Three isoflavonoids from Iris germanica

From the rhizome of Iris germanica one new hexaoxygenated isoflavone, two new polyoxygenated isoflavone glucosides, the known isoflavonoids irisolidone, irigenin and iridin and acetovanillone, sitosterol, α-amyrin and β-amyrin were isolated. The structures of the new compounds were established by chemical and spectroscopic means and by correlation with known constitutents.     

Brickellin,a novel flavone from brickellia veronicaefolia and b. chlorolepis

A new highly oxygenated flavone methyl ether has been isolated from Brickellia veronicaefolia and B. chlorolepis. It has been identified as 5,6′-dihydroxy-6,7,2′,3′,4′-pentamethoxyflavone and given the name brickellin.     

Effect of ozone on photosystem II in Spinacia oleracea chloroplasts

Spinach plants were treated with 0.35 ppm ozone and the photochemical activity of photosystem II determined after separation from the isolated chloroplasts using digitonin. Ozone impaired the activity of the system and also reduced the amount of β-carotene in the chloroplasts.     

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.     

Isoflavonoids from Phaseolus coccineus

After treatment with CuCl₂, the following isoflavonoids have been isolated from the runner bean, Phaseolus coccineus: daidzein, genistein, isoprunetin, 2′-hydroxygenistein, phaseoluteone, 2′-hydroxydihydrodaidzein, isoferreirin, kievitone, cyclokievitone, glycinol, phaseollidin, phaseollin, demethylvestitol, phaseollinisoflavan, 2′-hydroxyisoprunetin and 7,4′-dihydroxy-5,2′-dimethoxyisoflavanone. The latter two compounds are novel natural products.     

Flavonoids of Gardenia cramerii and G. fosbergii bud exudates

From the bud exudates of Gardenia cramerii and G. fosbergii, two species endemic to Sri Lanka, a new flavonoid with an unusual B-ring oxidation pattern, 5,5′-dihydroxy-6,7,2′,3′-tetramethoxyflavone, was characterized. Two other rare flavonoids, 5,3′,5′-trihydroxy-3,6,7,4′-tetramethoxyflavone and 5-hydroxy-6,7,3′,4′,5′-pentamethoxyflavone were also isolated from both Gardenia species.     

Flavans from Zephyranthes flava

A new optically active flavan aglucone, 7-hydroxy-3′,4′-methylenedioxyflavan, and its 7-glucoside have been isolated from the bulbs of Zephyranthes flava, collected at flowering. Additionally, two known flavans, 7,4′-dihydroxy-3′-methoxyflavan and 7-methoxy-2′-hydroxy-4′,5′-methylenedioxyflavan, have been isolated for the first time from this species. The structures of these flavans have been established by comprehensive analyses (UV, IR, ¹H NMR, ¹³C NMR, mass spectrometry, [α]_D) of the compounds and their acetates, and also by chemical correlation.     

Myricetin and quercetin methyl ethers from Haplopappus integerrimus var. Punctatus

Nine flavonoids including two new myricetin derivatives, myricetin 3′,4′-dimethyl ether and myricetin 3,3′, 4′-trimethyl ether, were obtained from Haplopappus integerrimus var. punctatus. The known compounds are quercetin 7,3′-dimethyl ether, querectin 3,3′-dimethyl ether, isorhamnetin, quercetin 3,7-dimethyl ether, quercetin 3-methyl ether, quercetin and quercetin 3-β-d-glucoside.     

Abiesin,a biflavonoid of abies webbiana

Abiesin, a new biflavonoid, has been isolated from the leaves of Abies webbiana and identified as 5,3″,7″- trihydroxy-7,4′,4?-trimethoxy-(3′,6″)-biflavone.     

Xanthones from Tovomita pyrifolium

The wood of Tovomita pyrifolium (Guttiferae) contains the novel tovopyrifolins A [1,6-dihydroxy-7-methoxy-5-prenyl-6′,6′-dimethylpyrano (2′,3′:3,2)xanthone], B (1,5-dihydroxy-3,4-dimethoxyxanthone) and C (1,3,5-trihydroxy-2-methoxyxanthone) and also the known tovophyllins A and B [structure revised to 1,6-dihydroxy-5-prenyl-6′, 6′-dimethylpyrano(2′,3′:3,2)-6″,6″-dimethylpyrano(2″,3″:7,8)xanthone].     

Chalcone glycosides of Antirrhinum majus

Three chalcones have been found in yellow flowers of A. majus, two of which have been identified as chalcononaringenin 4′-glucoside and 3,4,2′,4′,6′-pentahydroxychalcone 4′-glucoside.     

Synthesis of dihydrochalcones of Myrica gale

4,4,6-Trimethyl-2-(3-phenylpropionyl)cyclohexane-1,3,5-trione, 2′-hydroxy-4′,6′-dimethoxy-3′-methyldihydrochalcone, 2′,6′-dihydroxy-4′-methoxy-3′,5′-dimethyldihydrochalcone and 2,2,5-trimethyl-4(3-phenylpropionyl)cyclopent-4-ene-1,3-dione, constituents of Myrica gale, have been synthesized.     

