Biosystematics of the monocotyledoneae—flavonoid patterns in leaves of the liliaceae

In a leaf survey of 168 species of the Liliaceae, most of the major flavonoid classes were found to be represented in the family. Flavonols occurred most frequently: quercetin and kaempferol were detected in 40% and 42% of the sample respectively, while the flavones luteolin and apigenin were present in only 24% and 20% of the sample. Methylated derivatives, i.e. isorhamnetin, diosmetin and tricin were rare. Procyanidins were present in 17 species, flavonoid sulphates in only one species and flavone C-glycosides in only three species. Anthraquinone pigments were identified in species of Aloe Asphodeline and Asphodelus. Three new flavonoid glycosides were characterised during the course of the survey: diosmetin 7-diglucoside in Colchicum byzanthinum and tricin 7-fructosylglucoside and tricin 7-rutinoside-4′-glucoside in Hyacinthus orientalis cv. ‘Quean of the Pinks’. On the basis of the flavonoid survey, the subfamilies of the Liliaceae may be grouped into those containing flavonols only, those with flavones only or those having both flavonols and flavones. Members of the related families: Amaryllidaceae (17 species), Agavaceae (1 species) and Xanthorrhoeaceae (1 species) contained only flavonols. The subfamilies Scilloideae, Asphodeloideae and Melanthioideae show the most chemical variation whilst the Wurmbaeoideae and Lilioideae are the most homogeneous groups. The tribe Scilleae is unusual in that both flavone- and flavonol-containing genera occur and a wide variety of flavonoid types are represented. A comparison of the leaf flavonoids of the Liliaceae with those found in families related to the grasses showed that all except two classes of flavonoid compound (5-methylated flavones and 5-deoxyflavonoids) found in the Juncaceae. Cyperaceae, Palmae and Gramineae are present in the Liliaceae thus supporting the view that all four families could have arisen from Liliaceae-like ancestors.     

Involvement of Hydroxyl Radical Formation and Dna Strand Breakage in the Cytotoxicity of Anthraquinone Antitumour Agents

Four 9,10-anthraquinones (AQ) mono- or bis-substituted with the -NH(CH₂)₂ NH(CH₂)₂OH group were studied. 1-AQ, 1,5-AQ and 1,8-AQ but not 1,4-AQ (100°M) generated pBR322 plasmid DNA single strand breaks in the presence of purified NADPH dependent cytochrome P450 reductase. 1-AQ, 1,5-AQ and 1,8-AQ (at 100 °M) stimulated hydroxyl radical formation in MCF-7 S9 cell fraction (as measured by dimethyl pyrolline N-oxide spin trapping) and MCF-7 DNA strand breaks as measured by alkaline filter elution. In contrast 1,4-AQ did not stimulate hydroxyl radical formation and produced considerably less strand breaks in MCF-7 cells compared to the other AQ's. It would appear that the position of the -NH(CH₂)₂ NH(CH₂)₂OH groups on the chromophore is an important determinant in the metabolic activation of cytotoxic anthraquinones. This may contribute to the cytotoxicity (ID₅₀ values) of 1-AQ (0.06 °M), 1-8-AQ (0.5 °M) and 1,5-AQ (12.3 °M) but not the 1,4-AQ (1.2 °M).     

Microbial glycosylation of four free anthraquinones by Absidia coerulea

Absidia coerulea transformed four anthraquinones from rhubarb, chrysophanol, physcion, emodin and aloe-emodin to their corresponding glycosylated metabolites. The structures of the products were characterized as chrysophanol 8-O-beta-D-glucoside, physcion 8-O-beta-D-glucoside, emodin 6-O-beta-D-glucoside, and aloe-emodin 1-O-beta-D-glucoside, respectively.     

Anthraquinones from the Genus cortinarius

The anthraquinones 6-methylxanthopurpurin-3-methyl ether, xanthorin, and 1,4-dihydroxy-2-methoxy-7-methyl-9,10-anthraquinone (austrocortinin) have been isolated from fruit bodies of a red Australian toadstool belonging to the genus Cortinarius; austrocortinin is reported for the first time as a natural product.     

