An isoflavone diglycoside from the seeds of Dolichos biflorus

-5-Hydroxy-7,3′,4′-trimethoxy-8-methylisoflavone 5-neohesperidoside has been identified from the seeds of Dolichos biflorus.     

A coumarin from Perezia coerulescens

The roots of Perezia coerulescens contain ψ-taraxasteryl acetate, β-amyrin acetate, 8-hydroxypereflorin, pereflorin B and a new compound identified as 3,4,8-trimethoxy-5-formyl coumarin.     

Anthraquinones from Cassia sophera root bark

Two new anthraquinones have been isolated from the root bark of Cassia sophera and characterized as 1,8-dihydroxy-3,6-dimethoxy-2-methyl-7-vinylanthraquinone and 1,3-dihydroxy-5,7,8-trimethoxy-2-methylanthraquinone.     

Alkaloids and flavonoids of Melicope indica

The following substances were isolated from the leaves of Melicope indica: N-methylatanine dictamnine, evolitrine, meliternatin, melibentin and a new flavonoid which was shown to be 3,5,8-trimethoxy-6,7: 3′,4′-dimethylenedioxyflavone by its spectroscopic properties.     

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 Frasera albomarginata and F. speciosa

Seven 1-hydroxyxanthones have been isolated from the roots of Frasera albomarginata. There were 1-hydroxy-3,7-dimethoxy-, 1-hydroxy-3,5-dimethoxy-, 1,8-dihydroxy-3,5-dimethoxy-, 1-hydroxy-2,3,4,7-tetramethoxy-, 1-hydroxy-2,3,4,5-tetramethoxy-, 1-hydroxy-3,4,7-trimethoxy- and 1-hydroxy-2,3,5-trimethoxyxanthone. Six 1-hydroxyxanthones were obtained from the roots of F. speciosa. These were 1-hydroxy-2,3,4,5-tetramethoxy-, 1-hydroxy-2,3,4,7-tetramethoxy-, 1-hydroxy-2,3,5-trimethoxy-, 1,7-dihydroxy-2,3,4-trimethoxy-, 1,7-dihydroxy-2,3-dimethoxy- and 1,3-dihydroxy-4,5-dimethoxyxanthone.     

4-Arylcoumarins from Coutarea hexandra

Four new 4-arylcoumarins have been isolated from Coutarea hexandra and their structures established as 5,7,4′-trimethoxy-4-phenylcoumarin, 4′-hydroxy-5,7-dimethoxy-4-phenylcoumarin, 3′-hydroxy-5,7-4′-trimethoxy-4-phenylcoumarin and 3′,4′-dihydroxy-5,7-dimethoxy-4-phenylcoumarin.     

Isoflavones from Xanthocercis zambesiaca

In addition to the previously described 7-hydroxy-8,4′-dimethoxy- and 7,3′-dihydroxy-8,4′-dimethoxy-isoflavone the heartwood of Xanthocercis zambesiaca has been shown to contain 7-hydroxy-8,3′,4′-trimethoxy-,3′,4′-dimethoxy-6,7-methylenedioxy- and 8,3′,4′-trimethoxy-6,7-methylenedioxy-isoflavone. A technique of determining isoflavone hydroxylation patterns by deuterium labelling is described.     

The systematic implications of the complexity of leaf flavonoids in the bromeliaceae

In a leaf survey of 61 species of the Bromeliaceae, an unexpectedly wide spectrum of flavonoid constituents was encountered. The family is unique amongst the monocotyledons in the frequency and variety of flavonoids with extra hydroxylation or methoxylation at the 6-position. More common flavonols (in 43% of species) and flavones (in 13%) are distributed throughout the family whereas the rarer flavonoid classes are restricted to one or two of the three subfamilies. Thus 6-hydroxyflavones were found in both the Pitcairnioideae (in 50%) and the Tillandsioideae (in 14%) but patuletin (in 19%), gossypetin (in 1 species) and methylated 6-hydroxymyricetin derivatives (in 24%) were detected only in the Tillandsioideae. A new flavonol, 6,3′,5′-trimethoxy-3,5,7-4′-tetrahydroxyflavone, was identified as the 3-glucoside in Tillandsia usneoides and a new glycoside, patuletin 3-rhamnoside, in Vriesea regina. Myricetin glycosides were found only in the Bromelioideae and their presence here and the concomitant absence of 6-hydroxyflavonoids could indicate the primitive condition of this subfamily. The flavonoid results, in toto, confirm the view based on morphology, that the Bromeliaceae occupies an isolated position in relation to other monocot families.     

Synthesis of (±)-7,3′- and 7,4′-di-O-methyleriodictyol and of velutin and pilloin

Synthetic 2′-hydroxy-3,4′,6′-trimethoxy-4-benzyloxychalcone (I) affords (±)-7,3′-di-O-methyleriodictyol (II) and 7,3′-di-O-methylluteolin (or velutin, VII) identical with natural samples. Similarly synthetic 2′-hydroxy-4,4′,6′-trimethoxy-3-benzyloxychalcone (X) gives natural (±)-7,4′-di-O-methyleriodictyol (XI) and 7,4′-di-O-methylluteolin (or pilloin, IX). However, attempts to partially etherify II with one mole of prenyl bromide to obtain the natural prenyl ether failed; only the corresponding diprenyloxychalcone (IV) was obtained.     

