D (Maier et al. 1998), and first reported from Ophidiaster ophidianus (Jin et al.
1994). Anasterias minuta produced a new glucosylceramide: Anasterocerebroside
A, together with five other previously reported pure cerebrosides. Isolated as a
pure compound, Glucosylceramide 7, previously obtained as molecular species
from C. lurida and A. capensis, was characterized for the first time (Chludil et al.
2003a). The novel Inaequalocerebroside 1 was obtained from body walls and
gonads of A. capensis. The body walls also contained two other new glucosylceramides as nearly homogeneous mixtures and five known cerebrosides:
Phalluside 1, Ophidiacerebrosides C and D (Jin et al. 1994) and compounds 3 and
4, firstly isolated from C. lurida. Gonads had two new glucosylceramides (Inaequalocerebrosides 2 and 3), containing the new LCB (2S,3R,4E,15Z)-2-amino4,15-docosadien-1,3-diol and Phalluside 1 as major components. A comparative
analysis of the composition of the cerebroside mixtures obtained from body walls
and gonads of A. capensis showed differences in the fatty acid and LCB moieties:
the 9-methyl, D
4,8,10 triene-LCB and saturated or unsaturated (D
10 or D
15
)-24-C
fatty acids were the most abundant in the glucosylceramides obtained from body
walls, while the octadecatriene and the cis-D
15 -22-C LCBs and 2-hydroxyheptadecanoic acid were predominant moieties in cerebrosides from gonads. All fatty
acids isolated from body walls had normal chains whereas gonads had fatty acids
with iso chains as well (Díaz de Vivar et al. 2002).
Ophiuroidea
Secondary metabolites from three species collected at SMG: Ophioplocus januarii,
Ophiactis asperula and Ophiacantha vivipara were studied. Ophioplocus januarii
afforded four sulfated polyhydroxysteroids, one of them is new (Fig. 11.5d). The
antiviral activity of the four compounds was tested against herpes simplex virus
type 1, Junín virus, respiratory syncytial virus and polio virus. These studies showed
the importance of the unsaturation at C-22 for the inhibitory action towards
respiratory syncytial virus and at C24-28 for replication of Junín virus (Roccatagliata et al. 1996a). Ophiactis asperula and O. vivipara did not have sulfated
polyhydroxylated steroids as the major secondary metabolites, but showed
nucleosides and nucleobases in their ethanolic extracts instead. From O. asperula,
inosine (19.0 %), 2
0 -deoxyuridine (10.6 %), thymidine (14.9 %), and the bases
uracyil (17.4 %), cytosine (15.9 %) and thymine (22.2 %) were obtained. Ophiacantha vivipara afforded inosine (7.1 %), 2
0 -deoxyinosine (13.4 %), uridine
(3.8 %), 2
0 -deoxyuridine (7.1 %), 2
0 -deoxycytidine (1.4 %), and thymidine (4.6 %)
with the bases uracyl (8.1 %), cytosine (4.8 %), thymine (31.9 %) and hypoxanthine (17.8 %) (Murray et al. 2002). Considering echinoderms, 2
0 -deoxyribonucleosides had only been previously isolated from the sea stars A. planci and
L. maculata (Komori et al. 1978, 1980). Their importance as systematic markers
was suggested by Dematté et al. (1986), since they had only been isolated from
tunicates and echinoderms. This is currently under discussion as they have also been
purified from two marine sponges (Kondo et al. 1992; Searle and Molinski 1994).
11 Echinoderms from Argentina
385
1994). Anasterias minuta produced a new glucosylceramide: Anasterocerebroside
A, together with five other previously reported pure cerebrosides. Isolated as a
pure compound, Glucosylceramide 7, previously obtained as molecular species
from C. lurida and A. capensis, was characterized for the first time (Chludil et al.
2003a). The novel Inaequalocerebroside 1 was obtained from body walls and
gonads of A. capensis. The body walls also contained two other new glucosylceramides as nearly homogeneous mixtures and five known cerebrosides:
Phalluside 1, Ophidiacerebrosides C and D (Jin et al. 1994) and compounds 3 and
4, firstly isolated from C. lurida. Gonads had two new glucosylceramides (Inaequalocerebrosides 2 and 3), containing the new LCB (2S,3R,4E,15Z)-2-amino4,15-docosadien-1,3-diol and Phalluside 1 as major components. A comparative
analysis of the composition of the cerebroside mixtures obtained from body walls
and gonads of A. capensis showed differences in the fatty acid and LCB moieties:
the 9-methyl, D
4,8,10 triene-LCB and saturated or unsaturated (D
10 or D
15
)-24-C
fatty acids were the most abundant in the glucosylceramides obtained from body
walls, while the octadecatriene and the cis-D
15 -22-C LCBs and 2-hydroxyheptadecanoic acid were predominant moieties in cerebrosides from gonads. All fatty
acids isolated from body walls had normal chains whereas gonads had fatty acids
with iso chains as well (Díaz de Vivar et al. 2002).
Ophiuroidea
Secondary metabolites from three species collected at SMG: Ophioplocus januarii,
Ophiactis asperula and Ophiacantha vivipara were studied. Ophioplocus januarii
afforded four sulfated polyhydroxysteroids, one of them is new (Fig. 11.5d). The
antiviral activity of the four compounds was tested against herpes simplex virus
type 1, Junín virus, respiratory syncytial virus and polio virus. These studies showed
the importance of the unsaturation at C-22 for the inhibitory action towards
respiratory syncytial virus and at C24-28 for replication of Junín virus (Roccatagliata et al. 1996a). Ophiactis asperula and O. vivipara did not have sulfated
polyhydroxylated steroids as the major secondary metabolites, but showed
nucleosides and nucleobases in their ethanolic extracts instead. From O. asperula,
inosine (19.0 %), 2
0 -deoxyuridine (10.6 %), thymidine (14.9 %), and the bases
uracyil (17.4 %), cytosine (15.9 %) and thymine (22.2 %) were obtained. Ophiacantha vivipara afforded inosine (7.1 %), 2
0 -deoxyinosine (13.4 %), uridine
(3.8 %), 2
0 -deoxyuridine (7.1 %), 2
0 -deoxycytidine (1.4 %), and thymidine (4.6 %)
with the bases uracyl (8.1 %), cytosine (4.8 %), thymine (31.9 %) and hypoxanthine (17.8 %) (Murray et al. 2002). Considering echinoderms, 2
0 -deoxyribonucleosides had only been previously isolated from the sea stars A. planci and
L. maculata (Komori et al. 1978, 1980). Their importance as systematic markers
was suggested by Dematté et al. (1986), since they had only been isolated from
tunicates and echinoderms. This is currently under discussion as they have also been
purified from two marine sponges (Kondo et al. 1992; Searle and Molinski 1994).
11 Echinoderms from Argentina
385