Terpenoid constituents of Pellia epiphylla

Cullmann, Frank; Becker, Hans

doi:10.1016/s0031-9422(97)00414-7

Cited by 26 publications

(32 citation statements)

References 28 publications

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“…The remaining three signals appearing in the lower field region of the spectrum are due to the quaternary carbons of one olefinic carbon (d 149.0) and two ketone carbonyls (d 208.6, 214.3). By the assistance of extensive 2D NMR study (COSY, HMQC, HMBC), the 4,5-seco-guaiane skeleton 6) of 1 was proposed (Fig. 1).…”

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Terpenoid-Related Metabolites from a Formosan Soft Coral Nephthea chabrolii

Dai

Huang

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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We recently reported a series of new meroditerpenoids including naphthoquinone derivatives, tetraprenyltoluquinone-related metabolites, and tetraprenyltoluquinol-related metabolites from the soft coral Nephthea chabrolii AUDOUIN (Alcyonacea, Nephthedae). 1,2) In continuation of our search for cytotoxic metabolites from a soft coral N. chabrolii, collected from Taiwanese waters, we have further isolated six new metabolites including two new sesquiterpenoids, chabrolidione A and B (1 and 2), two C 18 terpenoid-related carboxylic acids, ketochabrolic acid (3) and isoketochabrolic acid (4), and one naphthoquinone derivative chabrolonaphthoquinone C (5) along with two known compounds (ϩ)-aristolone (6) 3,4) and teuhetenone A (7).5) The structures of 1-5 were elucidated on the basis of extensive spectroscopic analyses and by comparison of the spectral data with those of the related metabolites. The relative configuration of 1 was established by careful analysis on the NOE correlations of their NOESY spectra. Cytotoxicity of these compounds toward several cancer cell lines was also evaluated.Soft corals specimen was collected off the coast of Pingtung county, southern Taiwan, and extracted exhaustively with in EtOH. After evaporation of the solvent, the residue of EtOH extract was triturated sequentially with n-hexane, and then with EtOAc. The EtOAc and n-hexane extracts were successively subjected to silica gel gravity column chromatography and normal phase HPLC purification to afford compounds 1-7.Chabrolidione A (1) was obtained as a colorless oil. On the basis of its HR-EI-MS (m/z 236.1773, M ϩ ) and 1 H-and 13 C-NMR spectral data, the molecular formula of 1 was established as C 15 H 24 O 2 . The existence of the ketone functional group (n max 1712 cm Ϫ1 ) in 1 was observed from IR spectrum. Inspection of the 13 C-NMR and DEPT spectral data (Table 1) of 1, indicated the presence of 15 carbon signals of a sesquiterpenoid. These signals were ascribable to carbons of three methyls, five sp 3 methylenes, one sp 2 methylene, and three sp 3 methines. The remaining three signals appearing in the lower field region of the spectrum are due to the quaternary carbons of one olefinic carbon (d 149.0) and two ketone carbonyls (d 208.6, 214.3). By the assistance of extensive 2D NMR study (COSY, HMQC, HMBC), the 4,5-seco-guaiane skeleton 6) of 1 was proposed (Fig. 1). The relative stereochemistry of 1 was confirmed to be 1S*, 7S*, 10S* from the following NOESY correlations (Fig. 2): H-10, H-8a (d 1.82), and H-6a (d 2.42) with H-1; H-7 with H-6b (d 2.62); H 3 -14 with H-9b (1.78). It was found that 1 has been obtained previously by chemical reaction.7) However, this compound was discovered for the first time from natural sources.The new metabolite chabrolidione B (2) Road, Checheng, Pingtung 944, Taiwan, R.O.C.: e Institute of Marine Biotechnology, National Dong Hwa University; Checheng, Pingtung 944, Taiwan, R.O.C.: and f Asian Pacific Ocean Research Center, National Sun Yatsen University; Kaohsiung 804, Taiwan, R.O.C. Rece...

