Alkaloidal Components in the Poisonous Plant, Ipomoea carnea (Convolvulaceae)
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Alkaloidal Components in the Poisonous Plant, Ipomoea carnea (Convolvulaceae). / Haraguchi, Mitsue; Gorniak, Silvana L.; Ikeda, Kyoko et al.
In: Journal of Agricultural and Food Chemistry, Vol. 51, No. 17, 11.07.2003, p. 4995-5000.Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Alkaloidal Components in the Poisonous Plant, Ipomoea carnea (Convolvulaceae)
AU - Haraguchi, Mitsue
AU - Gorniak, Silvana L.
AU - Ikeda, Kyoko
AU - Minami, Yasuhiro
AU - Kato, Atsushi
AU - Watson, Alison A.
AU - Nash, Robert J.
AU - Molyneux, Russell J.
AU - Asano, Naoki
N1 - Haraguchi, M., Gorniak, S. L., Ikeda, K., Minami, Y., Kato, A., Watson, A. A., Nash, R. J., Molyneux, R. J., Asano, N. (2003). Alkaloidal components in the poisonous plant, Ipomoea carnea (Convolvulaceae). Journal of Agricultural and Food Chemistry, 51, (17), 4995-5000.
PY - 2003/7/11
Y1 - 2003/7/11
N2 - Natural intoxication of livestock by the ingestion of Ipomoea carnea (Convolvulaceae) sometimes occurs in tropical regions of the world. Polyhydroxylated alkaloids were isolated from the leaves, flowers, and seeds of the poisonous plant and characterized. Chromatographic separation of the leaf extract resulted in the isolation of swainsonine (1), 2-epi-lentiginosine (2), calystegines B1 (3), B2 (4), B3 (5), and C1 (6), and N-methyl-trans-4-hydroxy-l-proline (7). The contents of 1 in the fresh leaves and flowers were 0.0029 and 0.0028%, respectively, whereas the contents of 1, 3, and 4 in the seeds were ∼10 times higher than those in the leaves and flowers. Alkaloids 3, 4, and 6 showed a potent inhibitory activity toward rat lysosomal β-glucosidase, with IC50 values of 2.1, 0.75, and 0.84 μM, respectively, and alkaloid 5 was a moderate inhibitor of α- and β-mannosidases. Although alkaloid 1 is known as a powerful inhibitor of lysosomal α-mannosidase (IC50 = 0.02 μM), alkaloid 2, which has been thought to be an intermediate in the biosynthesis of 1, was also a potent inhibitor of α-mannosidase with an IC50 value of 4.6 μM.
AB - Natural intoxication of livestock by the ingestion of Ipomoea carnea (Convolvulaceae) sometimes occurs in tropical regions of the world. Polyhydroxylated alkaloids were isolated from the leaves, flowers, and seeds of the poisonous plant and characterized. Chromatographic separation of the leaf extract resulted in the isolation of swainsonine (1), 2-epi-lentiginosine (2), calystegines B1 (3), B2 (4), B3 (5), and C1 (6), and N-methyl-trans-4-hydroxy-l-proline (7). The contents of 1 in the fresh leaves and flowers were 0.0029 and 0.0028%, respectively, whereas the contents of 1, 3, and 4 in the seeds were ∼10 times higher than those in the leaves and flowers. Alkaloids 3, 4, and 6 showed a potent inhibitory activity toward rat lysosomal β-glucosidase, with IC50 values of 2.1, 0.75, and 0.84 μM, respectively, and alkaloid 5 was a moderate inhibitor of α- and β-mannosidases. Although alkaloid 1 is known as a powerful inhibitor of lysosomal α-mannosidase (IC50 = 0.02 μM), alkaloid 2, which has been thought to be an intermediate in the biosynthesis of 1, was also a potent inhibitor of α-mannosidase with an IC50 value of 4.6 μM.
KW - Ipomoea carnea
KW - poisonous plant
KW - intoxication in livestock
KW - polyhydroxylated alkaloids
KW - glycosidase inhibition
UR - http://hdl.handle.net/2160/4171
U2 - 10.1021/jf0341722
DO - 10.1021/jf0341722
M3 - Article
C2 - 12903959
VL - 51
SP - 4995
EP - 5000
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 17
ER -