A. Sesquiterpenoids
11
8
9f ^^
8
ι οί b--îN -
4
Γ^^"^
9
5\^3^
2
^ « U
4
5
25c
25a
25b
25d
CTO.
25e
species. The subclass Opisthobranchia is entirely marine and consists of the
orders Tectibranchia (sea hares, bubbleshells), Pteropoda (sea butterflies),
and Nudibranchia (sea slugs). The sea hares, which lack a shell, are unspectacular animals in color and shape and are easily missed among the rocks
of a tidepool. Their trivial name stems from their appearance as they feed on
a stand of algae, which is said to be reminiscent of terrestrial rabbits in a lettuce
patch.
Yamamura and Hirata's (1963) work on the constituents of Aplysia
kurodai followed an earlier inconclusive study by Tanaka and Toyama
(1959). As part of an extensive investigation into the lipids of marine organisms these authors detected two crystalline bromine containing compounds
in the unsaponifiable portion of A. kurodai. One of the compounds, mp 69°71°, had the apparent composition C 16 H 2 iBrO and was characterized as a
bromophenol; the second compound, mp 146.5°-147.5°, was insufficiently
characterized.
Yamamura and Hirata (1963) followed up on the earlier work in an attempt
to verify the occurrence of the bromo constituents of sea hares. They extracted
whole dry animals with ether and saponified the extract with methanolic
potassium hydroxide. The unsaponifiable matter was again extracted with
ether, then hexane. The hexane-soluble residue was chromatographed first
on silica gel, then on alumina. From the hexane fraction the authors isolated
debromoaplysin (26) as an oil, which they converted to a mononitro derivative,
A. Sesquiterpenoids
11
4
6 •
10
•• 1
llX··
S
9
8
7
2
25c
25a
1
2Sd
1
_ _........... 10
2Sb
2Se
species. The subclass Opisthobranchia is entirely marine and consists of the
orders Tectibranchia (sea hares, bUbbleshells), Pteropoda (sea butterflies),
and Nudibranchia (sea slugs). The sea hares, which lack a shell, are unspectacular animals in color and shape and are easily missed among the rocks
of a tidepool. Their trivial name stems from their appearance as they feed on
a stand of algae, which is said to be reminiscent of terrestrial rabbits in a lettuce
patch.
Yamamura and Hirata's (1963) work on the constituents of Aplysia
kurodai followed an earlier inconclusive study by Tanaka and Toyama
(1959). As part of an extensive investigation into the lipids of marine organisms these authors detected two crystalline bromine containing compounds
in the unsaponifiable portion of A. kurodai. One of the compounds, mp 69°71°, had the apparent composition C 16 H 21 BrO and was characterized as a
bromophenol; the second compound, mp 146.5°-147.5°, was insufficiently
characterized.
Yamamura and Hirata (1963) followed up on the earlier work in an attempt
to verify the occurrence of the bromo constituents of sea hares. They extracted
whole dry animals with ether and saponified the extract with methanolic
potassium hydroxide. The unsaponifiable matter was again extracted with
ether, then hexane. The hexane-soluble residue was chromatographed first
on silica gel, then on aluDlina. From the hexane fraction the authors isolated
debromoaplysin (26) as an oil, which they converted to a mononitro derivative,
11
8
9f ^^
8
ι οί b--îN -
4
Γ^^"^
9
5\^3^
2
^ « U
4
5
25c
25a
25b
25d
CTO.
25e
species. The subclass Opisthobranchia is entirely marine and consists of the
orders Tectibranchia (sea hares, bubbleshells), Pteropoda (sea butterflies),
and Nudibranchia (sea slugs). The sea hares, which lack a shell, are unspectacular animals in color and shape and are easily missed among the rocks
of a tidepool. Their trivial name stems from their appearance as they feed on
a stand of algae, which is said to be reminiscent of terrestrial rabbits in a lettuce
patch.
Yamamura and Hirata's (1963) work on the constituents of Aplysia
kurodai followed an earlier inconclusive study by Tanaka and Toyama
(1959). As part of an extensive investigation into the lipids of marine organisms these authors detected two crystalline bromine containing compounds
in the unsaponifiable portion of A. kurodai. One of the compounds, mp 69°71°, had the apparent composition C 16 H 2 iBrO and was characterized as a
bromophenol; the second compound, mp 146.5°-147.5°, was insufficiently
characterized.
Yamamura and Hirata (1963) followed up on the earlier work in an attempt
to verify the occurrence of the bromo constituents of sea hares. They extracted
whole dry animals with ether and saponified the extract with methanolic
potassium hydroxide. The unsaponifiable matter was again extracted with
ether, then hexane. The hexane-soluble residue was chromatographed first
on silica gel, then on alumina. From the hexane fraction the authors isolated
debromoaplysin (26) as an oil, which they converted to a mononitro derivative,
A. Sesquiterpenoids
11
4
6 •
10
•• 1
llX··
S
9
8
7
2
25c
25a
1
2Sd
1
_ _........... 10
2Sb
2Se
species. The subclass Opisthobranchia is entirely marine and consists of the
orders Tectibranchia (sea hares, bUbbleshells), Pteropoda (sea butterflies),
and Nudibranchia (sea slugs). The sea hares, which lack a shell, are unspectacular animals in color and shape and are easily missed among the rocks
of a tidepool. Their trivial name stems from their appearance as they feed on
a stand of algae, which is said to be reminiscent of terrestrial rabbits in a lettuce
patch.
Yamamura and Hirata's (1963) work on the constituents of Aplysia
kurodai followed an earlier inconclusive study by Tanaka and Toyama
(1959). As part of an extensive investigation into the lipids of marine organisms these authors detected two crystalline bromine containing compounds
in the unsaponifiable portion of A. kurodai. One of the compounds, mp 69°71°, had the apparent composition C 16 H 21 BrO and was characterized as a
bromophenol; the second compound, mp 146.5°-147.5°, was insufficiently
characterized.
Yamamura and Hirata (1963) followed up on the earlier work in an attempt
to verify the occurrence of the bromo constituents of sea hares. They extracted
whole dry animals with ether and saponified the extract with methanolic
potassium hydroxide. The unsaponifiable matter was again extracted with
ether, then hexane. The hexane-soluble residue was chromatographed first
on silica gel, then on aluDlina. From the hexane fraction the authors isolated
debromoaplysin (26) as an oil, which they converted to a mononitro derivative,