Trans-β-Caryophyllene: An Effective Antileishmanial Compound Found in Commercial Copaiba Oil (Copaiferaspp.)

Abstract

This study investigated the leishmanicidal activity against Leishmania amazonensis of four commercial oils from Copaifera spp. named as C1, C2, C3, and C4, the sesquiterpene and diterpene pools obtained from distilling C4, and isolated β-caryophyllene (CAR). Copaiba oils chemical compositions were analyzed by gas chromatography and correlated with biological activities. Diterpenes-rich oils C2 and C3 showed antipromastigote activity. Sesquiterpenes-rich C1 and C4, and isolated CAR presented a dose-dependent activity against intracellular amastigotes, with IC50s of 2.9 µg/mL, 2.3 µg/mL, and 1.3 µg/mL (6.4 µM), respectively. Based on the highest antiamastigote activity and the low toxicity to the host cells, C4 was steamdistillated to separate pools of sesquiterpenes and diterpenes. Both pools were less active against L. amazonensis and more toxic for the macrophages than the whole C4 oil. The leishmanicidal activity of C3 and C4 oils, as well as C4 fractions and CAR, appears to be independent of nitric oxide production by macrophages. This study pointed out β-caryophyllene as an effective antileishmanial compound and also to its role as potential chemical marker in copaiba oils or fractions derived thereof, aiming further development of this rainforest raw material for leishmaniasis therapy.

β‐Caryophyllene, the major constituent of copaiba oil, reduces systemic inflammation and oxidative stress in arthritic rats

“…40,41 Therefore, the effects of treatment with β-caryophyllene on gluconeogenesis were evaluated in perfused livers using as substrate L-lactate, which is one of the main gluconeogenic substrates in humans and rodents and in addition allows evaluating the complete gluconeogenic machinery from pyruvate up to glucose. 40,41 Therefore, the effects of treatment with β-caryophyllene on gluconeogenesis were evaluated in perfused livers using as substrate L-lactate, which is one of the main gluconeogenic substrates in humans and rodents and in addition allows evaluating the complete gluconeogenic machinery from pyruvate up to glucose.…”

Immunomodulatory action of Copaifera spp oleoresins on cytokine production by human monocytes

“…Although several authors have investigated the biological and therapeutic properties of Copaifera spp, such as antifungal, antileishmanial, alveolar wound healing after tooth extraction in rats, anti-inflammatory, antioxidant, antimutagenic and others [23][24][25][26], our data exhibited the immunomodulatory action of Copaifera oleoresins.…”

In Vitro Antileishmanial Activity of Falcaria vulgaris Fractions on Leishmania major

“…Previous studies have shown that beta-caryophyllene, alpha-pinene, and limonene are compounds with antileishmanial activities (19)(20)(21). In this regard, one previous study showed that F. vulgaris is rich in these compounds (10).…”