In:
Chemistry & Biodiversity, Wiley, Vol. 14, No. 7 ( 2017-07)
Abstract:
Four limonoids, 1 – 4 , five alkaloids, 5 – 9 , and four phenolic compounds, 10 – 13 , were isolated from a Me OH extract of the bark of Phellodendron amurense (Rutaceae). Among these, compound 13 was new, and its structure was established as rel‐ (1 R ,2 R ,3 R )‐5‐hydroxy‐3‐(4‐hydroxy‐3‐methoxyphenyl)‐6‐methoxy‐1‐(methoxycarbonylmethyl)indane‐2‐carboxylic acid methyl ester ( γ ‐di(methyl ferulate)) based on the spectrometric analysis. Upon evaluation of compounds 1 – 13 against the melanogenesis in the B16 melanoma cells induced with α ‐melanocyte‐stimulating hormone ( α ‐ MSH ), four compounds, limonin ( 1 ), noroxyhydrastinine ( 6 ), haplopine ( 7 ), and 4‐methoxy‐1‐methylquinolin‐2(1 H )‐one ( 8 ), exhibited potent melanogenesis‐inhibitory activities with almost no toxicity to the cells. Western blot analysis revealed that compound 6 inhibited melanogenesis, at least in part, by inhibiting the expression of protein levels of tyrosinase, TRP ‐1, and TRP ‐2 in α ‐ MSH ‐stimulated B16 melanoma cells. In addition, when compounds 1 – 13 were evaluated for their cytotoxic activities against leukemia ( HL 60), lung (A549), duodenum ( AZ 521), and breast ( SK ‐ BR ‐3) cancer cell lines, five compounds, berberine ( 5 ), 8 , canthin‐6‐one ( 9 ), α ‐di‐(methyl ferulate) ( 12 ), and 13 , exhibited cytotoxicities against one or more cancer cell lines with IC 50 values in the range of 2.6 – 90.0 μ m . In particular, compound 5 exhibited strong cytotoxicity against AZ 521 ( IC 50 2.6 μ m ) which was superior to that of the reference cisplatin ( IC 50 9.5 μ m ).
Type of Medium:
Online Resource
ISSN:
1612-1872
,
1612-1880
DOI:
10.1002/cbdv.201700105
Language:
English
Publisher:
Wiley
Publication Date:
2017
detail.hit.zdb_id:
2139001-0
SSG:
12
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