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Keywords = callitrisic acid

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11 pages, 627 KiB  
Article
Biological Profiling of Semisynthetic C19-Functionalized Ferruginol and Sugiol Analogues
by Miguel A. González-Cardenete, Fatima Rivas, Rachel Basset, Marco Stadler, Steffen Hering, José M. Padrón, Ramón J. Zaragozá and María Auxiliadora Dea-Ayuela
Antibiotics 2021, 10(2), 184; https://doi.org/10.3390/antibiotics10020184 - 12 Feb 2021
Cited by 9 | Viewed by 3212
Abstract
The abietane-type diterpenoids are significant bioactive compounds exhibiting a varied range of pharmacological properties. In this study, the first synthesis and biological investigation of the new abietane-diterpenoid (+)-4-epi-liquiditerpenoid acid (8a) together with several of its analogs are reported. The compounds were generated from [...] Read more.
The abietane-type diterpenoids are significant bioactive compounds exhibiting a varied range of pharmacological properties. In this study, the first synthesis and biological investigation of the new abietane-diterpenoid (+)-4-epi-liquiditerpenoid acid (8a) together with several of its analogs are reported. The compounds were generated from the readily available methyl callitrisate (7), which was obtained from callitrisic acid present in Moroccan Sandarac resin. A biological evaluation was conducted to determine the effects of the different functional groups present in these molecules, providing basic structure–activity relationship (SAR) elements. In particular, the ferruginol and sugiol analogs compounds 1016 were characterized by the presence of a phenol moiety, higher oxidization states at C-7 (ketone), and the hydroxyl, methyl ester or free carboxylic acid at C19. The biological profiling of these compounds was investigated against a panel of six human solid tumor cell lines (HBL-100, A549, HeLa, T-47D, SW1573 and WiDr), four parasitic Leishmania species (L. donovani, L. infantum, L. guyanensis and L. amazonensis) and two malaria strains (3D7 and K1). Furthermore, the capacity of the compounds to modulate gamma-aminobutyric acid type A (GABAA) receptors (α1β2γ2s) is also described. A comparison of the biological results with those previously reported of the corresponding C18-functionalized analogs was conducted. Full article
(This article belongs to the Special Issue Search of New Natural Products with Antimicrobial Activity)
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13 pages, 2645 KiB  
Article
Terpenoid Compositions of Resins from Callitris Species (Cupressaceae)
by Bernd R. T. Simoneit, Robert E. Cox, Daniel R. Oros and Angelika Otto
Molecules 2018, 23(12), 3384; https://doi.org/10.3390/molecules23123384 - 19 Dec 2018
Cited by 23 | Viewed by 6073
Abstract
The environmental fate of conifer resins and their natural product compounds as mixtures is of importance for source, alteration, and transport studies. The compound compositions of resins of the common Callitris species (Cupressaceae) based on gas chromatography-mass spectrometry have not been [...] Read more.
The environmental fate of conifer resins and their natural product compounds as mixtures is of importance for source, alteration, and transport studies. The compound compositions of resins of the common Callitris species (Cupressaceae) based on gas chromatography-mass spectrometry have not been reported. Results show that diterpenoids were the most abundant components and callitrisic acid was present in the resin extracts of all Callitris species analyzed. Significant amounts of 4-epi-pimaric and sandaracopimaric acids, with lesser communic, ozic, and lambertianic acids, were also in the mixtures. Phenolic diterpenoids, for example, ferruginol, hinokiol, were found in trace quantities in some samples. Thus, callitrisic acid and 4-epi-pimaric acid are the characteristic diterpenoids of Callitris species that are amenable to molecular biomarker analyses in geological or environmental applications. Full article
(This article belongs to the Special Issue Diversity of Terpenoids)
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