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Using countercurrent chromatography to assist in the purification of new Annonaceous acetogenins from Annona squamosa
Author(s) -
Hopp D. Craig,
Conway Walter D.,
McLaughlin Jerry L.
Publication year - 1999
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/(sici)1099-1565(199911/12)10:6<339::aid-pca474>3.0.co;2-l
Subject(s) - chemistry , acetogenin , annona squamosa , ring (chemistry) , stereochemistry , diastereomer , tetrahydrofuran , countercurrent chromatography , column chromatography , annonaceae , chromatography , organic chemistry , botany , solvent , biology
Three new Annonaceous acetogenins, (2,4‐ cis and trans )‐9‐hydroxy asimicinone ( 1 ), (2,4‐ cis and trans )‐squamoxinone B ( 2 ) and (2,4‐ cis and trans ) squamoxinone C ( 3 ), were isolated from the bark of Annona squamosa with the help of countercurrent chromatography. Additionally found was isoannoreticuin ( 4 ), which is new to this species. Compound 1 is an adjacent bis‐tetrahydrofuran (THF) ring acetogenin with a hydroxyl group at the nine position and two more hydroxyls flanking the bis‐THF system, while compounds 2–4 are all mono‐THF ring acetogenins also possessing three hydroxyl groups. All four compounds are ketolactone‐type acetogenins, and all show impressive cytotoxicities in a panel of six human tumour cell lines. Copyright © 1999 John Wiley & Sons, Ltd.