TY - JOUR
T1 - Phytotoxic activity of bibenzyl derivatives from the orchid Epidendrum rigidum
AU - Hernández-Romero, Yanet
AU - Acevedo, Laura
AU - De Los Ángeles Sánchez, María
AU - Shier, W. Thomas
AU - Abbas, Hamed K.
AU - Mata, Rachel
PY - 2005/8/10
Y1 - 2005/8/10
N2 - A whole plant chloroform-methanol extract of the orchid Epidendrum rigidum inhibited radicle growth of Amaranthus hypochondriacus seedlings (IC 50 = 300 μg/mL). Bioassay-guided fractionation furnished four phytotoxins, namely, gigantol (1), batatasin III (2), 2,3-dimethoxy-9,10- dihydrophenathrene-4,7-diol (9), and 3,4,9-trimethoxyphenanthrene-2,5-diol (11), along with the known flavonoids apigenin, vitexin, and isovetin and the triterterpenoids 24,24-dimethyl-9,19-cyclolanostane-25-en-3β-ol (14) and 24-methyl-9,19-cyclolanostane-25-en-3β-ol (15). Stilbenoids 1, 2, 9, and 11 inhibited radicle growth of A. hypochondriacus with IC50 values of 0.65, 0.1, 0.12, and 5.9 βM, respectively. Foliar application of gigantol (1) at 1 βM to 4 week old seedlings of A. hypochondriacus reduced shoot elongation by 69% and fresh weight accumulation by 54%. Bibenzyls 1 and 2, as well as synthetic analogues 4′-hydroxy-3,3′,5-trimethoxybibenzyl (3), 3,3′,4′,5-tetramethoxybibenzyl (4), 3,4′-dihydroxy-5- methoxybibenzyl (5), 3′-O-methylbatatasin III (6), 3,3′,5- trihydroxybibenzyl (7), and 3,4′,5-trihydroxybibenzyl (8), were tested for phytotoxicity in axenic cultures of the small aquatic plant Lemna pausicostata. All bibenzyls derivatives except 7 and 8 inhibited growth and increased cellular leakage with IC50 values of 89.9-180 and 89.9-166 μM, respectively. The natural and synthetic bibenzyls showed marginal cytotoxicity on animal cells. The results suggest that orchid bibenzyls may be good lead compounds for the development of novel herbicidal agents.
AB - A whole plant chloroform-methanol extract of the orchid Epidendrum rigidum inhibited radicle growth of Amaranthus hypochondriacus seedlings (IC 50 = 300 μg/mL). Bioassay-guided fractionation furnished four phytotoxins, namely, gigantol (1), batatasin III (2), 2,3-dimethoxy-9,10- dihydrophenathrene-4,7-diol (9), and 3,4,9-trimethoxyphenanthrene-2,5-diol (11), along with the known flavonoids apigenin, vitexin, and isovetin and the triterterpenoids 24,24-dimethyl-9,19-cyclolanostane-25-en-3β-ol (14) and 24-methyl-9,19-cyclolanostane-25-en-3β-ol (15). Stilbenoids 1, 2, 9, and 11 inhibited radicle growth of A. hypochondriacus with IC50 values of 0.65, 0.1, 0.12, and 5.9 βM, respectively. Foliar application of gigantol (1) at 1 βM to 4 week old seedlings of A. hypochondriacus reduced shoot elongation by 69% and fresh weight accumulation by 54%. Bibenzyls 1 and 2, as well as synthetic analogues 4′-hydroxy-3,3′,5-trimethoxybibenzyl (3), 3,3′,4′,5-tetramethoxybibenzyl (4), 3,4′-dihydroxy-5- methoxybibenzyl (5), 3′-O-methylbatatasin III (6), 3,3′,5- trihydroxybibenzyl (7), and 3,4′,5-trihydroxybibenzyl (8), were tested for phytotoxicity in axenic cultures of the small aquatic plant Lemna pausicostata. All bibenzyls derivatives except 7 and 8 inhibited growth and increased cellular leakage with IC50 values of 89.9-180 and 89.9-166 μM, respectively. The natural and synthetic bibenzyls showed marginal cytotoxicity on animal cells. The results suggest that orchid bibenzyls may be good lead compounds for the development of novel herbicidal agents.
KW - Amaranthus hypochondriacus
KW - Batatsin III
KW - Bibenzyls
KW - Cytotoxicity
KW - Duckweed
KW - Epidendrum rigidum
KW - Gigantol
KW - Lemna pausicostata
KW - Orchidaceae
KW - Phenantrenes
KW - Phytotoxicity
KW - Stilbenoids
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U2 - 10.1021/jf0508044
DO - 10.1021/jf0508044
M3 - Article
C2 - 16076106
AN - SCOPUS:23844540961
SN - 0021-8561
VL - 53
SP - 6276
EP - 6280
JO - Journal of agricultural and food chemistry
JF - Journal of agricultural and food chemistry
IS - 16
ER -