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Cas Database




  • Product Name:D-Galactopyranose

  • CAS Number: 10257-28-0

  • EINECS:233-595-2

  • Molecular Weight:180.158

  • Molecular Formula: C6H12O6

  • HS Code:2924199090

  • Mol File:10257-28-0.mol

Synonyms:Galactopyranose,D- (8CI);NSC 8102;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Galactose Pharmaceutical Secondary Standard; Certified Reference Material
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  • Product Description:(3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraol 97%
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Relevant articles and documentsAll total 188 Articles be found


Waage, Susan K.,Hedin, Paul A.

, p. 243 - 246 (1985)

A new flavonol glycoside, quercetin 3-O-galactosyl-(1 -> 6)-glucoside, has been isolated from above-ground parts of narrowleaf vetch, Vicia angustifolia.Its antibacterial activity against Pseudomonas maltophilia and Enterobacter cloacae is compared with that of several other flavonol glycosides.Key Word Index - Vicia angustifolia; Leguminosae; flavonol glycoside; quercetin; antibacterial.

75. New Triterpenoid N-Acetylglycosides with Molluscicidal Activity from Tetrapleura tetraptera TAUB

Maillard, Marc,Adewunmi, Clement O.,Hostettmann, Kurt

, p. 668 - 674 (1989)

Activity-guided fractionation of the MeOH extract of the fruits of Tetrapleura tetraptera TAUB. (Mimosaceae) afforded 4 saponins 1-4, which exhibited strong molluscicidal properties against the schistosomiasis-transmitting snails Biomphalaria glabrata.Chemical, enzymatic, and spectral methods (DCI-MS, 1H-NMR, 13C-NMR) showed that they were N-acetylglycosides of oleanolic acid and of echinocystic acid.Apart from saponin 1 (aridanin), previously isolated from this plant, glycosides 2-4 are new naturally occuring compounds.

Synthesis of some trifluoromethylated cyclodextrin derivatives and analysis of their properties as artificial glycosidases and oxidases

Bjerre, Jeannette,Fenger, Thomas Hauch,Marinescu, Lavinia G.,Bols, Mikael

, p. 704 - 710 (2007)

Cyclodextrin derivatives containing trifluoromethyl groups at C6 of the A and D rings were synthesized for the purpose of creating artificial enzymes. The compounds were synthesized by perbenzylation of β-cyclodextrin followed by selective A,D-debenzylation according to Sinay. Subsequent oxidation to dialdehyde with Dess-Martin periodinane followed by addition of CF3 by using Arduengo carbene and TMSCF3 led to the C6- bistrifluoromethylated alcohols. These were either deprotected by hydrogenolysis or subjected to another round of oxidation to provide the corresponding ketones that were deprotected. The trifluoromethylated alcohols were found to be weak artificial enzymes catalysing hydrolysis of nitrophenyl glycosides at neutral pH with a kcat/kuncat of up to 56. It is proposed that this catalysis is analogues to the catalysis performed by related cyanohydrins. The trifluoro ketones were likewise weak articial enzymes catalysing oxidation of amines to nitro derivatives or alcohols to ketones with a kcat/k uncat of up to 133. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.


Narantuya, S.,Batsuren, D.,Rashkes, Ya. V.,Mil'grom, E. G.

, p. 197 - 199 (1994)

The coumarin composition of the epigeal part of Stellera chamaejasme has been studied.Together with the known coumarins daphnoretin, daphnetin, daphnin, and daphnorin, we have isolated the new bicoumarin glycoside chamaejasmoside and have established its structure by chemical transformations and a study of its spectral properties.Of the know coumarins, this is the first time that daphnorin and daphnin have been isolated from this plant.

Comparative study of new α-galactosidases in transglycosylation reactions

Spangenberg, Petra,Andre, Corinne,Dion, Michel,Rabiller, Claude,Mattes, Ralf

, p. 65 - 73 (2000)

We have studied the potential of several newly cloned α-galactosidases to catalyze the regioselective synthesis of disaccharides using 4-nitrophenylgalactoside as a donor. The kinetics of the reactions were followed by in situ NMR spectroscopy. The following thermophilic enzymes have been tested: Aga A and an isoenzyme Aga B obtained from the strain KVE39 and Aga 285 from the strain IT285 of Bacillus stearothermophilus; Aga T is an α-galactosidase from Thermus brockianus (strain IT360). Two other non-thermophilic α-galactosidases have also been evaluated: Aga 1 (Streptococcus mutans, strain Ingbritt) and Raf A (Escherichia coli, strain D1021). For all of the enzymes studied, high regioselectivity was observed leading to two (1 → 6)-disaccharides: 4-nitrophenyl α-D-galactopyranosyl-(1 → 6)-α-D-galactopyranoside and methyl α-D-galactopyranosyl-(1 → 6)-α-D-galactopyranoside, which were obtained in 54% (Aga B) and 20% (Aga T) yields, respectively. (C) 2000 Elsevier Science Ltd.

