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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Kusano, Jun-ichi Kato, Saori Hasuda, Tomoyo Fukaya, Haruhiko Hitotsuyanagi, Yukio Odagiri, Masumi Takeya, Koichi |
| Description | Author Affiliation: Hitotsuyanagi Y ( School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.) |
| Abstract | 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. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 10 |
| Volume Number | 18 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2012-03-05 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Peptides, Cyclic Chemical Synthesis Rubia Chemistry Crystallography, X-Ray Drug Screening Assays, Antitumor HCT116 Cells HL-60 Cells Molecular Conformation Pharmacology Plant Roots Structure-Activity Relationship Tyrosine |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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