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1.
Elfahmi Komar Ruslan Sieb Batterman Rein Bos Oliver Kayser Herman J. Woerdenbag Wim J. Quax 《Biochemical Systematics and Ecology》2007
The lignan profile of the aerial part of Piper cubeba L. (Piperaceae) was determined using GC, GC–MS and HPLC. The number of lignans found in the leaves was 15, followed by berries and the stalks with respectively 13 and five lignans. This is the first investigation of lignans from the leaves and the stalks of P. cubeba. Cubebin, hinokinin, yatein, isoyatein are common lignans in the genus Piper and appeared as major components in all parts of P. cubeba investigated. 相似文献
2.
Feeding experiments in Podophyllum hexandrum plants with labelled aryltetralin lignans have established much of the biosynthetic interrelationships existing amongst Podophyllum lignans. Thus, desoxypodophyllotoxin is converted into podophyllotoxin, which in turn is oxidized to podophyllotoxone, although this latter step appears to be reversible. A similar sequence is proposed for the corresponding 4′-demethyl derivatives. Although 4′-demethyldesoxy-podophyllotoxin is readily converted into 4′-demethylpodophyllotoxin, neither compound is incorporated into lignans of the 4′-methyl series such as podophyllotoxin. The Podophyllum lignans may be subdivided biogenctically into two groups, those with 3,4,5-trimethoxy substitution in the pendent aryl ring, and those with a 4-hydroxy-3,5-dimethoxy substituted pendent ring, although these probably arise from a common precursor. A biogenetic scheme interrelating all of the known Podophyllum aryltetralin lignans is proposed. 相似文献
3.
Gisele B. Messiano 《Phytochemistry》2009,70(5):590-6648
Holostylis reniformis biosynthesizes 8-8′ linked lignans without 9,9′-oxygenation. To elucidate the biosynthetic pathways to these lignans, the reputed precursors [U-14C]phenylalanine, [9-3H1]coniferyl alcohol, and [9-3H1]isoeugenol were administered to roots of the plant, which led to the incorporation of 3H and 14C into ten 2,7′ linked-lignans (aryltetralone lignans) and two 7,7′-epoxylignans (furan lignans). These administration experiments demonstrated that the lignans were propenylphenol-derived and that H. reniformis can exhibit regioselective control over radical-radical coupling (via isoeugenol radicals). Regiospecific control over propenylphenol-derived lignan biosynthesis was observed, together with diastereoselective control of C2-C7′ bond formation for the aryltetralone lignans (7′R). These experiments provide evidence that isoeugenol is a biosynthetic intermediate to the aryltetralone and furan lignans. 相似文献
4.
Qiu-Yan Song Chun-Jiang Zhang Ya Li Juan Wen Xiao-Wei Zhao Zhen-Ling Liu Kun Gao 《Phytochemistry letters》2013,6(2):174-178
The systematic isolation of the EtOAc extract from Schisandra sphenanthera fruit was performed during a search for HSV-2 and adenovirus inhibitors. Sixteen lignans were obtained, with compound 1 representing a new and rare type of lignan in the genus Schisandra. Their structures were elucidated by spectroscopy and comparison with literature data. Among all the lignans tested for their antiviral activities, compound 14 was the most active against HSV-2 with a selectivity index value up to 29.83. Moreover, the new compound 1, and the known ones (4, 6, 7, 10 and 14) also exhibited moderate inhibition of HSV-2 and adenovirus. To the best of our knowledge, this is the first report that these lignans from Schisandra genus were shown to have modest activity against HSV-2 and adenovirus. Meanwhile, structure–activity relationships of some lignans for the inhibitory activity against HSV-2 and adenovirus were discussed in this study. 相似文献
5.
