Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities.

Abstract

Two new compounds heliotropiumides A (1) and B (2), phenolamides each with an uncommon carbamoyl putrescine moiety, were isolated from the seeds of a naturalized Hawaiian higher plant, Heliotropium foertherianum Diane & Hilger in the borage family, which is widely used for the treatment of ciguatera fish poisoning. The structures of compounds 1 and 2 were characterized based on MS spectroscopic and NMR analysis, and DP4+ calculations. The absolute configuration (AC) of compound 1 was determined by comparison of its optical rotation with those reported in literature. Compound 2 showed inhibition against NF-κB with an IC50 value of 36μM.

• Authors: You-Sheng Cai, Ariel M Sarotti, Daniela Gündisch, Tamara P Kondratyuk, John M Pezzuto, James Turkson, Shugeng Cao
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 27 Issue 20 Pg. 4630-4634 (10 15 2017) ISSN: 1464-3405 [Electronic] England
• PMID: 28927792 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2017 Elsevier Ltd. All rights reserved.

Chemical References

• Amides
• Anti-Infective Agents
• Antineoplastic Agents, Alkylating
• Benzofurans
• NF-kappa B
• Phenols
• Plant Extracts
• heliotropiumide A
• heliotropiumide B
• Putrescine

Topics

• Amides (chemistry, pharmacology, toxicity)
• Anti-Infective Agents (chemistry, isolation & purification, pharmacology)
• Antineoplastic Agents, Alkylating (chemistry, isolation & purification, pharmacology)
• Benzofurans (chemistry, pharmacology, toxicity)
• Cell Line, Tumor
• Cell Survival (drug effects)
• Fungi (drug effects)
• Gram-Negative Bacteria (drug effects)
• Gram-Positive Bacteria (drug effects)
• Heliotropium (chemistry, metabolism)
• Humans
• Magnetic Resonance Spectroscopy
• Molecular Conformation
• NF-kappa B (antagonists & inhibitors, metabolism)
• Phenols (chemistry, pharmacology, toxicity)
• Plant Extracts (chemistry, pharmacology, therapeutic use)
• Putrescine (chemistry)
• Shellfish Poisoning (prevention & control)