Four spiromeroterpenoids, chermesins A–D (219–222) (Fig. 13), were isolated
from the solid rice culture extract of Penicillium chermesinum EN-480, an endophyte obtained from the inner tissue of the marine red alga Pterocladiella tenuis
collected at Rongcheng, Shandong Province. Chermesins A and B (219 and 220)
O
O
HO
219 (chermesin A)
O
O
220 R = H (chermesin B)
222 R = COOH (chermesin D)
R
O
O
O
HO
221 (chermesin C)
OH
O
O
O
O
O
O
OH
OH
228 R
1 = OH, R
2 = H
(chrodrimanin P)
231 R
1 = H, R
2 = OMe
(chrodrimanin S)
R 1
O
O
O
HO
OH
OH
Cl
225 R
1 = OH, R
2 = H
(chrodrimanin M)
226 R
1 = H, R
2 = OAc
(chrodrimanin N)
R 1
O
O
O
O
O
OH
229 (chrodrimanin Q)
AcO
O
O
O
O
OH
OH
Cl
223 R
1 = R
2 = H (chrodrimanin K)
224 R 1 = Cl, R 2 = H (chrodrimanin
L)
227 R 1 = R 2 = Cl (chrodrimanin O)
232 (verruculide B2)
O
O
HO
OH
O
OH
HO
O
O
HO
OH
O
OH
HO
233 (verruculide B3)
R 1
R 2
R 2
R 2
O
O
O
O
OH
HO
234 (arisugacin K)
O
O
O
OAc
AcO
OAc
235 (phenylpyropene A 5-olefin)
O
O
N
O
R 3
OAc
R 1
236 R
1 = R
2 = OAc, R 3 = H
(13-dehydroxypyripyropene A)
237 R
1 = R
2 = OH, R 3 = H
(13-dehydroxy-1,11deacetylpyripyropene A)
238 R
1 = R 3 = OH, R
2 = OAc
(1-deacetylpyripyropene A)
R 2
O
O
O
HO
OH
OH
230 (chrodrimanin R)
AcO
Fig. 13 Structures of merosesquiterpenes (part 3)
Secondary Metabolites from Marine-Derived Fungi from China
103