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.     

Methoxyspheroidene and methoxyspheroidenone,two carotenoids from Rhodopseudomonas spheroides

Two new carotenoids isolated from Rhodopseudomonas spheroides (Rhodospirillaceae) have been identified as methoxyspheroidene (1,1′-dimethoxy-3,4-didehydro-1,2,1′,2′,7$\text{,}\text{?}$8′-hexahydro-ψ,ψ-carotene) obtained from anaerobic cultures and methoxyspheroidenone (1,1′-dimethoxy-3,4-didehydro-1,2,1′,2′,7′,8′-hexahydro-ψ,ψ-caroten-2-one) recovered from aerobic cultures.     

Isoetine,nouvelle flavone isolee de Isoetes delilei et de Isoetes durieui

A new flavone isolated from Isoetes has been identified as 2′,4′,5,5′,7-pentahydroxy flavone.     

7′,8′,11′,12′-Tetrahydro-γ-carotene: A novel carotene from Phycomyces blakesleeanus

The natural occurrence of 7′,8′,11′,12′-tetrahydro-γ-carotene (7′,8′,11′,12′-tetrahydro-γ-carotene, IV) is predicted and its isolation from diphenylamine-inhibited cultures of a mutant of Phycomyces blakesleeanus and characterization are described. The possible role of this novel monocyclic carotene in β-carotene biosynthesis is discussed.     

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.     

Octasubstituted flavones from Ageratum houstonianum

Two new highly oxygenated flavones, were isolated from aerial parts of Ageratum houstonianum. Their structures were established as 3′-hydroxy-5,6,7,8,2′,4′,5′-heptamethoxyflavone and 5,3′-dihydroxy-6,7,8,2′,4′,5′-hexamethoxyflavone on the basis of spectral data and chemical degradation. The structure of the latter compound was confirmed by X-ray analysis.     

Dihydrochalcones from lindera umbellata

Two dihydrochalcones, 2′,6′-dihydroxy-4′-methoxydihydrochalcone and 2,4′,6′-trihydroxydihydrochalcone have been isolated from leaves of Lindera umbellata.     

An octamethoxyflavone from Pogostemon purpurascens

3,5,6,7,8,2′,4′,5′-Octamethoxyflavone has been isolated from the whole plant of Pogostemon purpurascens.     

Six 2′-hydroxyflavonols from Gutierrezia microcephala

Six 2′-hydroxyflavonols were isolated from Gutierrezia microcephala, including four new compounds, 5,7,2′-trihydroxy-3,6,4′,5′-tetramethoxyflavone, 5,7,2′-trihydroxy-3,6,8,4′,5′-pentamethoxyflavone, 5,2′-dihydroxy-3,6,7,8,4′,5′-hexamethoxyflavone and 5,7,2′,4′-tetrahydroxy-3,8,5′-trimethxoyflavone and two known compounds, 5,7,2′,5′-tetrahydroxy-3,6,8,4′-tetramethoxyflavone and 5,7,2′,4′-tetrahydroxy-3,6,8,5′-tetramethoxyflavone.     

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.     

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.     

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.     

A glycosidic germacradienolide from Eupatorium altissimum

The isolation and structure determination of a glycosidic germacradienolide from Eupatorium altissimum are reported. Eupatorin and 5-hydroxy-3′,4′,6,7-tetramethoxyflavone were also found.     

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].     

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.     

Viridiflorin,an isoflavone from Tephrosia viridiflora

A new isoflavone, viridiflorin, has been isolated from Tephrosia viridiflora. Its structure was established as 4′,5,7-trihydroxy-2′,5′-dimethoxy-6-prenylisoflavone based on spectral evidence and chemical transformation.     

Flavones from Eupatorium leucolepis

Chloroform extraction of Eupatorium leucolepis gave the new flavones 3′-hydroxy-5,6,7,8,4′,5′-hexamethoxyflavone, 4′-hydroxy-5,6,7,8,3′,5     

Neolignans from Nectandra miranda

Seven neolignans, isolated from a C₆H₆ extract of Nectandra miranda (Lauraceae) trunk wood, included the hitherto undescribed (2S, 3S, 3aS)- and (2S, 3S, 3aR)-5-allyl-3a-methoxy-2-(3′, 4′, 5′-trimethoxyphenyl)-3-methyl-2, 3, 3a, 6-tetrahydro-6-oxobenzofurans (respectively mirandin-A and mirandin -B), 7-allyl-6-hydroxy-5-methoxy-2-(3′, 4′, 5′-trimethoxyphenyl)-3-methylbenzofuran and (2R, 3R)-7-methoxy-2-(3′, 4′, 5′-trimethoxyphenyl)-3-methyl-5 -(E)-propenyl-2, 3-dihydrobenzofuran (licarin C).     

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.     

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.