Structure of a novel epidithiodioxopiperazine, emethallicin A, a potent inhibitor of histamine release from Emericella heterothallica.
A new epidithiodioxopiperazine derivative, emethallicin A (1), was isolated along with ergosterol from the mycelial extract of the heterothallic fungus, Emericella heterothallica (mating type A). The structure of emethallicin A (1) was established on the basis of chemical and spectroscopic investigations and finally by chemical transformation to apoaranotin (11). Emethallicin A (1) has the same basic skeleton as apoaranotin (11), with C6-C2 carboxylic acid (mandelic and phenylacetic acids) diester moieties, and showed a potent inhibitory activity on histamine release from mast cells.
Kawahara
N
N
Nakajima
S
S
Yamazaki
M
M
Kawai
K
K
D001203:Ascomycota / Q000378:metabolism*; D055598:Chemical Phenomena; D002621:Chemistry; D006636:Histamine Release / Q000187:drug effects*; D008407:Mast Cells / Q000187:drug effects / Q000378:metabolism; D010879:Piperazines / Q000032:analysis / Q000494:pharmacology*
D010879:Piperazines; C062853:emethallicin A