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1.
Two novel ceramides, Candidamide A (1) with a phytosphingolipid structure, and Candidamide B (2) with a tertiary amide structure, together with 12 known compounds (3–14) have been isolated from the bulbs of Zephyranthes candida, The structures of 1 and 2 have been elucidated to be 1,3,5,6-tetrahydroxy-2-(2′-hydroxytetracosanoyl amino)-8-(E)-octadecadiene (1) and (2S,3S,4R,8E,2′R)-2-[N-(2′-hydroxyoctadecanoyl)-N-(1′′,2′′-dihydroxyethyl)-amino]-8-hexacosene-1,3,4-triol (2) on the basis of spectroscopic evidence including IR, MS, NMR (1H-NMR, 13C-NMR, DEPT, 1H–1H COSY, HSQC, HMBC). The known compounds were identified as (2S)-3′,7-dihydroxy-4′-methoxyflavan (3), (2S)-4′-hydroxy-7-methoxyflavan (4), (2S)-4′,7-dihydroxyflavan (5), 7-hydroxy-3′, 4′-methylenedioxyflavan (6), ambrettolide (7), β-sitostero1 (8), β-daucosterin (9), rutin (10), pancratistatin (11), lycorine (12), haemanthidine (13), and haemanthamine (14). In the antimicrobial assay, candidamide A (1) and candidamide B (2) displayed moderate activities against bacteria Staphylococcus aureus and Escherichia coli, and fungi Aspergillus niger, Candida albicans and Trichophyton rubrum. 相似文献
2.
The new substance hemsleyin imine A (1) was isolated along with (2S,3S,4R,2′R)-2-(2′-hydroxytetracosanoylamino)-octadecan-1,3,4-triol (2), (2S,3R,4E,8E)-1-O-β-d-glucopyranosyl-3-hydroxy-2-(2′R-hydroxypalmitoylamino)-4,8-octadecadiene (3) from the rhizomes of Hemsleya macrocarpa var. clavata. Their chemical structures were established mainly by spectral analysis and chemical evidence. Compound 1 possesses the skeleton of an imine moiety, which is novel in natural products. 相似文献
3.
A new phytosphingosine-type ceramide (1) was isolated along with nine other compounds—5α,8α-epidioxy-(22E,24R)-ergosta-6,22-dien-3β-ol, 5α,8α-epidioxy-(24S)-ergosta-6-en-3β-ol, (24S)-ergosta-7-ene-3β,5α,6β-triol,(22E,24R)-ergosta-7, 22-dien-3β,5α,6β-triol, inosine, adenine, l-pyroglutamic acid, fumaric acid, and d-allitol from the ethanol and chloroform/methanol extract of the fruiting bodies of the basidiomycete Russula cyanoxanotha (Schaeff.) Fr. The structure of (1) was established as (2S,3S,4R,2′R)-2-(2′-hydroxytetracosanoylamino) octadecane-1,3,4-triol by means of spectroscopic and chemical methods. 相似文献
4.
New glyceroglycolipid and ceramide from <Emphasis Type="Italic">Premna microphylla</Emphasis> 总被引:1,自引:0,他引:1
Iwo new compounds (1,2) were isolated from the ethanolic extract of the leaves of Premna microphylla, together with five known compounds. The structures of compounds 1 and 2 were elucidated as (2S,3S,4R,11E)-2-[(2R)-2-hydroxytetracosanoylamino]-11-octadecene-1,3,4-triol (1) and 1-O(9Z,12Z, 15Z-octadecatrienoyl)-3-O-[β-d-galactopyranosyl-(1→6)-O-β-d-galactopyranosyl-(1→6)-α-d-galactopyranosyl] glycerol (2) by means of spectroscopic and chemical methods. 相似文献
5.
Asperamides A (1) and B (2), a sphingolipid and their corresponding glycosphingolipid possessing a hitherto unreported 9-methyl-C20-sphingosine moiety, were characterized from the culture extract of Aspergillus niger EN-13, an endophytic fungus isolated from marine brown alga Colpomenia sinuosa. The structures were elucidated by spectroscopic and chemical methods as (2S,2′R,3R,3′E,4E,8E)-N-(2′-hydroxy-3′-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (1) and 1-O-β-d-glucopyranosyl-(2S,2′R,3R,3′E,4E,8E)-N-(2′-hydroxy-3′-hexadecenoyl)-9-methyl-4,8-icosadien-1,3-diol (2). In the antifungal assay, asperamide A (1) displayed moderate activity against Candida albicans. 相似文献
6.
