Part F | 32.3
766 Part F Marine Derived Metabolites
1
17
18
19
25
30
24
29
22 (Z ):
23 (E):
20
21
28
9
1 5
2: R 1 = CH 3 COO, R 2 = H
3: R 1 = OH , R 2 = OH
4: R 1 = CH 3 COO, R 2 = OH
12: R 1 = OCH 3 , R 2 = H, R 3 = OH
13: R 1 = OH , R 2 = H, R 3 = H
14: R 1 = H, R 2 = OH, R 3 = H
8: R 1 =
31: R 1 =
26: R = O
27: R = H 2
, R 2 = C 2 H 4 OH
32: R 1 = R 2 = H
, R 2 =
10: R 1 =
, R 2 =
11: R 1 =
, R 2 =
5: R = CH 3 COO
6: R = OH
7
H
HN
H
H
O
O
O
O
O
O
O
O
O
O
O
O
O
N
N
R
O
O
O
O
R 1
R 2
O
O
O
O
O
O
N
N
N
N
O
N
H
N
H
N
H
N
H
N
H
N
H
OH
OH
OH
OH
HO
OCH 3
O
N
H
OH
OH
OH
OH
HO
HO
OH
OH
H 3 CO
HN
OH
NH
N
N
N
N
N
N
N
N
N
N
O
O
O O
O
O
N
N
H
O
O
O
R
OH
NH
NH 2
OCH 3
O
N
H
OH
R 2
R 1
R 1
R 2
R 3
R 1
R 2
HN
HO
H
O
O
O
O
R
OH
HN
HN
H
N
16
HN
N
O
O
O
O
OH
CH 2
OH
Fig. 32.5 Chemical structures of compounds 1–32
incarnatum (HKI0504), isolated from the mangrove
plant Aegiceras corniculatum [32.78]. In the antiproliferative activity assay, only 2-acetyl-1,2,3,4-tetrahydro-ˇ-carboline (18), fusamine (20), and 3-(1-aminoethylidene)-6-methyl-2H-pyran-2,4(3H)-dione (21) exhibited weak cytotoxic activities against human umbilical vascular endothelial cells (HUVEC), human cervix
carcinoma cells (HeLa), and human chronic myeloid
leukemia cells (K562) with IC 50 values of 41:1, 23:3,
and 9:0 M, respectively [32.78].
Two putative tyrosine-derived metabolites, stachylines A (22) and B (23), together with two O-prenylated
derivatives, stachylines C and D, were purified from
the fungal extract of Stachylidium sp., a marine-derived
fungus isolated from the Australian sponge Callyspongia cf. C. flammea [32.79]. Stachylines are tyrosinederived metabolites featuring oxime moiety which is
incorporated in biosynthesis of marine natural products such as bastadins and psammaplins, which may
suggest a metabolic relation between the marine-de-
766 Part F Marine Derived Metabolites
1
17
18
19
25
30
24
29
22 (Z ):
23 (E):
20
21
28
9
1 5
2: R 1 = CH 3 COO, R 2 = H
3: R 1 = OH , R 2 = OH
4: R 1 = CH 3 COO, R 2 = OH
12: R 1 = OCH 3 , R 2 = H, R 3 = OH
13: R 1 = OH , R 2 = H, R 3 = H
14: R 1 = H, R 2 = OH, R 3 = H
8: R 1 =
31: R 1 =
26: R = O
27: R = H 2
, R 2 = C 2 H 4 OH
32: R 1 = R 2 = H
, R 2 =
10: R 1 =
, R 2 =
11: R 1 =
, R 2 =
5: R = CH 3 COO
6: R = OH
7
H
HN
H
H
O
O
O
O
O
O
O
O
O
O
O
O
O
N
N
R
O
O
O
O
R 1
R 2
O
O
O
O
O
O
N
N
N
N
O
N
H
N
H
N
H
N
H
N
H
N
H
OH
OH
OH
OH
HO
OCH 3
O
N
H
OH
OH
OH
OH
HO
HO
OH
OH
H 3 CO
HN
OH
NH
N
N
N
N
N
N
N
N
N
N
O
O
O O
O
O
N
N
H
O
O
O
R
OH
NH
NH 2
OCH 3
O
N
H
OH
R 2
R 1
R 1
R 2
R 3
R 1
R 2
HN
HO
H
O
O
O
O
R
OH
HN
HN
H
N
16
HN
N
O
O
O
O
OH
CH 2
OH
Fig. 32.5 Chemical structures of compounds 1–32
incarnatum (HKI0504), isolated from the mangrove
plant Aegiceras corniculatum [32.78]. In the antiproliferative activity assay, only 2-acetyl-1,2,3,4-tetrahydro-ˇ-carboline (18), fusamine (20), and 3-(1-aminoethylidene)-6-methyl-2H-pyran-2,4(3H)-dione (21) exhibited weak cytotoxic activities against human umbilical vascular endothelial cells (HUVEC), human cervix
carcinoma cells (HeLa), and human chronic myeloid
leukemia cells (K562) with IC 50 values of 41:1, 23:3,
and 9:0 M, respectively [32.78].
Two putative tyrosine-derived metabolites, stachylines A (22) and B (23), together with two O-prenylated
derivatives, stachylines C and D, were purified from
the fungal extract of Stachylidium sp., a marine-derived
fungus isolated from the Australian sponge Callyspongia cf. C. flammea [32.79]. Stachylines are tyrosinederived metabolites featuring oxime moiety which is
incorporated in biosynthesis of marine natural products such as bastadins and psammaplins, which may
suggest a metabolic relation between the marine-de-