A Fungal Metabolite as the Male Wing Gland Pheromone of the Bumble-Bee Wax Moth, Aphomia sociella L.

Abstract

3,4-Dihydro-9-hydroxy-3-methylisocoumarin [R(-)-mellein] was identified as the major component of the male wing gland pheromone of the bumble-bee wax moth, Aphomia sociella L. (Pyralidae, Galleriinae). The presence of Aspergillus ochraceus Wilhelm, a mellein producing microorganism, was detected in the intestines of last-instar larvae and in bumble-bee nests. Arguments for a new type of insect-fungus relationship are presented.

Polyketides in insects: ecological role of these widespread chemicals and evolutionary aspects of their biogenesis

“…Endosymbionts do seem to produce mellein in several other insects. For example, the bumblebee wax moth Aphomia sociella (Kunesch et al , 1987) contains mellein in male hairpencils. The gut of this moth is inhabited by a mellein‐producing fungus ( Aspergillus ochraceus ), suggesting polyketide production by this fungus (Kunesch et al , 1987).…”

“…For example, the bumblebee wax moth Aphomia sociella (Kunesch et al , 1987) contains mellein in male hairpencils. The gut of this moth is inhabited by a mellein‐producing fungus ( Aspergillus ochraceus ), suggesting polyketide production by this fungus (Kunesch et al , 1987). A mellein‐producing fungus ( Lasiodiplodia theobromae ) was found on the body surface of the giant white danaine Idea leuconoe .…”

Synthesis, Characterization, Anti-Inflammatory and in Vitro Antibacterial Activity of Some (±)-1-Aryl-7,8-Dichloroisochromans

“…Isochroman (3,4-dihydro-1H-benzo[c]pyran) is a common oxa-heterocycle structural motif in a variety of bioactive natural products such as 1,6,8-trihydroxy-3-heptyl-7-carboxyisochroman [1,2], an antibiotic and topoisomerase II inhibitor from the Penicillum sp., pseudodeflectusin [3], a selective human cancer cytotoxin from Aspergillus pseudodeflectus, isochromans from softwood lignin [4], and the male wing gland pheromone of bumblebee wax moth, Aphomia sociella [5]. Hydroxy-1-aryl-isochromans such as 1-phenyl-6,7-dihydroxyisochroman and 1-(3-methoxy-4-hydroxy)phenyl-6,7-dihydroxyisochroman have been identified in extra-virgin olive oil [6].…”

Microwave‐accelerated Synthesis of Some (±)‐1‐Aryl‐5‐chloroisochromans

“…4 Isochroman structures are also part of complex natural products such as stephaoxocanine, 5 a novel dihydroisoquinoline alkaloid from Stephania cepharantha, and glucoside B, an aphid insect pigment derivative. 6 Hydroxy-1-arylisochromans such as 1-phenyl-6,7-dihydroxyisochroman and 1-(3-methoxy-4-hydroxyphenyl)-6,7-dihydroxyisochroman have been identified in extra-virgin olive oil.…”