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At least 19 recordsLinked to original sources
PubMed2005

Asimitrin and 4-hydroxytrilobin, new bioactive annonaceous acetogenins from the seeds of Asimina triloba possessing a bis-tetrahydrofuran ring.

Bioactivity-directed fractionation of the seeds of Asimina triloba resulted in the isolation of asimitrin (1) and 4-hydroxytrilobin (2). Compound 1 represents an adjacent ring-hydroxylated bis-tetrahydrofuran (THF) acetogenin. Compound 2 has an adjacent bis-THF ring with two flanking hydroxyl groups and a alpha,beta-unsaturated gamma-lactone with a 4-hydroxyl group. Compounds 1 and 2 showed cytotoxic selectivity, with 100-10 000 times the potency of adriamycin against prostate adenocarcinoma (PC-3) and colon adenocarcinoma (HT-29) cell lines.

Animals↗
PubMed1996

(2,4-cis)-asimicinone and (2,4-trans)-asimicinone: two novel bioactive ketolactone acetogenins from Asimina triloba (Annonaceae).

Two novel bioactive ketolactone Annonaceous acetogenins, (2,4-cis)-asimicinone (1) and (2,4-trans)-asimicinone (2), have been isolated from Asimina triloba (Annonaceae) by bioactivity directed fractionation. The separation of these two epimeric compounds was achieved by HPLC methods using a Si gel normal phase column eluted with acetone in hexane gradients. The assignments of cis or trans stereochemistry of the ketolactone moieties were made on the bases of 1H-1H COSY and NOESY experiments. 1 and 2 showed selective cytotoxicities against A-549 (human lung cancer) and MCF-7 (human breast cancer) cell lines with ED50 values as low as < 10(-7) micrograms/ml with 2 being the more active isomer.

Acetylation↗
PubMed1999

Lipids of the pawpaw fruit: Asimina triloba.

The fatty acid composition and structure of pawpaw fruit (Asimina triloba) triglycerides were examined and found to contain fatty acids ranging from C6 to C20. Octanoate represented 20% of the fatty acids while other medium-chain fatty acids were present in low amounts. Analysis of the intact triglycerides by high-temperature gas-liquid chromatography gave an unusual three-cycle carbon number distribution. Analysis of triglyceride fractions separated according to degree of unsaturation suggested that one octanoate was paired with diglyceride species containing long-chain fatty acids. Determination of the double-bond positions of monoene fatty acids revealed cis delta9 and cis delta11 hexadecenoate and cis delta9, cis delta11, and cis delta13 octadecenoate isomers were present in significant quantities. Octanoate and positional monoene fatty acid isomers were found only in the fruit lipids and not in the seed lipids. Phenacyl esters of fatty acids were found to be useful derivatives for structure determination using multiple types of analyses.

Chromatography↗
PubMed1993

Biologically active acetogenins from stem bark of Asimina triloba.

In continuing our research with cytotoxic and pesticidal components from the stem bark of the North American paw paw, Asimina triloba, the novel cytotoxic monotetrahydrofuran Annonaceous acetogenins, cis- and trans-annonacin-A-one, cis- and trans-gigantetrocinone and cis-isoannonacin, in addition to the known compounds, trans-isoannonacin and squamolone, have been identified. Brine shrimp lethality testing was used to direct the fractionation. The structures were elucidated by spectral analysis and/or chemical synthesis. These acetogenins have potent cytotoxicities against the human tumour cell lines of A-549 (lung carcinoma), MCF-7 (breast carcinoma) and HT-29 (colon adenocarcinoma).

Animals↗
PubMed1996

The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba.

A novel acetogenin, asiminocin (1), was isolated by activity-directed fractionation from the stem bark of the paw paw tree, Asimina triloba. By spectral and chemical methods, 1 was identified as (30S)-hydroxy-4-deoxyasimicin. The absolute configuration of 1, along with those of previously reported acetogenins asimin, asiminacin, bullatin, (30S)-bullanin, and (30R) bullanin, was determined by Mosher ester methodology. Compound 1 was highly inhibitory to three human solid tumor cell lines with over a billion times the potency of adriamycin.

Animals↗
PubMed1996

Longifolicin, longicoricin, and gigantetroneninone, three novel bioactive mono-tetrahydrofuran annonaceous acetogenins from Asimina longifolia (Annonaceae).

Longifolicin (1), longicoricin (2) and (2,4-cis and trans)-gigantetroneninone (3), three novel bioactive mono-tetra-hydrofuran (THF) gamma-lactone acetogenins, were isolated from the leaves and twigs of Asimina longifolia (Annonaceae) by directing the fractionation with the brine shrimp lethality test (BST). The structures were elucidated based on spectroscopic and chemical methods. Compounds 1-3 showed selective and potent cytotoxicities to certain human tumor cell lines.

Animals↗
PubMed1999

Asitrilobins A and B: cytotoxic mono-THF annonaceous acetogenins from the seeds of Asimina triloba.

