Dynamic aspect of male gamete-attracting activity in marine algae.

经鉴定，田间栽培的花管藻雌配子体分泌的吸引雄配子的物质为hormosirene。此外，在本研究中，为了防止真菌和细菌产生的挥发性化合物的污染，培养了S.lomentaria。结果表明，其配子体分泌的吸引雄配子的物质为hormosirene。同样地，阐明了与S.lomentaria同属Scytosiphonaceae的田间生长和培养的Petalonia fascia的雌性配子也分泌hormosirin作为雄性配子吸引物质。(-)以（+）-（1 S，5 R）-3-氧杂双环[3，3，0]辛-6-烯-2-酮为原料，合成了（3R，4 R）-3-丁基-4-乙烯基环戊烯[（-）-1]。在手性气相色谱（CP-Cyclodex 236 M）中，合成的（-）-1与外消旋的（-）-1保留时间较晚的峰相吻合<plus-minus>，而褐藻、Dicyopterisprolifera和D.sp.挥发油中的天然1与保留时间较早的峰相吻合。结果表明，该化合物的绝对构型为（+）-（3S，4S），对映体过量约为100%。

It had been identified that the male gamete-attracting substances secreted from female gametes of fied-grown Scytosiphon lomentaria was hormosirene. In this investigation, furthermore, with preventing contamination from volatile compounds formed from epiphytes and bacteria, S.lomentaria had been cultured. And it was revealed that the male gamete-attracting substance secreted from gametes of its was hormosirene. Similarly, it was elucidated that female gametes of field-grown and cultural Petalonia fascia, which is classified into same family of Scytosiphonaceae, as S.lomentaria, also secreted hormosiren as the male gamete-attracting substance.(-) (3R,4R) -3-butyl-4-vinylcyclopentene [(-) -1] was synthesized via (+) - (1S,5R) -3-oxabicyclo [3,3,0] oct-6-en-2-one. The synthetic (-) -1 coincided with the peak with later retention time of racemic (<plus-minus>) -1 in a chiral GC (CP-Cyclodex 236M), while the natural 1 in essential oils from the marine brown algae, Dicyopteris prolifera and D.sp.was identical with the earlier retention time peak. Thus, the absolute configuration of the natural product in Dictyopteris oils was determined as (+) - (3S,4S) with ca.100% enantiomeric exce