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1.
Chemical investigation of the aerial part of Chonemorpha griffithii has led to the isolation of 20 compounds, comprising six lignans (16), six triterpenoids (712), four phenolic acids (1316), two flavonoids (17 and 18), one cyclitol (19) and one aliphatic acid (20). Among them, 5′-methoxy-7′-oxomatairesinol (1) was identified to be a new lignan. It is the first report of the presence of those compounds in this genus. Two 24-methyl-29-norcycloartane triterpenoids (10 and 11) were considered as the chemotaxonomic markers for the species C. griffithii.  相似文献   

2.
Convenient structure modification of (+)-catechin (1) induced by nonthermal dielectric barrier discharge (DBD) plasma treatment afforded three novel methylene-linked flavan-3-ol oligomers, methylenetetracatechin (2), methylenetricatechin (3), and methylenedicatechin (4), together with two known catechin dimers, bis 8,8′-catechinylmethane (5) and bis 6,8′-catechinylmethane (6). The structures of the three new catechin oligomers 24 with methylene bridges were elucidated by detailed 1D- and 2D-NMR analysis, and the absolute configurations were established by the observation of circular dichroism (CD). The novel products 2 and 3 showed significantly enhanced anti-adipogenic capacities against both pancreatic lipase and differentiation of 3T3-L1 preadipocytes compared to the parent (+)-catechin.  相似文献   

3.
The phytochemical investigation of the roots of Triosteum himalayanum Wall. led to the isolation of eleven iridoids (16 and 812), one monoterpene diglycoside (7), and four flavonoids (1316), of which 4′,6′-di-O-isopropylidene sweroside (1) and secologanin diethylacetal (2) were new iridoid glucosides. The existence of iridoids and flavonoids provided further confirmation of the typical profile of the secondary metabolites found in the genus Triosteum, suggesting a close relationship among the species of Caprifoliaceae.  相似文献   

4.
Sixteen known lignans were isolated from the 95% alcohol extract of the whole plant of Serissa japonica (Thunb.) Thunb., including nine furofurans (19), three tetrahydrofurans (1012) and four arylnaphthalenes (1316). In the present report, compounds (+)-epipinoresinol (1), (+)-1-hydroxy-6-epipinoresinol 4,4″-di-O-methyl ether (3), (−)-pinoresinol (4), (+)-8-hydroxypinoresinol (6), pseuderesinol (7), (+)-1-hydroxysyringaresinol (8), (−)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one (10), wikstrone (11), 7'-(+)-oxomatairesinol (12), (+)-cycloolivil (13), (+)-isolariciresinol (14), 5-methoxy-(+)-isolariciresinol (15) and cyclolignans (16) were reported from the Serissa genus for the first time, and compounds (+)-lirioresinol A (2) and (−)-lirioresinol B (5) were firstly isolated from the plant. Their structures were elucidated on the basis of extensive spectroscopic and chemical analyses. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.  相似文献   

5.
Chemical study of the aerial parts of Anthospermum emirnense led to the isolation of one original iridoid glycoside (1) along with six known iridoids (2–7), three lignans (8–10), two flavonoids (11–12), one coumarin (13), two anthraquinones (14–15), two benzoic acids (16–17) and three triterpenoids (18–20). These results are the first chemical data on non-volatile constituents of this genus. The chemotaxonomic significance of these compounds is discussed.  相似文献   

6.
Sixteen compounds were isolated from the whole herbs of Peperomia tetraphylla (Forst. F.) Hooker et Arnott by phytochemical methods, including eight flavonoids (1–3, 6, 7, 1416), three lignans (8–10), three beta sitosterols (4, 5, 11), and two phenolic acids (12, 13). Their structures were identified by the analysis of NMR and MS, as well as the comparisons to the reported data. Among them, 2″-O-xylosylisoswertisin (14) was firstly isolated from the Piperaceae family, as well as ten compounds (1–4, 7, 10–11, 13, 15–16) were isolated from P. tytraphylla for the first time. Moreover, the chemotaxonomic significance of constituents isolated from P. tytraphylla was also discussed.  相似文献   