Thomas J. Schmidt Shiva Hemmati Michael Klaes Belma Konuklugil Abdolali Mohagheghzadeh Iliana Ionkova Elisabeth Fuss A. Wilhelm Alfermann 《Phytochemistry》2010,71(14-15):1714-1728
The aerial parts of 54 accessions representing 41 Linum species and four species of related genera were analysed for lignans by means of HPLC-ESI/MS–MS-UV/DAD. In total, 64 different lignans of the aryltetralin-, arylnaphthalene-, aryldihydronaphthalene-, dibenzylbutyrolactone-, and furofuran type were identified. According to their lignan profile, the Linum species can be divided in two groups accumulating as major lignan types either cyclolignans of the aryltetralin-series on one hand, or aryldihydronaphthalenes/arylnaphthalenes, on the other. Five of the investigated Linum species did not contain any detectable amounts of these lignans under the chosen analytical conditions. Furthermore, none of the lignans identified in Linum species was detectable in representatives of three related genera, namely, Reinwardtia (Linaceae, Linoideae), Hugonia and Indorouchera (Linaceae, Hugonioideae).The two species groups differing in the types of the dominating cyclolignans comprise representatives of the major taxonomic sections. Representatives of sections Syllinum, Cathartolinum and Linopsis accumulate mainly aryltetralins while those of sections Linum and Dasylinum were found to contain mainly aryldihydronaphthalenes/-naphthalenes. These phytochemical data correlate very well with a recent study on the molecular phylogeny of Linum/Linaceae, where a subdivision of Linum into two major clades comprising representatives of the two mentioned groups was found. Thus, the distribution of lignans apparently reflecting phylogenetic interrelations at the infrageneric level, a plausible scenario for the evolution of lignan biosynthesis in the genus Linum can now be presented. 相似文献
6.
Eleven of the major non-polar constituents of the dried bark of Virola elongata were isolated. A new neolignan, virolongin, two new lignans, dihydrosesartemin and β-dihydroyangambin, as well as the neolignan, eusiderin, the lignans, epi-sesartemin, epi-yangambin and yangambin, the cis and trans isomers of 3,5,4′-trimethoxystilbene and sitosterol were identified. The structures of virolongin, dihydrosesartemin and β-dihydroyangambin were determined. 相似文献
7.
Four lignans were isolated from the flower buds of Magnolia fargesii Cheng, two of which were known lignans, pinoresinol dimethyl ether and lirioresinol-B dimethyl ether; the other two were new lignans, magnolin and fargesin, and their structures have been determined by spectroscopic studies. 相似文献
8.
《Phytochemistry》2012
Mature seeds of 20 Linum species were analyzed for their content of lignans. The seeds of common flax (Linum usitatissimum L.) are known to contain as characteristic lignan sesoisolariciresinol diglucoside (SDG), whose presence in seeds of some other Linum species has also been reported. In order to investigate the material for the presence of such very polar lignans as well as for less polar non-glycosidic lignans as frequently found in aerial parts of Linum species, polar and non-polar extracts of each sample were analyzed by HPLC/ESI-MSMS.SDG was detected in 15 of 16 investigated seed samples of taxa representing sections Linum and Dasylinum. None of eight samples of taxa from sections Syllinum and Linopsis contained detectable amounts of SDG. Quite interestingly, most of the SDG-positive samples contained the 8R,8′R-isomer exclusively while only three (including L. usitatissimum) contained the 8S,8′S-stereoisomer as the predominant form. As a most noteworthy finding, the dichloromethane extracts obtained from seeds of several Linum species were found to contain significant concentrations of non-polar cyclolignans of the arylnaphthalene/-dihydronaphthalene lactone type or, alternatively of the aryltetralin lactone type. Thus, seeds of Linum perenne L. as well as those of several other representatives of sections Linum and Dasylinum were found to contain significant concentrations of the arylnaphthalene justicidin B along with further compounds of this type and some aryldihydronaphthalene-type lignans. On the other hand, seeds of Linum flavum and further representatives of section Syllinum were found to contain aryltetralin-type lignans, mainly in the form of esters with aliphatic carboxylic acids, such as 6-methoxypodophyllotoxin-7-O-n-hexanoate, whose occurrence in L. flavum seeds has very recently been reported by us for the first time.Various chemosystematic and biogenetic aspects are discussed in the light of these results. 相似文献
9.
A new bis-iridoid, pterhookeroside (1) was isolated from the roots of Pterocephalus hookeri along with three known iridoids (2–4) and five lignans (5–9). The structure elucidation of the isolates was accomplished by extensive 1D and 2D-NMR experiments as well as HRESI-MS. The bis-iridoid and lignans were encountered for the first time in the genus Pterocephalus. 相似文献
10.