Distinct substrate specificities of three glycoside hydrolase family 42 β-galactosidases from Bifidobacterium longum subsp. infantis ATCC 15697

Viborg, Alexander H.,Katayama, Takane,Abou Hachem, Maher,Andersen, Mathias C.F.,Nishimoto, Mamoru,Clausen, Mads H.,Urashima, Tadasu,Svensson, Birte,Kitaoka, Motomitsu

, p. 208 - 216 (2014)

Glycoside hydrolase family 42 (GH42) includes β-galactosidases catalyzing the release of galactose (Gal) from the non-reducing end of different β-d-galactosides. Health-promoting probiotic bifidobacteria, which are important members of the human gastrointestinal tract microbiota, produce GH42 enzymes enabling utilization of β-galactosides exerting prebiotic effects. However, insight into the specificity of individual GH42 enzymes with respect to substrate monosaccharide composition, glycosidic linkage and degree of polymerization is lagging. Kinetic analysis of natural and synthetic substrates resembling various milk and plant galactooligosaccharides distinguishes the three GH42 members, Bga42A, Bga42B and Bga42C, encoded by the probiotic B. longum subsp. infantis ATCC 15697 and revealed the glycosyl residue at subsite +1 and its linkage to the terminal Gal at subsite -1 to be key specificity determinants. Bga42A thus prefers the β1-3-galactosidic linkage from human milk and other β1-3- and β1-6-galactosides with glucose or Gal situated at subsite +1. In contrast, Bga42B very efficiently hydrolyses 4-galactosyllactose (Galβ1-4Galβ1-4Glc) as well as 4-galactobiose (Galβ1-4Gal) and 4-galactotriose (Galβ1-4Galβ1-4Gal). The specificity of Bga42C resembles that of Bga42B, but the activity was one order of magnitude lower. Based on enzyme kinetics, gene organization and phylogenetic analyses, Bga42C is proposed to act in the metabolism of arabinogalactan- derived oligosaccharides. The distinct kinetic signatures of the three GH42 enzymes correlate to unique sequence motifs denoting specific clades in a GH42 phylogenetic tree providing novel insight into GH42 subspecificities. Overall, the data illustrate the metabolic adaptation of bifidobacteria to the β-galactoside-rich gut niche and emphasize the importance and diversity of β-galactoside metabolism in probiotic bifidobacteria. The Author 2013.

Two new triterpene saponins from Acanthophyllum laxiusculum

Pertuit, David,Baghery Lotfabad, Tayebe,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Lacaille-Dubois, Marie-Aleth

, p. 611 - 617 (2015)

Two new triterpene glycosides, 1 and 2, together with three known ones, were isolated from roots of Acanthophyllum laxiusculum Schiman-Czeika. The structures of the new compounds were established by extensive 1D- and 2D-NMR spectroscopic experiments and MS analyses as 23-O-β-D-galactopyranosylgypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (1) and gypsogenic acid 28-O-{β-D-glucopyranosyl-(1→2)-6-O-[4-carboxy-3-hydroxy-3-methyl-1-oxobutyl]-β-D-glucopyranosyl-(1→6)}-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranosyl ester (2).


Gupta, K. C.,Sharma, Anita,Misra, V. D.

, p. 2887 - 2893 (1981)

Kinetics of oxidation of lactose, maltose, cellobiose and melibiose has been studied by hexacyanoferrate(III) in the presence of ammonia.A general mechanism involving the formation of intermediate enodiol anion has been suggested.The effects of dielectric constant and salts have been studied in detail.The oxidation products have been characterised by descending paper chromatography.Compensation effects have been observed.

