초록
<P>Marine-derived <I>Trichoderma</I> sp. TPU199 (cf. <I>T. brevicompactum</I>) produced gliovirin (<B>1</B>), pretrichodermamide A (<B>2</B>), and trichodermamide A (<B>3</B>) in a freshwater medium. Compounds <B>1</B> and <B>2</B> are rare epidithiodiketopiperazines possessing an unusual disulfide linkage. In the seawater medium, the strain biosynthesized the 5-chloro-5-deoxy derivatives (<B>4</B> and <B>5</B>) of <B>3</B> and <B>2</B>. The production of <B>5</B> was proportional to the concentration of seawater (NaCl). Therefore, 5-bromo-5-deoxy (<B>6</B>) and 5-deoxy-5-iodo (<B>7</B>) derivatives were biosynthesized in the freshwater media supplemented with NaBr and NaI, respectively. The structure of a new iodo derivative (<B>7</B>) was elucidated on the basis of its spectroscopic data.</P><P><B>Graphic Abstract</B><BR><IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jnprdf/2015/jnprdf.2015.78.issue-10/acs.jnatprod.5b00669/production/images/medium/np-2015-006693_0004.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/np5b00669'>ACS Electronic Supporting Info</A></P>