Xin-ping Fang

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.

Novel cytotoxic annonaceous acetogenins: (2,4-cis and trans)-bulladecinones from annona bullata (annonaceae)

Abstract A mixture of two novel cytotoxic adjacent bis-tetrahydrofuran (THF) ketolactone acetogenins, (2,4- cis and trans )-bulladecinones ( 1 and 2 ), was isolated from the bark of Annona bullata Rich. (Annonaceae). Adjacent bis-THF rings, located at C-12 and C-16 and having only one adjacent hydroxyl group, and the presence of an erythro vicinal diol in 1 and 2 are new features for the Annonaceous acetogenins.

New cytotoxic annonaceous acetogenins: Bullatanocin and cis- and trans-Bullatanocinone, from Annona bullata (Annonaceae)

Abstract Further bioactivity-directed fractionation of the ethanol extract of the bark of Annona bullata Rich. (Annonaceae) has led to the isolation of the new nonadjacent bis-tetrahydrofuran acetogenins, bullatanocin ( 1 ), cis- bullatanocinone ( 2 ) and trans-bullatanocinone ( 3 ). A known adjacent bis-tetrahydrofuran acetogenin, desacetyluvaricin ( 4 ), which is new to this species, was also isolated. Brine shrimp lethality test (BST) data and cytotoxicities against human solid tumor cell lines of 1–4 were compared with those of the diastereoisomers, bullatalicin ( 5 ), cis- and trans-bullatalicinone ( 6 and 7 ) and 4-deoxyasimicin ( 8 ). 1 shows cytotoxic potencies 10,000 times those of adriamycin in the lung and colon cancer cell lines.

Goniocin from Goniothalamus giganteus: The first tri-THF annonaceous acetogenin

A novel cytotoxic Annonaceous acetogenin, the first member of this class of compounds having a tri-tetrahydrofuran (THF) moiety, has been isolated from Goniothalamus giganteus. The structure was elucidated by spectral data, and the absolute configuration was determined by advanced Moshers methodology.

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

Two new bioactive triterpenoids from Melia volkensii (Meliaceae)

Abstract Meliavolin ( 1 ), a new triterpene with an apotirucallane skeleton, and meliavolkin ( 2 ), a new tetranortriterpene, together with melianin A, a known compound, have been isolated from the root bark of Melia volkensii (Meliaceae) by using activity-directed fractionation with brine shrimp. The structures have been elucidated by spectral data. The relative and absolute stereochemistry of meliavolin ( 1 ) was determined by analysis of Mosher ester derivatives, 1e and 1f , and by X-ray crystallographic analysis of meliavolin diacetate, 1c. 1 and melianin A showed marginal cytotoxicities to certain human tumor cell lines, but 2 was significantly more cytotoxic, showing equivalent potency to adriamycin against the human breast tumor cell line (MCF-7).

A new type of cytotoxic annonaceous acetogenin: Giganin from goniothalamus giganteus

A new cytotoxic Annonaceous acetogenin, giganin (1), was isolated from the bark of Goniothalamus giganteus (Annonaceae). This compound represents a new type of Annonaceous acetogenin lacking tetrahydrofuran or epoxide rings along the aliphatic chain, and its structure was elucidated by 1H and 13C NMR, MS, COSY, and single-relayed COSY.