Isolation of a new butenolide from the South China Sea gorgonian coral Subergorgia suberosa.
Chemical investigation on the South China Sea gorgonian coral Subergorgia suberosa has led to the isolation of one new butenolide (5R)-5-(1-ethoxypropyl)-5-hydroxy-3,4-dimethylfuran-2(5H)-one (1) as a pair of inseparable epimers, along with two known butenolides (S)-5-hydroxy-3,4-dimethyl-5-propylfuran-2(5H)-one (2) and (S)-5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one (3). Their structures including absolute configurations were determined unambiguously by detailed analyses of spectroscopic data and by comparison with the available literature. Compounds 1-3 exhibited moderate antifouling activities against the settlement of Balanus amphitrite larvae, whereas compound 4, the acetyl derivative of 3, showed no antifouling activity at the concentrations up to 25 μg/mL.
a College of Pharmacy, Jinan University , Guangzhou 510632 , P.R. China.
Jun
J
Zhang
Yan
Y
Liang
Xiao-Jian
XJ
Liao
Zhou
Z
Deng
Shi-Hai
SH
Xu
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D001468:Thoracica / Q000187:drug effects; D014874:Water Pollutants, Chemical / Q000037:antagonists & inhibitors
C000590960:(5R)-5-(1-ethoxypropyl)-5-hydroxy-3,4-dimethylfuran-2(5H)-one; D014874:Water Pollutants, Chemical; C004511:butenolide; D015107:4-Butyrolactone