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13-Epi-9-Deacetylxenicin Derivatives from a Taiwanese Soft Coral Asterospicularia laurae and Treir Cytotoxic Activity
Ist Teil von
Chemistry of natural compounds, 2022-07, Vol.58 (4), p.659-668
Ort / Verlag
New York: Springer US
Erscheinungsjahr
2022
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
The xenicane-type diterpene 13-epi-9-deacetylxenicin (
1
) was isolated from polar extract of the soft coral
Asterospicularia laurae
. The structure of 13-epi-9-deacetylxenicin was determined by X-ray diffraction analysis, and the absoulte configuration was determined using the modified Mosher′s method. Eleven acylation products of 13-epi-9-deacetylxenicin were prepared: 13-epi-9-
O
-p-anisoylxenicin (
2
), 13-epi-9-
O
-2-furoylxenicin (
3
), 13-epi-9-
O
-2-thiophenecarbonylxenicin (
4
), 13-epi-9-
O
-2-benzoylxenicin (
5
), 13-epi-9-
O
-p-toluoylxenicin (
6
), 13-epi-9-
O
-4-chlorobenzoylxenicin (
7
), 13-epi-9-
O
-4-fluorobenzoylxenicin (
8
), 13-epi-9-
O
-4-propylbenzoylxenicin (
9
), 13-epi-9-
O
-4-nitrobenzoylxenicin (
10
), and 13-epi-9-
O
-cinnamoylxenicin (
11
) are new compounds, and one known compound, 13-epixenicin (
12
). The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis, particularly mass spectroscopy and 2D NMR (
1
H–
1
H COSY, HMQC, HMBC, and NOESY) spectroscopy. The in vitro cytotoxic activities of the twelve compounds were evaluated against Molt4, K562, U937, and SUP-T1 human tumor cell lines.