Sedigheh Esmaeilzadeh Bahabadi Mozafar Sharifi Najme Ahmadian Chashmi Jun Murata Honoo Satake 《Acta Physiologiae Plantarum》2014,36(12):3325-3331
Linum album has been shown to accumulate some lignans with antiviral and anticancer properties such as podophyllotoxin (PTOX) and 6-methoxy podophyllotoxin (MPTOX). In this research, we examined the effects of fungal elicitors on the production of lignans in L. album hairy root cultures. The biosynthesis of lignans was differentially affected by fungal elicitors. Fusarium graminearum extract induced the highest increase of PTOX, 190 μg g?1 dry weight (DW), and lariciresinol, 260 μg g?1 DW, which was two-fold and three-fold greater than the untreated control, respectively, while Trichoderma viride extract enhanced the accumulation of MPTOX, instead of PTOX, up to 160 µg g?1 DW, which was 2.4-fold greater than the control. The enhancing effects of fungal elicitors on lignans production was correlated with the increased expression of some key genes involved in the biosynthesis of these compounds, phenylalanine ammonia-lyase, cinnamoyl-CoA reductase, cinnamyl-alcohol dehydrogenase and pinoresinol-lariciresinol reductase. 相似文献
11.
《Phytomedicine》2015,22(2):301-307
Arctium lappa is a well-known traditional medicinal plant in China (TCM) and Europe that has been used for thousands of years to treat arthritis, baldness or cancer. The plant produces lignans as secondary metabolites which have a wide range of bioactivities. Yet, their ability to reverse multidrug resistance (MDR) in cancer cells has not been explored. In this study, we isolated six lignans from A. lappa seeds, namely arctigenin, matairesinol, arctiin, (iso)lappaol A, lappaol C, and lappaol F. The MDR reversal potential of the isolated lignans and the underlying mechanism of action were studied using two MDR cancer cell lines, CaCo2 and CEM/ADR 5000 which overexpress P-gp and other ABC transporters. In two-drug combinations of lignans with the cytotoxic doxorubicin, all lignans exhibited synergistic effects in CaCo2 cells and matairesinol, arctiin, lappaol C and lappaol F display synergistic activity in CEM/ADR 5000 cells. Additionally, in three-drug combinations of lignans with the saponin digitonin and doxorubicin MDR reversal activity was even stronger enhanced. The lignans can increase the retention of the P-gp substrate rhodamine 123 in CEM/ADR 5000 cells, indicating that lignans can inhibit the activity of P-gp. Our study provides a first insight into the potential chemosensitizing activity of a series of natural lignans, which might be candidates for developing novel adjuvant anticancer agents. 相似文献
12.
Two lignans, grandisin and (+)-eudesmin have been isolated from Litsea grandis and L. gracilipes respectively. 相似文献
13.
Sixteen compounds were isolated from the root barks of Ailanthus altissima (Mill.) Swingle, including thirteen lignans (1–13), two coumarins (14–15), and one chalcone (16). This is the first report on the occurrence of compounds 1–16 in the genus Ailanthus. Their structures were elucidated on the basis of NMR spectroscopic data. The plant distribution network of all isolated compounds was described to illustrate the significance of taxonomy. The presence of these congenetic lignans (1–13) and their biosynthetic relationships may be used for identification of Ailanthus genus. 相似文献
14.
Due to their linear, freely rotatable, structure many natural 7,7-diaryl-8,8′-dimethylbutan-7′-ol lignans are reported without any stereochemical assignment. Analysis of synthetic 8,8′-dimethylbutanol lignans and analogues reveals significant differences between the NMR data of syn- and anti-isomers. This information was then used to determine the relative stereochemistry of the C-8 and C-8′ methyl groups in previously undefined natural products. 相似文献
15.
From the petrol extract of Piper clusii five lignans were isolated. One of the lignans (?)-clusin is assigned the structure (?)-2-furanol-4(1,3-benzodioxol-5-ylmethyl) tetrahydro-3(3,4,5-trimethoxyphenyl) methyl. This is the first report of this compound from a natural source. Asaronaldehyde and sitosterol were also present. 相似文献
16.
