Antifungal constituents from roots of Virola surinamensis

Chromatographic fractionation of the dichloromethane extract from roots of Virola surinamensis yielded two new natural products, 3-epi-juruenolide C and 2'-hydroxy-7,4'-dimethoxyisoflavone, as well as various known steroids, lignans, isoflavones, flavonoids and diarylpropanes. of these, alpha,2'-dihydroxy-4,3'-dimethoxydihydrochal biochanin A and 2'-hydroxy-7,4'-dimethoxyisoflavone displayed antifungal activity against Cladosporium cladosporioides at a minimum amount of 5 mu g, whereas 7-hydroxyflavanone and 7-hydroxy-4'-methoxyisoflavone exhibited an antifungal activity 10-fold higher than the positive control Nystatin. (C) 1999 Elsevier B.V. Ltd. All rights reserved.

COUMARINS AND A FLAVONOID FROM PTEROCAULON ALOPECUROIDES

From a CH2Cl2 extract of the aerial parts of Pterocaulon alopecuroides, two oxyprenyl coumarins, 7-(2,3-dihydroxy-3-methylbutyloxy)-6-methoxy coumarin and 7-(2,3-dihydroxy-3-methylbutyloxy)-5-hydroxy-6-methoxy coumarin and one flavononol, 3,5,3',4'-tetrahydroxy-7-(2,3-en-3-methylbutyloxy)-2,3-dihydroflavonol, were isolated.

Neolignans, styrylpyrones and flavonoids from an Aniba species

The trunk wood and barks from an Aniba species contain four esters of benzoic acid with cinnamyl alcohol, five benzofuran neolignans, licarin-A, burchellin, cis-burchellin, burchellin-rearranged and cis-burchellin-rearranged, one tetrahydrofuran neolignan, aristolignin, three bicyclooctane guianin-type neolignans, (7S, 8S, 1'R, 5'R)-4-hydroxy-3,3'-dimethoxy-4',6'-dioxo-8.1', 7.5'-neolignan-Delta: 1,3,5,2',8' and the new (7S, 8S, 1'R, 4'R, 5'S)-4'-hydroxy-3,4,3'-trimethoxy-6'-oxo-8.1', 7.5'-neolignan-Delta: 1,3,5,2',8' and (7S, 8S, 1'R, 4'R, 5'S)-4,4'-dihydroxy-3,3'-dimethoxy-6'-oxo-8.1', 7.5'-neolignan-Delta: 1,3,5,2',8', one new bicyclooctane canellin-type neolignan (7S, 8S, 1'S, 4'R, 5'R, 6'S)-4',6'-dihydroxy-3,4-dimethoxy-3'-oxo-8.1', 7.5'-neolignan-Delta: 1,3,5,8', two styrylpyrones, 4-methoxy-6-(11,12-dimethoxy-trans-styryl)-2-pyrone and 6-(11,12-methylenedioxy-trans-styryl)-4-methoxy-2-pyrone, two styrylpyrone dimers: 4'-methoxy-8-(11,12-dimethoxyphenyl)-7-[6-(4-methoxy-2-pyronyl)-6-(E)-styryl-1'-oxabicyclo[4,2,0]octa-4'-en-2'-one and the new 11,12-dimethoxyphenyl-7,7'-di-[6-(4-methoxy-2-pyronyl)]-cyclobutane and six flavonoids, 3,5-dihydroxy-7,4'-dimethoxyflavone, 5-hydroxy-3,7,4'-trimethoxyflavone, 3,5,4'-trihydroxy-7-methoxyflavone, 2,3-dihydro-5-hydroxy-7,4'-dimethoxyflavone, 2,3-dihydro-3,5-dihydroxy-7-methoxyflavone, 2,3-dihydro-3,5-dihydroxy-7,4'-dimethoxyflavone and a new flavan, 6,7,3',4',5'-pentamethoxyflavan. (C) 1997 Elsevier B.V. Ltd.

