331-39-5Relevant articles and documents
Ladroside (=6'-Caffeoyl-mussaenoside), a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae) and the Elucidation of the Absolute Configuration at C(8) of Mussaenoside
Affifi-Yazar, Fatma Ue.,Sticher, Otto,Uesato, Shinichi,Nagajima, Kimiko,Inouye, Hiroyuki
, p. 16 - 24 (1981)
A new iridoid glucoside, named ladroside, together with mussaenoside (1) , has been isolated from Veronica officialis L.The structure of ladroside (4) and the identity of mussaenoside have been established by spectral analysis.Additionally, the absolute configuration at C(8) carrying hydroxyl group has been established by chemical evidence.
MALONATED FLAVONOL GLYCOSIDES AND 3,5-DICAFFEOYLQUINIC ACID FROM PEARS
Wald, Burkard,Wray, Victor,Galensa, Rudolf,Herrmann, Karl
, p. 663 - 664 (1989)
Key Word Index--Pyrus communis; Rosaceae; pears; malonated flavonol glucosides; 3,5-dicaffeoylquinic acid.Abstract--3-O-(6''-O-malonyl)-β-Glucosides of quercetin, kaempferol, isorhamnetin and 3,5-dicaffeoylquinic acid were isolated and identified from leaves of pears.The compounds are also present in the fruits.
Two new monoterpenes and one dicaffeic acid ester from Sibiraea angustata with hypolipidemic activities in HepG2 cells in Vitro
Li, Bin,Chen, Xiaotian,Wang, Zhangwei,Liu, Hongdong,Liu, Bo,Yu, Shishan,Lai, Xuewen,Xu, Xianghong,Hayashi, Toshimitsu
, p. 319 - 323 (2015)
Two new monoterpenes, named sibiscolacton B (1) and sibiscolacton C (2), together with a sorbate obtained from the natural product 1, 6-sorbitol-O-dicaffeic acid ester (3), were isolated from an aqueous extract of the aerial portion of Sibiraea angustata. The compounds' structures were elucidated on the basis of extensive spectroscopic analysis, as well as literature comparisons. A preliminary in vitro bioassay showed that all of the compounds exhibited hypolipidemic effects in HepG2 cells.
Rhamnetin Glycosides from the Genus Spiraea
Olennikov,Chirikova
, p. 41 - 45 (2018)
Rhamnetin (7-O-methylquercetin,1) and its glycosides were found for the first time in the genus Spiraea (Rosaceae) during chromatographic studies of representatives from the subgenus Protospiraea. Leaves of S. salicifolia yielded1, rhamnetin-3-O-β-D-glucopyranoside (2), and two new flavonoids3and4that were identified by UV, IR, and NMR spectroscopy and mass spectrometry as rhamnetin-3-O-(6″-O-p-coumaroyl)-β-D-glucopyranoside (spiraearhamnin A,3) and rhamnetin-3-O-(6″-O-caffeoyl)-β-D-glucopyranoside (spiraearhamnin B,4). Leaves of S. betulifolia and S. betulifolia var. aemiliana afforded1and2and glycosides of kaempferol, quercetin, and isorhamnetin. Species of the subgenus Metaspiraea (S. alpina, S. chamaedryfolia, S. dahurica, S. hypericifolia, and S. media) did not contain1or its derivatives.
Cizmarik,Matel
, p. 713 (1970)
New thiophene and flavonoid from tagetes minuta leaves growing in saudi arabia
Al-Musayeib, Nawal M.,Mohamed, Gamal A.,Ibrahim, Sabrin R. M.,Ross, Samir A.
, p. 2819 - 2828 (2014)
Phytochemical investigation of the methanolic extract of Tagetes minuta L. (Asteraceae) leaves resulted in the isolation and identification of two new compounds: 5-methyl-2,2',5',2'',5'',2''',5''',2''''-quinquethiophene (1) and quercetagetin-6-O-(6-Ocaffe
Cytotoxic triterpenoid saponins from Clematis tangutica
Zhao, Min,Da-Wa, Zhuo-Ma,Guo, Da-Le,Fang, Dong-Mei,Chen, Xiao-Zhen,Xu, Hong-Xi,Gu, Yu-Cheng,Xia, Bing,Chen, Lei,Ding, Li-Sheng,Zhou, Yan
, p. 228 - 237 (2016)
Eight previously undescribed oleanane-type triterpenoid saponins, clematangoticosides A-H, together with eight known saponins, were isolated from the whole plants of Clematis tangutica (Maxim.) Korsh. Their structures were elucidated by extensive spectroscopic analysis, in combination with chemical methods (acid hydrolysis and mild alkaline hydrolysis). Clematangoticosides D-G were found to be unusual 23, 28-bidesmosidic glycosides. The cytotoxic activities of all of the isolated saponins were evaluated against the four human cancer cell lines SGC-7901, HepG2, HL-60 and U251MG. Clematoside S, sapindoside B, kalopanax saponin A, and koelreuteria saponin A exhibited cytotoxicity against all of the test cancer cell lines with IC50 values in the range of 1.88–27.20?μM, while clematangoticoside D and F showed selective cytotoxicity against SGC-7901 with IC50 values of 24.22 and 21.35?μM, respectively.
