59-23-4Relevant articles and documents
Hydrolysis of β-galactosyl ester linkage by β-galactosidases
Kiso, Taro,Nakano, Hirofumi,Nakajima, Hirofumi,Terai, Tadamasa,Okamoto, Katsuyuki,Kitahata, Sumio
, p. 1702 - 1706 (2000)
p-Hydroxybenzoyl β-galactose (pHB-Gal) was synthesized chemically to examine the hydrolytic activity of β-galactosyl ester linkage by β-galactosidases. The enzyme from Penicillium multicolor hydrolyzed the substrate as fast as p-nitrophenyl β-galactoside (pNP-Gal), a usual substrate with a β-galactosidic linkage. The enzymes from Escherichia coli and Aspergillus oryzae hydrolyzed pHB-Gal with almost the same rates as pNP-Gal. The enzymes from Bacillus circulans, Saccharomyces fragilis, and bovine liver showed much lower activities. pH-activity profiles, inhibition analysis, and kinetic properties of the enzymic reaction on pHB-Gal suggested that β-galactosidase had only one active site for hydrolysis of both galactosyl ester and galactoside. The Penicillium enzyme hydrolyzed pHB-Gal in the presence of H218O to liberate galactose containing 18O. This result suggests the degradation occurs between the anomeric carbon and an adjacent O atom in the ester linkage of pHB-Gal.
SBA-15 supported ionic liquid phase (SILP) with H2PW12O40- for the hydrolytic catalysis of red macroalgal biomass to sugars
Malihan, Lenny B.,Nisola, Grace M.,Mittal, Neha,Lee, Seong-Poong,Seo, Jeong Gil,Kim, Hern,Chung, Wook-Jin
, p. 33901 - 33909 (2016)
A supported ionic liquid phase (SILP) catalyst for biomass hydrolysis was prepared via immobilization of an acidic ionic liquid (IL) with a phosphotungstic counter-anion H2PW12O40- (HPW) on ordered mesoporous silica (SBA-15). Characterization results from XRD, N2 physisorption, FT-IR, TGA and SEM/TEM image analyses confirmed the successful preparation of the SILP catalyst (SBA-IL-HPW). Meanwhile, its catalytic performance was evaluated in terms of sugar production from the hydrolysis of different biomasses in water. Under optimal hydrolysis conditions, SBA-IL-HPW yielded 73% d-galactose from agarose and 58% d-glucose from cellobiose. Moreover, SBA-IL-HPW effectively hydrolyzed the red macroalgae G. amansii as it afforded 55% total reducing sugar and 38% d-galactose yields. SBA-IL-HPW was easily separated from the hydrolysates after reaction and was re-used five times without significant loss of activity. Overall findings reveal the potential of SBA-IL-HPW as a durable, environmentally benign catalyst for sugar production from renewable resources.
Adxanthromycins A and B, new inhibitors of ICAM-1/LFA-1 mediated cell adhesion molecule from streptomyces sp. NA-148. II. Physico-chemical properties and structure elucidation
Takahashi, Senji,Nakano, Takayuki,Koiwa, Tsukasa,Noshita, Toshiro,Funayama, Shinji,Koshino, Hiroyuki,Nakagawa, Akira
, p. 163 - 170 (2000)
Adxanthromycins A and B are new inhibitors of ICAM-1/LFA-1 mediated cell adhesion molecule isolated from the fermentation broth of Streptomyces sp. NA-148. The molecular formula of adxanthromycins A and B were determined as C42H40O17 and C48H50O22, respectively by FAB-MS and NMR spectral analyses, and the structures of both compounds were elucidated to be a dimeric anthrone peroxide skeleton containing α-D-galactose by various NMR spectral analyses and chemical degradation.
Binkley,Binkley
, p. 163,165, 166 (1970)
An unusual galactofuranose lipopolysaccharide that ensures the intracellular survival of toxin-producing bacteria in their fungal host
Leone, Maria R.,Lackner, Gerald,Silipo, Alba,Lanzetta, Rosa,Molinaro, Antonio,Hertweck, Christian
, p. 7476 - 7480 (2010)
Dress code for living in a fungus: Analysis of the carbohydrate coating of the toxin-producing endobacterium of the phytopathogenic fungus Rhizopus microsporus revealed an unprecedented lipopolysaccharide (LPS) structure, which is important for infection and colonization of the fungal host. A mutant lacking the unusual [→2)-β-D-galactofuranose-(1→]n O antigen (red in the schematic illustration) was incapable of forming a stable symbiosis with the fungus.
Hudson,Yanovski
, p. 1022 (1917)
Structural and serological studies on the O-antigen show that Citrobacter youngae PCM 1505 must be classified to a new Citrobacter O-serogroup
Katzenellenbogen, Ewa,Kocharova, Nina A.,Gorska-Fraczek, Sabina,Gamian, Andrzej,Shashkov, Alexander S.,Knirel, Yuriy A.
, p. 52 - 55 (2012)
The O-polysaccharide obtained by mild acid hydrolysis of the lipopolysaccharide of Citrobacter youngae PCM 1505 was studied by sugar and methylation analyses along with 1D and 2D 1H and 13C NMR spectroscopies. The following structure of the tetrasaccharide repeating unit of the polysaccharide was established: Structural and serological data obtained earlier and in this work show that the strain studied is a candidate to a new Citrobacter O-serogroup.