Remarkable supramolecular catalysis of glycoside hydrolysis by a cyclodextrin cyanohydrin

Ortega-Caballero, Fernando,Rousseau, Cyril,Christensen, Brian,Petersen, Torben Ellebaek,Bols, Mikael

, p. 3238 - 3239 (2005)

(6AR,6DR)-6A,6D-di-C-cyano-β-cyclodextrin (3) was synthesized and shown to catalyze hydrolysis of nitrophenyl glycosides with the reaction following Michaelis-Menten kinetics. At pH 7.4 and 25 °C, hydrolysis of 4-nitrophenyl-β-glucopyranoside (2) was catalyzed with KM = 15 mM, kcat = 8.2 × 10-6 s-1, and kcat/kuncat = 1217. Catalysis was observed with concentration of 3 as low as 10 μM. Hydrolysis of the corresponding α-glucoside, α-galactoside, α-mannoside, and 2-nitrophenyl-β-galactoside was also catalyzed by 3, with kcat/kuncat ranging from 283 to 2147. A series of analogues of 3 was prepared and investigated for catalysis of the hydrolysis of 2: (6AR,6DR)-6A,6D-di-C-propyl-β-cyclodextrin (9) was not catalytic, while 6A,6D-di-C-cyano-6A,6D-dideoxy-β-cyclodextrin (12) had a low catalytic activity (kcat/kuncat = 4). A kcatkuncat = 48 was found for 6A,6D-dialdehydo-β-cyclodextrin dihydrate (11). It was proposed that 3 acts by general acid catalysis on the bound substrate. Copyright

Steroidal saponins from the rhizomes of Smilacina henryi

Zhang, Xiao,Su, Yan-Fang,Chen, Lei,Huang, Xiong,Yan, Shi-Lun,Chai, Xin,Gao, Xiu-Mei

, p. 478 - 487 (2013)

Five steroidal saponins, namely henryiosides A-E (1-5), were isolated from the EtOH extract of the rhizomes of Smilacina henryi. Their structures were elucidated by the extensive use of 1D- and 2D-NMR experiments, along with HR-MALDI-MS analysis and the results of acid hydrolysis. The aglycones of henryiosides A-E possess a C(7)=C(8) or C(9)=C(11) bond and were not previously found in saponins. Copyright

Structures of steroidal alkaloid oligoglycosides, robeneosides A and B, and antidiabetogenic constituents from the Brazilian medicinal plant Solarium lycocarpum

Yoshikawa, Masayuki,Nakamura, Seikou,Ozaki, Kenichi,Kumahara, Akira,Morikawa, Toshio,Matsuda, Hisashi

, p. 210 - 214 (2007)

In the course of our studies on antidiabetogenic compounds from natural medicines and medicinal foodstuffs, a methanolic extract of the fruits of Solanum lycocarpum showed an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. Through bioassay-guided separation, three known steroidal alkaloid oligoglycosides, solamargine (1), solasonine (3), and 12-hydroxysolasonine (5), were isolated from the active fraction together with two new steroidal alkaloid oligoglycosides, robeneosides A (2) and B (4). The major constituents, solamargine (1) and solasonine (3), exhibited an inhibitory effect on the increase of serum glucose levels in oral sucrose-loaded rats. In addition, these compounds suppressed gastric emptying in mice. However, this methanolic extract from S. lycocarpum fruits did not have any effect on intestinal a-glucosidase (sucrase and maltase) in vitro. It was concluded that these steroidal alkaloid oligoglycosides, 1 and 3, inhibited the increase of rat serum glucose levels by suppressing the transfer of sucrose from the stomach to the small intestine.


Somme, Randi

, p. 325 - 332 (1980)

After partial, acid hydrolysis of the extracellular, acid polysaccharide from Rh. trifolii Bart A, the following products were isolated and characterised: 3,4-O-(1-carboxyethylidene)-D-galactose, 4,6-O-(1-carboxyethylidene)-D-galactose, 3-O-D-glucose, 3-O--D-glucose, O--(13)-O-β-D-glucopyranosyl-(14)-D-glucose, and O--(13)-O-β-D-glucopyranosyl-(14)-D-glucose.The presence of pyruvic acid linked either to O-3 and O-4 or to O-4 and O-6 of the D-galactopyranosyl group of these saccharides indicates that both structures may be present in the original polysaccharide.

Illuminating the binding interactions of galactonoamidines during the inhibition of β-galactosidase (E. coli)

Fan, Qiu-Hua,Pickens, Jessica B.,Striegler, Susanne,Gervaise, Cédric D.