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confidence: 99%

Terpenoid-Related Metabolites from a Formosan Soft Coral Nephthea chabrolii

Dai

Huang

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The infrared (IR) spectrum (Supplemental Figure S21) revealed the presence of a hydroxy group (3429 cm −1 ), and due to its strong, wide, and scattered characteristics, there may be intramolecular hydrogen bonds. The 1 H-NMR spectrum (Supplemental Figure S11; Table 2) of 2 showed 3 methyl groups at δ The NMR spectroscopic data for 2 were quite similar to those of 4,5-seco-guaiane, 26 which was isolated from Pellia epiphylla, except that the isopropenyl group attached to C-7 replaces the isopropyl group. The HMBCs (Supplemental Figure S17; Table 2) from 2 olefin protons H 2 -12 (δ H 4.74) and a unimodal methyl group H 3 -13 (δ H 1.76) to a tertiary carbon C-11 (δ C 149.0) indicated the presence of an isopropenyl group.…”

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confidence: 71%

“…C-4 of compound 2 was a hemiacetal, indicating the existence of an equilibrium mixture. When the hydroxy group at C-4 has a βorientation, it could form a stable intramolecular hydrogen bond linked to the ketone at C-5 26 , therefore it was determined as the dominant configuration. In the ROESY spectrum, major cross-peaks from H 3 -14 (δ H 0.90) to H 3 -15 (δ H 1.31) were observed, and the H atoms distance of H 3 -14 and H 3 -15 was 2.7 × 10 -10 m (Figure 3), indicating that Me-14 and Me-15 were on the same side and thus had an αorientation.…”

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Two New Sesquiterpenoids Isolated From Cyperus rotundus L

Qiang

Duan

et al. 2021

Natural Product Communications

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Two new sesquiterpenoids, isocyperotundone (1) and 1,4-epoxy-4-hydroxy-4,5-seco-guain-11-en-5-one (2), together with 6 known sesquiterpenoids, cyperotundone (3), cyperenoic acid (4), sugetriol triacetate (5), cyperusol A3 (6), cyperusol A2 (7), and cyperusol A1 (8), were isolated from the methanol extract of the rhizomes of Cyperus rotundus L. High-resolution electrospray ionization mass spectrometry and 1-dimensional (1D) and 2D nuclear magnetic resonance spectroscopy were used to establish the structures of all the compounds. All the compounds were tested for activity on nuclear factor kappa-light-chain-enhancer of activated B cells (NF- κB) signaling. Compounds 1-7 exhibited inhibitory activity on tumor necrosis factor- α-induced activation of the NF- κB pathway, with half-maximal inhibitory concentration values ranging from 34.5 to 73.7 μmol/L.

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“…In africanane derivatives unsubstituted at C-1, the signal for H-11α always appears at higher fields than the signal for H-11β, usually in the range 0.10 -0.30 ppm. 13,[22][23][24] Based on the same reasoning, the hydroxyl group of 3 should also be α-orientated. At this point, only the stereochemistry of the C-15 methyl group remains to be settled.…”

Section: Resultsmentioning

confidence: 99%

Chemical composition, seasonal variation and a new sesquiterpene alcohol from the essential oil of Lippia integrifolia

Coronel

Cerda-Garcı́a-Rojas

Joseph‐Nathan

et al. 2006

Flavour & Fragrance J

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Chemical investigations on the essential oil of Lippia integrifolia performed by column chromatography, HPLC, GC-MS, 1 H-and 13 C-NMR spectroscopy led to the identification of 78 components. A new sesquiterpene alcohol, trans-africanan-1α α α α α-ol (4), was characterized as a significant component of the oil. Additionally, six samples obtained at monthly intervals through the annual cycle of the shrub (November-April) were studied. The oil was characterized by large amounts of oxygenated sesquiterpenes (53.3 -69.4%) and sesquiterpene hydrocarbons (14.3 -27.9%), along with small amounts of monoterpenoids (1.4-2.9%).Lippifoli-1(6)-en-5-one (2), african-5-en-1α α α α α-ol (3), β β β β β-caryophyllene oxide, 4,5-seco-africanan-4,5-dione (10), trans-africanan-1α α α α α-ol (4), humulene epoxide II, integrifolian-1,5-dione (1) and lippifoli-1(6)-en-4β β β β β-ol-5-one (7) were the main oxygenated constituents. Although the qualitative composition appeared to be constant, there were large quantitative variations in the content of most components through the studied period. Copyright

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Terpenoid constituents of Pellia epiphylla

Cited by 26 publications

References 28 publications

Terpenoid-Related Metabolites from a Formosan Soft Coral Nephthea chabrolii

Terpenoid-Related Metabolites from a Formosan Soft Coral Nephthea chabrolii

Two New Sesquiterpenoids Isolated From Cyperus rotundus L

Chemical composition, seasonal variation and a new sesquiterpene alcohol from the essential oil of Lippia integrifolia

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