Neurologically active plant compounds and peptide hormones: a chirality connection

FEBS Letters

Anselmi, Claudio²  Fraternali, Franca¹  Temussi, Piero Andrea³ 

[1] Division of Molecular Structure, National Institute for Medical Research, MRC, Mill Hill, The Ridgeway, London NW7 1AA, UK;Dipartimento di Chimica, Università La Sapienza, Ple A. Moro 5, 00185 Rome, Italy;Dipartimento di Chimica, Università Federico II, via Mezzocannone 4, I-80134 Naples, Italy

关键词: Alkaloid;    Peptide;    Signaling system;    Bioactive conformation;    SAR;    structure-activity relationship;    SIOM;    7-spiroindanyloxymorphine;    Standard IUPAC single- and triple-letter codes for amino acids are used throughout;   

DOI  :  10.1016/S0014-5793(99)00244-6

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The most dramatic, but seldom mentioned, difference between alkaloid and peptide opioids is the change of chirality of the α carbon of the tyramine moiety. We propose that the presence of Gly² or d-Ala² in the two most common message domains compensates this change by allowing the attainment of unusual conformations. A thorough conformational search of Tyr-d-Ala-Phe-NH-CH₃ and of its isomer Tyr-l-Ala-Phe-NH-CH₃ backs this view and establishes a solid link between alkaloid and peptide opioids. This finding supports the notion that morphine, like other neurologically active plant compounds, may bind to endogenous receptors in plants to regulate cell-to-cell signaling systems.

【 授权许可】

Unknown