The seeds of Asimina triloba have yielded two novel cytotoxic mono-tetrahydrofuran (THF) Annonaceous acetogenins, asitrilobins A (1) and B (2). In addition, annonacin, asimin and asiminacin, which are known, and annomontacin and xylomaticin, which are known but are new in this species, were obtained. Compounds 1 and 2 have a relative stereochemical relationship of erythro/cis/threo across the mono-THF ring with its two flanking hydroxyls and they, thus, represent a new type of acetogenin. Their structures were established on the basis of chemical and spectral evidence. 1 and 2 showed potent bioactivities in the brine shrimp lethality test (BST) and among six human solid tumor cell lines with notable selectivity for the pancreatic cell line (MIA PaCa-2) at ten to one-hundred times the potency of adriamycin.

Animals↗
PubMed1997

Additional bioactive annonaceous acetogenins from Asimina triloba (Annonaceae).

Trilobalicin (1), a new nonadjacent bis-THF ring annonaceous acetogenin, 2,4-cis- (2) and 2,4-trans-trilobacinone (3), the ketolactones of trilobacin, an adjacent bis-THF ring acetogenin, were isolated from the stem bark of Asimina triloba (L.) Dunal (Annonaceae). Their structures were established based on chemical and spectral evidence. The relative stereochemistry of 1 was determined as trans/threo/threo/trans/erythro from C-10 to C-22 by comparisons of NMR data with those of model compounds. Compound 1 is the first example of a nonadjacent bis-THF acetogenin being isolated from the title species and represents a new type of these compounds. Bioactivities of these new structures against brine shrimp larvae and six human solid tumor cell lines were determined, and cytotoxic selectivities were shown for the lung (A-549) and breast (MCF-7) cell lines with up to a million times the potency of adriamycin.

4-Butyrolactone↗
PubMed2000

Asitrilobins C and D: two new cytotoxic mono-tetrahydrofuran annonaceous acetogenins from Asimina triloba seeds.

Two new bioactive mono-tetrahydrofuran (THF) gamma-lactone acetogenins, asitrilobins C (1) and D (2), were isolated from the seeds of Asimina triloba (Annonaceae) by directing the fractionation with brine shrimp lethality. Compounds 1 and 2 have a relative stereochemical relationship of threo/trans/threo across the mono-THF ring with its two flanking hydroxyls. Their structures were established on the basis of chemical and spectral evidence. Compounds 1 and 2 showed selective cytotoxicity comparable with adriamycin for the breast carcinoma (MCF-7) and the colon adenocarcinoma (HT-29) cell lines.

4-Butyrolactone↗
PubMed1994

Asimin, asiminacin, and asiminecin: novel highly cytotoxic asimicin isomers from Asimina triloba.

Activity-directed fractionation of the stem bark extracts of the North American paw paw tree, Asimina triloba (Annonaceae), has yielded three further acetogenins: asimin (2), asiminacin (3), and asiminecin (4). 2-4 are structural isomers of asimicin (1), which is a potent inhibitor of mitochondrial NADH:ubiquinone oxidoreductase, and thus exhibits potent antitumor and pesticidal effects. 2-4 have the same carbon skeleton and configurations as those of 1, but they have the third hydroxyl group located at C-10, C-28, and C-29, respectively, rather than at C-4. The determinations of the hydroxyl group locations were largely based on mass spectral analyses of TMSi and TMSi-d9 derivatives. 2-4 all showed highly potent cytotoxicities (ED50 values as low as < 10(-12) micrograms/mL) with notable selectivities for the HT-29 human colon cancer cell line. The presence of a third hydroxyl at C-4, C-10, C-28, or C-29, as in 1-4, greatly enhances the bioactivity of 4-deoxyasimicin (5).

Antineoplastic Agents, Phytogenic↗
PubMed1996

Longimicins A-D: novel bioactive acetogenins from Asimina longifolia (annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins.

Bioactivity-directed fractionation of the ethanol extract of Asimina longifolia led to the isolation of four novel bioactive annonaceous acetogenins: longimicins A-D (1-4). Compounds 1-4 represent the asimicin type of acetogenins; however, the locations of the adjacent bis-tetrahydrofuran (THF) ring moieties are shifted along the aliphatic chains compared to the known compounds of this type. They are the first examples among this type of acetogenins with the placements of the ring systems altered. Compounds 1-4 showed bioactivities in several bioassays, but they are less active than their structural isomers. Study of their structure-activity relationships (SAR) reveals that the position of the adjacent bis-THF ring moiety is essential for maximization of the bioactivities among these asimicin type annonaceous acetogenins.

Animals↗
PubMed2000

Asitrocin, (2,4)-cis- and trans-asitrocinones: novel bioactive mono-tetrahydrofuran acetogenins from Asimina triloba seeds.