Naphthalenes and naphthoquinones from Ventilago species

Two new naphthalene derivatives and three naphthoquinones have been found in the root bark of Ventilago maderaspatana. Their structures are 2-acetyl-6,7-dimethoxy-3-methyl-1,8-methylenedioxynaphthalene (ventilaginone) and 1,3-dihydro-6,9-dihydroxy-7,8-dimethoxy-1-methylnaphtho[2,3-c]furan-3-one (ventilagol), 2(2′-acetoxypropyl)-3-hydroxy-5,7,8-trimethoxy-1,4-naphthoquinone (maderone), cordeauxione and isocordeauxione. The root bark of V. calyculata contains 2-methoxystypandrone and 1-hydroxy-6-methoxy-3-methylxanthone-8-carboxylic acid (calyxanthone).     

Isoflavones from Pterodon apparicioi

The trunk wood of Pterodon apparicioi contains five known compounds: 7-hydroxy-6,4′-dimethoxy-, 7-hydroxy-6-methoxy-3′,4′-methylenedioxy-, 6,7,2′,3′,4′-pentamethoxy-, 6,7,2′,4′,5′-pentamethoxy- and 6,7,2′-trimethoxy-4′,5′-methylenedioxyisoflavone. In addition, there are four new substances, namely 7,3′-dihydroxy-6,4′-dimethoxy-, 7-hydroxy-6,2′,4′,5′-tetramethoxy-, 7,2′-dimethoxy-4′,5′-methylenedioxy- and 7,8,2′-trimethoxy-4′,5′-methylenedioxyisoflavone.     

New water soluble flavone and xanthone glycosides from Hypericum canariense L.

The water soluble portion of the aerial parts of Hypericum canariense L. yielded after acetylation the 5,7,3′4′-tetra- and 7,3′4′-triacetates of a new flavonoid 5,7,3′,4′-tetrahydroxy-3-O-β-d-(methyl 2,3,4-triacetoxypyranuronyl)-quercetin, the 3′-acetate of a new flavonoid 3′-hydroxy-5,7,4′-trimethoxy-3-O-β-d-(methyl 2,3,4-triacetoxypyranuronyl)-quercetin, the 3′-acetate and the 3′5′-diacetate of the new flavonoid 5,3′dihydroxy-7,4′-dimethoxy-3-β-d-(methyl 2,3,4-triacetoxypyranuronyl)-quercetin, the xanthone derivative mangiferin 2′,3′,4′,6′-tetraacetate and the latter's new 1,3,6,7′-tetramethoxy, 1,3,6-trimethoxy-4-acetoxy and 1,7-diacetoxy-3,6-dimethoxy analogs.     

Melovinone,an open chain analogue of melochinone from Melochia tomentosa

Melovinone, a new alkaloid isolated from the roots of Melochia tomentosa has been characterized as 3,7,8-trimethoxy-2-methyl-5(5′-phenylpentyl)-4-quinolinone.     

A berbine alkaloid,lienkonine from Corydalis ochotensis

Lienkonine, a further alkaloid from Corydalis ochotensis, has been isolated and elucidated as (?)-2,3,10-trimethoxy-8α-methyl-13aαH-berbine-9-ol by the spectral data and chemical properties.     

An aporphinoid alkaloid from Pseuduvaria macrophylla

Chromatographic separation of the alkaloid fraction of the methanol extract from the stem bark of Pseuduvaria macrophylla resulted in the isolation of a new aporphinoid alkaloid, 1,2,3-trimethoxy-4,5-dioxo-6a,7-dehydroaporphine, together with possibly the known O-methylmoschatoline.     

Acridone alkaloids from pleiospermium alatum (rutaceae)

The stem of Pleiospermium alatum has yielded two acridone alkaloids, 1,6-dihydroxy-2,3,5-trimethoxy-10-methyl-9-acridone and 1,5-dihydroxy-2,3-dimethoxy-10-methyl-9-acridone. The significance of their occurrence in this genus is discussed.     

Myricetin methyl ethers from Solanum pubescens

3,7,3′,5′-Tetramethoxy-5,4′-dihydroxyflavone and a novel flavonol 3,7,3′-trimethoxy-5,4′,5′-trihydroxyflavone were isolated from the leaves of Solanum pubescens and characterized by both physical and chemical methods.     

Xanthones and C-glucosylflavones from Gentiana corymbifera

A new xanthone and twelve known compounds were isolated from the aerial parts of Gentiana corymbifera. The new xanthone was shown to be 3-methylcorymbiferin (1,8-dihydroxy-3,4,5-trimethoxy-9H-xanthen-9-one) by spectral and chemical procedures. The chemotaxonomic implications are discussed.     

Formation of three new flavones by differentiating callus cultures of andrographis paniculata

Differentiating tissue cultures of Andrographis paniculata produce three new flavones, 5-hydroxy-7,8,2′-trimethoxy-, 5,2′-dihydroxy-7,8-dimethoxy- and 5-hydroxy-7,8-dimethoxy-flavones. Flavones are not synthesized by the de-differentiated callus. Closely related flavones have been isolated from intact plants of Andrographis species.