Bioactive compounds from some Kenyan ethnomedicinal plants: Myrsinaceae,Polygonaceae and Psiadia punctulata

There are several described medicinal plants in Kenya from a flora of approximately 10,000 members. Strong cross-medical information from the 42 ethnic groups points to the high potential of some of these species. The Myrsinaceae are well established ethno-anthelmintics and anti-bacterials. They are harbingers of long alkyl side chain benzoquinones which clearly have a protective function from their histochemical disposition. The main benzoquinone in the sub-family Myrsinodae is embelin while for the Maesodae it is maesaquinone together with its 5-acetyl derivative; the distribution of these benzoquinones by their alkyl side chain length or the presence/absence of a 6-methyl group is in accord with morphological sub-family de-limitation. The benzoquinones showed anti-feedant, anti-microbial, phytotoxic, acaricidal, insecticidal and nematicidal activity. Many other benzoquinones of medium and minor concentration were also isolated and characterised. Some plants belonging to the Polygonaceae which are widely used as ethno-anthelmintics have been studied. The common anthelmintic anthraquinones were obtained from all five Rumex species while the naphthalenic acetogenin derivative, nepodin was more selectively distributed. The leaf of Polygonum senegalense is up to 17% surface exudate; about thirteen non polar flavonoid derivatives (chalcones, dihydrochalcones, flavanones and a flavone) have been isolated from it. From the internal aerial tissues of this plant, the major flavonoids were common flavonoids, quercetin, kaempferol, luteolin and their glycosides. The only unique compound isolated from this plant was 2′-glucosyl-6′-hydroxy-4′-methoxydihydrochalcone whose aglycone, uvangolatin is part of the exudate mixture. Other leaf exudate plants studied include the stomach-ache medicine, Psiadia punctulata (Compositae) from which novel methylated flavonoids, kaurene and trachyloban diterpenes have been found. This revised version was published online in June 2006 with corrections to the Cover Date.     

Chemical signals mediating interactions betweenGaleruca tanaceti L. (Coleoptera, Chrysomelidae) and its egg parasitoidOomyzus galerucivorus (Hedqvits) (Hymenoptera, Eulophidae)

Chemical signals mediating interactions betweenGaleruca tanaceti and its egg parasitoidOomyzus galerucivorus (Hymenoptera, Eulophidae) were studied. Neither odor of gravid females ofG. tanaceti nor volatiles of their feces were attractive to the parasitoid. However, the presence of the beetles’ feces on a substrate arrested the parasitoid and elicited frequent antennal drumming. Thus, feces may contain a kairomone important for host finding. Odors of damaged and undamaged host plants had no effect on the parasitoids.O. galerucivorus did not detect its host eggs at close range but encountered them by chance. Neither the structure nor the dark color of the egg surface play a key role in host recognition, but chemicals of the extrachorion which could be isolated by dichloromethane. Fractionation of the dichloromethane extract by TLC revealed a single active fraction which induced host recognition behavior. Since the eggs ofG. tanaceti contain anthraquinones and anthrones which are active as feeding deterrents against predators, we hypothesized that reproductive success ofO. galerucivorus is due to sequestration of these protective compounds. However, GC-MS analyses revealed that there was no transfer of them from the host egg into the adult parasitoid.     

Biosynthesis of naphthoqinones and anthraquinones in streptocarpus dunnii cell cultures

Administration of ^p13C- and ^p2H-labelled precursors to Streptocarpus dunnii cell cultures demonstrated that the naphthoquinones formed through aunique prenylation mode are biosynthesized via 4-(2'-carboxyphenyl)-4-oxobutanoic acid, 1,4-dihydroxy-2-naphthoic acid, lawsone and lawsone 2-prenyl ether, and that the anthraquinones are biosynthesized through prenylation of 2-carboxy-4-oxo-1-tetralone at the carboxy-bearing carbon atom to form 2-carboxy-2-prenyl-4-oxo-1-tetralone,or through ipso attack of the prenyl group on the corresponding carbon atom of 1,4-dihydroxy-2-naphthoic acid.     

Anthracen-derivate in kalluskulturen aus Cassia angustifolia

Callus cultures from cotyledons of Cassia angustifolia were shown to contain dianthrones. Proof of their structures was obtained by co-chromatography (TLC), oxidative cleavage and UV analysis. The basic components chrysophanol, physcion, rheum emodin, aloe emodin and rhein have been isolated and identified by UV and IR analysis.     

蔓生百部的化学成分研究

从蔓生百部(Stemona japonica)根中分离得到13个化合物,通过波谱数据,它们鉴定为β-谷甾醇(1)、豆甾醇(2)、5,11-豆甾二烯-3β-醇(3)、苯甲酸(4)、4-甲氧基苯甲酸(5)、1,8-二羟基-3-甲基蒽醌(6)、1,8-二羟基-6-甲氧基-3-甲基蒽醌(7)、氧代狭叶百部碱(8)、百部定碱(9)、异狭叶百部碱(10)、绿原酸(11)、栀子苷(12)和藏红花素A(13).所有化合物均为首次从该植物中分离得到.