Intraspecific variation of meroditerpenoids in the brown alga Stypopodium zonale guiding the isolation of new compounds

Abstract

Abstract Intraspecific variation on meroditerpenoids production by the brown marine alga Stypopodium zonale at four different populations along the Brazilian coast was analyzed using Principal Component Analysis over high-performance liquid chromatography profiles from algae extracts. The ordination of the samples by the similarities of their chromatographic traits showed the existence of three chemotypes: (i) the populations Búzios and Abrolhos which were characterized by the presence of atomaric acid (1), (ii) the population Atol das Rocas which contained the compound stypoldione (2), and (iii) the population Marataízes which was characterized by other peaks that guided the isolation of three new meroditerpenoids stypofuranlactone (3), 10,18-dihydroxy-5′a-desmethyl-5′-acetylatomaric acid (4), and the 10-keto-10-deisopropyliden-5′a-desmethyl-5′-acetylatomaric acid (5) together with the known compound the 10-keto-10-deisopropyliden-atomaric acid (6). The structures and relative stereochemistry of 3, 4 and 5 were elucidated by NMR and MS techniques. The observed chemical differences among populations of S. zonale can be related to its geographic distribution and can open an avenue to the discovery of new compounds in algae.