Prenylated flavonoids from Desmodium caudatum and evaluation of their anti-MRSA activity

Seven prenylated flavonoids and a prenylated chromanochroman derivative, together with eight known flavonoids, were isolated from roots of Desmodium caudatum. The 15 structures were elucidated by extensive spectroscopic analyses. The antibacterial activity of many of other compounds was evaluated against methicillin-resistant Staphylococcus aureus (MRSA: COL and 5) by a disc diffusion method, and the minimum inhibitory concentrations (MICs) to MRSA were determined.     

Prenylated flavonoids from Moghania philippinensis

Five prenylated flavonoids, 8-(1,1-dimethylallyl)genistein (1), 5,7,3',4'-tetrahydroxy-2',5'-di(3-methylbut-2-enyl)isoflavone (2), 5,7,3'-trihydroxy-2'-(3-methylbut-2-enyl)-4',5'-(3,3-dimethylpyrano)isoflavone (3), (2R)-5,2',4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4a) and (2S)-5, 2', 4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4b), were isolated from the roots of Moghania philippinensis. The structures of these compounds were determined on the basis of spectroscopic and chemical means.     

Prenylated flavonoids from Tephrosia purpurea seeds

Two new prenylated flavonoids, purpuritenin purpureamethide, have been characterized from the seeds of Tephrosia purpurea together with the known c     

Distribution of flavonoids and their systematic significance in Clematis subsection Viornae

Fifteen flavonoids were identified in the eight taxa of Clematis subsection Viornae. Flavonols, flavones, and C-glycosyl flavones were present. The compounds were based primarily on luteolin, apigenin, quercetin, and kaempferol. The systematic significance of the distribution of these compounds among the taxa is discussed.     

Prenylated flavonoids from seeds of Calopogonium mucunoides

The seeds of Calopogonium mucunoides furnished 7-O-γ,γ-dimethylallyl-8-methoxy-3′,4′-dioxymethylene-isoflavone, 7-O-γ,γ-dimethylallyl-3′-hydroxy-4′-methoxyisoflavone, 7-O-γ,γ-dimethylallyl-3′,4′-dimethoxyisoflavone and 2S-di[6′',6′'-dimethylpyrano (2′',3′':7,8;2′',3′':4′,3′)]-flavanone whose structures were established by spectroscopic means involving the use of 400 MHz ¹H NMR with double irradiation and INDOR techniques.     

Prenylated flavonoids from the aerial parts of Dorstenia mannii

Four new prenylated flavanones, dorsmanins 1, J and epi-dorsmanins F, G, identified, respectively, as 6,7-(2,2-dimethylpyrano)-8-prenyl-5,3',4'-trihydroxyflavanone, 6,7-(2,2-dimethyldihydropyrano)-8-prenyl-5,3',4'-trihydroxflavanone, and 2'-epimers of dorsmanins F and G were isolated from the aerial parts of Dorstenia mannii together with 13 known flavonoids: 4-hydroxylonchocarpin, 4-methoxylonchocarpin, 6-prenylchrysoeriol, 6,8-diprenyleriodictyol, gancaonin P and dorsmanins A-H. The structures of these secondary metabolites were determined by spectroscopic means and by comparison with published data and with authentic specimens for some of the known compounds.     

Prenylated flavonoids of Erythrina lysistemon grown in Egypt

Three prenylated flavonoid derivatives; 5,7,4′-trihydroxy-8-(3-methylbut-2-enyl)-6-(2″-hydroxy-3″-methylbut-3″enyl) isoflavone (isoerysenegalensein E), 5,7,2′-trihydroxy-4′-methoxy-5′-(3″-methylbut-2″-enyl) isoflavanone (lysisteisoflavanone), 5, 4′-dihydroxy-6-(3-methylbut-2-enyl)-2″-hydroxyisopropyl dihydrofurano [4″,5″:8,7] isoflavone (isosenegalensin), together with the four known flavonoids abyssinone V-4′-methylether, alpinumisoflavone, wighteone and burttinone were isolated from the stem bark of Erythrina lysistemon Hutch. (Leguminosae). Structures were elucidated by spectroscopic methods.     

