4-deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteus.

4-Deoxyannomontacin (1) and a mixture of (2,4-cis and trans)-annomontacinone (2), new bioactive mono-tetrahydrofuran (THF) gamma-lactone and keto-lactone acetogenins, respectively, as well as five known mono-THF acetogenins [xylomaticin, longifolicin, longicoricin, (2,4-cis and trans)-gigantetrocinone, and (2,4-cis and trans)-gigantetroneninone], were isolated from the bark of Goniothalamus giganteus (Annonaceae) by activity-directed fractionation using the brine shrimp lethality test (BST). The structures were elucidated based on spectroscopic and chemical methods. The absolute stereochemistries of 1 and 2 were determined by the advanced Mosher ester method and by circular dichroism (CD). Determination of the absolute stereochemistry at C-10 as R for 1 is the first example of the direct determination of the absolute stereochemistry of a carbinol position isolated from other functional groups in the annonaceous acetogenins. 1 and 2 showed selective and potent cytotoxicities to certain human tumor cell lines and were comparable to the activity of rotenone against yellow fever mosquito larvae.

Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.

Three new adjacent bis-tetrahydrofuran ring Annonaceous acetogenins with four hydroxy groups, bullatetrocin (1), 10-hydroxyasimicin (2), and 10-hydroxytrilobacin (3), were isolated by activity-directed fractionation from the stem bark of Asimina triloba. Their structures were established on the basis of chemical and spectral evidence. The absolute stereochemistry at the C-10 hydroxy position was determined by converting 2 and 3 to their ketolactone isomers, 2,4-cis/trans 10-hydroxyasimicinones and 2,4-cis/trans 10-hydroxytrilobacinones, respectively. The bioactivities of the new compounds against brine shrimp larvae and six human solid-tumor cell lines are reported, and structure-activity relationships between trihydroxylated and tetrahydroxylated acetogenins are discussed. In addition to 1-3, gigantetrocin A, 2,4-cis/trans-gigantetrocin A-ones, annonacin, and annonacin A were also isolated for the first time from this species.

New bioactive adjacent bis-THF annonaceous acetogenins from Annona bullata.

Five new adjacent bis-THF annonaceous acetogenins, 32-hydroxybullatacin, 31-hydroxybullatacin, 30-hydroxybullatacin, and (2,4-cis and trans)-28-hydroxybullatacinones, were isolated from the ethanolic extract of the bark of Annona bullata Rich. (Annonaceae). The absolute configurations of the above five compounds, as well as those of (2,4-cis and trans)-32-, 31-, and 30-hydroxybullatacinones and (2,4-cis and trans)-bulladecinones, previously isolated from the same extract, were defined by the application of the advanced Mosher ester [methoxy(trifluoromethyl)phenyl acetate or MTPA] methodology. The determination of the absolute configuration of C-20 of (2,4-cis and trans)-bulladecinones to be S supports our hypothesis that the cyclization of the THF rings of (2,4-cis and trans)-bulladecinones starts from C-12 (the right side). The first five compounds listed above showed potent bioactivities in the brine shrimp lethality test (BST) and among six human solid tumour cell lines.

Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata.

In a continuation of our research on bioactive components from the leaves of Annona muricata, three novel monotetrahydrofuran Annonaceous acetogenins, namely, annomutacin [1], (2,4-trans)-10R-annonacin-A-one [2], and (2,4-cis)-10R- annonacin-A-one [3], have been identified. Their structures were deduced by ms, nmr, ir, and uv spectral and chemical methods, and the absolute configurations were determined by Mosher ester methodology. A known bioactive amide, N-p-coumaroyl tyramine, was also found. Compound 1 and the mixture of compounds 2 and 3 showed selective cytotoxicities against the human A-549 lung tumor cell line.

Muricatocins A and B, two new bioactive monotetrahydrofuran Annonaceous acetogenins from the leaves of Annona muricata.

The leaves of Annona muricata have yielded the novel monotetrahydrofuran Annonaceous acetogenins, muricatocins A [1] and B [2]. Each compound possesses five hydroxyl groups, with two hydroxyl groups at the C-10 and C-12 positions. The absolute configurations of 1 and 2 (except for positions C-10 and C-12) were determined by Mosher ester methodology. The C-10, C-12 acetonides (1c, 2c) suggested relative stereochemistry and significantly enhanced cytotoxicity against the A-549 human lung tumor cell line. Three known monotetrahydrofuran acetogenins, annonacin A, (2,4-trans)-isoannonacin, and (2,4-cis)-isoannonacin, were also found.

New bioactive monotetrahydrofuran Annonaceous acetogenins, annomuricin C and muricatocin C, from the leaves of Annona muricata.

The leaves of Annona muricata have yielded two additional monotetrahydrofuran Annonaceous acetogenins, annomuricin C [1] and muricatocin C [2]. Compounds 1 and 2 each possess five hydroxyl groups; two hydroxyl groups are at the C-10/C-11 and C-10/C-12 positions in 1 and 2, respectively. The absolute configurations of 1 and 2, except for positions C-10 and C-11 or C-12, were determined by Mosher ester methodology. The C-10/C-11 and C-10/C-12 acetonides (1c, 2c) suggested relative stereochemistry and significantly enhanced the cytotoxicities against the A-549 human lung and the MCF-7 human beast solid tumor cell lines. One known monotetrahydrofuran acetogenin, gigantetronenin, not described previously from this plant, was also found.