Β. Hydrocarbons
173
(1969), e.g., have shown that compound 10 isomerized to dictyopterene
C (7) at 15°.
10
In a fascinating parallel investigation Müller (1968) was able to isolate the
sex attractant produced by the female gametes of the brown alga Ectocarpus
siliculosus and could show that this chemotactic substance was volatile and
possessed a characteristic odor. By mass culturing the alga (14,900 culture
dishes) over two years Müller et al. (1971) were able to isolate 92 mg of
chromatographically pure biologically active substance and to demonstrate
its structure to be 6-(cz>but-r-enyl)cyclohepta-l,4-diene (11). The German
workers (Jaenicke et al, 1971) have since synthesized racemic dictyopterene
D' (11) as has the Weinstein group (Ali et al, 1971) by rearranging dictyopterene Β (3). The full structural elucidation of a sex attractant in a lower
plant is the first for a marine plant and only the second such compound from
any environment. The first compound, sirenin (12), was isolated by Machlis
et al. (1966) from the fresh water mold of the genus Allomyces and its structure was elucidated by Machlis et al. (1968). In view of this precedent Müller
Me
Me^^^CH 2 OH
11
12
et al. (1971) suggest that the algal sex attractant (11) may be referred to as
Ectocarpus sirenin. Regardless of whether plant pheromones will in the future
be referred to by the generic name sirenin, this research will doubtless be
followed by structural elucidation of other chemotactic principles. It will
be recalled (vide supra) that Youngblood et al. (1971) observed that in the
alga Ascophyllum nodosum the polyunsaturated hydrocarbons occur exclusively in the reproductive tissue. Attempts to define chemically a gamone
of a marine alga in fact go back to some work by Cook et al. (1948, 1951) who
suggested that the sex attractant material released by the mature eggs of the
brown algae Fucus vesiculosus and F. serratus may be a C-6 hydrocarbon.
Müller (1972) has reisolated the attractant released by the eggs of F. serratus
and has found that it is a small lipophilic molecule with a volatility between
C 8 and C 9 alkanes on a silicone column. Hlubucek et al. (1970) have recently
confirmed that «-hexane is the major peak (ca 60 percent) of the volatiles
extracted from the ripe female tips of F. vesiculosus.
173
(1969), e.g., have shown that compound 10 isomerized to dictyopterene
C (7) at 15°.
10
In a fascinating parallel investigation Müller (1968) was able to isolate the
sex attractant produced by the female gametes of the brown alga Ectocarpus
siliculosus and could show that this chemotactic substance was volatile and
possessed a characteristic odor. By mass culturing the alga (14,900 culture
dishes) over two years Müller et al. (1971) were able to isolate 92 mg of
chromatographically pure biologically active substance and to demonstrate
its structure to be 6-(cz>but-r-enyl)cyclohepta-l,4-diene (11). The German
workers (Jaenicke et al, 1971) have since synthesized racemic dictyopterene
D' (11) as has the Weinstein group (Ali et al, 1971) by rearranging dictyopterene Β (3). The full structural elucidation of a sex attractant in a lower
plant is the first for a marine plant and only the second such compound from
any environment. The first compound, sirenin (12), was isolated by Machlis
et al. (1966) from the fresh water mold of the genus Allomyces and its structure was elucidated by Machlis et al. (1968). In view of this precedent Müller
Me
Me^^^CH 2 OH
11
12
et al. (1971) suggest that the algal sex attractant (11) may be referred to as
Ectocarpus sirenin. Regardless of whether plant pheromones will in the future
be referred to by the generic name sirenin, this research will doubtless be
followed by structural elucidation of other chemotactic principles. It will
be recalled (vide supra) that Youngblood et al. (1971) observed that in the
alga Ascophyllum nodosum the polyunsaturated hydrocarbons occur exclusively in the reproductive tissue. Attempts to define chemically a gamone
of a marine alga in fact go back to some work by Cook et al. (1948, 1951) who
suggested that the sex attractant material released by the mature eggs of the
brown algae Fucus vesiculosus and F. serratus may be a C-6 hydrocarbon.
Müller (1972) has reisolated the attractant released by the eggs of F. serratus
and has found that it is a small lipophilic molecule with a volatility between
C 8 and C 9 alkanes on a silicone column. Hlubucek et al. (1970) have recently
confirmed that «-hexane is the major peak (ca 60 percent) of the volatiles
extracted from the ripe female tips of F. vesiculosus.