Ceramicines M–P from Chisocheton ceramicus: isolation and structure–activity relationship study
Ceramicines are a series of limonoids which were isolated from the bark of Malaysian Chisocheton ceramicus (Meliaceae) and show various biological activities. Ceramicine B, in particular, has been reported to show a strong lipid droplet accumulation (LDA) inhibitory activity on a mouse pre-adipocyte...
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Veröffentlicht in: | Journal of natural medicines 2018-01, Vol.72 (1), p.64-72 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Ceramicines are a series of limonoids which were isolated from the bark of Malaysian
Chisocheton ceramicus
(Meliaceae) and show various biological activities. Ceramicine B, in particular, has been reported to show a strong lipid droplet accumulation (LDA) inhibitory activity on a mouse pre-adipocyte cell line (MC3T3-G2/PA6). With the purpose of discovering compounds with stronger activity than ceramicine B, we further investigated the constituents of
C. ceramicus
. As a result, from the bark of
C. ceramicus
four new ceramicines (ceramicines M–P,
1
–
4
) were isolated, and their structures were determined on the basis of NMR and mass spectroscopic analyses in combination with NMR chemical shift calculations. LDA inhibitory activity of
1
–
4
was evaluated. Compounds
1
–
3
showed LDA inhibitory activity, and
3
showed better selectivity than ceramicine B while showing activity at the same order of magnitude as ceramicine B. Since
3
, which possess a carbonyl group at C-7, showed better selectivity than
5
, which possess a 7α-OH group, while showing activity at the same order of magnitude as
5
, we also investigated the effect of the substituent at C-7 by synthesizing several derivatives and evaluating their LDA inhibitory activity. Accordingly, we confirmed the importance of the presence of a 7α-OH group to the LDA inhibitory activity. |
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ISSN: | 1340-3443 1861-0293 |
DOI: | 10.1007/s11418-017-1109-2 |