Sesquiterpenoids fromTithonia diversifoliawith Potential Cancer Chemopreventive Activity

Abstract

Activity-guided fractionation of an ethyl acetate extract of the aerial parts of Tithonia diversifolia, using an antiproliferation bioassay performed with human colon cancer (Col2) cells, led to the isolation of three new sesquiterpenoids, 2alpha-hydroxytirotundin (1), tithofolinolide (2), and 3alpha-acetoxydiversifolol (3), along with eight known sesquiterpene lactones, 3beta-acetoxy-8beta-isobutyryloxyreynosin (4), tagitinin C (5), 1beta,2alpha-epoxytagitinin C (6), 4alpha,10alpha-dihydroxy-3-oxo-8beta-isobutyryloxyguaia-11(13)-en-12,6alpha-olide (7), 3alpha-acetoxy-4alpha-hydroxy-11(13)-eudesmen-12-oic acid methyl ester, 17,20-dihydroxygeranylnerol, tagitinin A, and tirotundin. These isolates were evaluated for their potential as cancer chemopreventive agents, by measuring antiproliferative activity in Col2 cells and induction of cellular differentiation in human promyelocytic leukemia (HL-60) cells. Selected compounds were then investigated for their ability to inhibit 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in a mouse mammary organ culture assay. Among these isolates, 5 and 6 showed significant antiproliferative activity, 2, 4, and 7 induced HL-60 cellular differentiation, and 4 significantly inhibited (63.0% at 10 microg/mL) lesion formation in the mouse mammary organ culture assay. The chemical structures of 1-3 were elucidated by spectroscopic analysis. The absolute configurations of 1 and 2 were determined by Mosher ester methodology.

Costunolide induces G1/S phase arrest and activates mitochondrial-mediated apoptotic pathways in SK-MES 1 human lung squamous carcinoma cells

“…Sesquiterpene lactones are phytochemicals derived from Chinese medicinal herbs, and have been demonstrated previously to have anti-neoplastic and anti-inflammatory activities (8). Costunolide is a well-known sesquiterpene lactone and a number of previous studies have shown that it has a broad spectrum of cytotoxicity against human cancer cell lines of different origins (6,18,(20)(21)(22)26,27).…”

“…Sesquiterpene lactones are predominantly isolated from members of the Compositae and Magnoliaceae plant families, and have attracted widespread attention due to their anti-tumor and anti-inflammatory activity, (8,9). Costunolide, a sesquiterpene lactone, which is isolated from Chinese herb Saussurea lappa, is a popular herbal remedy, with anti-ulcer (10), anti-inflammatory (11), anti-fungal (12) and anti-viral properties (13).…”

Histopathology, haematology and serum chemistry of growing pigs fed varying levels of wild sunflower (Tithonia diversifolia) leaf meal as protein supplements

“…The phytochemical profile of TDLM revealed high levels of flavonoids and phytin [25]. Moreover, sesquiterpene lactones in TDLM were reported to be free radical scavengers [26]. It is therefore conceivable that these components may have competed with haemoglobin (Hb) in red blood cell (RBC) for oxygen, resulting in hypoxea which stimulated synthesis and RBC production.…”

Xylariaceae Endophytic Fungi Metabolites Against Salmonella

“…Borges et al (2006) described the presence of derivatives anthraquinones produced by Phoma sorghina, and endophytic fungus associated to a medicinal plant Tithonia diversifolia (Asteracea). This plant extracts are used for the treatment of malaria, diarrhea, fever, hepatitis and wounds (Gu et al, 2002, Cos et al, 2002. There are also attributed anti-inflammatory, amebic, antispasmodic, antifungal, antibacterial and antiviral activities (Goffin et al, 2002, Cos et al, 2002.…”