Recently, we reported the isolation of the potent protein kinase C inhibitor balanol (1) from the fungus Verticillium balanoides.In an earlier study, Konig et al. reported the isolation of ophiocordin (3), a structural isomer of 1, from the fungus Cordyceps ophioglossoides. The present study was designed to clarify whether or not balanol and ophiocordin are different compounds. The results indicated that the two fungi produced the same compound, the structure being that assigned to balanol. In addition, a thirty-fold increase in the production of balanol from V. balanoides was observed whenthe culture mediumwas changed from cornmeal/tomato paste to soy meal/glycerol.In our search for protein kinase C (PKC) inhibitors from microbial sources, we recently disclosed the isolation and structure elucidation of the potent inhibitor balanol (1) from the fungus Verticillium balanoides.^Balanol represents a novel class of PKCinhibitors and is the most potent inhibitor reported since the discovery of staurosporine.2~4) HumanPKCenzymes a, /ft, /ftl, y, <5, e, and y\ were inhibited by 1 with IC50 values of 4~9nM. The structure of balanol was unambiguously determined by ID and 2D NMRdata and chemical degradation. The absolute stereochemistry of 1 was assigned by X-ray diffraction of a /rara-bromobenzoyl derivative of 2.1} Very recently, the structure of balanol was confirmed by total
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