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Absolute Configuration and Synthesis of (+)-Caudoxirene, the Gamete-Releasing and Gamete-Attracting Pheromone of the Brown Alga Perithalia caudata (Phaeophyceae)

✍ Scribed by Dieter Wirth; Wilhelm Boland; Dieter G. Müller

Publisher
John Wiley and Sons
Year
1992
Tongue
German
Weight
548 KB
Volume
75
Category
Article
ISSN
0018-019X

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✦ Synopsis

Introduction. ~ During sexual reproduction, fertile female gametes of the marine brown alga Perithalia caudata release caudoxirene (1) as a specific chemical messenger. The signal is secreted together with two inactive by-products, namely viridiene (2, ca. 4%) and multifidene (3, ca. 8%) [l] [2] (Scheme I ) . Caudoxirene (1) triggers a cascade of events that culminate in the fusion of the male and female cells forming a zygote. Upon Scheme I 1 caudoxirene 2 viridiene ((+)-(3R,4S)-2 shown) 3 multifidene ((3.54.9-3 shown) F (+)-(3R,4S)-2 ( ~a . 10%) + KSeCn (+)-I (in extract of Fcaudafa) H (+)-(3R,4S)-4 (ca. 90%)

contact with ripe antheridia, 1 induces within ca. 30 s the discharge of spermatozoids. The motile microgametes then follow the gradient of the pheromone trail towards the egg cell and fertilization takes place. Data regarding the intrinsinc efficiency of the chemotactic response are not available. The obligatory function of caudoxirene (1) for sperm release implies that pheromone-free spermatozoids can not be obtained for chemotaxis

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