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1.
A new diarylheptanoid glucoside,(8R,9R)-17-methoxy-2-oxatricyclo[13.2.2.13.7]icosa-l(17),3(20),4,6, 15,18-hexaene-4,9,10-triol-9-O-β-D-glucopyranoside(1),namely jugcathayenoside,together with two known diarylheptanoids,(+)-galeon(2) and 4-hydroxy-17-methoxy-2-oxatricyclo[13.2.2.13,7 ]icosa-1(17),3(20),4,6,15,18-hexaene-9-one(3),were isolated from the root bark of Juglans cathayensis. Their structures were elucidated on the basis of extensive spectroscopic data analysis.  相似文献   

2.
Methanol extracts of intact specimens of Cadlina luteomarginata, collected in Howe Sound and Barkley Sound, British Columbia, have been shown to contain sesquitepenoids and a degraded terpenoid. Albicanol (2) and its acetate 1 possess the drimane skeleton. Furodysin (4) and microcionin-2 (5) and microcionin-2 (6) are furanosesquiterpenoids of sponge origin. Luteone (8), the degraded terpenoid, represents a new carbon skeleton.  相似文献   

3.
Quan-Xiang Wu  Yan-Ping Shi 《Tetrahedron》2005,61(44):10529-10535
Four novel eremophilane-type sesquiterpene lactones, 6β,10α-dihydroxy-1-oxoeremophila-7(11),8(9)-dien-12,8-olide (1), 6β-acetyl-2-oxoeremophila-1(10),7(11), 8(9)-trien-12,8-olide (2), 6β,8β-diacetyl-2-oxoeremophila-1(10),7(11)-dien-12,8-olide (3), dimeric eremophilane ligulolide B (5), and known sesquiterpenoid, 6β,8α-diacetyleremophila-1(10),7(11)-dien-12,8-olide (4), were isolated from an extract of the whole plant of Ligularia virgaurea spp. oligocephala. The structure of 1 was confirmed by NMR spectra and single crystal X-ray crystallography investigation, as well as 2, 3, and 5 were elucidated by spectroscopic methods including 1D and 2D NMR spectra. A discussion of biogenesis of 5 was described. Cytotoxicities of compound 1 were measured in vitro against selected cancer cells human promyelocytic leukemia (HL-60), human ovarian (HO-8910) and human lung epithehial (A-549).  相似文献   

4.
《Comptes Rendus Chimie》2007,10(3):251-258
A variety of new chiral N-arylsulfonyl-1,3-oxazolidin-2-ones were prepared in three steps starting from (d)- and (l)-amino acid. N-Arylsulfonyl amino alcohols, derived from amino acids, were carbonylated with the bis-(trichloromethyl) carbonate (BTC), in the presence of triethylamine, to provide optically pure N-phenylsulfonyloxazolidin-2-ones 3af, N-naphthylsulfonyloxazolidin-2-ones 3gj and N-tosylsulfonyloxazolidin-2-ones 3kp in good yields.  相似文献   

5.
The structures of mortonins A (1), C (2a) and D (3) were previously deduced from chemical transformations and spectral data. The LAH reductions of mortonin A, mortonin C and their derivatives are discussed. Structure 2a, previously proposed for mortonin C, is proved by single crystal X-ray diffraction study. The transformation of Mortonin C (2a) into Mortonin A (1) and Mortonin D (3), proves the structure and stereochemistry proposed for all of them.  相似文献   

6.
From the wood stem and stem bark of the Panamanian plant Rondeletia panamensis (Rubiaceae), three novel diterpenes have been isolated. The structure of oxidopanamensin (2) was determined by single crystal X-ray crystallography of the diacetate derivative. Panamensin (4) was correlated with oxidopanamensin (2) by epoxidation under alkali conditions and with rondeletin (6) by hydrogenation to 14,15-dihydrorondeletin (8). Of the three isolates, panamensin (4) and oxidopanamensin (2) were cytotoxic in the KB test system but rondeletin was inactive.  相似文献   

7.
From Ligularia atroviolacea, four new eremophilendiolides, 81$-hydroxy-eremophil-3,7 (11)-dien-12,8α(14,6α)-diolide (1), 8β-methoxy-eremophil-3,7(11)-dien-12,8α(14,6α)-diolide (2), 8α-hydroxy-eremophil-3,7(11)-dien-12,8lβ(14,6α)-diolide (3) and eremophil-3,7(11),8-trien-12,8 (14,6α)-diolide (4), as well as a known diolide (5) were isolated. Their structures were elucidated on the basis of 1D and 2D NMR as well as ESI-MS spectral data.  相似文献   