, p. 661 - 671 (2016)

Several galactonoamidines were previously identified as very potent competitive inhibitors that exhibit stabilizing hydrophobic interactions of the aglycon in the active site of β-galactosidase (Aspergillus oryzae). To elucidate the contributions of the glycon to the overall inhibition ability of the compounds, three glyconoamidine derivatives with alteration in the glycon at C-2 and C-4 were synthesized and evaluated herein. All amidines are competitive inhibitors of β-galactosidase (Escherichia coli) and show significantly reduced inhibition ability when compared to the parent. The results highlight strong hydrogen-bonding interactions between the hydroxyl group at C-2 of the amidine glycon and the active site of the enzyme. Slightly weaker H-bonds are promoted through the hydroxyl group at C-4. The inhibition constants were determined to be picomolar for the parent galactonoamidine, and nanomolar for the designed derivatives rendering all glyconoamidines very potent inhibitors of glycosidases albeit the derivatized amidines show up to 700-fold lower inhibition activity than the parent.

Immobilization of β-Galactosidase from Aspergillus oryza on Magnetic Poly(GMA-ST) Beads

Sun, Sufang,Zhao, Xiuying,Xu, Xiaobing

, p. 381 - 384 (2013)

In this study, novel magnetic beads were prepared from glycidylmethacrylate (GMA) and styrene (ST) via suspension polymerization with cyclohexanol and lauryl alcohol as porogenic agent. The magnetic poly (GMA-ST) beads were characterized with scanning electron microscope (SEM), magnetic scales and X-ray spectroscopy. The magnetic susceptibility of the porous poly (GMA-ST) beads was 1.25 × 10-4 cm3/g. Under the optimum conditions, β-galactosidase was immobilized on the magnetic poly (GMA-ST) beads described above, the results obtained showed that the activity of the immobilized β-galactosidase reached 412.09 U/g and the activity recovery was 61.32 %. Finally, the basic properties of the immobilized enzyme were determined separately and satisfactory results were obtained in pH stability, thermal stability, operational stability and Michaelis constants Km.

Oleanane glycosides from the roots of Alhagi maurorum

Hamed, Arafa,Perrone, Angela,Mahalel, Usama,Oleszek, Wieslaw,Stochmal, Anna,Piacente, Sonia

, p. 782 - 787 (2012)

Three new oleanane-type triterpene glycosides (1-3), along with four known compounds (4-7) glycosides, were isolated from the roots of Alhagi maurorum. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. The antiproliferative activity of the isolated compounds was evaluated against a small panel of cancer cell lines including human breast cancer (MCF-7), human lung adenocarcinoma (A549), human prostate cancer (PC-3) and human leukemia (U937) cell lines. None of the tested compounds, in a range of concentrations between 1 and 50 μM, caused a significant reduction of the cell number.

Two new glycosides from Duboscia macrocarpa Bocq.

Tchuendem, Marguerite H.K.,Douanla, Pascal D.,Tabopda, Turibio K.,Tchinda, Alembert T.,Tamze, Véronique,Nkengfack, Augustin E.,Abegaz, Berhanu M.,Connolly, Joseph D.

, p. 1 - 4 (2014)

Two new compounds namely dubosciasides A (1) and B (2) were isolated from stem bark of Duboscia macrocarpa Bocq. together with three known flavonoids. Their structures were determined by spectroscopic methods including one- and two-dimensional NMR, EIMS and HRESIMS. The new compounds were identified as 6-C-β-d-apiofuranosyl-(1 → 4)-β-d-galactopyranosylnaringetol (1) and 1-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-xylopyranosyl-3,4,5- trimethoxyphenol (2).

Two new acylated flavonol glycosides from the seeds of Lepidium sativum

Fan, Qing-Lu,Zhu, Yin-Di,Huang, Wen-Hua,Qi, Yun,Guo, Bao-Lin

, p. 11341 - 11349 (2014)

Two new acylated flavonol glycosides named kaempferol-3-O-(2-O-sinapoyl)- β-D-galactopyranosyl-(1→2)-β-D-glucopyranoside-7-O-α-L- rhamnopyranoside (1) and quercetin-3-O-(6-O-benzoyl)-β-D-glucopyranosyl- (1→3)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside

High-throughput, quantitative enzyme kinetic analysis in microdroplets using stroboscopic epifluorescence imaging

Hess, David,Rane, Anandkumar,Demello, Andrew J.,Stavrakis, Stavros

, p. 4965 - 4972 (2015)

