NEW DIARYLHEPTANOIDS FROM THE SEEDS OF ALPINIA KATSUMADAI WITH HEAT SHOCK PROTEIN MODULATION ACTIVITY

Abstract

초두구 (Alpinia katsumadai)의 에칠아세테이트 분획으로부터 23개의 단일 물질을 분리하였으며, 이 중 14개가 새로운 다이아릴헵타노이드 유도체인, alpinikatin A-D (51-54), ent-calyxin H (55), katsumain C-H (58, 63-67), 7-epi-katsumain C (59), ent-alpinnanin B (60), ent-alpinnanin A (61)로 확인되었다. 추가적으로 9개의 알려진 물질인 (3S,5S)-3,5-dihydroxy-1,7-diphenyl-6E-heptene (2), cardamonin (12), helichrysetin (13), alpinetin (15), 5-methoxynaringenin (17) 5,6-dehydrokawain (23), epicalyxin H (56), calyxin H (57), alpinnanin B (62)이 분리되었으며 이 중, epicalyxin H (56), calyxin H (57), alpinnanin B (62)는 초두구에서 처음 분리되었다. 새로운 화합물의 구조는 각종 이화학적 및 분광학적 기법을 사용하여 분석하였다. 열충격단백질 조절인자 1 (HSF1) 및 이에 의해 발현되는 열충격단백질 70 과 27 (HSP70, HSP27)의 조절 활성 실험에서, 3종의 입체이성질체 혼합물 (이성질체혼합물 55-57, 58-59, 60-62)과 단일 물질 63-65은 세포독성 없이 HSF1및 HSP70과 27의 발현을 증가시켰다. 나아가 A. katsumadai로부터 분리된 물질들의 HSF1 및 HSP 조절 활성 검색은 처음 보고되는 바이다.;Fourteen new diarylheptanoid derivatives, namely, alpinikatin A-D (51-54), ent-calyxin H (55), katsumain C-H (58, 63-67), 7-epi-katsumain C (59), ent-alpinnanin B (60), and ent-alpinnanin A (61) were isolated from an ethyl acetate extract of the seeds of Alpinia katsumadai together with nine known compounds, (3S,5S)-3,5-dihydroxy-1,7-diphenyl-6E-heptene (2), cardamonin (12), helichrysetin (13), alpinetin (15), 5-methoxynaringenin (17), 5,6-dehydrokawain (23), epicalyxin H (56), calyxin H (57), and alpinnanin B (62). The three known compounds 56, 57, and 62 have never been isolated previously from this plant. The structures of the new compounds were elucidated by spectroscopic data analysis including 1D and 2D NMR experiments. Absolute configurations of 51 and 52 were resolved by Mosher’ esterification. Also, The established method was also applied to determine the absolute stereochemistry at C-3 and C-7 of 55-62. The three isomer mixtures of 55-57, 58 and 59, 60-62, and compounds 63-65 increased expression of heat shock factor 1 (HSF1), which was accompanied with increased expressions of heat shock protein (HSP) 27 and HSP70 without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers.