spectroscopic analysis,including 1D NMR,2D NMR,and HR-ESI-MS.     

A mild and efficient new synthesis of aryl sulfones from boronic acids and sulfinic acid salts

A new efficient and mild preparation of sulfones from boronic acids and sulfinic acid salts is reported. The cross-coupling reaction mediated by cupric acetate gives access to a variety of sulfones in excellent yield.     

A new carbamic acid from Dryopteris wallichiana

A new carbamic acid, (1,7a-dihydro-1H-inden-2(7aH)-ylidene)methylcarbamic acid (1), along with three known ones, 12-ursen-28-oic acid-3-O-β-D-glucopyranoside (2), 12-ursen-3-O-β-D-glucopyranoside (3), and 3,7,11,15-tetramethyl-2-hexadecen-1-ol (4), was isolated and identified from Dryopteris wallichiana.