Sesquiterpenoids and Other Constituents from Senecio argunensis

Abstract

Three new sesquiterpenoids, isodauc-7(14)-en-6a,10b-diol (1), 10b-hydroxyisodauc-6-en-14-al (2), and (7S*)-opposit-4(15)-en-1b,7-diol (4), along with ten known compounds have been isolated from the aerial parts of Senecio argunensis. Their structures were established by means of detailed spectroscopic analysis including IR, HR-MS, and 1D NMR and 2D NMR data. The sesquiterpenoids were assayed against Escherichia coli, Staphylococcus aureus and Bacillus subtilis. Compounds 4 exhibited weak antibacterial activity against Escherichia coli and Bacillus subtilis.

Two new sesquiterpenes from the fruits of Fissistigma villosissimum

“…Structures of the known compounds 10β-hydroxyisodauc-6-en-14-al (3) [5], 4(15)-eudesmene-1β,7α,11-triol (4) [6], 4(15)-eudesmene-1β,6α-diol (5) [7][8][9], spathulenol (6) [10][11][12], alloromadendran-4β,10α-diol (7) [13], 10α-hydroxycadin-4-en- 15-al (8) [14,15], shikimic acid (9) [16], protocatechuic acid (10) [17], vanillic acid (11) [18], protocatechualdehyde (12) [19] were determined by spectral data analysis and comparison with reported data.…”

Eremophilane Sesquiterpenoids from Farfugium japonicum

“…The antibacterial activity of isolates against Escherichia coli, Staphylococcus aureus and Bacillus subtilis was evaluated with the cup-plate method. 17 …”

“…The absence of NOESY correlation between H 3 -14 and H-3 suggested the angeloyoxyl group be β orientation. 17 Therefore, the structure of 1 was determined as 3β-angeloyloxy-6α-hydroxy-8β-methoxy-9α-senecioyloxyeremophila-7(11)-en-12, 8α-lactone (Figure 1).…”

Two Novel Guaiane Sesquiterpenes from the Whole Plant of Youngia japonica

“…The molecular formula of 1 was established as C 15 (3). The chemical shifts and coupling constants of all of the proton signals of 1 were highly similar to those of 3, which implied that 1 might be an isomer of 3.…”

“…The HMBC experiment of 2 showed two distinct correlations, i.e., the anomeric proton (Glc H-1, δ 5.06) with C-3 (δ 80.9), and Glc H-4 (δ 5.69) with C-8′ (δ 172.3), which supported the connectivity between the glucose moiety with the 3-hydroxy group of the sesquiterpene skeleton and also the linkage point of the p-hydroxyphenylacetyl group on the G-4 position. Therefore, the structure of 2 was identified as 4′-p-hydroxyphenylacetyl crepiside E. The other purified components 3-10 were identified as isolipidiol (3) [12], isoamberboin (4) [13], grosheimin (5) [14], annuionone D (6) [15], loliolide (7) [16], youngiajaponicoside A (8) [17], crepiside H (9) [18], and crepiside E (10) [18] by direct comparison of their spectral data with those in the literature. All isolated compounds (1-10) from Y. japonica were examined for inhibitory effects on proliferative of human cancer cell lines A549 (nonsmall cell lung carcinoma), SK-OV-3 (ovary malignant ascites), SK-MEL-2 (skin melanoma), and HCT15 (colon adenocarcinoma), according to the SRB assay in vitro [19].…”