Isopentenyladenine from Dictyostelium discoideum

Phytochemistry
1978.0

Abstract

First study: Discadenine, a spore germination inhibitor in Dictyostelium discoideum, is synthesized from isopentenyladenine (ip6Ade). This work demonstrated ip6Ade exists in D. discoideum at the culmination stage. The purified compound matched synthetic ip6Ade in UV absorption (273 nm in 0.1 N HCl, 268 nm in EtOH, 275 nm in 0.1 N NaOH), Rf values (0.50, 0.87, 0.76 with solvents A, B, C), and mass spectral peaks (m/e 203, 188, 160, etc.). Ip6Ade content was ~3 µg/g wet wt, consistent with discadenine levels (1.2-2.4 mg per 2500 plates) and 20x higher than in Agrobacterium tumefaciens, confirming it as a discadenine precursor. Second study: Pyrethrin biosynthesis in Tanacetum cinerariifolium was hindered by low precursor incorporation and seasonal variation. Undifferentiated callus and root-differentiated callus lacked pyrethrins, but shoot-differentiated callus contained six pyrethrin esters (cinerin I, jasmolin I, pyrethrin I, cinerin II, jasmolin II, pyrethrin II) in proportions (3:14:76:0.2:0.8:6) similar to seedlings. Authenticity was confirmed by GC-MS and PMR.

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