8.
A strain of Chaetomium globosum (DAOM 240359) was isolated from an indoor air sample in Ottawa, Ontario, Canada. When fermented in liquid culture, this strain produced a number of known metabolites including chaetoglobosins A (6), C, and F (7), chaetomugilin D (5), chaetoviridin A (4), and three new nitrogenous azaphilones; 4′-epi-N-2-hydroxyethyl-azachaetoviridin A (1), N-2-butyric-azochaetoviridin E (2), and isochromophilone XIII (3). The structures were elucidated by spectroscopic analysis including; HRMS, 1D and 2D NMR, UV, and ORD. Compounds 27 were antimicrobial when tested using quantitative growth inhibition assays.  相似文献   

9.
The presence of terpenoids in the order Stolonifera has been established by the isolation of three novel diterpenes, 1α,4β-dihydroxyclavular-17-ene (1), 4β-hydroxyclavulara-1(15),17-diene (2) and 3α.4β-dihydroxyclavulara-1(15), 17-diene (3) from Clavularia infiata. The structure of 1 has been determined by X-ray diffraction analysis and those of 2 and 3 by chemical intercorrelation with 1.  相似文献   

10.
Two new guaianolide-type sesquiterpenoids,4β,9β-dihydroxy-1α,5α-H-guaia-6,10(14)-dien(1) and 4β,9β,10α-trihydroxy-1α,5α-H-guaia-6-en(2),along with four known sesquiterpenoids(3a,3b,4 and 5),were isolated from Kadsura interior.Their structures and configurations were elucidated by spectroscopic methods including 2D-NMR and HR-MS techniques.Compounds 3a and 3b were obtained as a pair of enantiomers,and their structure and absolute configuration were established from their extensive NMR spectra and by single-crystal X-ray analysis.  相似文献   

11.
Two new sesquiterpenoids,attributable to eudesmane-type(1 and 2,named solajiangxins F and G),were isolated from the whole plant of Solanum lyratum.Their structures were elucidated on the basis of integrated spectroscopic techniques.In vitro,compounds 1 and 2 were found to show signifcant cytotoxic activity against selected cancer cells,including P-388,HONE-1 and HT-29.  相似文献   

12.
《Tetrahedron》2014,70(51):9726-9730
Four new eremophilane type sesquiterpenoids, a new bakkane type sesquiterpenoid, and a new secoeremophilane type sesquiterpenoid were isolated from Ligularia brassicoides Hand.-Mass. (Asteraceae) collected in China, and were an epoxy lactone derived from 6-acyloxyeuryopsin 1, 6-acyloxy-9-oxoeuryopsin 2, 6-acyloxy-9-oxofuranoeremophilane 3, 6-acyloxyeuryopsin 4, 6-acyloxy bakkane type epoxy lactone 5, and secovirgaurenol 6-O-(2′-hydroxymethyl)acrylate (6), respectively. All but one had a 2′-hydroxymethylacryloyloxy group at C-6. This is the first study to describe the chemical constituents of this species.  相似文献   

13.
The present study has focused on the isolation and structure determination of phenanthrenes from Juncus atratus Krock. Nine compounds, among them five phenanthrenes, have been isolated from the methanol extract of the plant. Two compounds [juncatrins A (1) and B (2)] are new natural products, three phenanthrenes [juncuenin B (3), effusol (4), and dehydroeffusol (5)], the flavones apigenin (7) and luteolin (8), the diterpene phytol and 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trien-oic acid (9) were isolated for the first time from the plant. Juncatrin A (1) is substitued with an acetyl group, while in case of juncatrin B (2), an unprecedented acetylene group is connected to the phenanthrene skeleton. The isolated phenanthrenes were evaluated for their antiproliferative activity against HeLa, SiHa and MDA-MB-231 human tumor cell lines. Four phenanthrenes (2, 3, 4 and 5) were more effective [IC50s 3.48?μM (2), 2.91 (3), 3.68 (4), and 7.75?μM (5)] than cisplatin (IC50 12.43?μM) on HeLa cells.  相似文献   