7.
Four new lignans, strebluslignanol F (1), (7′R,8′S,7″R,8″S)-erythro-strebluslignanol G (2), isomagnaldehyde (3) and isostrebluslignanaldehyde (4), along with 12 known lignans (516) were isolated from the ethyl acetate-soluble part of MeOH extract of the root of Streblus asper. Their structures were elucidated through various spectroscopic methods, including 1D NMR (1H NMR, 13C NMR), 2D NMR (HMQC, HMBC and NOESY) and HRMS. The stereochemistry at the chiral centers was determined using CD spectra, as well as analyses of coupling constants and optical rotation data. The isolated lignans were evaluated for their anti-HBV activities in vitro using the HBV transfected HepG2.2.15 cell line. The most active lignans, (7′R,8′S,7″R,8″S)-erythro-strebluslignanol G, magnolol, isomagnolol and isolariciresinol, exhibited significant anti-HBV activities with IC50 values of 1.58, 2.03, 10.34 and 3.67 μM, respectively, for HBsAg with no cytotoxicity, and of 3.24, 3.76, 8.83 and 14.67 μM, respectively, for HBeAg with no cytotoxicity. (7′R,8′S,7″R,8″S)-erythro-Strebluslignanol G and magnolol showed significant anti-HBV activities to inhibit the replication of HBV DNA with the IC50 values of 9.02 and 8.67 μM, respectively.  相似文献   

8.
Two new compounds named cleroserroside C (1), schisphenlignan O (2), as well as twenty-one known compounds (3–23) were isolated from the roots of Tripterygium regelii. The structures of the new compounds were determined by 1D and 2D NMR spectra and HR-ESI-MS data. The known compounds were determined by comparing the 1D NMR data in the literature. All compounds were evaluated for anti-inflammatory activity using the LPS-induced RAW264.7 inflammatory cell model, and the results showed that compounds 1, 8-11, 15-16, and 20-21 had good anti-inflammatory activity (IC50 < 20 μM). The cytotoxicity of all compounds was tested by CCK-8 assay, using RAW264.7 cells. The results showed that all compounds had no cytotoxicity to RAW264.7 in the range of 0 ~ 200 μM.  相似文献   

9.
A phytochemical investigation on the aerial part of Phyllodium pulchellum led to the isolation of 16 compounds including five flavonoids (15), three lignans (68), four indole alkaloids (912), and four other-type compounds (1316). Their structures were elucidated by their spectroscopic data analysis. Among them, 12 compounds (1, 2, 49, and 1114) are reported from the genus Phyllodium for the first time, while compound 14 was isolated from the Leguminosae family for the first time and compound 11 was firstly reported in the plant kingdom. The chemotaxonomic significance of these compounds was also summarized.  相似文献   

10.
Four new lignans, (7′R,8′S)-4,4'-Dimethoxy-strebluslignanol (1), 3'-Hydroxy-isostrebluslignaldehyde (2), 3,3'-Methylene-bis(4-hydroxybenzaldehyde) (3), and 4-Methoxy-isomagnaldehyde (4), and six known lignans (510), were isolated from the roots of Streblus asper. The structures of these molecules were elucidated through various spectroscopic methods of analysis, including 1D and 2D NMR. The stereochemistry at the chiral centres was determined using the CD spectrum and from coupling constant and optical rotation data. Compounds 1–6 showed good antimicrobial activity against Saccharomyces cerevisiae (ATCC 9763), Bacillus subtilis (ATCC 6633), Pseudomonas aeruginosa (ATCC 9027), Escherichia coli (ATCC 11775), and Staphylococcus aureus (ATCC 25923), with MIC values ranging from 0.0150 to 0.0940 μM.  相似文献   

