Lignans, Flavonoids and Phenolic Derivatives from Taxus mairei
TL;DR: From the twigs of Taxus mairei, 35 lignans, 2 sesquilignans and 4 flavonoids, 3 bisflavonoid, 13 phenolic derivatives, 2 bisnorsesquiterpenes, 3 long-chain carboxylic acids and 4 steroids were isolated as mentioned in this paper.
Abstract: From the twigs of Taxus mairei, 35 lignans, 2 sesquilignans, 4 flavonoids, 3 bisflavonoids, 13 phenolic derivatives, 2 sesquiterpenes, 3 bisnorsesquiterpenes, 3 long-chain carboxylic acids and 4 steroids were isolated. The new lignans and phenolic glucosides include 7′-hydroxynortrachelogenin, 7-hydroxymatairesinol, 3′-O-demethylepipinoresinol, taxiresinol 9-acetate, 3′-O-demethyltanegool, 8′-epitanegool, 3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one, 3-O-demethyldihydrodehydrodiconiferyl alcohol, taxumaiglucoside A heptaacetate, taxumaiglucoside B heptaacetate, and taxumaiglucoside C heptaacetate. Their structures were determined by spectral methods.
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TL;DR: Methods and procedures for analysis of lignans in trees and other plants are reviewed and the recent development of HPLC-electrospray ionisation (ESI)-iontrap MS (MS(n)) and corresponding techniques with high sensitivity and selectivity has proven valuable in lignan analysis.
168 citations
TL;DR: Lee et al. as mentioned in this paper demonstrate the potential of innately undifferentiated cells from Taxus cuspidata as an industrial source of the anticancer drug paclitaxel.
Abstract: The culture of dedifferentiated plant cells to produce commercially important chemicals has met with limited success. Lee et al. demonstrate the potential of innately undifferentiated cells from Taxus cuspidata as an industrial source of the anticancer drug paclitaxel.
157 citations
TL;DR: It is concluded that sesame seed is a rich source of mammalian lignan precursors and sesamin is one of them.
Abstract: Plant lignans occur in many foods, with flaxseed presently recognized as the richest source. Some plant lignans can be converted by intestinal microbiota to the mammalian lignans, enterodiol and enterolactone, which may have protective effects against hormone-related diseases such as breast cancer. This study determined whether plant lignans in sesame seed, particularly sesamin, could be metabolized to the mammalian lignans. The total plant lignan concentration in sesame seed (2180 micromol/100 g) was higher than that in flaxseed (820 micromol/100 g). In vitro fermentation with human fecal inoculum showed conversion of sesamin to the mammalian lignans, although at a lower rate (1.1%) compared with that of secoisolariciresinol diglucoside (57.2%). However, when fed to female Sprague-Dawley rats for 10 d, sesamin (15 mg/kg body weight) and a 10% sesame seed diet resulted in greater (P < 0.05) urinary mammalian lignan excretion (3.2 and 11.2 micromol/d, respectively), than the control (< 0.05 micromol/d). We conclude that sesame seed is a rich source of mammalian lignan precursors and sesamin is one of them. From intermediate metabolites of sesamin identified in rat urine by GC-MS, a tentative metabolic pathway of sesamin to mammalian lignans is suggested.
146 citations
01 Jan 2010
TL;DR: To bypass the dedifferentiation step, isolated and cultured innately undifferentiated cambial meristematic cells (CMCs) and identified marker genes and transcriptional programs consistent with a stem cell identity using a combination of deep sequencing technologies.
Abstract: A plethora of important, chemically diverse natural products are derived from plants. In principle, plant cell culture offers an attractive option for producing many of these compounds. However, it is often not commercially viable because of difficulties associated with culturing dedifferentiated plant cells (DDCs) on an industrial scale. To bypass the dedifferentiation step, we isolated and cultured innately undifferentiated cambial meristematic cells (CMCs). Using a combination of deep sequencing technologies, we identified marker genes and transcriptional programs consistent with a stem cell identity. This notion was further supported by the morphology of CMCs, their hypersensitivity to γ-irradiation and radiomimetic drugs and their ability to differentiate at high frequency. Suspension culture of CMCs derived from Taxus cuspidata, the source of the key anticancer drug, paclitaxel (Taxol), circumvented obstacles routinely associated with the commercial growth of DDCs. These cells may provide a cost-effective and environmentally friendly platform for sustainable production of a variety of important plant natural products.
144 citations
TL;DR: Of the 12 compounds isolated from the roots of Bursera tonkinensis Guillaum, only 4'-demethyldesoxypodophyllotoxin exhibited significant cytotoxic activities against KB, Col2 and LNCaP cell lines.
106 citations
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3,761 citations
TL;DR: A new phenolic glycoside, icariside A1 (IV), and six terpenic glycosides have been isolated from Epimedium grandiflorum MORR. var. thunbergianum (MIQ.) NAKAI as discussed by the authors.
Abstract: A new phenolic glycoside, icariside A1 (IV), and six new terpenic glycosides, icariside B1 (V), B2 (VI), C1 (VII), C2 (VIII), C3 (IX), and C4 (X), have been isolated from Epimedium grandiflorum MORR. var. thunbergianum (MIQ.) NAKAI, together with three known glycosides, salidroside (I), thalictoside (II) and benzyl glucoside (III). The structures of IV-X were established on the basis of chemical evidence and spectral data.
263 citations
TL;DR: In this paper, the natural dibenzylbutyrolactone type lignanolide (−)-arctigenin (2), an inhibitor of human immunodeficiency virus type-1 (HIV-1) replication in infected human cell systems, was found to suppress the integration of proviral DNA into the cellular DNA genome.
Abstract: The natural dibenzylbutyrolactone type lignanolide (−)-arctigenin (2), an inhibitor of human immunodeficiency virus type-1 (HIV-1) replication in infected human cell systems, was found to suppress the integration of proviral DNA into the cellular DNA genome.11b In the present study 2 was tested with purified HIV-1 integrase and found to be inactive in the cleavage (3‘-processing) and integration (strand transfer) assays. However, the semisynthetic 3-O-demethylated congener 9 characterized by a catechol substructure exhibited remarkable activities in both assays. Structure−activity relationship studies with 30 natural (1−6), semisynthetic (7−21), and synthetic (37−43, 45, 46) lignans revealed that (1) the lactone moiety is crucial since compounds with a butane-1,4-diol or tetrahydrofuran substructure and also lignanamide analogues lacked activity and (2) the number and arrangement of phenolic hydroxyl groups is important for the activity of lignanolides. The congener with two catechol substructures (7) was...
197 citations
TL;DR: Three new ionone glucosides named corchoionosides A, B, and C were isolated from the leaves of Corchorus olitorius and were found to inhibit the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.
Abstract: Three new ionone glucosides named corchoionosides A, B, and C were isolated from the leaves of Corchorus olitorius, commonly called "moroheiya" in Japanese, together with seven known compounds, an ionone glucoside (6S,9R)-roseoside, a monoterpene glucoside betulalbuside A, two flavonol glucosides astragalin and isoquercitrin, two coumarin glucosides scopolin and cichoriine, and chlorogenic acid. The absolute stereostructures of corchoionosides A, B, and C were determined by chemical and physiochemical evidence, which included the result of application of a modified Mosher's method, the CD helicity rule, and chemical correlation with (6S,9R)-roseoside. Corchoionosides A and B and (6S,9R)-roseoside were found to inhibit the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.
125 citations
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109 citations