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Search for "sesquiterpenoids" in Full Text gives 33 result(s) in Beilstein Journal of Organic Chemistry.
Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography
Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68
- chromatography): ethyl acetate–ethanol–water (9:2:10, v/v/v). The separation was carried out isocratically at a flow rate of 25 mL/min at 1200 rpm, affording seven fractions A to G. TLC of fractions B, C and F displayed a single spot corresponding to three new glycosylated sesquiterpenoids. Their structures were
- the polyphenols identified in Jungia species, sesquiterpenoids with guaiane, guaiene, nortrixane, trixane (isocedrene), and cyperane scaffolds are also representative of this genus [6][7][8][9]. These terpenoids demonstrated a wide range of bioactivities [10][11][12], and hit compounds such as
- configuration previously reported for trixanolides [34], led to identify compound 1 as a new member of the trixane sesquiterpenoids. The trivial name jungioside A was assigned. Compound 2 was obtained as a colourless gum. The molecular formula C21H30O8 was determined from its ESI–HRMS which gave the cationic
Total synthesis of panicein A2
Beilstein J. Org. Chem. 2015, 11, 1991–1996, doi:10.3762/bjoc.11.215
- with the earlier report that stated 5 exhibits in vitro cytotoxicity against a number of cell lines (ED50 = 5 μg/mL). Members of the panicein family of aromatic sesquiterpenoids. Proposed biogenesis of panicein A2 (5). Retrosynthetic analysis of panicein A2 (5). Synthesis of ketone 13. Synthesis of
Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system
Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298
- molecules (more bulky cyclic mono- and sesquiterpenoids) play an important role for encapsulation competitivity. However, the most concentrated sesquiterpene alcohol in the raw essential oil (α-cadinol (18), 6.2%) was more weakly encapsulated in β-CD (approximately 1%), likely due to its rigid structure and
- lower hydrophobicity in comparison with other sesquiterpenoids. The same observation was made for spathulenol (16), which had relative concentrations of 2.2% and 1.4%, respectively. Most of the other compounds were encapsulated at similar relative concentrations. Generally, oxygenated monoterpenes were
- degradation temperature (an of 83%, in comparison with 250% for non-encapsulated essential oil samples, Table 2 and Table 3). Similar behavior was observed for the case of sesquiterpenoids. An increase of 2.8–11.6% was observed for most of the sesquiterpene hydrocarbons and alcohols. For example, β-elemene (8
Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis
Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14
- place prior to the rearrangement to access the required boat transition state of the rearrangement. Intermediate 58 was converted to the natural product 59 in four additional steps. Two other sesquiterpenoids, prezizaene (63) [59][60] and prezizanol (64) [60], isolated from Eremophilia georgei or
Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin
Beilstein J. Org. Chem. 2013, 9, 1333–1339, doi:10.3762/bjoc.9.150
- remedy, and venereal aid [4]. In recent years, we have become interested in studying the bioactive constituents of A. balsamea. Our work allowed the identification of antibacterial sesquiterpenoids, active against S. aureus, from balsam fir essential oil [5]. We also isolated two cytotoxic
Caryolene-forming carbocation rearrangements
Beilstein J. Org. Chem. 2013, 9, 323–331, doi:10.3762/bjoc.9.37
- intermediates; terpene; Introduction The cytotoxic sesquiterpenol caryol-1(11)-en-10-ol (1, Figure 1) was isolated by Barrow et al. in 1988 during an investigation of antiviral/antitumor compounds from New Zealand marine invertebrates [2]. Similar sesquiterpenoids were also found in Campanella fungi
- isotropic values into chemical shifts [11][12][13]. Caryol-1(11)-en-10-ol (1) and similar sesquiterpenoids. Note that a different atom numbering was used in the paper describing the isolation of 1 [2]. Computed (top) and experimental (bottom, underlined italics) [2] 1H and 13C chemical shifts for 1 (lowest
Carbamate derivatives and sesquiterpenoids from the South China Sea gorgonian Melitodes squamata
Beilstein J. Org. Chem. 2012, 8, 170–176, doi:10.3762/bjoc.8.18
- (1, 2), dimethyl ((carbonylbis(azanediyl))bis(2-methyl-5,1-phenylene))dicarbamate (3), obtucarbamates A and B (4, 5), and four aromadendrane-type sesquiterpenoids, (+)-4β-N-methenetauryl-10β-methoxy-1β,5α,6β,7β-aromadendrane (6), (−)-4β-N-methenetauryl-10β-methoxy-1β,5β,6α,7α-aromadendrane (7
- rarely found in marine natural compounds, and 7 showed moderate antibacterial activity. The possible biosynthesis routes of 1–5 were conjectured. Keywords: carbamate; gorgonian; Melitodes squamata; sesquiterpenoid; Introduction Gorgonians are recognized to mainly produce acetogenins, sesquiterpenoids
- aromadendrane-type sesquiterpenoids, (+)-4β-N-methenetauryl-10β-methoxy-1β,5α,6β,7β-aromadendrane (6), (−)-4β-N-methenetauryl-10β-methoxy-1β,5β,6α,7α-aromadendrane (7), (−)-4α,10β-aromadendranediol) (8) [7], (+)-4β,10β-aromadendranediol) (9) [7] (Figure 1) from the EtOH/CH2Cl2 extracts of M. squamata. Compounds
Toward an integrated route to the vernonia allenes and related sesquiterpenoids
Beilstein J. Org. Chem. 2011, 7, 937–943, doi:10.3762/bjoc.7.104
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