Structure of a Novel Epidithiodioxopiperazine, Emethallicin A, a Potent Inhibitor of Histamine Release, from Emericella heterothallica

• Published in: Chemical & pharmaceutical bulletin Vol. 37; no. 10; pp. 2592 - 2595
• Main Authors: KAWAHARA, Nobuo, NAKAJIMA, Shoichi, YAMAZAKI, Mikio, KAWAI, Ken-ichi
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1989; Maruzen; Japan Science and Technology Agency
• Subjects: aranotin; Ascomycota - metabolism; Biological and medical sciences; Chemical Phenomena; Chemistry; Emericella heterothallica; emethallicin A; epidithiodioxopiperazine; General pharmacology; heterothallic fungus; Histamine Release - drug effects; histamine release inhibition; mandelic acid; Mast Cells - drug effects; Mast Cells - metabolism; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phenylacetic acid; Piperazines - analysis; Piperazines - pharmacology; Fungi; Emericella; Histamine; Molecular structure; Pharmacognosy; Ascomycetes; Mast cell; Antihistaminic; In vitro; Biological activity; Thallophyta; Medicinal plant
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.37.2592

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.