Diarylheptanoids from the Seeds of <i>Alpinia katsumadai</i> as Heat Shock Factor 1 Inducers

다국어 초록 (Multilingual Abstract)

<P>Seven new diarylheptanoids, (−)-(<I>R</I>)-4″-hydroxyyashabushiketol (<B>1</B>), (3<I>S</I>,5<I>S</I>)-alpinikatin (<B>2</B>), katsumain C (<B>3</B>), 7-<I>epi</I>-katsumain C (<B>4</B>), <I>ent</I>-alpinnanin B (<B>5</B>), <I>ent</I>-alpinnanin A (<B>6</B>), and <I>ent</I>-calyxin H (<B>8</B>), were isolated from the EtOAc extract of the seeds of <I>Alpinia katsumadai</I> together with three known compounds, alpinnanin B (<B>7</B>), epicalyxin H (<B>9</B>), and calyxin H (<B>10</B>). Each isomer mixture of <B>3</B> and <B>4</B>, <B>5</B>–<B>7</B>, and <B>8</B>–<B>10</B> was separated successfully by preparative HPLC using a chiral column. The three isomer mixtures (<B>3</B> and <B>4</B>, <B>5</B>–<B>7</B>, <B>8</B>–<B>10</B>) at 1 μM increased expression of heat shock factor 1 (HSF1) with fold increases of 1.438, 1.190, and 1.316, respectively, which was accompanied with increased expression of heat shock protein (HSP) 27 (1.403-, 1.250-, and 1.270-fold, respectively) and HSP70 (1.373-, 1.313-, and 1.229-fold, respectively) without cellular cytotoxicity, suggesting a possible application of these compounds as HSP inducers. Celastrol was used as a positive control of HSP induction, producing fold increases of 1.066 (HSF1), 1.216 (HSP27), and 1.371 (HSP70) at 1 μM. Compounds <B>1</B> and <B>2</B> did not affect the induction of HSF1 protein.</P><P><B>Graphic Abstract</B>
<IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2011/jnprdf.2011.74.issue-10/np200355n/production/images/medium/np-2011-00355n_0002.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np200355n'>ACS Electronic Supporting Info</A></P>