82 発がんプロモーターTeleocidin類の化学構造研究

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The present authors studied on isolation and purification of the metabolites (having strong cancer promoter activity) of Streptomyces mediocidus and Streptoverticillium olivoreticuls, and succeeded in elucidating their structures. (I) Metabolites of Streptoverticillium olivoreticuls: As shown in Table 1, six compounds, i.e. olivoretin A,B,C and D, des-O-methylolivoretin C and L-N-methylvalyl-L-trypthanol(10), were isolated. Structures of B,C and D were clarified with X-ray structure analysis to be 3, 4 and 1, respectively. Demethylation of A and C with BBr_3 gave D and des-O-methylolivoretin C, respectively. These findings allowed us to assign the formula 2 to A and formula 5 to des-O-methylolivoretin C. Further-more, structure of D(1) was found to be identical to that formerly proposed to teleocidin B (amorphous). In addition, D(1) was identified with teleocidin B-4 (mp 230-232.5℃), a metabolite of S. mediocidus, by means of mixed fusion, retention time of HPLC and all sorts of spectral data. (see below) (II) Metabolites of Streptomyces mediocidus: As shown in Table 3, teleocidins B-1, B-2, B-3 and B-4, together with teleocidins A-1 (=lyngbyatoxin A) and A-2 (amorphous), were obtained in crystalline states. B-1 was found to be identical to des-O-methylolivoretin B, which was obtainded from olivoletin B through BBr_3 demethylation. B-4 was proved to be same as olivoretin D (named as teleocidin B by Hirata). These findings allowed us to assign the structural formulae 7 and 1 to teleocidin B-1 and B-4, respectively. The mass and NMR spectral data suggested that B-2 and B-3 were the remaining two isomers concerning the chiral centres in the cyclohexene ring. Enantiomeric relationships in regard to the stereochemistry at the cyclohexane ring moiety were found to exist in the respective pairs of B-1/B-2 and B-3/B-4. Structural formulae 8 and 9 were assigned to B-2 and B-3, respectively, by means of ^<13>C-NMR data as shown in Fig. 6. Structure of B-2 was confirmed to be 8 by means of X-ray structural analysis. Study on the absolute configurations of the chiral centres in the side chains of teleocidins A-1 and A-2 is in progress.
天然有機化合物討論会の論文
1985-09-07

82 発がんプロモーターTeleocidin類の化学構造研究

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