A new glucoceramide from the watermelon begonia, <Emphasis Type="Italic">Pellionia repens</Emphasis> 总被引:1,自引:0,他引:1
A new glucoceramide named pellioniareside (1) was isolated from the aqueous ethanolic extract of whole plants of Pellionia repens, together with lupeol (2), uracil (3), (22E,20S,24R)-5α,8α-epidioxyergosta-6,22-dien-3-β-ol (4), and daucosterol (5). The structure and relative configurations of pellioniareside were identified as (2S,3S,4R,6E,8E)-1-O-β-d-glucopyranosyl-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octadecanetriol-6,8-diene by analysis of spectral data and by chemical evidence. 相似文献
7.
A new C18-ceramide congener named pecipamide (1), together with the known ergosta-4,6,8(14),22-tetraen-3-one (2), was isolated from the solid fermentations of the basidiomycetous fungus Polyporus picipes. The structure of the new metabolite was established as (2′R,2S,3R)-N-2′-hydroxyheptadecanoyl-2-amino-octadecane-1,3-diol on the basis of spectroscopic data, including 1D- and 2D- nuclear magnetic
resonance spectroscopy (NMR) experiments, as well as by means of mass spectrometric measurements (MS). 相似文献
8.
Louis Pergaud Sandjo Abdou Tchoukoua Hippolyte Nga Ntede Mehdi Yemloul Enrico Perspicace Felix Keumedjio François Couty Gilbert Kirsch Bonaventure Tchaleu Ngadjui 《Journal of the American Oil Chemists' Society》2010,87(10):1167-1177
To highlight the role of plants in traditional healing, the leaves and the stems of cultivated Triumfetta cordifolia were phytochemically studied yielding a new nor-ursane type (1), a new ceramide (2) and a new piperidinic ceramide derivative (3) named, respectively, 2α,19α-dihydroxy-3-oxo-23-nor-urs-12-en-28-oic acid, (2R)-2-hydroxy-N-[(2S,3S,4R,26E)-1,3,4-trihydroxy-26-triaconten-2-yl] tetradecanamide and (2R,8Z)-2-hydroxy-{(2S,3R,5R,6S)-3,5-dihydroxy-6-[(1E,5Z)-hexadeca-1,5-dienyl]-2-(β-d-glucopyranosyloxy)methyl piperidine-1-yl} tetracos-8-enamide (3). These were obtained together with lupeol (4), stigmasterol (5), 3-O-β-d-glucopyranoside of β-sitosterol (6), tormentic acid (7) from stems and heptadecanoic acid (8), β-carotene (9), oleanolic acid (10), and 24-hydroxytormentic acid (11) from leaves. The structures were determined on the basis of NMR data (1H-, 13C-, 2D-NMR analyses), mass spectrometry and confirmed by chemical transformations as well as comparison of spectral data with
those reported in the literature. The FRAP method was used to evaluate the antioxidant activity of fractions collected from
flash chromatography and isolated compounds. Among the fractions, four reduced FeIII-TPTZ to FeII-TPTZ while isolated pure compounds showed no activity. 相似文献
9.
New glycosphingolipid containing an unusual sphingoid base from the basidiomycete Polyporus ellisii 总被引:1,自引:0,他引:1
A new 9-methyl-sphinga-4,8-dienine-containing glucocerebroside (1), together with two additional known analogs, cerebrosides B and D, was isolated from the chloroform-soluble lipid fraction
of the ethanol and chloroform/methanol extract of the fruiting bodies of the basidiomycete Polyporus ellisli Berk. and characterized. The structure and relative stereochemistry of the new compound were identified as (2S,3R,4E,8E)-1-(β-d-glucopyranosyl)-3-hydroxy-2-[(R)-2′-hydroxyheptadecanoyl]amino-9-methyl-4,8-octadecadiene by means of spectroscopic (1H, 13C, and two-dimensional nuclear magnetic resonance; mass spectrometry) and chemical methods. 相似文献
10.
