Abstract
Eleven new alkaloids (1-11), classified as the 12-acetylplicamine (1), N-deformyl-seco-plicamine (2), plicamine (3-6), 4a-epi-plicamine (7), seco-plicamine (8), and lycorine (9-11) framework types, along with 15 known alkaloids (12-26) were isolated from the whole plants of Zephyranthes carinata. The structures of the new alkaloids 1-11 were established by extensive spectroscopic data interpretation. The absolute configurations of 9 and 10 were defined by single-crystal X-ray diffraction analysis. Zephycarinatines A (1), B (2), and G (7) represent the first examples of 12-acetylplicamine, N-deformyl-seco-plicamine, and 4a-epi-plicamine alkaloids, respectively. Alkaloids 6, 11, 17, and 20-23 exhibited AChE inhibitory activities with IC50 values ranging from 1.21 to 184.05 μM, and a preliminary structure-activity relationship is discussed.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Acetylcholinesterase / chemistry
-
Acetylcholinesterase / isolation & purification*
-
Acetylcholinesterase / metabolism*
-
Alkaloids / chemistry
-
Alkaloids / isolation & purification*
-
Alkaloids / pharmacology*
-
Amaryllidaceae / chemistry*
-
Amaryllidaceae Alkaloids / chemistry
-
Amaryllidaceae Alkaloids / isolation & purification*
-
Amaryllidaceae Alkaloids / pharmacology*
-
Cholinesterase Inhibitors / chemistry
-
Cholinesterase Inhibitors / isolation & purification*
-
Cholinesterase Inhibitors / pharmacology*
-
Heterocyclic Compounds, 4 or More Rings / chemistry
-
Heterocyclic Compounds, 4 or More Rings / isolation & purification*
-
Heterocyclic Compounds, 4 or More Rings / pharmacology*
-
Inhibitory Concentration 50
-
Liliaceae / chemistry*
-
Molecular Structure
-
Phenanthridines / chemistry
-
Phenanthridines / isolation & purification*
-
Phenanthridines / pharmacology*
-
Structure-Activity Relationship
-
X-Ray Diffraction
Substances
-
Alkaloids
-
Amaryllidaceae Alkaloids
-
Cholinesterase Inhibitors
-
Heterocyclic Compounds, 4 or More Rings
-
Phenanthridines
-
Zephycarinatine G
-
plicamine
-
zephycarinatine A
-
zephycarinatine B
-
Acetylcholinesterase
-
lycorine