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Wolfrom et al.
, p. 1529 (1959)
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Structural analysis of kappa-carrageenan isolated from Hypnea musciformis (red algae) and evaluation as an elicitor of plant defense mechanism
Arman, Muhammad,Qader, Shah Ali Ul
, p. 1264 - 1271 (2012)
High molecular weight crude and purified polysaccharide fractions obtained from Hypnea musciformis, red algae were evaluated for their elicitor activity in terms of induced browning and phytoalexins production in the cotyledons of Chickpea and Peas. Intense browning was performed from purified fraction of algae that was extracted with water, dilute alkali and acid for elicitor preparations and maximum yield (30.2%) was obtained in aqueous extraction. Chemical composition of these extracted polysaccharides in terms of total sugar, protein, sulfate and uronic acid was performed and found that purified fractions contained sugar content (67.6%) and galactose as a major sugar component. using. Gel Permeation Chromatography of purified fraction identified molecular range ≥70,000 Da. On the basis of FTIR, 1H and 13C NMR studies, the purified fraction was safely characterized as k-carrageenan.
Houttuynoid M, an Anti-HSV Active Houttuynoid from Houttuynia cordata Featuring a Bis-houttuynin Chain Tethered to a Flavonoid Core
Li, Jiao-Jiao,Chen, Guo-Dong,Fan, Hong-Xia,Hu, Dan,Zhou, Zheng-Qun,Lan, Kang-Hua,Zhang, Hui-Ping,Maeda, Hideaki,Yao, Xin-Sheng,Gao, Hao
, p. 3010 - 3013 (2017)
Houttuynoid M (1), a new houttuynoid, and the related known compound houttuynoid A (2) were isolated from Houttuynia cordata. Their structures were defined using NMR data analysis, HR-MSn experiment, and chemical derivatization. Houttuynoid M is the first example of a houttuynoid with a bis-houttuynin chain tethered to a flavonoid core. A putative biosynthetic pathway of houttuynoid M (1) is proposed. The anti-herpes simplex virus (anti-HSV) activities of 1 and 2 (IC50 values of 17.72 and 12.42 μM, respectively) were evaluated using a plaque formation assay with acyclovir as the positive control.
Chain conformations and steady-shear viscosity properties of pectic polysaccharides from apple and tomato
Hu, Shihao,Nie, Shaoping,Wang, Junqiao,Wang, Qiang,Xu, Xiaojuan
, (2022/04/03)
In this study, apple pectin (AP) and tomato pectin (TP) were demonstrated to be a high-ester (74.8%) polysaccharide with the weight-average molecular weight (Mw) of ~ 243 kDa and a low-ester (45.9%) polysaccharide with the Mw of ~ 19 kDa, respectively. The semi-rigid chain conformations of pectic polysaccharides in NaNO3 aqueous solution were deduced according to the Smidsr?d “B values” of AP (0.025) and TP (0.029), while AP and TP exhibited higher stiffness in water due to the electric repulsion of carboxyl groups, which was visually observed by AFM images. Under steady shear, the shear-thickening behaviors of AP and TP in NaNO3 aqueous solutions were observed in the shear rate range of ?1, which were attributed to the disruption of the ordered arrangement induced by semi-rigid pectin chains into randomly entangled structure by weak shear force. AP exhibited stronger shear-thickening behavior due to the formation of more entanglements resulted from the higher Mw and longer side chains highly branched at rhamngalacturonan region. This study provides the scientific basis for the construction of the relationship of steady-shear property with chain conformation and molecular weight of pectin.
Two new steroidal alkaloids from the mature fruits of Solanum nigrum
Lin, Li,Liu, LiangYu,Wang, JianNong,Wang, WenYi,Wu, Tong,Yang, YuKe
, p. 81 - 86 (2022/03/14)
Two previously undescribed steroidal alkaloids, compounds 1–2, were isolated from the ripe fruits of Solanum nigrum, along with seven known metabolites (3–9). Based on spectroscopic and chemical evidence, including IR, NMR, and HR-ESI-MS analyses, the structures of the isolated compounds were elucidated as 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)]-β-D-galacopyranoside and 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside. Four steroidal alkaloids (compounds 1–2 and 4–5) were tested for their anti-proliferative effects against the HT-29, A549, and Lewis cell lines. Both of the previously isolated compounds inhibited the proliferation of these three cell lines in a dose-dependent manner, with the most significant effect being in the A549 cells, but neither reached IC50 at 50 μM. These results revealed that S. nigrum had weak cytotoxicity, indicating its clinical safety as a traditional anti-tumor herbal medicine.
Steroidal glycosides from the underground parts of Hosta ventricosa and their anti-inflammatory activities in mice
Chu, Hong-Biao,Li, Nan-Nan,Zhang, Zong-Ping,Hu, Xiao-Yue,Yu, Cai-Yun,Hua, Lei
, p. 1766 - 1774 (2019/07/16)
Two new pregnane glycosides, 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside} (1) and 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(2), have been isolated along with two known spirostanol saponins from the underground parts of Hosta ventricosa. Their structures were elucidated on the basis of chemical and spectral evidence. The anti-inflammatory activities of these steroidal glycosides were evaluated using a xylene-induced ear edema model. Our results indicated that the compounds exhibited promising anti-inflammatory activities.