Five cerebrosides (1–5), including three new ones named cortenuamide A (1), cortenuamide B (2), and cortenuamide C (3), were isolated from the fruiting bodies of the basid-iomycete Cortinarius tenuipes. The structures of those compounds were elucidated as (4E,8E)-N-d-2′-hydroxytetracosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (1), (4E,8E)-N-d-2′-hydroxytricosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8 sphingadienine (2), (4E, 8E)-N-d-2′-hydroxydocosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (3), (4E, 8E)-N-d-2′-hydroxyoctadecanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (4), and (4E, 8E)-N-d-2′-hydroxypalmitoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (5) by spectral and chemical methods. 相似文献
11.
From the water-insoluble lipid fraction of the methylene chloride/methanol extract of the starfish Cosmasterias lurida, two new glucosylceramides together with a known glucosylceramide, ophidiacerebroside E, were isolated by chromatographic
procedures and characterized by spectroscopic (1H and 13C nuclear magnetic resonance, mass spectrometry) methods. The new compounds were identified as (2S, 3R, 4E, 8E, 10E)-1-(β-d-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxyheptadecanoyl)amino]-9-methyl-4,8,10-octadecatriene (3) and (2S,3R,4E,8E,10E)-1-(β-d-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxyoctadecanoyl)amino]-9-methyl-4,8,10-octadecatriene (4). 相似文献
12.
From the water-insoluble lipid fraction of the chloroform/methanol/water extract of the gonads and body walls of the Patagonian
starfish Allostichaster inaequalis, two new glucosylceramides (4 and 7) were isolated together with the known phalluside-1 (1) and two glucosylceramides (2 and 3) previously isolated from the starfish Cosmasterias lurida. The new compounds were characterized as (2S,3R,4E,8E,10E)-1-(β-d-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxy-15-tetracosenoyl] amino-4,8,10-octadecatriene (4) and (2S,3R,4E,15Z)-1-(β-d-glucopyranosyloxy)-3-hydroxy-2-[(R)-2-hydroxyhexadecanoyl] amino-4,15-docosadiene (7) by means of spectroscopic and chemical methods. 相似文献
13.
Two antibacterial and xanthine oxidase inhibitory cerebrosides, one of which is chemically new, were characterized from the
chloroform-methanol (1∶1) extract of Fusarium sp. IFB-121, an endophytic fungus in Quercus variabilis. By means of chemical and spectral methods [IR, electrospray ionization MS (ESI-MS), tandem ESI-MS, 1H and 13C NMR, distortionless enhancement by polarization transfer, COSY, heteronuclear multiple-quantum coherence, heteronuclear
multiple-bond correlation, and 2-D nuclear Overhauser effect correlation spectroscopy], the structure of the new metabolite
named fusaruside was established as (2S,2′R,3R,3′E,4E,8E,10E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8,10-sphingatrienine, and the structure of the other was identified as
(2S,2′R,3R,3′E,4E,8E)-1-O-β-d-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8-sphingadienine. Both new and known cerebrosides, although inactive to
Trichophyton rubrum and Candida albicans, showed strong antibacterial activities against Bacillus subtilis, Escherichia coli, and Pseudomonas fluorescens, with their minimum inhibitory concentrations being 3.9, 3.9, and 1.9 μg/mL, and 7.8, 3.9, and 7.8 μg/mL, respectively. Furthermore,
both metabolites were inhibitory to xanthine oxidase, with the IC50 value of fusaruside being 43.8±3.6 μM and the known cerebroside being 55.5±1.8 μM. 相似文献
14.
The oxylipin chemistry of the temperate red alga Polyneura latissima has been investigated. The structures of three novel oxylipins, 8-[1′(Z),3′(Z),6′(Z)-dodecatriene-1′-oxyl-5(Z),7(E)-octadienoic acid, 7(S
*)-hydroxy-8(S
*),9(S
*)-epoxy-5(Z), 11(Z),14(Z)-eicosatrienoic acid, 7(R
*)-hydroxy-8(S
*), 9(S
*)-epoxy-5(Z), 11(Z),14(Z)-eicosatrienoic acid, together with two known eicosanoids, 9(S)-hydroxy-5(Z), 7(E), 11(Z), 14(Z)-eicosatetraenoic acid, and 9, 15-dihydroxy-5(Z),7(E),11(Z),13(E)-eicosatetraenoic acid, were elucidated by spectroscopic methods and chemical degradation. The oxygenation pattern of these
oxylipins suggests that P. latissima metabolizes polyunsaturated fatty acids via a 9(S)-lipoxygenase. 相似文献
15.