Droplet-based microfluidic systems offer a range of advantageous features for the investigation of enzyme kinetics, including high time resolution and the ability to probe extremely large numbers of discrete reactions while consuming low sample volumes. Kinetic measurements within droplet-based microfluidic systems are conventionally performed using single point detection schemes. Unfortunately, such an approach prohibits the measurement of an individual droplet over an extended period of time. Accordingly, we present a novel approach for the extensive characterization of enzyme-inhibitor reaction kinetics within a single experiment by tracking individual and rapidly moving droplets as they pass through an extended microfluidic channel. A series of heterogeneous and pL-volume droplets, containing varying concentrations of the fluorogenic substrate resorufin β-d-galactopyranoside and a constant amount of the enzyme β-galactosidase, is produced at frequencies in excess of 150 Hz. By stroboscopic manipulation of the excitation laser light and adoption of a dual view detection system, "blur-free" images containing up to 150 clearly distinguishable droplets per frame are extracted, which allow extraction of kinetic data from all formed droplets. The efficiency of this approach is demonstrated via a Michaelis-Menten analysis which yields a Michaelis constant, Km, of 353 μM. Additionally, the dissociation constant for the competitive inhibitor isopropyl β-d-1-thiogalactopyranoside is extracted using the same method.

Flavonol glycosides with α-D-aldohexoses from Rhododendron irroratum

Yang, Ming Hua,Luo, Jian Guang,Huang, Xue Feng,Kong, Ling Yi

, p. 920 - 925 (2010)

Two new flavonol glycosides which contain rare α-D-galactose or α-D-glucose were obtained from the flowers of Rhododendron irroratum Franch., namely myricetin 3-O-β-D-galactoside-3′-O -α-D-glucoside (1) and myricetin 3-O-β-D-galactoside-3′-O- α-D-glucosid

Antifungal saponins from bulbs of white onion, Allium cepa L.

Lanzotti, Virginia,Romano, Adriana,Lanzuise, Stefania,Bonanomi, Giuliano,Scala, Felice

, p. 133 - 139 (2012)

Three saponins, named ceposide A, ceposide B, and ceposide C were isolated from the bulbs of white onion, Allium cepa L. Elucidation of their structure was carried out by comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry, and chemical evidences. The structures of the compounds were identified as (25R)-furost-5(6)-en-1β,3β,22α, 26-tetraol 1-O-β-d-xylopyranosyl 26-O-α-d-rhamnoyranosyl-(1 → 2)-O-β-d-galactopyranoside (ceposide A), (25R)-furost-5(6)-en-1β, 3β,22α,26-tetraol 1-O-β-d-xylopyranosyl 26-O-α-d- rhamnoyranosyl-(1 → 2)-O-β-d-glucopyranoside (ceposide B), and (25R)-furost-5(6)-en-1β,3β,22α,26-tetraol 1-O-β-d- galactopyranosyl 26-O-α-d-rhamnoyranosyl-(1 → 2)-O-β-d- galactopyranoside (ceposide C). The isolated compounds, alone and in combinations, were evaluated for their antimicrobial activity on ten fungal species. Antifungal activity of all three saponins increased with their concentration and varied with the following rank: ceposide B > ceposide A-ceposide C. We found a significant synergism in the antifungal activity of the three ceposides against Botrytis cinerea and Trichoderma atroviride, because growth of these fungi was strongly inhibited when the three saponins were applied in combination. In contrast, Fusarium oxysporum f. sp. lycopersici, Sclerotium cepivorum and Rhizoctonia solani were very little affected by saponins.

Karataviosides G-K, five new bisdesmosidic steroidal glycosides from the bulbs of Allium karataviense

Kuroda, Minpei,Ori, Kazutomo,Takayama, Hiroshi,Sakagami, Hiroshi,Mimaki, Yoshihiro

, p. 96 - 104 (2015)

We have analyzed the steroidal glycosides in Allium karataviense bulbs, and isolated five new bisdesmosidic steroidal glycosides: karataviosides G-K (1-5). The structures were elucidated by extensive spectroscopic analysis, including 2D NMR and enzymatic and hydrolytic cleavage. Karatavioside G (1) is an entirely novel furostanol glycoside, which has an O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl unit at C-26 of the aglycone. Although a variety of cholestanol glycosides have been isolated, mainly from Liliaceae and Agavaceae, karataviosides J and K (4 and 5) are also notable because they are the most polar cholestanol bisdesmosides discovered, in which a lycotetraose is attached to C-3 of the aglycone, and a glucose or O-glucosyl-(1 → 3)-glucose is attached at C-16. The isolated glycosides were also evaluated for their cytotoxic activities against cultured tumor cell lines.


