Chemistry Reference
In-Depth Information
phospholipase A
2
(7). More than 50 halogenated C
15
acetogenins, which are
derived from fatty acids, have been isolated from red algae of the genus
Lau-
rencia
; laurencin (
4
) was first isolated from
L. nipponica
(8). These compounds
were reported to be antifeeding and insecticidal. Certain species of soft corals
are known to contain prostanoids, of which the most intriguing are punaglandins
[punaglandin 1 (
5
)], the first halogenated prostaglandins isolated from the soft
coral
Telesto riisei
(3). They are antiviral and cytotoxic.
OAc OAc
O
H
CO
2
CH
3
CH
3
O
Br
Cl
OAc
O
CO
2
H
O
O
OAc
CH
3
(CH
2
)
15
HO
4
5
6
Fatty acid-derived cyclic peroxides are often found in marine sponges of the
genus
Plakortis
; the first example was chondrillin (
6
). 1,2-Dioxane and 1,2-
dioxolane carboxylates were also discovered from
Plakortis
sponges (9). These
cyclic oxides show a range of biologic activities, for example, antimicrobial,
cytotoxic, and antimalarial activities.
In addition, a variety of bioactive fatty acid derivatives have been isolated
from marine organisms, including glycoceramides (10). Perhaps the most unusual
example is a highly chlorinated sulfolipid
7
isolated as a cytotoxic principle from
the mussel
Mytilus galloprovincialis
(10).
O
O
Cl
OSO
3
Cl
OH
Cl
OH
OH
Cl
CH
3
(CH
2
)
13
OH
Cl
Cl
Cl
Cl
Cl
Cl
Cl
OH
7
2.1.2 Polyacetylenes
Linear polyacetylenes are found frequently in marine sponges of the order Hap-
losclerida (11). Although the chain lengths vary from C
14
to C
49
, likely they
are to be derived from C
16
fatty acids. Polyacetylenes show a wide range of
bioactivities, including antimicrobial, cytotoxic, antiviral, and enzyme inhibitory.
Corticatic acid A (
8
), which is a C
31
polyacetylene carboxylic acid isolated from
Petrosia corticata
, is not only antimicrobial, but also it inhibits geranylgeranyl-
transferase I (12).
2.1.3 Polypropionates
The most prominent source of marine polypropionates are mollusks, in par-
ticular opisthobranchs (13). Among a variety of polypropionates, the simplest