Three species of brown algae,Laminaria sinclairii, L. saccharina andL. setchellii, have been investigated for the presence of oxylipins. From one,L. sinclairii, three new divinyl ether fatty acids have been characterized as methyl ester derivatives (methyl 12-[1′ (Z),3′(Z)-hexadienyloxy]-6(Z), 9(Z), 11(E)-dodecatrienoate, methyl 12-[1′ (Z), 3′ (Z)-hexadienyloxy]-9(Z), 11(E)-dodecatrienoate, and methyl 14-[1′ (Z),3′ (Z)-hexadienyloxy]-9(Z),11(E)-dodecadienoate, and methyl 14-[1′ (Z),3′(Z)-hexadienyloxy]-5(Z),8(Z),11(Z),13(E)-tetradecatetraenoate) by a variety of spectroscopic methods. In addition, one new [13(S)-hydroxy-6(Z),9(Z),11(E),15(Z)-octadecatetraenoic acid] and four known monohydroxy polyunsaturated fatty acids have been isolated from all three species
as their methyl ester derivatives. The occurrence of these compounds in brown algae strongly suggests that these organisms
possess an active lipoxygenase(s) with ω6 specificity.
A preliminary summary of this work was presented at the XIVth International Seaweed Symposium, Brest, France, August 1992
(10). 相似文献
16.
Spectroscopic and physical properties of Nd3+-doped alkali lead borate glasses of type 20R
2O · 30PbO · 49.5B2O3 · 0.5Nd2O3 (R = Li and K) and alkaline-earth lead borate glasses 20RO · 30PbO · 49.5B2O3 · 0.5Nd2O3 (R = Ca, Ba, and Pb) have been investigated. Optical absorption spectra have been used to determine the Slater-Condon (F2, F4, and F6), spin orbit ξ4f, and Racah parameters (E1, E2, and E3). The oscillator strengths and the intensity parameters Ω2, Ω4, and Ω6 have been determined by the Judd-Ofelt theory, which, in turn, provide the radiative transition probability (A), total transition probability (A
T
), radiative lifetime (τ
R
), and branching ratio (β
R
, %) for the fluorescent levels. The lasing efficiency of the prepared glasses has been characterized by the spectroscopic
quality factor (Ω4/Ω6), the value of which is in the range 0.2–1.5, typical of Nd3+ in different laser hosts. A red shift of the peak wavelength is observed upon addition of alkali or alkaline-earth oxides
to the lead borate glass. A higher value of the W2 parameter for potassium-doped glass indicates a higher covalency for this glass matrix. The relative intensity of the peaks
4I9/2 → 4F7/2, 4S3/2 has also been studied.
The text was submitted by the authors in English. 相似文献
17.
Mats Hamberg 《Lipids》1989,24(4):249-255
The major part (80%) of the fatty acid hydroperoxide isomerase activity present in homogenates of the fungus,Saprolegnia parasitica, was localized in the particle fraction sedimenting at 105,000×g.
13(S)-Hydroperoxy-9(Z),11(E)-octadecadienoic acid and 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid were both good substrates for the particle-bound hydroperoxide isomerase. The products formed from
the 13(S)-hydroperoxide were identified as an α,β- and a γ,δ-epoxy alcohol, i.e., 11(R),12(R)-epoxy-13(S)-hydroxy-9(Z)-octadecenoic acid and 9(S),10(R)-epoxy-13(S)-hydroxy-11(E)-octadecenoic acid, respectively. The 9(S)-hydroperoxide was converted in an analogous way into an α,β-epoxy alcohol, 10(R),11(R)-epoxy-9(S)-hydroxy-12(Z)-octadecenoic acid and a γ,δ-epoxy alcohol, 12(R),13(S)-epoxy-9(S)-hydroxy-10(E)-octadecenoic acid.
