Part F | 32.3
778 Part F Marine Derived Metabolites
OH
OH
OH
OH OH
OH
H
H
H
H
H
H
O
O
O
H
H
H
O
O
O
O O
O
O
O
O
O
H
O
O
O
O
O
R
7'
6'
O
OH
OH
OH
OH
OH OH
OH
OH
OH OH
HO
HO
OH
OH
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
R 1
R 2
HO
187: R 1 = OH, R 2 = H
189: R 1 , R 2 = O
194: R 1 , R 2 , R 3 = H
195: R 1 , R 3 = H, R 2 = OH
196: R 1 = H, R 2 , R 3 = OH
197: R 3 = OH, R 2 , R 3 = H
206: 6', 7'-Dihydro, R = H
207: 6', 7'-Dihydro, R = OH
208: Δ 6',7' , R = H
226: R = CH 2 OH
227: R = CH 3
228: R = COOH
229: R = CH 3
200: R 1 = OH, R 2 , R 3 = OH
201: R 1 , R 2 , R 3 = H
203: R 1 , R 2 = H, R 3 = OH
204: R 1 , R 2 = OH, R 3 = H
212: R 1 = α–H, R 2 = α–OH
213: R 1 = α–H, R 2 = α–OCH 3
214: R 1 = –H, R 2 = –OCH 3
188
197
209
210
216
222
223
224
225
217
218
219
211
198
202
205
215
190
191
192
193
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
R 1
R 1
R 3
R 2
OH
O
O
O
O
OH
OH
HO
HO
OH
OH
H
O
OH
HO
H
H
O
O
O
O
R
O
R
OH
OH
OH
OH
OH
OH
OH
OH
OH
OH
OH
OH
H
HO
HO
O
COOH
OH
HO
OH
OH
220
221
230
H
OH
OH
H
OH
OH
O
O
O
O
OH
OH
OH
R 1
R 3
R 2
R 2
Fig. 32.11 Chemical structures of compounds 187–230
Three new pimarane diterpenes, aspergilones A–C
(190–192), together with the known compound 193,
were isolated from the marine-derived fungus Epicoccum sp. HS-1 associated with Apostichopus japonicus
[32.138]. Absolute configurations of compounds (190–
192) were determined by CD spectroscopy [32.138]. In
the cytotoxicity (MTT) assay, compounds 190 and 193
revealed potent activities against KB and KBv200 cell
lines with IC 50 values of 10:0, 6:4 M, and 11:2 and
18:0 M, respectively [32.138].
778 Part F Marine Derived Metabolites
OH
OH
OH
OH OH
OH
H
H
H
H
H
H
O
O
O
H
H
H
O
O
O
O O
O
O
O
O
O
H
O
O
O
O
O
R
7'
6'
O
OH
OH
OH
OH
OH OH
OH
OH
OH OH
HO
HO
OH
OH
HO
HO
HO
HO
HO
HO
HO
HO
HO
HO
R 1
R 2
HO
187: R 1 = OH, R 2 = H
189: R 1 , R 2 = O
194: R 1 , R 2 , R 3 = H
195: R 1 , R 3 = H, R 2 = OH
196: R 1 = H, R 2 , R 3 = OH
197: R 3 = OH, R 2 , R 3 = H
206: 6', 7'-Dihydro, R = H
207: 6', 7'-Dihydro, R = OH
208: Δ 6',7' , R = H
226: R = CH 2 OH
227: R = CH 3
228: R = COOH
229: R = CH 3
200: R 1 = OH, R 2 , R 3 = OH
201: R 1 , R 2 , R 3 = H
203: R 1 , R 2 = H, R 3 = OH
204: R 1 , R 2 = OH, R 3 = H
212: R 1 = α–H, R 2 = α–OH
213: R 1 = α–H, R 2 = α–OCH 3
214: R 1 = –H, R 2 = –OCH 3
188
197
209
210
216
222
223
224
225
217
218
219
211
198
202
205
215
190
191
192
193
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
R 1
R 1
R 3
R 2
OH
O
O
O
O
OH
OH
HO
HO
OH
OH
H
O
OH
HO
H
H
O
O
O
O
R
O
R
OH
OH
OH
OH
OH
OH
OH
OH
OH
OH
OH
OH
H
HO
HO
O
COOH
OH
HO
OH
OH
220
221
230
H
OH
OH
H
OH
OH
O
O
O
O
OH
OH
OH
R 1
R 3
R 2
R 2
Fig. 32.11 Chemical structures of compounds 187–230
Three new pimarane diterpenes, aspergilones A–C
(190–192), together with the known compound 193,
were isolated from the marine-derived fungus Epicoccum sp. HS-1 associated with Apostichopus japonicus
[32.138]. Absolute configurations of compounds (190–
192) were determined by CD spectroscopy [32.138]. In
the cytotoxicity (MTT) assay, compounds 190 and 193
revealed potent activities against KB and KBv200 cell
lines with IC 50 values of 10:0, 6:4 M, and 11:2 and
18:0 M, respectively [32.138].
