Two New Guaiane Sesquiterpenes from the Fruits of Daucus carota

Abstract

Two new sesquiterpenes, 11-(acetyloxy)torilolone (1) and 1b-hydroxytorilolone (2) were obtained from the fruits of Daucus carota. Their structures were elucidated on the basis of various spectroscopic analyses and chemical evidence.Introduction. -Daucus carota L. is a biennial herb, belonging to the family Umbelliferae, which is commonly distributed throughout the world. The fruits of the plant are widely used as traditional Chinese medicines for the treatment of a variety of human diseases, such as ancylostomiasis, dropsy, chronic kidney disease, and bladder afflictions, etc.

Searching for Heracleum mantegazzianum allelopathy in vitro and in a garden experiment

“…Junttila (1976), who studied inhibitory effects of a seed extract of H. laciniatum, reported three bioactive fractions including furanocoumarins to suppress germination of assay species although other unknown compounds were also involved. In the highly phytotoxic exudates used for the May 2011 bioassay, we found compounds that were not previously reported from a Heracleum species; some of them, however, possibly represent sesquiterpene derivatives related to daucanes, which have been reported from different species of the Apiaceae family (Casinovi et al 1983;Pandita et al 1984;Miski and Mabry 1985;Yi et al 2009). As we do not know the identity of the phytotoxic compounds released by the invader, we cannot say whether they are novel and unique in invaded communities, as the novel weapons hypothesis predicts (Callaway and Aschehoug 2000;Fig4 Effects of root exudates, the soil microbiota and activated carbon on biomass of assay species in garden experiments.…”

“…Compound C17H26O4 was reported either as siol acetate in Sium latifolium (Casinovi et al 1983) and S. latijugum (Pandita et al 1984) or as 11-(acetyl)torilolone in Daucus carota (Yi et al 2009), whereas compound C27H36O5 may represent a trisubstituted daucane with angeloyloxy and benzoyloxy moiety that has been reported from Ferula communis (Miski and Mabry 1985). More research is needed to assign bioactivity to these compounds and to clarify their structure.…”

Two new sesquiterpenoids fromArtemisia annua

“…The 13 C NMR and DEPT‐135 spectra revealed the precence of 15 carbon signals, including a carbonyl ( δ C 209.7), a tetrasubstituted double bond ( δ C 144.6 and 166.3), three oxygenated quaternary carbons ( δ 94.0, 79.1 and 79.0), three methylenes ( δ C 40.7, 37.5 and 29.8), two methines ( δ C 77.4 and 34.1), as well as four methyl groups ( δ C 26.4, 25.4, 18.5 and 8.9). The comparison of these data with those of 1 β ‐hydroxytorilolone permited the full assignment of the resonances for 1 as shown in Table .…”

Two new eudesmane-type glucopyranosides from the fruits ofDaucus carotaL.

“…The fruits of the plant have been used in traditional Chinese medicine for the treatment of a variety of human diseases, such as ancylostomiasis, dropsy, chronic kidney disease and bladder afflictions, etc (Sun et al 2013). Our previous research on chemical constituents of D. carota L. was carried out using guaiane-type sesquiterpenes and eudesmane type sesquiterpenes Yi et al 2009;Fu et al 2010aFu et al , 2010bFu et al , 2010cFu, Zhang, Yi, Chen et al 2010). The ongoing phytochemical study from the EtOH extracts of the fruits of D. carota L. led to the isolation of two new eudesmane type sesquiterpene glycosides.…”