淫羊藿属植物中的黄酮类成分及其分类学意义

用HPLC法研究了具8位异戊烯基的黄酮醇甙类(A类)及一般结构的黄酮醇甙类(B类)在淫羊 藿属Epimedium L.中的存在和含量情况,得到一些具分类学意义的结论。1)依据化学成分可将 Epimedium 分为3群：A群,主要含A类成分;B群,主要含B类成分;AB群,两类化合物含量都高。B 群的8个类群(种或亚种)有多项演化程度较高的形态特征,它可能是Epimedium发展演化中较为进化 的一个分支群。—朋群的种类为本屑较原始的类群,因而在化学性状上有朋群→A群、AB群→B群的 演化趋势,与形态演化趋势基本相关。A、B、AB群的划分与现有分类系统不一致,也与花粉、染色体C 带的结果不很吻合。2)分布于地中海的E. alpinum因有较高含量的厶2类成分(A类中4'-OH的一类 化合物)而体现了与中国的原始类群的一些联系。3)E. davidii和E. ecalcaratum的化学成分几乎相 同,表明花瓣距的有无在Epimedium中的原始类群可能不具重要的分类价值。4)HPLC图谱为E.Х fanjingshanense这一杂交种的亲本来源提供了可靠的证据。本研究结果为建立一个合理的Epimedium的分类系统提供了新的依据。     

The flavonoids in Epimedium L. and their taxonomic significance

In this paper, the distribution and quantity of flavonol glycosides with isoprenyl in the eighth position (A kind) or without isoprenyl (B kind) in Epimedium were analyzed by HPLC. The following results of taxonomic significance were obtained: 1 )According to the chemical characteristics, Epimedium could be divided into three groups: A group, mainly with A kind of flavonol glycosides; B group, mainly with B kind of fiavonol glycosides; AB group, sharing the two kinds. Eight taxa (species or subspecies) in B group, which have many advanced charaetaristics, should represent a more advanced group of the genus. The species of AB group were relatively primitive in the genus. Hence the evolutionury trend from AB group to A group and then to B group was possible. This trend is basically correlated with that of morphological evolution. But the above groupings of A, B and AB do not accord with Stearn's taxonomic system and the results of pollen morphology and of chromosome C-bands. 2)E. alpinum, a species distributed in the Mediterranean area, contains a high quantity of A2 kind of compounds (those of A kind with 4'-OH), so it may be somewhat related to the primitive species in China. 3)The constituents of E. davidii and E. ecalcaratnm are almost identical, implying that the prescence or absence of the spur of the petal should be of unimportant systematic significance. 4)The chromngram of HPLC provided reliable evidence for determining the parental origin of the hybrid E. x fanjingshanense. The results of this work provided new evidence for establishing a more reasonable taxonomic system of Epimediurn, but the taxonomic research on Epimedium has a long way to go and more work must be done. Other chemical characteristics of Epimedium and its relationshipwith other groups in the Berberidaceae were also discussed. 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Prenylated flavonoids of Erythrina lysistemon grown in Egypt

Three prenylated flavonoid derivatives; 5,7,4′-trihydroxy-8-(3-methylbut-2-enyl)-6-(2″-hydroxy-3″-methylbut-3″enyl) isoflavone (isoerysenegalensein E), 5,7,2′-trihydroxy-4′-methoxy-5′-(3″-methylbut-2″-enyl) isoflavanone (lysisteisoflavanone), 5, 4′-dihydroxy-6-(3-methylbut-2-enyl)-2″-hydroxyisopropyl dihydrofurano [4″,5″:8,7] isoflavone (isosenegalensin), together with the four known flavonoids abyssinone V-4′-methylether, alpinumisoflavone, wighteone and burttinone were isolated from the stem bark of Erythrina lysistemon Hutch. (Leguminosae). Structures were elucidated by spectroscopic methods.     

Antimicrobial agents from higher plants: Prenylated flavonoids and other phenols from Glycyrrhiza lepidota

Bioassay directed fractionation of extracts of American licorice, Glycyrrhiza lepidota (Leguminosae), resulted in identification of the known bibenzyl, 3,5-dihydroxy-4-(3-methyl-2-butenyl)-bibenzyl, and the known flavanones, glabranin and pinocembrin, as well as the isolation and structure determination of the new flavonol, glepidotin A and the new dihydroflavonol, glepidotin B as antimicrobial agents.     

Prenylated flavonols and their distribution in flowering plants

The species of angiosperms known to contain prenylated flavonols and its glycosides have been listed family wise. It is present in 19 species in 14 genera and in six families of dicots only. The glycosides are confined to just two families. This review may suggest new sources for the compounds.     

The systematic significance of flavonoids in Persea of the Southeastern United States

The systematic significance of flavonoid distribution in the southeastern United States taxa of Persea is discussed. The compounds thus far elucidated are glycosides based on quercetin, kaempferol, apigenin or luteolin.     

Prenylated cinnamate and stilbenes from Kangaroo Island propolis and their antioxidant activity

A prenylated cinnamic acid derivative as well as six prenylated tetrahydroxystilbenes were isolated from the ethyl acetate extract of propolis that originated from Kangaroo Island, Australia. Furthermore, six known stilbenes and two known flavanones were also identified from the same sample. Stilbenes are not common in propolis; therefore, Kangaroo Island propolis is considered a unique type of propolis that is rich in prenylated stilbenes. Stilbene propolis from Kangaroo Island showed a stronger scavenging activity towards DPPH free radical than Brazilian green propolis. This strong activity can be explained by the presence of large number of stilbenes, most of them showed strong free radical scavenging activity.     

