Active sesquiterpene lactones against Leishmania amazonensis and Leishmania braziliensis

Abstract

Seventeen sesquiterpene lactones (SLs) isolated from five species of the tribe Vernonieae were evaluated for their in vitro activity against promastigotes of Leishmania amazonensis and Leishmania braziliensis. Additionally, a quantitative structure activity relationship has been made, since all these natural compounds were found to have potent to mild antileishmanial properties. The most active compounds against L. braziliensis were 16 and 17 (IC values 1.45 and 1.34 μM, respectively), followed by compound 15 with IC value of 1.60 μM against L. amazonensis. The three glaucolide-type SLs (4-6) were the least active against both parasites. The computational study allowed us to establish that lipophilicity and polarisability play an important role in the antiparasitic activity. This is the first report of the known germacradiendiolides 16 and 17 from Elephantopus mollis. The activity data of the compounds 1-17 assayed against Leishmania parasites are reported here for the first time.

Chemical Constituents, Antiproliferative and Antioxidant Activities of Vernonanthura nudiflora (Less.) H. Rob. Aerial Parts

“…Compound 15 were identified as 3-O-caffeoylquinic acid. 49 The triterpenes lupeol (1) and β-amyrin (3) and the flavones velutin (10), apigenin (11) and chrysoeriol (12) were previously isolated from V. nudiflora. 23 Despites the sesquiterpene lactones piptocarphin A (6), B (7) and D (8) already described in other Vernonanthura and Vernonia species, [50][51][52][53] this is the first report of piptocarphins in V. nudiflora.…”

“…Several Vernonanthura species are known in Brazil as "assa-peixe", and are used in traditional medicine for the treatment of flu and colds. 6,7 Species of this genus have also been reported to possess pharmacological activities, 8 such as antiplasmodial, 9 antileishmanial, [10][11][12] antimicrobial, [13][14][15] antioxidant, 11 antinociceptive and anti-inflammatory. 16,17 Vernonanthura nudiflora (Less.)…”

Maturation, processing and seed storage of Elephantopus mollis Kunth Maturação, processamento e armazenamento de sementes de Elaphantopus mollis Kunth.

“…The medicinal properties of the species are attributed to its essential oils, flavonoids, triterpenoids, and sesquiterpene lactones (Li et al, 2016c;Shao et al, 2016;Sosa et al, 2016). Pharmacological studies of the species have revealed anticarcinogenic activity by the sesquiterpene lactones (Hasegawa et al, 2010;Kitson, Millemaggi, & Taylor, 2009;Li et al, 2016c;Ooi, Tengku Muhammad, Tan, & Sulaiman, 2011;Ooi, Tengku Muhammad, Lam, & Sulaiman, 2014;Shao et al, 2016;Siedle et al, 2003;Tabopda et al, 2008;Tabopda et al, 2007).…”

“…Seven patent applications are registered in the European Patent Office for the use of the plant as a medicine (Li, Ye, Wang, Li, & Wang, 2016a;Li, Ye, Wang, Li, & Wang, 2016b;Hou, Lin, Wu, Chen, & Siao, 2012;Medeiros, Senna-Vale, Andreata, & Fernandes, 2008, Umishio, Maeda, & Kobayashi, 2006Kondo et al, 2000) due to its hepatoprotective (Ho, Yeap, Ho, Abdul Rahim, & Alitheen, 2012;Kabiru & Por 2013), antioxidant (Clemes, Beirith, & Zeni, 2015), anti-inflammatory (Wu et al, 2017), antimicrobial, antileishmaniasis, bone regeneration (Kabiru & Por, 2013;Ngueguim et al, 2012;Sosa et al, 2016), temperature-lowering, and antihypertensive properties, as well as its effects on intestinal transit (Poli et al, 1992).…”

Composition and leishmanicidal activity of the essential oil of Vernonia polyanthes Less (Asteraceae)

“…Lima et al (2016) evaluated the leishmanicidal activity of Calea uniflora Less. Shyaula et al (2016) showed the antileishmanial activity of the Aconitum spicatum (Bruhl) StapfAnd Sosa et al (2016) demonstrated that sesquiterpene lactones were active against against Leishmania amazonensis and Leishmania braziliensis. Vernonia polyanthes Less (Asteraceae) popularly known as 'assapeixe' is a common plant of the Brazilian 'Cerrado' .…”