Key cytokines of adaptive immunity are differentially induced in rainbow trout kidney by a group of structurally related geranyl aromatic derivatives

Chemical Fingerprinting, Isolation and Characterization of Polyphenol Compounds from Heliotropium taltalense (Phil.) I.M. Johnst and Its Endothelium-Dependent Vascular Relaxation Effect in Rat Aorta

“…For instance, the main compound in the aqueous extract was an opened filifolinoic acid, peak ([M − H] − ion at m / z 307.1553, C 17 H 23 O 5 − ). However, methyl ester derivatives of filifoninolic acid or filifolinol [ 6 , 22 ] were not detected in the aqueous and methanolic extract, but were previously detected in the resin exudate (chloroform extract) by us [ 7 ]. Thus peaks 9 ([M − H] − ion at m / z 339.14542, C 17 H 23 O 7 − ), peak 10 ([M − H] − ion at m / z 323.15051, C 17 H 23 O 6 − ), peak 34 ([M − H] − ion at m / z 307.15491, C 17 H 23 O 5 − ), peak 18 ([M − H] − ion at m / z 321.13434, C 17 H 21 O 6 − ), peak 19 ([M − H] − ion at m / z 305.13947, C 17 H 21 O 5 − ), peak 52 ([M − H] − ion at m / z 289.14450, C 17 H 21 O 4 − ), and peak 46 ([M − H] − ion at m / z : 289.1449038, C 17 H 21 O 4 − ), which were identified as opened 2,5-dihydroxy-filifolinoic acid, opened 5-hydroxy-filifolinoic acid, opened filifolinoic acid, 2,5-dihydroxy-filifolinoic acid, 5-hydroxy-filifolinoic acid, filifolinoic acid, and 4,5-dihydroxy-3-geranyl-benzoic acid, respectively [ 7 ].…”

“…The resin of this species is a producer of several interesting benzofuran derivatives and benzoic acid geranyl derivatives with several tested biological properties [ 4 , 5 , 6 ]. So far, only the exudates of this plant have been investigated [ 4 , 7 ].…”

Terpenoids as Source of Anti-Inflammatory Compounds

“…Filifolinone (4) is a semisynthetic terpenoid derivative obtained from Heliotropium filifolium. Filifolinone appeared responsible of an important upregulation of interferon (IFN)-a1, IFN-g, IL-4/13A, and IL-17D in the kidney [10]. Umbelliprenin (5) and methyl galbanate (6) was isolated from Ferula szowitsiana.…”

Obtainment and evaluation of adjuvant effect of the aromatic geranyl derivative Filifolinone in bacterin of Piscirickettsia salmonis

“…Previously, in our laboratory, Filifolinone was obtained by semi-synthesis from Filifolinol, main compound isolated from resinous exudates of Heliotropium filifolium (Heliotropiaceae) by conventional oxidation with CrO 3 and purified by column chromatography using benzene-ethyl acetate (Torres et al, 2002), but now was isolated directly as a secondary metabolite from resin of Heliotropium sclerocarpum Phil. (Valenzuela et al, 2016). We examined the levels of cytokine transcripts IFNc as marker of Th1 type immune response, which is necessary for the cellular activation.…”

“…For the analysis, 96 fish (healthy prestmolt Atlantic salmon) of approximately 20 g were randomly selected and divided into four groups: group 1 was injected intramuscularly with a dose of 100 μl of bacterin plus 100 μg of Filifolinone (BF); group 2 was injected with 100 μl bacterin and adjuvant Montanide ISA 763 A VG (BM); group 3 was injected with 100 μl bacterin plus adjuvant Montanide and 100 μg of Filifolinone (BMF), and group 4 was injected with physiological serum (CI). Six fish per group were collected and killed to 2, 10 and 20 days post‐immunization with benzocaine (Veterquimica), and whole kidneys were extracted and stored at −80°C for RT‐PCR analyses of cytokines, according to the laboratory standard operating procedures (Valenzuela et al., ). We examined the levels of cytokine transcripts IFNγ as marker of Th1 type immune response, which is necessary for the cellular activation.…”