Prenylated flavonoids, monoterpenoid furanocoumarins and other constituents from the twigs of Dorstenia elliptica (Moraceae)

A monoprenylated flavan and two monoterpenoid substituted furanocoumarins were isolated from the twigs of Dorstenia elliptica along with 3-(3,3-dimethylallyl)-4,2',4'-trihydroxylchalcone, psoralen, bergapten, O-[3-(2,2-dimethyl-3-oxo-2H-furan-5-yl)butyl]bergaptol, beta-sitosterol and its beta-D-glucopyranoside. The structure of the flavan was determined as 6(1,1-dimethylallyl)-7,4'-dihydroxylflavan and the monoterpenoid substituted furanocoumarins were assigned as O-[3-(2,2-dimethyl-3-oxo-2H-furan-5-yl)-3-hydroxybutyl]-bergaptol and O-[2-(5-hydroxy-2,6,6-trimethyl-3-oxo-2H-pyran-2-yl)ethyl]bergaptol, respectively, using spectroscopic analysis, especially, 2D NMR spectra.     

Prenylated xanthones from mangosteen as promising cholinesterase inhibitors and their molecular docking studies

Garcinia mangostana is a well-known tropical plant found mostly in South East Asia. The present study investigated acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of G. mangostana extract and its chemical constituents using Ellman's colorimetric method. Cholinesterase inhibitory-guided approach led to identification of six bioactive prenylated xanthones showing moderate to potent cholinesterases inhibition with IC₅₀ values of lower than 20.5 μM. The most potent inhibitor of AChE was garcinone C while γ-mangostin was the most potent inhibitor of BChE with IC₅₀ values of 1.24 and 1.78 μM, respectively. Among the xanthones, mangostanol, 3-isomangostin, garcinone C and α-mangostin are AChE selective inhibitors, 8-deoxygartanin is a BChE selective inhibitor while γ-mangostin is a dual inhibitor. Preliminary structure-activity relationship suggests the importance of the C-8 prenyl and C-7 hydroxy groups for good AChE and BChE inhibitory activities. The enzyme kinetic studies indicate that both α-mangostin and garcinone C are mixed-mode inhibitors, while γ-mangostin is a non-competitive inhibitor of AChE. In contrast, both γ-mangostin and garcinone C are uncompetitive inhibitors, while α-mangostin is a mixed-mode inhibitor of BChE. Molecular docking studies revealed that α-mangostin, γ-mangostin and garcinone C interacts differently with the five important regions of AChE and BChE. The nature of protein–ligand interactions is mainly hydrophobic and hydrogen bonding. These bioactive prenylated xanthones are worthy for further investigations.     

Prenylated proteins from kidney

When [5-3H]mevalonate is injected into mice, it is incorporated into macromolecules in the kidney. The incorporated material is stable to treatment with RNase or DNase but not protease, indicating that the radioactivity is associated with protein. Electrophoresis in sodium dodecyl sulfate-containing polyacrylamide gels indicates a molecular weight of about 25,000. The incorporated radioactivity can be released from the polypeptide and extracted into organic solvents after hydrolysis with acid or base or by treatment with protease. The conditions required for hydrolysis strongly suggest that the linkage between the protein and the mevalonate-derived material is an allylic ether. The chromatographic mobility of the incorporated material in several systems is similar to that of dolichol C95.     

Luteolin and daphnetin derivatives in the juncaceae and their systematic significance

During a chemosystematic survey of 38 representative species of the Juncaceae for leaf and stem flavonoids, the 5-methyl ether of luteolin was discovered for the first time in plants. It occurs both free and as the 7-glucoside; its identity was confirmed by synthesis. Flavone sulphates were also found in the family and the 7-glucosidesulphates of luteolin and chrysoeriol were characterised for the first time. 7,3′,4′-Trihydroxyflavone and its 7-glucoside, not previously reported in the monocotyledons, were found in three species. The presence of luteolin 5-methyl ether or its glucoside in 70% of the species surveyed serves to distinguish the Juncaceae from the morphologically related Centrolepidaceae, Restionaceae and Thurniaceae. Flavone C-glycosides, common in grasses and sedges, were found only in Prionium, a genus which on anatomical grounds is anomalous in the Juncaceae. Among other phenolics detected during the survey, the uncommon 7,8-dihydroxycoumarin, daphnetin, was identified in Juncus effusus and its 8-methyl ether in four Luzula species. Taken together, these chemical findings show that the Juncaceae are very distinctive in their phenolic pattern and confirm the correctness of assigning them an isolated position in a separate order, the Juncales. The results indicate that the Juncaceae are chemically specialized, in spite of the facts that the family has been regarded as ancestral to the Cyperaceae and Gramineae and that they have been assigned a low advancement index by Sporne.