New sesquiterpenoids from the root of Guatteria multivenia.
A phytochemical investigation of the CHCl(3) fraction of an ethanol extract of the root of Guatteria multivenia furnished nine compounds, of which four are sesquiterpenes (1-4) and five are alkaloids (5-9). Of the four sesquiterpenes, two are new (1, 3), named guatterin A (1) and dihydromadolin-K (3), and two are known (2, 4), identified as madolin-K (2) and madolin-W (4). The five known alkaloids were identified as liriodenine (5), lysicamine (6), lanuginosine (7), guadiscine (8), and O-methylpallidine (9). All the known compounds were isolated from this species for the first time. Structures of the new compounds were determined by extensive NMR studies, including DEPT, COSY, HMQC, HMBC, and NOESY. Compound 7 showed weak inhibitory effect against Candida albicans secreted aspartic proteases (SAP) with IC(50) of 45 microg/mL. Compound 5 was found to have antimicrobial activity against C. albicans, Cryptococcusneoformans, Staphylococcus aureus, and methicillin-resistant S. aureus (MRS) with IC(50)/MIC values of 3.5/6.25, 2.0/12.5, 2.0/3.13, and 2.0/3.13 microg/mL, respectively.
Zhang
Zhizhen
Z
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
ElSohly
Hala N
HN
Jacob
Melissa R
MR
Pasco
David S
DS
Walker
Larry A
LA
Clark
Alice M
AM
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029061:Annonaceae / Q000737:chemistry*; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001060:Aporphines / Q000494:pharmacology; D016282:Aspartic Acid Endopeptidases / Q000037:antagonists & inhibitors; D002176:Candida albicans / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010568:Peru; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011480:Protease Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D001060:Aporphines; D011480:Protease Inhibitors; D012717:Sesquiterpenes; C069090:lysicamine; D016282:Aspartic Acid Endopeptidases