Abstract
Ryania insecticide, the powdered stemwood of Ryania speciosa, was analyzed by HPLC and 1H NMR for the content (ppm, w/w) of 10 ryanoids. The compounds were isolated and their potencies compared for toxicity to housefly adults (injection, piperonyl butoxide as a synergist), flour beetle larvae (dietary exposure), and mice (intraperitoneal) and for competition with [3H]ryanodine for binding to the Ca2+ release channel complex. Ryanodine (range 450-600 ppm) and 9,21-dehydroryanodine (650-700 ppm) are essentially equipotent and account for almost all of the biological activity of ryania in each of these systems. 9-Hydroxy-10-epiryanodine (7-17 ppm) and three 8ax-hydroxy-10-epiryanodine derivatives [10-(O-methyl) (28-33 ppm), dehydro (30-64 ppm), and 10-(O-methyl)dehydro (22-32 ppm)] are very effective with houseflies but not in the other assays. 18-Hydroxyryanodine (<10 ppm), ryanodyl 3-(pyridine-3-carboxylate) (42-58 ppm), 8ax,18-dihydroxy-10-(O-methyl)-10-epiryanodine (5-10 ppm), and 9-hydroxyanhydroryanodine (12-17 ppm) are all of low activity. The potency of a ryanoid at the Ca2+ release channel is a better predictor of toxicity to mice and beetle larvae than to housefly adults.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 142-146 |
| Number of pages | 5 |
| Journal | Journal of Agricultural and Food Chemistry® |
| Volume | 40 |
| Issue number | 1 |
| State | Published - 1992 |
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ASJC Scopus subject areas
- Agricultural and Biological Sciences (miscellaneous)
- Food Science
- Chemistry (miscellaneous)
Cite this
Ryania insecticide : analysis and biological activity of 10 natural ryanoids. / Jefferies, Phillip R.; Toia, Robert F.; Brannigan, Brian; Pessah, Isaac; Pessah, Isaac N.
In: Journal of Agricultural and Food Chemistry®, Vol. 40, No. 1, 1992, p. 142-146.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Ryania insecticide
T2 - analysis and biological activity of 10 natural ryanoids
AU - Jefferies, Phillip R.
AU - Toia, Robert F.
AU - Brannigan, Brian
AU - Pessah, Isaac
AU - Pessah, Isaac N
PY - 1992
Y1 - 1992
N2 - Ryania insecticide, the powdered stemwood of Ryania speciosa, was analyzed by HPLC and 1H NMR for the content (ppm, w/w) of 10 ryanoids. The compounds were isolated and their potencies compared for toxicity to housefly adults (injection, piperonyl butoxide as a synergist), flour beetle larvae (dietary exposure), and mice (intraperitoneal) and for competition with [3H]ryanodine for binding to the Ca2+ release channel complex. Ryanodine (range 450-600 ppm) and 9,21-dehydroryanodine (650-700 ppm) are essentially equipotent and account for almost all of the biological activity of ryania in each of these systems. 9-Hydroxy-10-epiryanodine (7-17 ppm) and three 8ax-hydroxy-10-epiryanodine derivatives [10-(O-methyl) (28-33 ppm), dehydro (30-64 ppm), and 10-(O-methyl)dehydro (22-32 ppm)] are very effective with houseflies but not in the other assays. 18-Hydroxyryanodine (<10 ppm), ryanodyl 3-(pyridine-3-carboxylate) (42-58 ppm), 8ax,18-dihydroxy-10-(O-methyl)-10-epiryanodine (5-10 ppm), and 9-hydroxyanhydroryanodine (12-17 ppm) are all of low activity. The potency of a ryanoid at the Ca2+ release channel is a better predictor of toxicity to mice and beetle larvae than to housefly adults.
AB - Ryania insecticide, the powdered stemwood of Ryania speciosa, was analyzed by HPLC and 1H NMR for the content (ppm, w/w) of 10 ryanoids. The compounds were isolated and their potencies compared for toxicity to housefly adults (injection, piperonyl butoxide as a synergist), flour beetle larvae (dietary exposure), and mice (intraperitoneal) and for competition with [3H]ryanodine for binding to the Ca2+ release channel complex. Ryanodine (range 450-600 ppm) and 9,21-dehydroryanodine (650-700 ppm) are essentially equipotent and account for almost all of the biological activity of ryania in each of these systems. 9-Hydroxy-10-epiryanodine (7-17 ppm) and three 8ax-hydroxy-10-epiryanodine derivatives [10-(O-methyl) (28-33 ppm), dehydro (30-64 ppm), and 10-(O-methyl)dehydro (22-32 ppm)] are very effective with houseflies but not in the other assays. 18-Hydroxyryanodine (<10 ppm), ryanodyl 3-(pyridine-3-carboxylate) (42-58 ppm), 8ax,18-dihydroxy-10-(O-methyl)-10-epiryanodine (5-10 ppm), and 9-hydroxyanhydroryanodine (12-17 ppm) are all of low activity. The potency of a ryanoid at the Ca2+ release channel is a better predictor of toxicity to mice and beetle larvae than to housefly adults.
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UR - http://www.scopus.com/inward/citedby.url?scp=0000357180&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0000357180
VL - 40
SP - 142
EP - 146
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 1
ER -