Lignans are a group of compounds consisting of dimers of phenyl propane units. They are found in diverse forms distributed in a variety of plants. Sesame lignans in particular are obtained from Sesamum indicum, a highly prized oilseed crop cultivated widely in many countries in the east. The plant is the main source of clinically important antioxidant lignans such as sesamin, sesamolin, sesaminol and sesamol. These lignans exhibit antihypertensive, anticancerous and hypocholesterolemic activities as well especially in humans due to which they have become compounds of tremendous research interest in recent times. Sesamin is synthesized from shikimic acid through phenylpropanoid pathway and metabolised into enterolignans which play a pivotal role in protection against several hormone related diseases. In this paper we present an overview of current status of research on sesame lignans with respect to the analytical methods employed, the biological activities and biosynthesis of sesame lignans. 相似文献
17.
《Animal : an international journal of animal bioscience》2017,11(4):705-712
Flaxseed is a rich source of α-linolenic acid and phytoestrogens, mainly lignans, whose metabolites (enterodiol and enterolactone) can affect estrogen functions. The present study evaluated the influence of dietary flaxseed supplementation on reproductive performance and egg characteristics (fatty acids, cholesterol, lignans and isoflavones) of 40 Hy-Line hens (20/group) fed for 23 weeks a control diet or the same diet supplemented with 10% of extruded flaxseed. The flaxseed diet had approximately three times the content of lignans (2608.54 ng/g) as the control diet, mainly secoisolariciresinol diglucoside (1534.24 v. 494.72 ng/g). When compared with the control group, hens fed flaxseed showed a similar deposition rate (72.0% v. 73.9%) and egg yield. Furthermore, there was no effect of flaxseed on the main chemical composition of the egg and on its cholesterol content. Estradiol was higher in the plasma of the control group (1419.00 v. 1077.01 pg/ml) probably due to the effect of flaxseed on phytoestrogen metabolites. The plasma lignans were higher in hens fed flaxseed, whereas isoflavones were lower, mainly due to the lower equol value (50.52 v. 71.01 ng/ml). A similar trend was shown in eggs: the flaxseed group had higher level of enterodiol and enterolactone, whereas the equol was lower (198.31 v. 142.02 ng/g yolk). Secoisolariciresinol was the main lignan in eggs of the flaxseed group and its concentration was three times higher then control eggs. Flaxseed also improved the n-3 long-chain polyunsaturated fatty acids of eggs (3.25 v. 0.92 mg/g egg), mainly DHA, however, its oxidative status (thiobarbituric reactive substances) was negatively affected. In conclusion, 10% dietary flaxseed did not affect the productive performance of hens or the yolk cholesterol concentration, whereas the lignans and n-3 polyunsaturated fatty acid content of eggs improved. Further details on the competition between the different dietary phytoestrogens and their metabolites (estrogen, equol, enterodiol and enterolactone) should be investigated. 相似文献
18.
Jun Li Ai-Ping Meng Xin-Lan Guan Jian Li Qiang Wu Sheng-Ping Deng Xiao-Jian Su Rui-Yun Yang 《Bioorganic & medicinal chemistry letters》2013,23(7):2238-2244
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 (5–16) 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
19.
Xiao-Qi Zhang Ye-Cai Lai Lei Wang Fang-Fang Xu Mei-Hua Gao Hua Li Yao-Lan Li Wen-Cai Ye 《Biochemical Systematics and Ecology》2011,39(4-6):861-863
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20.
Phytochemical investigation on the stems of Tripterygium regelii resulted in the isolation of fourteen compounds, including six flavonoids (1–6), seven lignans (7–13), and one cyanogenic glycoside (14). This is the first report of the four dimeric flavonoids bis-8, 8′-catechinylmethane (2), bis (8-epicatechinyl) methane (3), bis-6, 8′-catechinylmethane (4) and montahomobisflavan B (5) from a species of Tripterygium. Previously, these dimeric flavonoids have been mainly identified from species of gymnosperms. This research has shown that the main secondary metabolisms identified in T. regelii were flavonoids and lignans. These data enable this species to be differentiated from T. wilfordii and T. hypoglaucum that contain the triptolide-resembling diterpenoids. 相似文献