Iridoid and phenylpropanoid glycosides from the roots of Lantana montevidensis

• Published in: Medicinal chemistry research Vol. 26; no. 6; pp. 1117 - 1126
• Main Authors: Mohamed, Nesma M., Makboul, Makboul A., Farag, Salwa F., Tarawneh, Amer H., Khan, Shabana I., Brooks, Tracy A., Wang, Yan-Hong, Ross, Samir A.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.06.2017; Springer Nature B.V
• Subjects: Amine oxidase (flavin-containing); Antioxidants; Antiprotozoal activity; Antiprotozoal agents; Biochemistry; Biomedical and Life Sciences; Biomedicine; Breast cancer; Cell Biology; Glycosides; Inflammation; Methanol; Nitric-oxide synthase; NMR; Nuclear magnetic resonance; Original Research; Oxidative stress; Pharmacology/Toxicology; Roots; Xylopyranoside; Phenylpropanoids; Iridoids; Reactive oxidative stress; Anticancer; Anti-inflammatory
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-017-1817-x

A new iridoid glycoside; 6- O - β -D-xylopyranoside-shanzhiside methyl ester ( 1 ) along with six known compounds; shanzhiside methyl ester ( 2 ), lamalbid ( 3 ), geniposidic acid ( 4 ), theveside ( 5 ), verbascoside ( 6 ) and arenarioside ( 7 ) were isolated from the roots of Lantana montevidensis . The structures of the compounds were determined through 1D and 2D NMR spectroscopic data analysis, HRESIMS, electronic circular dichorism and UPLC-UV/MS method. The total extract, chloroformic ( F1 ) and aqueous ( F2 ) fractions together with the isolated compounds were tested for their antimicrobial, antiprotozoal, antiplasmodial, anti-inflammatory, monoamine oxidase inhibition and cell viability activities in addition to free radical scavenging activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The phenylpropanoid compounds ( 6 and 7 ) resulted in a potent antioxidant activity. Total methanolic extract together with the aqueous fraction ( F2 ) showed decrease in reactive oxidative stress with 57 and 66%, respectively, while the chloroformic fraction ( F1 ), together with the total methanolic extract, showed a decrease in iNOS with IC 50 values 5 and 30 μg/mL, respectively. Compounds 1 , 2 , 3 , 6 , and 7 showed inhibition in the reactive oxidative stress with values 50, 60, 57, 63, and 52%, respectively. Both F1 and F2 fractions demonstrated measurable inhibition of MCF-7 breast cancer cell growth, with IC 50 value 0.3 mg/mL. Compounds 2 and 7 showed mild monoamine oxidase inhibition. None of the tested compounds showed antimicrobial, antiplasmodial or antiprotozoal activity.