Hydroxyalkenylresorcinols from Stylogyne turbacensis

Abstract

Two new compounds, 5-(11'(S)-hydroxy-8'-heptadecenyl)resorcinol (3) and 5-(12'(S)-hydroxy-8',14'-heptadecadienyl)resorcinol (4), were isolated from the leaves of Stylogyne turbacensis together with the known analogue metabolites 1 and 2. Compounds 3 and 4 showed the strongest activity in the leishmania assay, 7 and 3 microM, respectively, while compounds 1, 2, and 4 showed moderate activity against a drug-resistant strain of Trypanosoma cruzi with IC(50) values of 30, 25, and 22 microM, respectively. Additional testing in MCF-7 and NCI-H460 was performed for compounds 3 and 4. The structures of compounds 1-4 were elucidated using NMR, MS, and other spectroscopic data. The absolute stereochemistry of compounds 3 and 4 was also investigated using the Mosher ester approach. Peracetylated derivatives of these four metabolites were produced and their activities determined in the Trypanosoma cruzi assay.

Biological activity of phenolic lipids

“…Similarly, 5-(11 0 (S)-hydroxy-8 0 -heptadecenyl)resorcinol and 5-(12 0 (S)-hydroxy-8 0 ,14 0 -heptadecadienyl) resorcinol isolated from the leaves of Stylogyne turbacensis showed the strongest activity in the leishmania assay and only moderate activity against a drugresistant strain of Trypanosoma cruzi [163]. The anacardic acids present in the petroleum ether extract of Viola websteri Hemsl.…”

Omega-3 polyunsaturated lipophenols, how and why?

“…oxycardium contain the anacardic acid derivative 42 (0.016% of FM) and the AR 29 (0.005% from FM), which is the major allergen compound and a weapon defense of the plant [48]. The AR 29 has various origins and can also be isolated from liverwort Omphalantus filiformis [49] (mainly in the cuticle) and leaves of Stylogyne turbacensis [50]. Anacardic acid derivative 42 is also present in various other sources and has been isolated from leaves of Anacardium spondias [39], and leaves and stems of Spondias mombin [51].…”

“…Among the natural products, cytotoxicity of the ALAalkylresorcinol analogue 29 was observed on human breast cancer (MCF-7) and human lung cancer (NCIeH460) cell lines [50]. The n-6 LA analogue was equipotent compared to 29.…”

“…Complementary assays with synthesized analogues suggested that longer FA lead to increased antiplasmodial activity, while the presence of polar groups on the FA chain decreased the activity. The ALA-AR analogue 29 could also be considered as antiparasitic agent, as its LA analogue [50]. In vitro tests of 29 exhibited moderate activity (IC 50 ¼ 25 mM) against intracellular form of the parasite Trypanosoma cruzi (Chagas disease), and a significant activity (IC 50 ¼ 0.6 mM) against a unicellular kinotoplastid prozoane parasite Leishmania donovani (human visceral leishmaniasis).…”

Antifungal depsidone metabolites from Cordyceps dipterigena, an endophytic fungus antagonistic to the phytopathogen Gibberella fujikuroi

“…The International Cooperative Biodiversity Group program in Panama (ICBG-Panama) has been investigating cytotoxic, anti-parasitic and anti-microbial agents from various natural sources such as plants, 1 marine organisms, 2 and more recently, endophytic fungi. 3,4 From a total of 3582 endophytic fungal extracts, a number of active materials have been identified in our cytotoxic or anti-parasitic drug screening.…”