191. Agroclavine

Nomenclature

CAS number: 548-42-5
8,9-Didehydro-6,8-dimethylergoline.
C16H18N2; mol wt 238.33.
C 80.63%, H 7.61%, N 11.75%.

Description and references

A non-peptide ergot alkaloid obtained from cultures of fungi parasitic on Elymus mollis Trin.: Abe et al., JP 49 178336 (1949 to Takeda), C.A. 45, 6352c (1951); Annu. Rep. Takeda Res. Lab. 10, 145, 167, 171 (1951); JP 54 7498 (1954), C.A. 50, 6000b (1956); US 2835675 (1958). Found in fungi parasitic on Pennisetum typhoideum Rich.: Stoll et al., Helv. Chim. Acta 37, 1815 (1954). Structure and stereochemistry: Schreier, ibid. 41, 1984 (1958). Biosynthesis: Floss et al., J. Am. Chem. Soc. 90, 6500 (1968). Synthesis: Plieninger et al., Ann. 743, 95 (1971). Metabolism: Ramstad, Lloydia 31, 327 (1968).

Chemical structure

Properties

Rods from ether, dec 198-203°; needles from acetone, dec 205-206°. [α]D20 155° (c = 0.9 in chloroform); [α]D20 182° (c = 0.5 in pyridine). uv max: 225, 284, 293 nm (ε 4.47, 3.88, 3.81). Freely sol in alc, chloroform, pyridine; sol in benzene, ether; very slightly sol in water.