Cytotoxic polyoxygenated cyclohexene derivatives from the aerial parts of Uvaria cherrevensis

Three previously undescribed polyoxygenated cyclohexene derivatives named cherrevenol M (1), cherrevenol N (2), and cherrevenone (3), together with nine related known analogues 4–12 were isolated from the ethyl acetate fraction partitioned from the methanol extract of the aerial parts of Uvaria cher...

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Bibliographic Details
Published in:Fitoterapia 2019-09, Vol.137, p.104182, Article 104182
Main Authors: Jaipetch, Thaworn, Hongthong, Sakchai, Kuhakarn, Chutima, Pailee, Phanruethai, Piyachaturawat, Pawinee, Suksen, Kanoknetr, Kongsaeree, Palangpon, Prabpai, Samran, Nuntasaen, Narong, Reutrakul, Vichai
Format: Article
Language:English
Subjects:
Acetic acid
Annonaceae
Biotechnology
Circular dichroism
Configurations
Cyclohexene
Cytotoxic activity
Cytotoxicity
Derivatives
Dichroism
Ethyl acetate
Uvaria cherrevensis
X-ray diffraction
Zeylenol
Zeylenone
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Summary:Three previously undescribed polyoxygenated cyclohexene derivatives named cherrevenol M (1), cherrevenol N (2), and cherrevenone (3), together with nine related known analogues 4–12 were isolated from the ethyl acetate fraction partitioned from the methanol extract of the aerial parts of Uvaria cherrevensis (Annonaceae). The determination of the structures and their relative configurations of the isolated compounds were established by spectroscopic techniques, electronic circular dichroism (ECD) analysis as well as comparison with the literature data. For cherrevenone (3), the relative and absolute configurations were also confirmed by using X-ray diffraction and ECD techniques, respectively. Compounds isolated except for compounds 8 and 10 were evaluated for their cytotoxic activity and cherrevenone (3) showed moderate cytotoxic activity against all cancerous cell lines except for ASK cell line with ED50 values ranging from 1.04 ± 0.13 to 10.09 ± 4.31 μM. [Display omitted]
ISSN:0367-326X
1873-6971
DOI:10.1016/j.fitote.2019.104182