Asitrocin (1) and the mixture of (2,4)-cis- and trans-asitrocinones (2 and 3), new bioactive Annonaceous acetogenins, were isolated from the seeds of Asimina triloba by activity-directed fractionation using the brine shrimp lethality test. Asitrocin and the mixture of (2,4)-cis- and trans-asitrocinones have a configuration of erythro/trans/threo from C-15 to C-20, the mono-THF moiety with two flanking hydroxyl groups. The structures were determined by spectroscopic methods. These acetogenins showed potent bioactivities in the brine shrimp lethality test (BST) and among six human solid tumor cell lines with notable selectivity for the prostate (PC-3) and the pancreatic (MIA PaCa-2) cell lines at 10-100 times the potency of adriamycin.

Animals↗
PubMed1992

Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.

Fractionation of the EtOH extract of the bark of Asimina triloba, monitoring by brine shrimp lethality, has led to the isolation and structural elucidation of a novel highly cytotoxic Annonaceous acetogenin, trilobacin [1], in addition to six known compounds: asimicin 2], bullatacin [3], bullatacinone [4], N-p-coumaroyltyramine [5], N-trans-feruloyltyramine [6], and (+)-syringaresinol [7]. Acetogenin 1 was identified as a diastereomer of asimicin [2] by spectral and chemical methods, and both 1 and 2 showed potent and selective cytotoxicities in the NCI human tumor cell line screen.

Antineoplastic Agents, Phytogenic↗
PubMed1992

Bioactive constituents from the twigs of Asimina parviflora.

The EtOH extract of Asimina parviflora (Annonaceae), when subjected to activity-directed fractionation using lethality to brine shrimp, led to the isolation and identification of five bioactive compounds: asimicilone [1], which is a new 2-quinolone alkaloid, 6-cis-docosenamide [2], which is a new amide of a long hydrocarbon chain fatty acid, and three known compounds, asimicin, (+)-syringaresinol, and beta-sitosterol-beta-D- glucopyranoside. The structure determination of the new alkaloid was performed by extensive nmr analyses, including HMQC and HMBC. Selective cytotoxic activities of these compounds in three human solid tumor cell lines are also reported.

Animals↗
PubMed1995

Longicin and goniothalamicinone: novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia.

Longicin [1] and (2,4-cis and trans)-goniothalamicinone [2], two new monotetrahydrofuran Annonaceous acetogenins, have been isolated from the leaves and twigs of Asimina longifolia (the long leaf paw paw) by the use of the brine shrimp lethality test for bioactivity-directed fractionation. The structures were elucidated based on spectroscopic and chemical methods. Compound 1 was converted to its ketolactone isomer, (2,4-cis and trans)-longicinone [3], to aid the stereochemical elucidation of 1. Compounds 1-3 showed selective and potent cytotoxicities to certain human tumor cell lines, with the potency of 1 against pancreatic carcinoma (PaCa-2) over one million times that of adriamycin. Nine known cytotoxic acetogenins, annonacin, xylomaticin, isoannonacin, gigantetrocins A and B, muricatetrocins A and B, gigantetrocin-A-one and goniothalamicin, were also isolated for the first time from this species.

4-Butyrolactone↗
PubMed1995

Asimilobin and cis- and trans-murisolinones, novel bioactive Annonaceous acetogenins from the seeds of Asimina triloba.

Three new bioactive Annonaceous acetogenins, asimilobin [1], cis-murisolinone [2], and trans-murisolinone [3], have been isolated from an ethanolic extract of the seeds of Asimina triloba by directing the fractionation with brine shrimp lethality. The structure were elucidated based on spectroscopic and chemical methods, In addition, cis- and trans-bullatacinone, which are known compounds, were obtained. Asimilobin [1] has adjacent bis-THF rings, located at C-10 to C-17 and having only one flanking hydroxyl group at C-18. Compounds 1-3 showed cytotoxicity values comparable with adriamycin against six human solid tumor cell lines.

Animals↗
PubMed1996

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.

Animals↗
PubMed1992

Evaluation of various parts of the paw paw tree, Asimina triloba (Annonaceae), as commercial sources of the pesticidal annonaceous acetogenins.

Various plant parts of the paw paw tree (Asimina triloba Dunal, Annonaceae) were extracted and partitioned to concentrate the mixture of acetogenins into a standardized pesticidal extract (F005). A bioassay with brine shrimp larvae (Artemia salina Leach) was used to determine the relative potencies of the various extracts. The small twigs (0-0.5 cm diameter) yielded the most potent extract (LC50 = 0.04 ppm); the stem wood (LC50 = 4.9 ppm) and leaves (LC50 = 53.7 ppm) yielded the poorest activities. The unripe fruits, seeds, root wood, root bark, and stem bark were notably potent and, generally, yielded > 2% of their dry weight as F005. The smaller diameter stems were more potent than the larger stems. We conclude that, by pollarding the trees, the entire twigs and small branches of paw paw could be processed to produce a potent acetogenin mixture; this biomass could be made available in quantities needed for commercialization of the pesticidal product and could be renewable through regrowth from the parent trunk and larger branches.

Animals↗