6669. Nodulisporic acid

Nomenclature

CAS number: 163120-03-4
(2E,4E)-5-[(3S,4S,4aR,6aS,12aR,13S,15S,16bS,16cS)-2,3,4,4a,5,6,6a,7,10,12,12a,13,14,15,16b,16c-Hexadecahydro-3,13-dihydroxy-4,10,10,12,12,16b,16c-heptamethyl-15-(1-methylethenyl)-14-oxo-1H-benz[6,7]indeno[1,2-b]pyrano[3′,4′:4,5]cyclopenta[1,2-f]pyrrolo[3,2,1-hi]indol-4-yl]-2-methyl-2,4-pentadienoic acid; nodulisporic acid A; NsA A.
C43H53NO6; mol wt 679.88.
C 75.96%, H 7.86%, N 2.06%, O 14.12%.

Description and references

Indole diterpene alkaloid which activates glutamate-gated chloride channels. Isolated from the fungus Nodulisporium sp.; it occurs naturally as the (+)-form. Isoln: A. W. Dombrowski et al., US 5399582 (1995 to Merck & Co.); structure determination and insecticidal activity: J. G. Ondeyka et al., J. Am. Chem. Soc. 119, 8809 (1997). Mode of action: M. M. Smith et al., Biochemistry 39, 5543 (2000). Synthetic studies: A. B. Smith, III et al., Org. Lett. 3, 3967, 3971 (2001). Biosynthesis: K. M. Byrne et al., J. Am. Chem. Soc. 124, 7055 (2002). Systemic efficacy against fleas on dogs: W. L. Shoop et al., J. Parasitol. 87, 419 (2001). Review of chemical and biological properties: P. T. Meinke et al., Curr. Top. Med. Chem. 2, 655-674 (2002).

Chemical structure

Properties

Yellow powder, mp 250-255°. [α]D22 +13° (c = 0.4 in CHCl3). uv max (methanol): 241, 265, 385 nm (ε 43900, 49800, 7360).

Use

Insecticide.