9(R,S)-Hydroperoxy-10(E),12(E)-octadecadienoic acid and 13(R,S)-hydroperoxy-9(E),11(E)-octadecadienoic acid were poor substrates for theS. parasitica hydroperoxide isomerase. Experiments with 13(R,S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid showed that the 13(R)-hydroperoxy enantiomer was slowly isomerized by the enzyme. The major product was identified as α,β-epoxy alcohol 11(R),12(R)-epoxy-13(R)-hydroxy-9(Z)-octadecenoic acid. 相似文献
18.
Mats Hamberg 《Lipids》1998,33(11):1061-1071
[1-14C]α-Linolenic acid was incubated with a particulate fraction of homogenate of leaves of the meadow buttercup (Ranunculus acris L.). The main product was a divinyl ether fatty acid, which was identified as 12-[1′(Z),3′(Z)-hexadienyloxy]-9(Z), 11(E)-dodecadienoic acid. Addition of glutathione peroxidase and reduced glutathione to incubations of α-linolenic acid almost
completely suppressed formation of the divinyl ether acid and resulted in the appearance of 13(S)-hydroxy-9(Z), 11(E), 15(Z)-octadecatrienoic acid as the main product. This result, together with the finding that 13(S)-hydroperoxy-9(Z), 11(E), 15(Z)-octadecatrienoic acid served as an efficient precursor of the divinyl ether fatty acid, indicated that divinyl ether biosynthesis
in leaves of R. acris occurred by a two-step pathway involving an ω6-lipoxygenase and a divinyl ether synthase. Incubations of isomeric hydroperoxides
derived from α-linolenic and linoleic acids with the enzyme preparation from R. acris showed that 13(S)-hydroperoxy-9(Z), 11(E)-octadecadienoic acid was transformed into the divinyl ether 12-[1′(Z)-hexenyloxy]-9(Z), 11(E)-dodecadienoic acid. In contrast, neither the 9(S)-hydroperoxides of linoleic or α-linolenic acids nor the 13(R)-hydroperoxide of α-linolenic acid served as precursors of divinyl ethers. 相似文献
19.
Novel ceramides and a new glucoceramide from the roots of <Emphasis Type="Italic">Incarvillea arguta</Emphasis> 总被引:3,自引:0,他引:3
Novel ceramides, rel-(3S,4S,5S)-3-[(2R)-2-hydroxycosanoyl-hexacosanoylamino]-4-hydroxy-5-[(4Z)-tetradecane-4-ene]-2,3,4,5-tetrahydrofuran (1a-g), and a new glucoceramide, 1-O-β-d-glucopyranosyl-(2S,3S,4R,8E)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octodecanetriol-8-ene (2) were isolated from the aqueous ethanolic extract of the roots of Incarvillea arguta, together with eight known compounds: β-sitosterol (3), oleanolic acid (4), ursolic acid (5), piperin (6), maslinic acid (7), β-sitosterol 6′-O-acyl-β-d-glucopyranoside (8), 8-epideoxyloganic acid (9), and plantarenaloside (10). Their structures were elucidated on the basis of spectral data including IR, MS, NMR [1H NMR, 13C NMR (distortionless enhancement by polarization transfer), 1H−1H COSY, heteronuclear multiplequantum coherence, and heteronuclear multiple-bond coherence correlations]. The relative configurations
were established by nuclear Overhauser effect spectroscopy experiments and by comparison of the NMR spectral data and coupling
constants with those already reported in the literature. 相似文献
20.
Sharks are the most dangerous predators of people in the sea, resulting in people being mauled and killed each year. A shark
repellent could help to diminish this danger. The aglycone of the shark repellent pavoninin-5, (25R)-cholest-5-en-3β,15α,26-triol (5a), was synthesized from diosgenin (9). Removing mercury from the Clemmensen reduction of 9 gave a higher yield of (25R)-cholest-5-en-3β,16β,26-triol, 10a, and was also more environmentally friendly. Attempted methods for the transposition of the C-16β hydroxyl to the 15α position
are described. A successful method for this transposition via the 15α-hydroxy-16-ketone, 8a, using the Barton deoxygenation reaction on the 16-alcohol 14b, is reported. 相似文献