derived from the sea urchin Anthocidaris crassispina collected from the seashore of
Qionghai, Hainan. Three γ-butenolide derivatives, spiculisporic acids B–D (599–
601), were isolated from the solid MEA medium fermentation of A. candidus.
Spiculisporic acids B–D (599–601) showed no cytotoxicity against SGC-7901 and
SPC-A-1 cell lines, but displayed antibacterial activity against Staphylococcus
aureus with inhibition zones of 10, 12, and 12 mm at a concentration of 20 mg/
cm
3 , while the diameter of inhibition zone of the positive control (streptomycin
sulfate) was 24 mm at the same concentration level [187]. Two additional derivatives, spiculisporic acids F and G (602 and 603), were obtained when this fungus was
cultivated in liquid PDB medium. Both compounds 602 and 603 exhibited
antibacterial activity against Gram-positive Staphylococcus aureus and Gramnegative Pseudomonas solanacearum but did not show cytotoxicity against the
two cancer cell lines, SGC-7901 and SPC-A-1. The inhibitory diameters of
spiculisporic acid F (602) against S. aureus and P. solanacearum in the filter
paper disk diffusion assay at doses of 20 mg/cm
3 were 12 and 9 mm, respectively.
The inhibitory diameters of spiculisporic acid G (603) against S. aureus and
O
OH
HO
HO
OH
O
HN
O
HO
OH
593 (flavicerebroside A)
594 D (flavicerebroside B)
O
NH
RO
OH
OH
598 (4,5-ditridecyl-octanedioic acid)
HOOC
COOH
O
O
COOR
HOOC
599 D, R = H (spiculisporic acid B)
600 R = Me (spiculisporic acid C)
O
O
COOH
HOOC
601 (spiculisporic acid D)
602 D (spiculisporic acid F)
O
O
COOH
HOOC
603 (spiculisporic acid G)
6
7
OH
OH
6
7
OH
OH
606 R = H 2 (6R,7S) (harzianumol A)
607 R = H 2 (6S,7R) (harzianumol B)
608 R = O (6R,7R) (harzianumol C)
609 R = O (6S,7S) (harzianumol D)
610 R = H (6R,7S) (harzianumol E)
611 R = H (6S,7R) (harzianumol F)
612 R = OH (6R,7R) (harzianumol G)
613 R = OH (6S,7S) (harzianumol H)
604 R = OH (chondrosterin G)
605 R = Cl (chondrosterin H)
R
HO
OH
HO
OH
OH
O
597
R
R
595 R = H (asperamide A)
596 R = b-D-glucopyranosyl (asperamide B)
Fig. 35 Structures of lipids
Secondary Metabolites from Marine-Derived Fungi from China
137
Qionghai, Hainan. Three γ-butenolide derivatives, spiculisporic acids B–D (599–
601), were isolated from the solid MEA medium fermentation of A. candidus.
Spiculisporic acids B–D (599–601) showed no cytotoxicity against SGC-7901 and
SPC-A-1 cell lines, but displayed antibacterial activity against Staphylococcus
aureus with inhibition zones of 10, 12, and 12 mm at a concentration of 20 mg/
cm
3 , while the diameter of inhibition zone of the positive control (streptomycin
sulfate) was 24 mm at the same concentration level [187]. Two additional derivatives, spiculisporic acids F and G (602 and 603), were obtained when this fungus was
cultivated in liquid PDB medium. Both compounds 602 and 603 exhibited
antibacterial activity against Gram-positive Staphylococcus aureus and Gramnegative Pseudomonas solanacearum but did not show cytotoxicity against the
two cancer cell lines, SGC-7901 and SPC-A-1. The inhibitory diameters of
spiculisporic acid F (602) against S. aureus and P. solanacearum in the filter
paper disk diffusion assay at doses of 20 mg/cm
3 were 12 and 9 mm, respectively.
The inhibitory diameters of spiculisporic acid G (603) against S. aureus and
O
OH
HO
HO
OH
O
HN
O
HO
OH
593 (flavicerebroside A)
594 D (flavicerebroside B)
O
NH
RO
OH
OH
598 (4,5-ditridecyl-octanedioic acid)
HOOC
COOH
O
O
COOR
HOOC
599 D, R = H (spiculisporic acid B)
600 R = Me (spiculisporic acid C)
O
O
COOH
HOOC
601 (spiculisporic acid D)
602 D (spiculisporic acid F)
O
O
COOH
HOOC
603 (spiculisporic acid G)
6
7
OH
OH
6
7
OH
OH
606 R = H 2 (6R,7S) (harzianumol A)
607 R = H 2 (6S,7R) (harzianumol B)
608 R = O (6R,7R) (harzianumol C)
609 R = O (6S,7S) (harzianumol D)
610 R = H (6R,7S) (harzianumol E)
611 R = H (6S,7R) (harzianumol F)
612 R = OH (6R,7R) (harzianumol G)
613 R = OH (6S,7S) (harzianumol H)
604 R = OH (chondrosterin G)
605 R = Cl (chondrosterin H)
R
HO
OH
HO
OH
OH
O
597
R
R
595 R = H (asperamide A)
596 R = b-D-glucopyranosyl (asperamide B)
Fig. 35 Structures of lipids
Secondary Metabolites from Marine-Derived Fungi from China
137