title: Antiplasmodial and antimycobacterial cyclopeptide alkaloids from the root of Ziziphus mauritiana.
abstract: Investigation of the MeOH extract obtained from the root of the Ziziphus mauritiana grown in Thailand resulted in the isolation of two 14- and 13-membered cyclic alkaloids, mauritine L (1) and mauritine M (2), and three known cyclopeptide alkaloids, nummularines H (3), B (4) and hemsine A (5). Their structures were elucidated on the basis of extensive NMR spectroscopic analysis. The first single crystal X-ray diffraction study of the 13-membered ring cyclopeptide, nummularine B methiodide (4'), revealed all S configurations on the amino acid residues. The isolated alkaloids exhibited potent antiplasmodial activity against the parasite Plasmodium falciparum with the inhibitory concentration (IC50) ranging from 3.7 to 10.3 μM. Compounds 2 and 3 also demonstrated antimycobacterial activity against Mycobacterium tuberculosis with the MIC of 72.8 and 4.5 μM, respectively.
authors: Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand.
authors: Panomwan
authors: P
authors: Panseeta
authors: Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand.
authors: Kanlaya
authors: K
authors: Lomchoey
authors: Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
authors: Samran
authors: S
authors: Prabpai
authors: Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand; Center for Excellence in Protein Structure and Function, Faculty of Science, Mahidol University, Bangkok 10400, Thailand.
authors: Palangpon
authors: P
authors: Kongsaeree
authors: Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand.
authors: Apichart
authors: A
authors: Suksamrarn
authors: Chulabhorn Research Institute, Chemical Biology Program, Center for Environmental Health, Toxicology and Management of Chemicals (ETM), Chulabhorn Graduate Institute, Vipavadee Rangsit Highway, Bangkok 10210, Thailand.
authors: Somsak
authors: S
authors: Ruchirawat
authors: Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand.
authors: Sunit
authors: S
authors: Suksamrarn
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification; D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification; D018517:Plant Roots / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D013785:Thailand; D031957:Ziziphus / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000962:Antimalarials; D010456:Peptides, Cyclic