A new isoflavone from Blepharis ciliaris of an Egyptian origin
El-Shanawany, Mohamed A.,Sayed, Hanaa M.,Ibrahim, Sabrin R. M.,Fayed, Marwa A. A.,Radwan, Mohamed M.,Ross, Samir A.
, p. 2346 - 2350 (2013)
A phytochemical study of the aerial parts of Blepharis ciliaris (L.) B.L. Burtt. led to the isolation of one new isoflavone glycoside caffeic acid ester: genistein-7-O-(6″-O-E-caffeoyl-β-d-glucopyranoside) (4), along with seven known compounds: methyl veratrate (1), methyl vanillate (2), protocatechuic acid (3), naringenin-7-O-(3″-acetyl-6″-E-p-coumaroyl- β-d-glucopyranoside) (5), naringenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (6), apigenin-7-O-(6″-E-p-coumaroyl-β-d- glucopyranoside) (7), and acteoside (8). Their structures were established on the basis of detailed analyses of physical, chemical, and spectral data. Compounds 1, 2, 3, 6, and 8 were isolated for the first time from this plant. The antioxidant activity of the different extracts as well as for some of the isolated compounds was evaluated.
Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa1
Morikawa, Toshio,Pan, Yingni,Ninomiya, Kiyofumi,Imura, Katsuya,Matsuda, Hisashi,Yoshikawa, Masayuki,Yuan, Dan,Muraoka, Osamu
, p. 1882 - 1890 (2010)
The methanolic extract from fresh stems of Cistanche tubulosa (Orobanchaceae) was found to show hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. From the extract, three new phenylethanoid oligoglycosides, kankanosides H1 (1), H2 (2), and I (3), were isolated together with 16 phenylethanoid glycosides (4-19) and two acylated oligosugars (20, 21). The structures of 1-3 were determined on the basis of spectroscopic properties as well as of chemical evidence. Among the isolates, echinacoside (4, IC50 = 10.2 μM), acteoside (5, 4.6 μM), isoacteoside (6, 5.3 μM), 2′-acetylacteoside (8, 4.8 μM), and tubuloside A (10, 8.6 μM) inhibited d-GalN-induced death of hepatocytes. These five isolates, 4 (31.1 μM), 5 (17.8 μM), 6 (22.7 μM), 8 (25.7 μM), and 10 (23.2 μM), and cistantubuloside B1 (11, 21.4 μM) also reduced TNF-α-induced cytotoxicity in L929 cells. Moreover, principal constituents (4-6) exhibited in vivo hepatoprotective effects at doses of 25-100 mg/kg, po.
Three antibacterial compounds from the roots of Pteris multifida
Hao-Bin, Hu,Xu-Dong, Zheng,Huai-Sheng, Hu,Hong, Cao
, p. 45 - 48 (2009)
A new eudesmane-type sesquiterpenoid, 3β-caffeoxyl-1β,8α- dihydroxyeudesm-4(15)-ene (1), together with two known compounds including ludongnin V (2) and isoneorautenol (3), were isolated from the roots of Pteris multifida. Their structures were determined
A new naphthoquinone and a new neolignan from ligularia vellerea rhizomes
Wang,Zhao,Shi,Li,Zhang,Liu
, p. 184 - 186 (2010)
In the course of phytochemical investigations of Ligularia vellerea rhizomes, a new naphthoquinone, 2,5-dihydroxy-6,7-dimethylnaphthoquinone (1), and a new neolignan, 4-[(3',4'-dihydroxycinnamoyl)-oxy]-methyl cinnamate (2), have been isolated and characterized on the basis of spectroscopic methods (1H NMR, 13C NMR, 2D NMR, and MS).
Chemical structures of constituents from the whole plant of Bacopa monniera
Ohta, Tomoe,Nakamura, Seikou,Nakashima, Souichi,Oda, Yoshimi,Matsumoto, Takahiro,Fukaya, Masashi,Yano, Mamiko,Yoshikawa, Masayuki,Matsuda, Hisashi
, p. 404 - 411 (2016)
Two new dammarane-type triterpene oligoglycosides, bacomosaponins A and B, and three new phenylethanoid glycosides, bacomosides A, B1, and B2, were isolated from the whole plant of Bacopa monniera Wettst. The chemical structures of the new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, bacomosaponins A and B with acyl groups were obtained from the whole plant of B. monniera. This is the first report of acylated dammarane-type triterpene oligoglycosides isolated from B. monniera. In addition, dammarane-type triterpene saponins significantly inhibited the aggregation of 42-mer amyloid β-protein.
Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae)
Hamerski, Lidilhone,Bomm, Mauro Dionei,Silva, Dulce Helena Siqueira,Young, Maria Claudia Marx,Furlan, Maysa,Eberlin, Marcos Nogueira,Castro-Gamboa, Ian,Cavalheiro, Alberto Jose,Da Silva Bolzani, Vanderlan
, p. 1927 - 1932 (2005)
Phenylpropanoid glycosides, 1′-O-benzyl-α-l-rhamnopyranosyl- (1″ → 6′)-β-d-glucopyranoside (1) and α-l- xylopyranosyl-(4″ → 2′)-(3-O-β-d-glucopyranosyl)-1′- O-E-caffeoyl-β-d-glucopyranoside (2), together with the known derivatives, 1,6-di-O-caffeoyl-β-d-glucopyranoside (3), 1-O-(E)-caffeoyl-β-d- glucopyranoside (4) and 1-O-(E)-feruloyl-β-d-glucopyranoside (5), were isolated from leaves of Coussarea hydrangeifolia. Their structures were determined by IR, HRESIMS, and 1D and 2D NMR experiments, and their antioxidant activities, evaluated by assaying the free radical scavenging capacity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical as substrate. The antioxidant activities of 3 and 4 (IC50 values of 15.0 and 19.2 μM, respectively) were comparable to that of the standard positive control caffeic acid, whilst 2 and 5 were only weakly active and 1 was inactive.
Trisubstituted hydroxycinnamic acid spermidines from Quercus dentata pollen
Bokern,Witte,Wray,Nimtz,Meurer-Grimes
, p. 1371 - 1375 (1995)
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Engineered Bacterial Flavin-Dependent Monooxygenases for the Regiospecific Hydroxylation of Polycyclic Phenols
Dippe, Martin,Funke, Evelyn,Herrmann, Susann,Pecher, Pascal,Pietzsch, Markus,Wessjohann, Ludger A.
, (2022/02/19)
4-Hydroxyphenylacetate 3-hydroxylase (4HPA3H), a flavin-dependent monooxygenase from E. coli that catalyzes the hydroxylation of monophenols to catechols, was modified by rational redesign to convert also more bulky substrates, especially phenolic natural products like phenylpropanoids, flavones or coumarins. Selected amino acid positions in the binding pocket of 4HPA3H were exchanged with residues from the homologous protein from Pseudomonas aeruginosa, yielding variants with improved conversion of spacious substrates such as the flavonoid naringenin or the alkaloid mimetic 2-hydroxycarbazole. Reactions were followed by an adapted Fe(III)-catechol chromogenic assay selective for the products. Especially substitution of the residue Y301 facilitated modulation of substrate specificity: introduction of nonaromatic but hydrophobic (iso)leucine resulted in the preference of the substrate ferulic acid (having a guaiacyl (guajacyl) moiety, part of the vanilloid motif) over unsubstituted monophenols. The in vivo (whole-cell biocatalysts) and in vitro (three-enzyme cascade) transformations of substrates by 4HPA3H and its optimized variants was strictly regiospecific and proceeded without generation of byproducts.
Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information, p. 5905 - 5908 (2021/06/18)
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
Herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl
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Paragraph 0038; 0046; 0053; 0061; 0068; 0076, (2021/06/21)
The invention discloses a herbicide based on haloxyfop, flumetsulam and halosulfuron-methyl. The herbicide is prepared from the following raw materials in parts by weight: 1-15 parts of haloxyfop-R-methyl, 1-15 parts of flumetsulam, 1-37 parts of halosulfuron-methyl, 1-2 parts of a modified antioxidant, 10-12 parts of borax, 6-8 parts of a surfactant, 10-12 parts of triethanolamine, 10-12 parts of vegetable oil and 40-42 parts of deionized water. After the haloxyfop-R-methyl, the flumetsulam and the halosulfuron-methyl are mixed, the effects are complementary, the weeding spectrum is wider, the weeding activity is high, the weeding effect is more excellent. In addition, the modified antioxidant is added into the herbicide formula, so that the composite herbicide has the effects of resisting oxidation aging and ultraviolet aging, effective components are prevented from decomposing and losing efficacy in the presence of light, the pesticide effect is kept lasting, and the application prospect and popularization value are remarkably improved.