Tetrahydroisoquinoline alkaloids and 2-deoxyribonolactones from Aristolochia arcuata

2-Deoxyribonolactones and four tetrahydroisoquinoline alkaloids were isolated from the acetone extract of the leaves of Aristolochia arcuata Mast., together with pinitol, sequoyitol, glycerol, fructose, sucrose, eupomatenoid-7, salsolinol, and 6,7-dihydroxyl,1-dimethyl-1,2,3,4-tetrahydroisoquinoline. Their structures were determined on the basis of spectroscopic methods, mainly using H-1, C-13, N-15, and P-31 NMR. (C) 2003 Elsevier B.V. Ltd. All rights reserved.

Butanolides as a common feature of Iryanthera lancifolia and Virola surinamensis

A comparative phytochemical study between pericarps of Iryanthera lancifolia and Virola surinamensis showed that the first one contains a new pair of epimeric 2-alkenyl-gamma-lactones, besides an aryltetralinic lignan and one tocotrienol, while the second species contains the lignans, galgravin and veraguensin, seven juruenolides: juruenolides C, D, F, G and epi-juruenolides D, F, G, together with three pairs of epimeric aliphatic 2-alkenyl-gamma-lactones. Juruenolide F, epi-juruenolides D, F, G and the 2-alkenyl-gamma-lactones are new natural compounds. (C) 1998 Elsevier B.V. Ltd. All rights reserved.

Rearranged (4 -> 2)-abeo-clerodane and clerodane diterpenes from Aristolochia chamissonis

From stems of Aristolochia chamissonis Duch., five new diterpenes, one rearranged (4 --> 2)-abeo-clerodane and four ent-clerodanes, were isolated. Their structures were determined to be (+)-(4 --> 2)-abeo-kolavelool-3-oic acid, (-)-13-epi-2-oxokolavelool, (-)-2 beta-hydroxykolavelool, (-)-2 beta-hydroperoxykolavelool and (+)- 13-epi-2 alpha-hydroxykolavelool. In addition, lignans, sesquiterpenes, steroids and two known ent-clerodane diterpenes were isolated. (C) 1998 Elsevier B.V. Ltd. All rights reserved.

AN OLEANANE ACID FROM ALIBERTIA-EDULIS

A new oleanane, 3 beta,19 alpha,23,24-tetrahydroxy-12-oleanen-28-oic acid, was isolated together with nine known triterpene compounds from the leaves of Alibertia edulis, Rubiaceae.

2,3-Dihydrobenzofuran neolignans from Aristolochia pubescens

From a hexane extract of stems and roots of Aristolochia pubescens, the new neolignans (2S,3S,1'R,2'R)- and (2S,3S, 1'S,2'R)-2,3-dihydro-5-(1',2'-dihydroxypropyl)-2-(4-hydroxy-3-methylbenzofuran) and (2S,3S,1'R,2'R)- and (2S,3S,1'S,2'R)-2,3-dihydro-5-(1',2'-dihydroxypropyl)-2-(3,4-dimethoxyphenyl)-7-methoxy-3-methyl-benzofuran were isolated, together with the known neolignan licarin A, and its bisnor-neolignan aldehyde and acid derivatives. In addition, sitosterol, 8R,9R-oxide-beta-caryophyllene, kobusone, ent-kauran-16 alpha, 17-diol, vanillin, vanillic acid, (+)-sesamin, (+)eudesmin, and (-)-cubebin were isolated. The structures of the new compounds have been elucidated by spectroscopic methods and by chemical transformation using Mosher's acid chloride. (C) 1999 Elsevier B.V. Ltd. All rights reserved.