11.
Phytochemical investigation of the stems and leaves of Lonicera hypoglauca Miq. led to the isolation of one novel methoxylated flavone, acunminatin (7,2′,4′-trihydroxyl-5,5′- methoxyflavone) (1), and fourteen known compounds (215), including six flavonoids (mearnsetin 2, kaempferol 3, acacetin 4, 5,7,3′,4′-tetramethoxyflavone 5, tricin 6, and 5,7,3′,4′,5′-pentamethoxyflavone 7), two coumarins (umbelliferone 8 and scopoletin 9), two phenylpropanoids (trans-ferulic acid 10 and chlorogenic acid 11), two iridoid glycosides (loganin 12 and sweroside 13), and two triterpenoids (uvaol 14 and ursolic acid 15). The structures of the compounds were identified by spectroscopic analysis and by comparing their spectral data with those reported in the literature. Five of these compounds (1, 2, 4, 5, and 7) were isolated from the L. genus for the first time, and compounds 68 and 1415 were isolated for the first time from L. hypoglauca. The chemotaxonomic significance of the isolated compounds in the L. genus and the Caprifoliaceae family are discussed herein.  相似文献   

12.
A new yellow carotenoid, named 5,6-dihydrocrustaxanthin (6), was isolated together with five yellow xanthophylls: isoastaxanthin (1), 5,6-dihydropenaeusxanthin (2), penaeusxanthin (3), tetrahydroxypirardixanthin (4), and crustaxanthin (5) from three species of prawns: Marsupenaeus japonicus, Litopenaeus vannamei, and Metapenaeus joyneri, belonging to Penaeidae. The structure of (6) was determined to be (3R,4S,5R,6R,3′R,4′S)-5,6-dihydro-β,β-carotene-3,4,3′,4′-tetrol by UV-VIS, MS, 1H NMR, and CD spectral data. Distributions of yellow xanthophylls (16) in ten species of shrimps were investigated from a chemo-systematic point of view. Yellow xanthophylls (16) were present in only three species of prawns described above, among the ten species of shrimps investigated. Instead of 16, luteins and tunxanthins, having the 3-hydroxy-ε-end group, were present in other species of shrimps belonging to Penaeidae, Pandalidae, and Palaemonidae.  相似文献   

13.
Fourteen compounds were isolated from Cremanthodium brunneo-pilosum, including two steroids (1 and 14), five sesquiterpenoids (2–6), six flavonoids (7–12) and one isoflavone (13). Graveolide (2) was obtained from a plant for the first time. 5,7-Dihydroxy-3,6,3′,4′-tetramethoxy-flavone (9), centaureidin (10) and tectoridin (13) have not been isolated from the family Compositae. The chemotaxonomic data support the relationship between this species and others in the family Compositae.  相似文献   

14.
Phytochemical investigation of the rhizomes of Smilax trinervula led to isolation and structure elucidation of eight lignan glycosides, including five new lignans, namely, (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4′-O-β-d-glucopyranoside (1), (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4-O-β-d- glucopyranoside (2) (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-4′, 7-epoxy-8, 5′-neolignan 9′-O-β-d-glucopyranoside (3), (7R, 8R)-4, 9, 9′-trihydroxy-3, 5-dimethoxy-7.O.4′, 8.O.3′- neolignan 9′-O-β-d-glucopyranoside (4), and (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-8, 4′-oxy-neolignan 4-O-β-d-glucopyranoside (5), along with three known compounds (6-8). Their structures were established mainly on the basis of 1D and 2D NMR spectral data, ESI–MS and comparison with the literature. Compounds 1-8 were tested in vitro for their cytotoxic activity against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Compounds 3 and 5 exhibited cytotoxic activity against Lovo cells, with IC50 value of 10.4 μM and 8.5 μM, respectively.  相似文献   

15.
The present study reports about the phytochemical analysis of a sample of Daphne oleoides Schreb. subsp. oleoides (family Thymelaeaceae) collected from the Majella National Park. Twenty components, belonging to different classes of natural products, have been identified by means of spectroscopic and spectrometric techniques: [monomeric (4), bis- (5, 710, 20) and trimeric coumarins (11), including aglycones and glycosides, coumarinolignoid (6); flavonoids (1619); glycosidic furolignans (14, 15), glucosidic phenylpropanoids (12, 13), cyclic tetrapyrrole derivatives (2, 3), unsaturated triglyceride (1)]. Besides the chemosystematic markers of the genus (410, 12, 1418, 20) several other components were identified for the first time in the species (17, 20) and/or in the Daphne genus (13, 13, 19). The observed composition was discussed from the chemotaxonomic standpoint and compared with those recognized from a Sardinian accession. It was observed a pronounced difference in the two metabolites patterns, most probably attributable to geographic isolation of the studied populations and, in some extent, also by the different environmental conditions, evidencing a possible tendency of D. oleoides to the infraspecific chemovariability. Considering the wide traditional uses of Daphne spp. in ethnomedicine of several countries, also the pharmacologic potential of the identified secondary metabolites is discussed.  相似文献   

