• Archives of Pharmacal Research
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• v.22 no.5
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• pp.524-528
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• 1999

cis-Annonacin (1) and the mixture of (2,4)-cis-and trans-isoannonacins (2 and 3), three known mono-tetrahydrofuran annonaceous acetogenins, have been isolated form the seeds of Annona cherimolia by the use of the brine shrimp lethality test (BST) for bioactivity directed fractionation. Their structures were elucidated based on spectroscopic and chemical methods. 1 showed potent cytotoxicities in the brine shrimp lethality test (BST) and among six human solid tumor cell lines with notable selectivity for the pancreatic cell line (PaCa-2) at about 1,000 times the potency of adriamycin. The mixture of 2 and 3 is over 10,000 times cytotoxic as adriamycin in the pancreatic cell line (PaCa-2). All of the compounds are about 10 to 100 times as cytotoxic as adriamycin in the prostate cell line (PC-3).

• Archives of Pharmacal Research
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• v.24 no.4
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• pp.300-306
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• 2001

A novel and two known bioactive mono-tetrahydrofuran (THF) annonaceous acetogenins, annomocherin (1), annonacin (2) and annomontacin (3), have been isolated from the fractionated ethanolic extracts of the seeds of Annona cherimolia, guided by the brine shrimp lethality test (BST). Their structures were elucidated on the basis of spectroscopic and chemical methods. All compounds have a relative stereochemistry of threo/trans/threo for the mono-THF ring with two flanking hydroxyls. Compound 1 has a double bond at C-23/ 24 of aliphatic chain. Compound 1 was isolated from natural sources for the first time, and was named annomocherin. Two known Compounds 2 and 3 which have never been isolated from this species before, were obtained. Compound 1 exhibited potent and selective cytotoxicities against the breast carcinoma (MCF-7) and kidney carcinoma (A-498) cell lines with 100 to 1,000 times the potency of adriamycin. In brine shrimp lethality test (BST), 1-3 exhibited cytotoxicity.

• YAKHAK HOEJI
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• v.43 no.5
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• pp.584-590
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• 1999

Bioactivity-directed fractionation from the seeds of Annona cherimolia resulted in the isolation of two known cytotoxic compounds : corrosolin (1) and compound-2 (2). The structures of these compounds were characterized on the basis of chemical and spectral data. Corrosolin has a relative stereochemical relationship of threo/trans/threo for the mono-tetrahydrofuran (THF) ring with two flanking hydroxyls, from C-15 to C-20, which is the annonacin type. Compound-2 has a relative stereochemical relationship of threo/trans/threo/trans/threo for the adjacent bis-THF ring with two flanking hydroxyls, such as in the asimicin type. The absolute configurations of carbinol carbons in corrosolin in corrosolin were determined as 10R, 15R, and 20R by analysis of its Mosher ester derivatives. Corrosolin and compound-2 are known, but are first isolated in this plant.