Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Annonaceous Acetogenins from the Seeds of Annona squamosa.Non-adjacent Bis-tetrahydrofuranic Acetogenins
Yoshinori FUJIMOTOChikako MURASAKIHiroyasu SHIMADASeiichi NISHIOKAKatsumi KAKINUMASanjewon SINGHManorama SINGHYogesh Kumar GUPTAMahendra SAHAI
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1994 Volume 42 Issue 6 Pages 1175-1184

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Abstract

Four non-adjacent bis-tetrahydrofuranic acetogenins, named squamostatins-B (2), -C (3), -D (4) and -E (5), have been isolated from the petroleum ether extract of Annona squamosa seeds. The structures of these acetogenins have been established on the basis of spectral evidence. C-15/C-16-threo, C-19/C-20-threo, C-23/C-24-erythro stereochemistry was assigned for squamostatins-B and -D, whereas C-15/C-16-threo, C-19/C-20-threo, C-23/C-24-threo stereochemistry was assigened for squamostatins-C and -E. All of these acetogenins, including squamostatin-A, have been established to have C-12/C-15-trans, C-20/C-23-trans stereochemistry by 13C-NMR comparison with synthetic model mono-tetrahydrofuranic compounds. An improved <13>C-NMR assignment of squamostatin-A is presented.

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