Melanogenesis-Inhibitory Activities of Isomeric C-seco Limonoids and Deesterified Limonoids

被引:7
作者
Akihisa, Toshihiro [1 ]
Horiuchi, Maiko [2 ]
Matsumoto, Masahiro [2 ]
Ogihara, Eri [2 ]
Ishii, Kenta [2 ]
Zhang, Jie [3 ]
机构
[1] Akihisa Med Clin, 1086-3 Kamo, Sanda, Hyogo 6691311, Japan
[2] Nihon Univ, Coll Sci & Technol, Chiyoda Ku, 1-8-14 Kanda Surugadai, Tokyo 1018308, Japan
[3] China Pharmaceut Univ, Dept Nat Med Chem, 24 Tongjiaxiang, Nanjing 24210009, Peoples R China
关键词
C-seco Limonoids; Isomeric C-seco limonoids; Deesterified limonoids; Melanogenesis-inhibitory activity; INDICA VAR. SIAMENSIS; VAR-JAPONICA-MAKINO; A; JUSS; NEEM; AZADIRACHTA-INDICA; CYTOTOXIC ACTIVITIES; MELIA-AZEDARACH; GLYCOSIDIC INHIBITORS; CARBONYL-COMPOUNDS; HEXANE EXTRACT; ACER-NIKOENSE;
D O I
10.1002/cbdv.201600100
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Treatment of eight C-seco limonoids including six of salannin-type, 1 - 6, and two of nimbin-type, 7 and 8, with a combination of BF3 Et2O and iodide ion yielded the isomeric C-seco derivatives, i.e., six isosalannins, 1a - 6a, and two isonimbins, 7a and 8a, respectively. Ohchinin (1) was further subjected to LiAlH4 reduction which yielded a deesterified trihydroxy limonoid, nimbidinol (9). In addition, ten limonoids including seven of azadirone-type, 10 - 16, and three of gedunin-type, 17 - 19, all of which possess no ester functionality in the molecule, were obtained from the neutral fraction of Azadirachta indica seed extract after alkaline hydrolysis. Among the above, twelve compounds, i.e., 1a - 4a, 6a, 9, 13 - 16, 18, and 19, were new compounds, and their structures were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of all these limonoids for their inhibitory activities against melanogenesis in B16 melanoma cells induced with -melanocyte-stimulating hormone (-MSH), five structurally modified limonoids, 3-deacetyl-28-oxosalannin (6a), 9, 17-epi-17-hydroxynimbocinol (14), 17-epi-17-hydroxy-15-methoxynimbocinol (15), and 7-deacetyl-17-epinimolicinol (18), in addition to a natural limonoid, 1, exhibited potent inhibitory activities with 26 - 66% reduction of melanin content at 100 m concentration with almost no or low toxicity to the B16 melanoma cells (70 - 99% cell viability at 100 m).
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页码:1410 / 1421
页数:12
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