Stemodin-derived analogues with lipid peroxidation, cyclooxygenase enzymes and human tumour cell proliferation inhibitory activities

Stemodia maritima L. Extract Decreases Inflammation, Oxidative Stress, and Alveolar Bone Loss in an Experimental Periodontitis Rat Model

“…Chemical studies on S. maritima reported the isolation of diterpenes and flavonoids showing antiviral, cytotoxic, and larvicidal activities (Hufford et al, 1991 ; Rodrigues et al, 2010 ). Further, it was showed that S. maritima compounds have in vitro inhibitory activity of both lipids peroxidation and cyclooxygenase 1 and 2 (Hufford et al, 1992 ; Russell et al, 2011 ). Besides, our research group demonstrated that S. maritima has antioxidant activity in vitro and it also has activity against some bacterial strains (da Silva et al, 2014 ).…”

“…In this regard, earlier chemical studies on Stemodia maritima L. (Plantaginaceae family, formely Scrophulariaceae), which is used in traditional medicine to treat inflammatory disorders, reported the isolation of flavonoids, diterpenes, and other compounds associated with larvicidal and antiviral activities (Rodrigues et al, 2010 ; Russell et al, 2011 ). Our group studied the phytochemicals in S. maritima L., and described the isolation of the natural compound, stemodinol along with seven known compounds (da Silva et al, 2014 ).…”

Stemodane Diterpenes and Diterpenoids: Isolation, Structure Elucidation, Biogenesis, Biosynthesis, Biological Activity, Biotransformations, Metabolites and Derivatives Biological Activity, Rearrangements

“…(+)-Stemodin (1) and several analogues exhibited weak antiviral activity (Table 6). 1) and (+)-stemodinone (2) by Reese and colleagues to evaluate their lipid peroxidation (LPO) activity, cyclooxygenase enzyme-1 (COX-1) and -2 (COX-2) activity, and tumour cell proliferation inhibitory activity [83] (Figure 16).…”

Aphidicolin: Its Chemistry and Biosynthesis

“…[32][33][34][35] They inhibit lipid peroxidation and the proliferation of some human tumour cell lines. 36 Stemarin 29, obtained from S. maritima, also has a related carbon skeleton. 37 Although aspects of their chemistry resemble that of aphidicolin and other tetracyclic diterpenoids, there are stereochemical differences associated with rings C and D, and hence they are not discussed in this review.…”

“…These rearrangements have their parallels in the bromination of similar alkenes in stemadinone chemistry. 51,52 They all have as their driving force the relief of the steric strain of the bicyclo[3,2,1]octane by the formation of a bicyclo[2,2,2]octane.…”