JACK L. BEAL and RAYIIOSD IT. DOSKOTCH Di; isioii q i Piinriizocog~!os~ mid A\7atiirol Prodzlcts Cheviistr?., College of Pharniacy, The Ohio Stete L-ni;,ersitj, Coliimbics, Ohio 43210.IssTR.~cr.-.ldditional alkaloids were obtained from T . ri(gosiim and characterized by spectral methods. These minor constituents were obtained from the tertiary alkaloid fractions by extensive chromatograph>-. The ether-soluble nonphenolic fraction gave ozJ-berberine ( l ) , thalriigosinone ( 2 ) , thalicthuberine 13), obaberine (l), protopine i s ) and neothalibrine (6). The ether-soluble phenolic fraction afforded aromoline ( 8 ) and coryalline 19) : while the chloroform-soluble fraction yielded rugosinone norosl-hrdrastinine (12 I and 1,2-dih~-dro-G,T-n~etli~-lenedioz~--l-osoisoq~iinoline 113 1. .111 a& i e a alkaloids for the source, x i t h thalriigosinone i2), rugosinone (10) and I,?dih:-dro-A,T-meth?-lenedios\--l-osoisoqi~inoline 113) also new natural products. -4nt1microbial activity is reported for nine alkaloids and one derivative.-4s part of a detailed study of tlie alkaloids from the genus TIzalictrztm! T . rzigoszim Xit. ( T . glamzinz Desf.) investigated in our laboratory has yielded over 20 alkaloids (see reference 1 and others therein) to whjcli we n-ish to add, in this report. eleven others present in minor amounts. They It-ere isolated from fractions which previously gave the major constituents for which details of isolation and structure elucidation are published (l).3The ether-soluble tertiary nonplienolic alkaloid fraction afforded in the order of elution from the silica gel column the following six compounds : oxyberberine (l), thalrugosinone (2): thalicthuberine (3), obaberine (4), protopine ( 5 ) and neothalibrine (6). Of these! all but tlialicthuberine (3) and neothalibrine are n-ell-characterized knon-n compounds. Sone have been reported, previously, from T . rzigoszim, and all n-ere identified from their physical and spectral properties on direct comparison with authentic samples or from values reported in tlie literature. Seothalibrine (6), a recently characterized nen-alkaloid from the fruit of T . re.ilolzitztm was identified by direct comparison It-ith tlie known compound (2j.Thalrugosinone (2) is a new bisbenzylisoquinoline alkaloid, representing a first example of a variation not previously encountered, in u-hich both tlie benzylic carbons are oxidized to the level of a ketone while the hetero ring of the isoquinoline system remains fully reduced. The limited quantities of material prevented a chemical characterization, but the apectral data is consistent n-ith a unique structure. The high resolution mass spectrum showed an intense niolecular ion that on accurate m a s measurement is in excellent agreement with the formula C3sH38S209. Its intensity supports the presence of two diphenyl ether groups (3), and the nmr spectrum clearly revealed peaks for one S-methyl and five 0-methyls. Of the four remaining oxygens, tn-o as stated are diphenyl ethers, and the other two must be carbonyls, since tlie mol...
