Growth inhibitory alkaloids from mesquite ( Prosopis juliflora (Sw.) DC.) leaves

• Published in: Phytochemistry (Oxford) 2004-03, Vol.65 (5), p.587-591
• Main Authors: Nakano, Hiroshi, Nakajima, Eri, Hiradate, Syuntaro, Fujii, Yoshiharu, Yamada, Kosumi, Shigemori, Hideyuki, Hasegawa, Koji
• Format: Article
• Language: English
• Subjects: 3-Oxo-juliprosine; 3⁗-Oxo-juliprosopine; Alkaloid; Alkaloids - chemistry; Alkaloids - pharmacology; Biological and medical sciences; Biological Assay; Chemical constitution; Fundamental and applied biological sciences. Psychology; Growth Inhibitors - chemistry; Growth Inhibitors - pharmacology; Leguminosae; Lepidium sativum - drug effects; Lepidium sativum - growth & development; Mesquite; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant growth inhibitors; Plant Growth Regulators - chemistry; Plant Growth Regulators - pharmacology; Plant Leaves - chemistry; Plant physiology and development; Plant Structures - drug effects; Plant Structures - growth & development; Prosopis - chemistry; Prosopis juliflora; Secojuliprosopinal
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2004.01.006

Plant growth inhibitory alkaloids were isolated from the extract of mesquite [ Prosopis juliflora (Sw.) DC.] leaves. Their chemical structures were established by ESI-MS, 1H and 13C NMR spectra analysis. The I 50 value (concentration required for 50% inhibition of control) for root growth of cress ( Lepidium sativum L.) seedlings was 400 μM for 3⁗-oxo-juliprosopine, 500 μM for secojuliprosopinal, and 100 μM for a (1:1) mixture of 3-oxo-juliprosine and 3′-oxo-juliprosine, respectively. On the other hand, the minimum concentration exhibiting inhibitory effect on shoot growth of cress seedlings was 10 μM for 3⁗-oxo-juliprosopine, 100 μM for secojuliprosopinal, and 1 μM for a (1:1) mixture of 3-oxo-juliprosine and 3′-oxo-juliprosine, respectively. Among these compounds, a (1:1) mixture of 3-oxo-juliprosine and 3′-oxo-juliprosine exhibited the strongest inhibitory effect on the growth of cress seedlings. Plant growth inhibitory alkaloids, 3⁗-oxo-juliprosopine ( 1), secojuliprosopinal ( 2), and a (1:1) of 3-oxo-juliprosine ( 3a) and 3′-oxo-juliprosine ( 3b) were isolated from the extract of mesquite [ Prosopis juliflora (Sw.) DC.] leaves.