Two new quassinoids, javanicolides C and D, and five new quassinoid glucosides, javanicosides B-F, were isolated from the seeds of Brucea javanica, along with eight known quassinoids, i.e., yadanziolides A, C, D, and S, bruceins D and E, brusatol, and the aglycone of yadanzioside D, and 19 known quassinoid glucosides, i.e., yadanziosides A-G, I, and K-P, bruceosides A-C and E, and bruceantinoside A. Their structures were elucidated by analysis of spectroscopic data and chemical evidence.
Two bicyclic hexapeptides, allo-RA-V (4) and neo-RA-V (5), and one cyclic hexapeptide, O-seco-RA-V (6), were isolated from the roots of Rubia cordifolia L. Their gross structures were elucidated on the basis of spectroscopic analysis and X-ray crystallography of compound 5. The absolute stereochemistry of compounds 4 and 5 were established by their total syntheses, and the absolute stereochemistry of compound 6 by chemical correlation with deoxybouvardin (3). Comparison of the 3D structures of highly active RA-VII (1) with less-active compounds 4 and 5 suggests that the orientation of the Tyr-5 and/or Tyr-6 phenyl rings plays a significant role in their biological activity. The isolation of peptides 4-6, along with compound 3, and the comparison of their structures seem to indicate that peptide 6 may be the common precursor to bicyclic peptides 3-5 in the plant.
Four new abietane diterpenoids (1-4), a new 9(10→20)-abeo-abietane diterpenoid (5), and a new sesquiterpene pyridine alkaloid (6) were isolated from the roots of Euonymus lutchuensis along with 19 known compounds. The structures of the new compounds were elucidated by interpretation of the spectroscopic data.
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