Sesquiterpenoids with antialgal activity against the common red tide microalgae from marine macroalga Porphyra yezoensis

Abstract

Previous studies showed that methanol extracts from Porphyra yezoensis significantly inhibited Karenia mikimitoi and Skeletonema costatum. Five sesquiterpenoids (1–5) were successfully isolated from this marine macroalga through a combination of silica gel column chromatography and repeated preparative thin-layer chromatography in this paper. Their structure was identified as gossonorol (1), 7,10-epoxy-ar-bisabol-11-ol (2), cyclonerodiol (3), cadinol, (4) and 4-cadinen-1-ol (5) on the basis of spectroscopic data. These sesquiterpenoids were isolated from Porphyra yezoensis for the first time, and cyclonerodiol (3) and cadinol (4) isolated from marine macroalgae for the first time. Further, a quantitative relationship between the inhibition of algal growth and the concentration of each antialgal sesquiterpenoid (gossonorol, 7,10-epoxy-ar-bisabol-11-ol and cyclonerodiol) was determined and important parameters, e.g., EC_50-96h for future practical HAB control are to be obtained. Results showed that three sesquiterpenoids (1–3) had selective antialgal activity against the growth of red tide microalgae (Amphidinium carterae, Heterosigma akashiwo, Karenia mikimitoi, Phaeocystis globosa, Prorocentrum donghaiense, and Skeletonema costatum). More than two test red tide microalgae were significantly inhibited by these three sesquiterpenoids (1–3). Their antialgal activity against red tide microalgae has not been previously reported. Furthermore, EC_50-96h of gossonorol (1) and 7,10-epoxy-ar-bisabol-11-ol (2) for specific test red microalgae were not only significantly less than 10 μg/mL, but also were smaller than/or very close to those of potassium dichromate. Gossonorol (1) and 7,10-epoxy-ar-bisabol-11-ol (2) possessed good application potential than potassium dichromate as a characteristic antialgal agent against the specific harmful red tide microalgae (Heterosigma akashiwo, Phaeocystis globosa, and Prorocentrum donghaiense) (or Heterosigma akashiwo and Karenia mikimitoi).