16.
One new flavonoid, named (R)-2-hydroxynaringenin (1), along with fifteen known compounds, including six flavonoids (27), six lignans (813), two phenolic glycosides (1415) and one alkaloid (16) were isolated from the roots of Zizyphus jujuba Mill. var. spinosa (Bunge) Hu ex H. F. Chou. Their structures were established on the basis of spectroscopic evidence, including 1D and 2D NMR, circular dichroism (CD) curve analysis, and by comparison with literature data. Compounds 2, 3 and 816 were found in Z. jujuba Mill. var. spinosa for the first time, while compounds 8, 10 and 1315 were new to the Rhamnaceae family. In addition, the chemotaxonomic significance of the isolates was discussed in this paper.  相似文献   

17.
Phytochemical investigation of Caragana tangutica Maxim. resulted in the isolation of ten flavonoids, melilotocarpan A (1), medicarpin (2), maackiain (3), 2-(2′4′-dihydroxyphenyl)-3-methyl-6-methoxy benzofuran (4), cajanin (5), formononetin (6), 7,3′-dihydroxy-5-methoxy isoflavone (7), texasin (8), 2′,4,4′-trihydroxy chalone (9) and bolusanthin III (10), as well as one aromatic acid, p-ethoxy benzoic acid (11). Compounds 1, 4, 9, 10 and 11 were isolated for the first time from the genus Caragana. The chemotaxonomic significance of these compounds was summarized.  相似文献   

18.
Two new dimeric lignans, zanthpodocarpins A (1) and B (2), and five known lignans, eudesmin (3), (1R,2R,5R,6S)-2-(3,4-dimethoxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (4), dimethoxysamin (5), rel-(1R,5R,6S)-6-(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-2-one (6), and magnone A (7), were isolated from the barks of Zanthoxylum podocarpum. Their structures were identified by using spectroscopic methods. Compounds 1 and 2 are rare dilignans bearing an unusual α,β-unsaturated ketone group from a natural source. Bioassay showed that compounds 1 and 2 could inhibit nitric oxide (NO) production in LPS stimulated RAW 264.7 cells with IC50 values of 5.31 μM and 12.15 μM, respectively.  相似文献   

19.
Three new flavonoids, 6,7-dimethoxy-4′-hydroxy-8-formylflavon (1), 8-formyl-4′,6,7-trimethoxyflavon (2), 4′,7-dihydroxy-8-formyl-6-methoxyflavon (3), together with fifteen known flavonoids (418) were isolated from the leaves of oriental tobacco (a variety of Nicotiana tabacum L). Their structures were determined by means of HRESIMS, extensive 1D and 2D NMR spectroscopic studies and chemical evidences. The cytotoxicity against five human tumor (NB4, A549, SHSY5Y, PC3, and MCF7) cell lines of compounds 13 were also evaluated. The results showed that compounds 1 and 3 showed high cytotoxicity against PC3 and A549 cell lines with IC50 values of 2.6 and 1.6 μM, respectively.  相似文献   

20.
6-Prenylapigenin (1) and 8-prenylapegenin (2) were semi-synthesized from apigenin by nuclear prenylation. Morusin (3) was isolated from the root bark of Morus alba L. The microbial transformation studies of these three bioactive prenylated apigenin derivatives were performed using eighteen cell cultures in order to select microorganisms capable of transforming them. It was identified that Mucor hiemalis (KCTC 26779) showed the ability to metabolize the parent compounds (1–3) into three new (46) and one known (7) glucosylated derivatives with high efficiency. Their structures were established as 6-prenylapigenin 7-O-β-d-glucopyranoside (4), 8-prenylapigenin 7-O-β-d-glucopyranoside (5), morusin 5-O-β-d-glucopyranoside (6), and morusin 4′-O-β-d-glucopyranoside (7) by the spectroscopic methods.  相似文献   

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