14.
《Tetrahedron: Asymmetry》2001,12(2):279-285
The enzymatic resolution of 2-fluoroarylacetonitriles (RS)-3 using nitrilase from the plant Arabidopsis thaliana is described. Racemic 2-fluoronitriles 3 are easily accessible from O-silylated aromatic cyanohydrins 2 by reaction with DAST. The nitriles (RS)-3 were hydrolysed with the nitrilase as a catalyst, not to the expected 2-fluoroarylacetic acids but to the corresponding (R)-2-fluoroarylacetamides (R)-5 as the main products. After optimization of reaction conditions (pH 9, 7°C), the enantiomeric excesses of (R)-5a,c and f (R=H, 3-Me, 3-OMe) could be improved to >99% by one recrystallization. The acid catalysed hydrolysis of (R)-5a,5c and 5f afforded the corresponding (R)-2-fluoroarylacetic acids (R)-4a,4c and 4f without racemization.  相似文献   

15.
Mufolinin A(1), a ring A-seco rearranged limonoid with an unprecedented ethyl at C-10 and novel 6/6/6/5 fused-ring skeleton, together with three new potential precursors(ring A-seco limonoids, 2–4) were isolated from Munronia unifoliolata. Their structures and absolute configurations were confirmed by nuclear magnetic resonance(NMR), high resolution electrospray ionization mass spectroscopy(HRESIMS), X-ray crystallography, electronic circular dichroism(ECD) calculations and NMR calculations with...  相似文献   

16.
Three novel diterpenes, phomactins K–M (13), were isolated from the cultures of an unidentified marine-derived fungus. The structures of 13 were elucidated from spectroscopic data (NMR, MS, IR), and the absolute configurations of 1, 2, and the relative configuration of 3 were determined by X-ray diffraction analysis.  相似文献   

17.
Bioassay-guided fractionation of the diethyl ether extract of the liverwort Asterella angusta led to the isolation of two antifungal bis(bibenzyl)s,riccardin I(1),and angustatin A(2).Their structures were established by spectroscopic analysis(1D NMR and 2D NMR,IR,MS).Compound 1 is a novel variant riccardin-type bis(bibenzyl),while compound 2 is the first nonheteratom-containing variant bis(bibenzyl)possessing a bibenzyl-phenanthrene skeleton.  相似文献   

18.
Two new myrinsol diterpenoids, euphordracunculins A(1) and B(2), together with three known analogues, euphorprolitherin B(3), proliferins A(4) and B(5),were isolated from the petroleum ether extract of the aerial parts of Euphorbia dracunculoides Lam. Their structures were elucidated by means of extensive spectroscopic analysis(NMR and ESI-MS) and comparison with data reported in the literature.  相似文献   

19.
《中国化学快报》2022,33(8):4121-4125
Two novel seco-polycyclic polyprenylated acylphloroglucinols (PPAPs), hyperbenzones A (1) and B (2), were isolated from the roots of Hypericum beanii, together with one known biosynthetic congener 3. Compound 1 incorporates a 6/5/5 ring system with an unprecedented spiro[bicyclo[3.3.0]octane-3,1?-cyclohexane]-2,2??dione motif. The structures of 1 and 2 were determined by a combination of high resolution electrospray ionization mass spectroscopy (HRESIMS), nuclear magnetic resonance (NMR) spectroscopic analyses, gage-independent atomic orbital (GIAO) NMR chemical shift calculation with DP4+ analyses, electronic circular dichroism (ECD) calculation, and X-ray diffraction analysis. A 1,2-seco retro-Claisen rearrangement from a bicyclo[3.3.1]nonane PPAP precursor and following chemodivergent radical cascade cyclizations are proposed as the key steps in the biosynthetic pathway to yield compounds 1 and 2. Biological investigations indicated that compounds 1 and 3 could decrease intracellular lipid accumulation in a palmitic acid-induced nonalcoholic steatohepatitis (NASH) cell model.  相似文献   

20.
Melaleucadines A and B (1 and 2), two rare benzylic phloroglucinol-terpene hybrids (meroterpenoids), have been isolated and identified from the branches and leaves of the Australian “tea tree” Melaleuca leucadendron L. Their structures including absolute configurations were determined by 1D/2D NMR, HR-MS, and the CD exciton chirality method. Compound 1 was a hybrid of a benzylic phloroglucinol and rearranged β-pinene via a rare 2,3,4,5-tetrahydrooxepine ring, and 2 was the adduct of a benzylic phloroglucinol and a humulene-type sesquiterpene via an oxa-heterocycle. Bioactivity screening revealed that compounds 1 and 2 exhibited neuroprotective effects at a concentration of 50.0?μM.  相似文献   

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