A new pigment, C2IH22O5, rubropunctatin has been isolated from Monascus rubropunctatus SBto. With aqueous ammonia this gives a nitrogen analogue, rubropunctatamine, C,,H2,0,N, which, on reduction with zinc and acetic acid is degraded to an 8-hydroxyisoquinoline derivative, aporubropunctatamine, C,,H2,O2N, and one mol. of carbon dioxide. From degradative studies on the parent compound and these derivatives, aporubropunctatamine is shown to have structure (XII) , whilst structures (XIXa) and (XVIII) are proposed for rubropunctatin and rubropunctatamine respectively.Exhaustive hydrogenation of rubropunctatin gives hexahydroaporubropunctatin, C2oH3003, for which structure (XXIa) is proposed.The probable biogenesis of rubropunctatin is discussed and possible structural implications for the related compound rotiorin are tentatively suggested.
DURING an investigation into the metabolic products of the Monascus genus in thisDepartment, a new red pigment, rubropunctatin was isolated from the mycelium of M . rubvopunctatus %to. In a preliminary account of this work2 a close relation was pointed out between the properties of the pigments s~l e r o t i o r i n ,~~~~~,~~~ rotiorin,' monascin,8 monascorubrin? and rubropunctatin.The present paper describes the structural investigations on rubropunctatin which have been carried out during the last five years.Rubropunctatin has the molecular formula, C2lH2205, although the formula, C2,H,0,, Part XXXVI, Dean, Staunton, and Whalley,