Jon E. Anderson

Three new bioactive styryllactones from Goniothalamus giganteus (Annonaceae)

Three new styryllactones, goniobutenolides A (1) and B (3) and goniofupyrone (5), have been isolated from the bark of Goniothalamusgiganteus (Annonaceae). The structures were elucidated by ir, ms, 1H nmr, 13C nmr, 1H-1H COSY, nOe difference, and NOESY spectra. These compounds are marginally cytotoxic to human tumor cells in culture.

Gonioheptolides A and B: Novel eight-membered-ring lactones from Goniothalamus giganteus (Annonaceae)

Two novel eight-membered-ring lactones, gonioheptolides A (1 and B (3), have been isolated from the bark of Goniothalamus giganteus. The structures were elucidated by IR, MS, 1H and 13C NMR, COSY, HMQC, HMBC, and NOESY spectra. 1 and 3 showed marginal cytotoxicities to certain human solid tumor cells in culture. A biogenetic pathway of the 14 styryllactones found in G. giganteus is proposed.

Reticulatacin: A new bioactive acetogenin from Annona reticulata (Annonaceae)

Abstract A new bioactive monotetrahydrofuran acetogenin, reticulatacin, containing 37 carbons, has been isolated from a 95% EtOH extract of the bark of A. reticulata by directing the fractionation with brine shrimp lethality. Another previously reported highly potent antitumor, adjacent ring bistetrahydrofuran acetogenin, bullatacin, has also been isolated in large quantity. Two known diterpenes, (−)-kau-16-en-19-oic acid and methyl 16β,17-dihydro-(−)-kauran-19-oate and a known alkaloid, liriodenine, have also been isolated. Some of these compounds showed selective cytotoxic activities for certain human tumor cell lines.

Novel bioactive styryl-lactones: goniofufurone, goniopypyrone, and 8-acetylgoniotriol from Goniothalamus giganteus(annonaceae). X-Ray molecular structure of goniofufurone and of goniopypyrone

By use of brine shrimp lethality for activity-directed fractionation, three novel styryl-lactones which are cytotoxic to human tumour cells, goniofufurone, goniopypyrone, and 8-acetylgoniotriol, have been isolated from ethanolic extracts of the stem bark of Goniothalamus giganteus Hook, f., Thomas (Annonaceae). The structures were elucidated by IR, mass, 1H NMR, 13C NMR, and 2D NMR (1H–1H COSY, and 1H–13C HETCOR) spectra. The structures of goniofufurone and goniopypyrone, which represent unusual natural skeletons, were confirmed by X-ray crystallographic analysis, to help establish the relative configurations. Goniopypyrone was the most bioactive, showing nonselective ED50 values of ∼6.7 × 10–1µg/ml in each of our three human tumour cell lines.

Giganenin, a Highly Potent Monotetrahydrofuran Acetogenin and 4-Deoxygigantecin from Goniothalamus giganteus

Giganenin, a novel monotetrahydrofuran acetogenin with a double bond along the hydrocarbon chain, and 4-deoxygigantecin, a new nonadjacent bistetrahydrofuran acetogenin, have been isolated from the bark of Goniothalamus giganteus (Annonaceae) by the use of brine shrimp lethality for bioactivity-directed fractionation. The structures were elucidated based on spectral and chemical methods. Giganenin, which shows selective and highly potent cytotoxicities to human tumor cells in culture (ED 50 values as low as 5.80×10 #758 μg/ml) and toxicity to brine shrimp, is the most cytotoxic of the monotetrahydrofuran acetogenins reported thus far

Bullatalicin, a novel bioactive acetogenin from Annona bullata (Annonaceae)

Abstract Bullatalicin, a novel bioactive acetogenin having two nonadjacent tetrahydrofuran rings, has been isolated from the bark of Annona bullata (Annonaceae). Its structure has been elecidated from chemical and spectral data. This compound showed potent and selective cytotoxic activities for certain human tumor cell lines with ED50 values as low as 10−7 mcg/ml.

Majoranolide: A δ-lactone from Persea major

Abstract From the ethanol extract of the bark of Persea major , an additional new bioactive δ-lactone, majoranolide, has been isolated and characterized. The absolute stereochemistries of majoranolide and two previously isolated δ-lactones, majorynolide and majorenolide, have been determined by Horeaus method and CD spectra. Brine shrimp lethality was used to guide the fractionation, and the new lactone is moderately cytotoxic and inhibits crown gall tumours on potato discs.

Bioactive Benzyl Benzoates from the Roots of Endlicheria Dysodantha

AbstractFractionation of the bioactive constituents of the roots of endlicheria dysodantha mez. (lauraceae) using the brine shrimp lethality bioassay led to the isolation of four bioactive derivatives of benzyl benzoate: benzyl 2-hydroxybenzoate (1), benzyl 2-hydroxy-6-methoxybenzoate (2), benzyl 2,6-dimethoxybenzoate (3), and benzyl 2,5-dimethoxybenzoate (4). the structures of these compounds were identified by spectroscopic methods. this is the first report of these benzyl benzoates being isolated from the genus endlicheria.

Additional bioactive neolignans from the roots of Endlicheria dysodantha

Three additional new neolignans, dysodanthins D, E, and F, one known neolignan, megaphyllone acetate, have been isolated from the ethanol extract of the roots of Endlicheria dysodantha (Lauraceae). Their structures were solved using spectral data. Results of biological testing suggest further evaluation of megaphyllone acetate as an antitumor agent