An unusual C-6-C-6 '' linked flavonoid from Miconia cabucu (Melastomataceae)

Chromatographic fractionation of the methanolic extract from the leaves of Miconia cabucu Hoehne (Melastomataceae) afforded the first example of a C-6-C-6 linked flavone dimer, 5-hydroxy-4',7-dimethoxyflavone-(6-C-6)-5-hydroxy-3 4',7-trimethoxyflavone as well as the known compounds, quercetin- 3-O-alpha-L- rhamnopyranosyl-(2 -> 1)-O-beta-D-xylopyranoside, quercetin-3-O-alpha-L-rhamnopyranoside, myricetin-3-O-alpha-L-rhamnopyranoside, quercetin-3-O-beta-D-glucopyranoside, kaempferol -3-O-beta-D-(6-coumaroyl) -glucopyranoside and gallic acid. Their chemical identities were established by application of NMR spectroscopic methods including 2D-NMR, as well as UV and ESI-MS analyses. (c) 2007 Elsevier Ltd. All rights reserved.

Flavonoids from Iryanthera sagotiana

Leaves and inflorescences of Iryanthera sagotiana were found to contain three known dihydrochalcones, two flavonol rhamnosides, four flavanonol rhamnosides, one dihydrocoumaric acid, besides the new 3,'3'''-bis-2',4',6'-trihydroxy-4-methoxydihydrochalcone and 4',6'-dihydroxy-4-methoxydihydrochalcone-2'-O-beta-D-glucopyranoside. (C) 1997 Elsevier B.V. Ltd.

seco-Irldoids from Calycophyllum spruceanum (Rubiaceae)

Three seco-iridoids 7-methoxydidcrrosidc, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochernistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosonla Cruzi, with IC50 values of 59.0, 90.2, 74,2 and 84.9 mug/mL, respectively and were compared to the standard gentian violet (IC50 7.5 mug/ml). (C) 2003 Elsevier Ltd. All rights reserved.

Biosynthesis of friedelane and quinonemethide triterpenoids is compartmentalized in Maytenus aquifolium and Salacia campestris

Maytenus aquifolium (Celastraceae) and Salacia campestris (Hippocrateaceae) species accumulate friedelane and quinonemethide triterpenoids in their leaves and root bark, respectively. Enzymatic extracts obtained from leaves displayed cyclase activity with conversion of the substrate oxidosqualene to the triterpenes, 3 beta -friedelanol and friedelin. In addition, administration of (+/-)5-H-3 mevalonolactone in leaves of M. aquifolium seedlings produced radio labelled friedelin in the leaves, twigs and stems, while the root bark accumulated labelled maytenin and pristimerin. These experiments indicated that the triterpenes once biosynthesized in the leaves are translocated to the root bark and further transformed to the antitumoral quinonemethide triterpenoids. (C) 2000 Elsevier B.V. Ltd. All rights reserved.

Antifungal polysulphides from Petiveria alliacea L.

Bioactivity-directed fractionation of the CH2Cl2/MeOH (2:1, v/v) extract of the roots of Petiveria alliacea, using mutant yeast strains of Saccharomyces cerevisiae and fungi Cladosporium cladosporioides and C. sphaerospermum led to the isolation of dipropyl disulphide (1), dibenzyl sulphide (2), dibenzyl disulphide (3), dibenzyl trisulphide (4), dibenzyl tetrasulphide (5), benzylhydroxymethyl sulphide (6) and di(benzyltrithio) methane (7). of these, 5-7 are new compounds and this is the first report of the natural occurrence of 2 and 3. (C) 2001 Elsevier B.V. Ltd. All rights reserved.

Bioactive sesquiterpene pyridine alkaloids from Maytenus aquifolium

Two new sesquiterpene evoninate alkaloids, were isolated together with the known compounds syringaresinol and 4'-O-methyl-(-)-epigallocatechin from the root bark of Maytenus aquifolium. The structures of the two alkaloids were elucidated by interpretation of their spectral data, and both exhibited very weak activity in a mechanism-based DNA-modifying yeast assay. (C) 1998 Elsevier B.V. Ltd. All rights reserved.

ALKALOIDS FROM ARISTOLOCHIA-ARCUATA

Phytochemical studies with Aristolochia arcuata led to the isolation of KNO3, fructose, sucrose, sitosterol, calarene, its 2-oxo derivative, and three neolignans. Besides which, two new 13-oxidodibenzo[a, g]-quinolizinium alkaloids were isolated. They present only one oxygenated substituent at rings A and D.