Flavonoids from Haplophyllum pedicellatum, H. robustum AND H. glabrinum

Haplophyllum pedicellatum, H. robustum and H. glabrinum all yielded the known compound gossypetin 8,3′-dimethyl ether 3-rutinoside. In addition the first two species afforded isorhamnetin and its 3-rutinoside. A new glycoside, gossypetin 8,3′-dimethyl ether 3-glucoside was obtained from H. pedicellatum together with the 3-malonylrutinoside, 3-malonylglucoside and 3-galactoside of isorhamnetin plus kaempferol 3-malonylglucoside. H. robustum yielded isorhamnetin 7-glucoside and 3-glucoside and quercetin 3-galactoside, while H. glabrinum was found to contain gossypetin 8-methyl ether 3-malonylrutinoside in addition to kaempferol and isorhamnetin 3-glucoside.     

Flavonoids of Plummera: Taxonomic implications at the generic level within the gaillardiinae

Four populations each of Plummera floribunda and P. ambigens were examined for flavonoid content. Six compounds were isolated and identified as flavone and flavonol aglycones and flavonol glycosides. In all cases, both taxa were found to be identical in flavonoid content. Plummera was then compared to other genera in the subtribe Gaillardiinae. At the present time, it is the opinion of the author that Plummera is very closely related to, but not congeneric with Hymenoxys.     

Flavonols and C-Glycosylflavonoids of the caryophyllales

A survey of 112 species of the Caryophyllales showed the presence of flavonols in all eleven families and of C-glycosylflavonoids in nine families, being absent from the Aizoaceae and Cactaceae. 18% of the species contained both classes of compound. C-glycosylflavonoids are reported for the first time in the Amaranthaceae, Basellaceae, Didieraceae, Nyctaginaceae, Phytolaccaceae, Portulacaceae and Molluginaceae. The Caryophyllaceae contained prodominantly C-glycosylflavonoids, suggesting they are the most advanced family in the order.     

Two new C-methylated flavonoids from Myrica gale

From the leaves of Myrica gale 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone has been isolated. The fruits yielded 2′-hydroxy-4′,6′-dimethoxy-3′-methyldihydrochalcone. The constitutions were deduced from spectroscopic data and confirmed by synthesis.     

The contribution of symbiotic yeast to toxin resistance of the cigarette beetle (Lasioderma serricorne)

Representative plant allelochemicals were tested for toxicity to larvae of the cigarette beetle Lasioderma serricorne (F.) that were either untreated, treated with fungicides, or treated to render them free of symbiotic yeast (aposymbiotic) through surface sterilization of eggs. Insects rendered symbiont-free had higher mortality and/or developmental rates than controls when fed diets containing flavone, resorcinol or tannic acid. Fungicides reduced symbiont populations and/or caused morphological abnormalities. Two hydrolytic enzymes, which made up a significant protion of mycetome hydrolytic activity, were absent when symbionts were not present, as indicated by gel electrophoresis. This information indicates symbionts do contribute to the survival of their host by detoxifying toxins.

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Résumé La toxicité relative de substances allélochimiques végétales typiques a été examinée sur des larves de L. serricorne F. traitées aux fongicides et rendues aposymbiotiques par stérilisation superficielle des ufs. La toxicité de la nicotine est relativement inaffectée chez les larves aposymbiotiques; cependant les toxicités des resorcinol, flavone et acide tannique sont significativement augmentées chez les insectes ayant reçu un traitement pour éliminer leurs symbiontes. L'électrophorèse sur gel a montré que quelques enzymes responsables de l'hydrolyse du 1-naphthyl acétate, réaction enzymatique de la détoxification enzymatique, sont absentes chez les insectes aposymbiotiques. L'acide sorbique a réduit significativement l'effectif de symbiontes, tandis que le bénomyl a réduit leur gamme provoquant la multiplication anormale d'autres espèces. Ces résultats montrent que les symbiontes contribuent aux possibilités de détoxification de l'insecte. L'élimination des symbiontes peut être une technique efficace pour lutter contre les insectes qui en contiennent, puisqu'elle les priverait de leur contribution à l'alimentation et à la détoxification. Cette stratégie est vraisemblablement compatible avec des programmes de lutte intégrée, puisque les prédateurs et parasites ne contiennent pas de symbiontes.

     

Modification of the B-ring during flavonoid synthesis in Petunia hybrida: Effect of the hydroxylation gene Hf1 on dihydroflavonol intermediates

The white flowering mutant W48 of Petunia hybrida is dominant for the hydroxylation gene Hf1 and homozygous recessive for the hydroxylation gene Ht1 and the anthocyanin gene An1. Flower buds of this mutant accumulate dihydrokaempferol-glucosides. Thus the effect of Hf1 being dominant is not the hydroxylation of the C15 skeleton, as is the case in mutants that are able to synthesize anthocyanins. This can be explained either by a feed-back inhibition of the hydroxylation by small amounts of dihydromyricetin (glucosides), or by a controlling effect of the gene An1 on the expression of Hf1. However, the white flowering mutant W58, which is homozygous recessive for the gene An6 and dominant for Hf1, accumulates dihydromyricetin (glucosides). This excludes a possible feed-back inhibition by dihydromyricetin and we conclude that An1 controls the expression of Hf1. Feeding of radioactive malonic acid to isolated flower limbs of mutants able to synthesize anthocyanins, leads to the incorporation of radioactivity into dihydrokaempferol (glucosides) and dihydroquercetin (glucosides). These results show that glucosylation of dihydroflavonols is a normal event in anthocyanin biosynthesis and is not induced by an inhibition of anthocyanin synthesis.     

Altered Glycoflavone expression in induced Autotetraploids of Phlox drummondii

The effects of colchicine induced autotetraploidy on non-anthocyanin flavonoid expression were determine for 15 cultivars of Phlox drummondii and for the naturally occuring P. drummondii ssp. mcallisteri. Collectively, the taxa express a total of nine glycoflavonoid derivatives (C, O-diglycosides or di-C-glycosides) of either apigenin or luteolin. The autotetraploids of 14 cultivars and those of the natural subspecies exhibit altered glycoflavone profiles relative to their respective diploid sources. The qualitative alternations in the cultivars may be grouped into three phenotypic categories: (1) the expression of novel glycoflavones, (2) the absence of diploid glycoflavones, and (3) the deregulation of tissue-specific glycoflavone production. Alterations in mcallisteri autotetraploids include only the latter two categories. Each of the novel compounds is otherwise expressed among other diploid cultivars or in other wild P. drummondii subspecies. Quantitatively, the phenolic content of most autotetraploid flowers is significantly greater than in respective diploid flowers. However, on a dry weight basis, phenolic titre in comparable 4n and 2n floral or leaf tissues is not significantly different. Floral tissues express from 5 to 10 times the phenolic titre of leaves. The results are discussed in terms of the possible origins of novel flavonoids in natural polyploid Phlox species.     

Les flavonoides des rameaux vegetatifs de Periploca graeca

The flavonoid content of the vegetative stems of Periploca graeca include derivatives of flavonols (quercetin and kaempferol), anthocyanidins (     

Die flavonolglykoside von Equisetum silvaticum

Ten glycosides of kaempferol and quercetin, including the hitherto unknown kaempferol and quercetin 3-rutinoside-7-rhamnosides, have been isolated from Equisetum silvaticum L.