Flavonoids from the exudate of Acacia neovernicosa

2′,4′-Dihydroxychalcone, 4′-hydroxy-2′-methoxychalcone and 2′,4′-dihydroxy-3′-methoxychalcone were isolated and characterized from the resinous exudate produced by Acacia neovernicosa. Smaller amounts of isoliquiritigenin, pinocembrin and chrysin were also found and identified by their chromatographic properties and UV spectra. The material of one collection contained galangin, 3-methylkaempferol and 3,3′ -dimethylquercetin.     

Flavonoids from Artemisia ludoviciana var. ludoviciana

Nineteen flavonoids were isolated from Artemisia ludoviciana var. ludoviciana, including a new 2′- hydroxy- 6-methoxyflavone, 5,7,2′,4′-tetrahydroxy-6,5′-dimethoxyflavone. The known compounds include quercetagetin 3,6,3′,4′-tetramethyl ether, eupatilin, 5,7-dihydroxy-3,6,8,4′-tetramethoxyflavone, luteolin 3′,4′-dimethyl ether, jaceosidin, 5,7,4′-trihydroxy-3,6-dimethoxyflavone, tricin, hispidulin, chrysoeriol, kaempferol 3-methyl ether, apigenin, axillarin, eupafolin, selagin and luteolin together with three flavones which were previously isolated for the first time from Artemisia frigida: 5,7,4′-trihydroxy-6, 3′,5′-trimethoxyflavone, 5,7,3′-trihydroxy-6,4′,5′-trimethoxyflavone and 5,7,3′,4′-tetrahydroxy-6,5′- dimethoxyflavone.     

Identification of natural tricetin-derived C-glycosides through synthesis

C-Glycosylation of 5,7-dihydroxy-3′,4′,5′-trimethoxyflavone was carried out with acetobromo-α-d-glucose, -α-d-galactose, -α-d-xylose, -β-l-arabinose and -αt-L-rhamnose. The respective 6-C-glycosides and 6, 8-di-C-glycosides (excepted for galactose) were isolated and permethylated. MS and TLC comparison confirmed the proposed structures of five natural tricetin-derived C-glycosides.     

Flavonoids of the citrus cultivar calamondin and synthetic 2′β-dihydroxychalcones

Eight methoxyflavones were isolated and identified from the peel of calamondin. Citromitin and 5-O-desmethylcitromitin are actually nobiletin and 5-O-desmethylnobiletin, respectively. 5,6,7,8,3′,4′-Hexamethoxyflavanone and 5-hydroxy-6,7,8,3′,4′-pentamethoxyflavanone are not constituents of calamondin, although previously reported.     

Synthesis of phosphatidylglycerol by chloroplasts from leaves of Spinacia oleracea L. (spinach)

Purified chloroplasts from leaves of Spinacia oleracea L. (spinach) incorporated glycerol 3-phosphate into diacylglycerol, monoacylglycerol, phosphatidylglycerol, phosphatidic acid, and lysophosphatidic acid. The omission of ATP or CTP, CoA or illumination decreased the incorporation markedly. The fraction of incorporated glycerol 3-phosphate found in phosphatidylglycerol was greatly reduced by the omission of bicarbonate, acetate, and ATP, or in darkness, low-osmolarity medium, or high magnesium ion concentration (10 mM). Incorporation of glycerol 3-phosphate into lipid and specifically into phosphatidylglycerol was optimal at a $\text{Mg}{}^{\mathrm{2+}}\text{CTP}$ ratio of 1, whereas the optimal ratio for $\text{Mg}{}^{\mathrm{2+}}\text{ATP}$ was closer to 2. The $\text{Mg}{}^{\mathrm{2+}}\text{CTP}$ gave lower total incorporation but a higher fraction of incorporation in phosphatidylglycerol. Triton X-100 inhibited incorporation of glycerol 3-phosphate into lipid, especially into phosphatidylglycerol.     

Flavonoids from the external leaf resins of four hemizonia species (asteraceae)

The external leaf resins of four Hemizonia species afforded nine methylated flavonoids, including flavanones, flavones and flavonols. Besides the rare compounds 7-methyleriodictyol and 3,6,8-trimethoxy-5,7,3′,4′-tetrahydroxyflavone the new 6-methoxy-5,7,8,3′,4′-pentahydroxyflavone was isolated and identified by spectroscopic means.     

Flavonols and coumarins from the fruit of Murraya omphalocarpa

Separation of the ethanolic extract of the fruit of Murraya omphalocarpa afforded a new flavonol, murrayanol, which was characterized as 5,4′-dihydroxy-3,6,7,3′,5′-pentamethoxyflavone, together with the known substances coumurrayin, mexoticin, 3,5,6,7,3′,4′,5′-heptamethoxyflavone, 5,7-dimethoxy-8-(3′-methyl-2′-oxobutyl) coumarin and sitosterol.