Antifungal amides from Piper arboreum and Piper tuberculatum

In continuation of our study of the Piperaceae we have isolated several amides, mainly those bearing isobutyl, pyrrolidine, dihydropyridone and piperidine moieties. Bioactivity-guided fractionation of extracts from leaves of Piper arboreum yielded two new amides, N-[10-(13,14-methylenedioxyphenyl)-7(E),9(Z)-pentadienoyl]-pyrrolidine (1), arboreumine (2) together with the known compounds N-[10-(13,14-methylenedioxyphenyl)-7(E)-pentaenoyl]-pyrrolidine (3) and N-[10-(13,14-methylenedioxyphenyl)-7(L, 9(E)-pentadienoyl]-pyrrolidine (4). Catalytic hydrogenation of 3 yielded the amide iV-[10-(13,14-methylenedioxyphenyl)-pentanoyl]-pyrrolidine (5). We also have isolated six amides (6-11) and two antifungal cinnamoyl derivatives (12, 13) from seeds and leaves of Piper tuberculatum. Compounds 1-11 showed antifungal activity as determined by direct bioautography against Cladosporium sphaerospermum while compounds 3-4 and 6-13 also showed antifungal activity against C. cladosporioides. (C) 2002 Published by Elsevier B.V. Ltd.

Clerodane diterpenes from Aristolochia species

The investigation of Aristolochia brasiliensis and A. esperanzae afforded 12 clerodane derivatives, including the following six novel ones: rel (5S, 8R, 9S, 10R)-2-oxo-ent-3-cleroden-15-oic acid, rel (5S, 8R, 9S, 10R)-2-oxo-ent-clerod-3,13-dien-15-oic acid methyl ester, (5R, 8R, 9S, 10R)-ent-3-cleroden-15-oic acid, rel (5S, 8R, 9S, 10R)-ent-clerod-3,13-dien-15-oic acid, (2S, 5R, 8R, 9S, 10R)-2-hydroperoxy-ent-3-cleroden-15-oic acid methyl ester and (2S, 5R, 8R, 9S, 10R)-2-hydroperoxy-ent-clerod-3,13-dien-15-oic acid methyl ester. The structures were assigned on the basis of spectral data and derivatization by chemical reactions. The occurrence of this type of diterpene has not previously been reported in Aristolochiaceae. © 1987.

Isocoumarin from Paepalanthus bromelioides

The new isocoumarin, 9,10-dihydroxy-5, 7-dimethoxy-1H-naphtho(2,3c)pyran-1-one, was isolated from the capitula of Paepalanthus bromelioides. The structure was established by means of the spectral data of the natural product and its derivatives. The natural isocoumarin isolated has strong antibiotic activity. © 1990.

Soluble and bound peroxidases from papaya fruit

Soluble and bound peroxidases were isolated from the pulp of ripening papaya fruit. During papaya ripening, soluble and bound peroxidase activities increased 2.5- and 4.2-fold, respectively. Soluble peroxidase was purified 59-fold by ammonium sulphate precipitation and chromatography on Sephadex G-25, DEAE-cellulose and Sephadex G-100. Bound peroxidase was purified 140-fold by ammonium sulphate precipitation and chromatography on Sephadex G-100 and DEAE-cellulose. Polyacrylamide gel electrophoresis of the purified preparations revealed that both enzymes were highly purified by the procedures adopted. The soluble and bound forms had a Mr of 41 000 and 54 000, respectively. Soluble and bound peroxidases showed optimum activity at pH 6.0 and 5.5, respectively, and were inhibited by p-chloromercuribenzoate, iodoacetamide, N-ethylmaleimide, potassium cyanide and Fe2+. Soluble peroxidase was activated by ammonium sulphate and this activation was prevented by cyanide. © 1990.

Diterpenic adducts from Xylopia species

Xylopia emarginata and X. amazonica contain diterpene adducts probably originating from Diels-Aider reaction between labdane and kaurane derivatives. This type of substance seems to be characteristic of the genus Xylopia. © 1991.

OLEO ESSENCIAL EM ALGUMAS ESPECIES DE EUCALYPTUS

In this work we used leaves of four species of Eucalyptus - E. bicostata Maiden, E. deanei Maiden, E. dunnii Maiden and E. viminalis Labill, grown in Colombo, Parana State, Brazil. Preliminary studies were done, in the following sequence: botanic identification, olfactory research, extraction and purification of the essential oil of each species. The physical and chemical tests done were the following: relative density, refractive index, optical rotation, solubility, coagulation point and cineol percentage. The essential oils analysed through gaseous chromatography, presented the following cineol percentage: E. bicostata Maiden - 26.92%, E. deanei Maiden - 70.21%, E. dunnii Maiden - 53.16% and E. viminalis Labill - 23.05%.

Diterpenes from Guarea Trichilioides

Chemical investigation of the leaves of Guarea trichilioides afforded six diterpenoids, including four labdane and two clerodane derivatives. The following four are new: 3-oxolabd-8(17),12Z,14-triene, 3α-hydroxylabd-8(17),12Z,14-triene, 3β-hydroxylabd-8(17),12Z,14-triene and(-)-2-oxo-13-hydroxy,3,14-clerodandiene. Copyright © 1996 Elsevier Science Ltd. All rights reserved.

Coumarins and terpenoids from Dorstenia asaroides Gardn. in Hook

Phytochemical investigation of rhizomes and leaves of Dorstenia asaroides Gardn. in Hook. (Moraceae) afforded the furocoumarins psoralen and bergapten, the triterpenes α-amyrin, α-amyrin acetate, β-amyrin acetate, lupeyl acetate and simiarenol and saccharose.

Iridoids from Tocoyena formosa

The leaves of Tocoyena formosa afforded two antifungal iridoids α- and β-gardiol, and the new iridoids, mollugoside methyl ester and formosinoside. Formosinoside was characterized as its hexaacetyl derivative.

Lignoids; flavonoids and polyketides of Virola surinamensis

From the seeds of Virola surinamensis, which were collected near Altamira and near Maraba, Para State, Brazil, the following substances were isolated by chromatographic techniques: two dibenzylbutanediol lignans, dihydrocubebin and the new dihydrocubebin monolaurate, two furofuran lignans, sesamin and asarinin, three dibenzylbutyrolactol lignans, cubebin, β-O- methylcubebin and α-O-methylcubebin, one dibenzylbutyrolactone lignan, hinokinin, one aryltetralin neolignan, galbulin, two tetrahydrofuran neolignans, galgravin and the new 4'-hydroxy-3'-methoxy-3,4-methylenedioxy- 8.8',7.O.7'-neolignan, one flavone, tithonine, one isoflavone, irisolidone, and two new polyketides, 3-hydroxy-1-(15-phenylpentadecanoyl)-2,6- cyclohexanedione and 1-(5-phenylpentanoyl)-2,6-cyclohexanedione. Different chemical constitutions of the fruits from the two localities were observed.

Neolignans from leaves of Ocotea catharinensis

A hexane extract of Ocotea catharinensis leaves afforded, by chromatographic fractionation, 11 neolignans, eight of the benzofuran- type (including three new compounds) and three of the bicyclo[3.2.1] octane-type (including two new compounds).

Naphthopyranone glycosides from Paepalanthus bromelioides

Two new naphtho[2,3-C]pyran-1-one glycosides, paepalantine-9-O-β-D- glucopyranoside and paepalantine-9-O-β-D-allopyranosyl(1 → 6)glucopyranoside, were isolated from an ethanolic extract of capitula from Paepalanthus bromelioides and identified from their spectrometric data.