Kodaka, Masato

, p. 797 - 800 (1983)

The rate of hydrolysis of o-nitrophenyl-β-D-glucopyranoside was largely enhanced in the presence of cationic micelle and phenylboronic acid under alkaline conditions, while that of o-nitrophenyl-β-D-galactopyranoside was much less enhanced.


Etcheberrigaray, Juan Lorenzo,Vattuone, Marta Amelia,Sampietro, Antonio Rodolfo

, p. 49 - 52 (1981)

Key Word Index - Saccharum officinarium; Gramineae; sugar cane; β-galactosidase; cell wall. β-Galactosidase activity occurs in all of the organs of the sugar cane plant, and is also of general occurrence among different cultivars and species.Most of the activity was associated with the cell wall, and only ca 12-16 percent was an intercellular form.Both activities posess similar optimum pH and Km, both are activated by Mn2+ and ethanol, and inhibited by Hg2+, and both attack the same substrates.

Flavonol glycosides acylated with 3-hydroxy-3-methylglutaric acid as systematic characters in Rosa

Porter, Elaine A.,Van Den Bos, Alexander A.,Kite, Geoffrey C.,Veitch, Nigel C.,Simmonds, Monique S.J.

, p. 90 - 96 (2012)

LC-UV-MS/MS analysis of leaf extracts from 146 accessions of 71 species of Rosa revealed that some taxa accumulated flavonol O-glycosides acylated with 3-hydroxy-3-methylglutaric acid, which are relatively uncommon in plants. The structures of two previou

Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property

Pereira, Gabriela Moysés,Ribeiro, Marcela Gon?alves,da Silva, Bernadete Pereira,Parente, José Paz

, p. 4345 - 4349 (2017)

A new furostane steroidal saponin was isolated from the leaves of Agave angustifolia var. marginata. On the basis of chemical conversions and spectroscopic analyses, its structure was established as 3-[O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→3)-O]-[O-6-deoxy-α-L-mannopyranosyl-(1→4)-β-D-xylopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl)oxy]-(3β,5α,22α,25R)-26-(β-D-glucopyranosyloxy)-22-methoxy-furostane (1). Results of preliminary biological investigations indicated that compound 1 showed significant protective effects against induced gastric ulcers using in vivo experimental models and demonstrated negligible toxicity on membrane integrity in the in vitro assays.

Phenolic constituents of the inflorescences of Sorbus torminalis (L.) Crantz

Olszewska, Monika A.,Roj, Joanna Marta

, p. 151 - 157 (2011)

Torminaloside, a new acylated flavonol glycoside (3,5,7,4′- tetrahydroxy-3′-methoxyflavone-3-O-[6″-O-(3?-hydroxy- 3?-methylglutaroyl)]-β-d-galactopyranoside, 6), together with five further methoxylated flavones 1-5, hyperoside (7), isoquercitrin (8), chlorogenic acid (9) and neochlorogenic acid (10), were isolated for the first time from Sorbus torminalis (L.) Crantz. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D- and 2D-NMR, LSI-MS and HR-LSI-MS experiments. In addition to torminaloside, three further flavonoids: 5,7,4′-trihydroxy-3′-methoxyflavone-7-O-β-d- glucopyranoside (1), 3,5,7,4′-tetrahydroxy-8,3′-dimethoxyflavone-3- O-β-d-glucopyranoside (2), and 3,5,7,4′-tetrahydroxy-3′- methoxyflavone-3-O-β-d-galactopyranoside (4) were found for the first time in the genus Sorbus.

Isolation, characterization and anti-inflammatory property of Thevetia Peruviana

Thilagavathi,Kavitha, Helen P.,Venkatraman

, p. 1584 - 1590 (2010)

Thevetia peruviana seeds contain glucosides of neriifolin, acetylneriifolin and thevetin. Seed oil distillates of Thevetia peruviana have been found to contain anti-bacterial activity. In the persent work, the fresh flowers of Thevetia peruviana was subjected to phytochemical studies. The results of the study showed that the flowers contain quercetin, kaempferol and quercetin-7-o-galactoside. The structure of the isolated compound was characterized by UV, 1H NMR and 13C NMR spectra. The anti-inflammatory character of the isolated compound was tested by in vitro method and the results of the study revealed that the isolated compound showed a biphasic property.

Houttuynoids A-E, anti-herpes simplex virus active flavonoids with novel skeletons from Houttuynia cordata

Chen, Shao-Dan,Gao, Hao,Zhu, Qin-Chang,Wang, Ya-Qi,Li, Ting,Mu, Zhen-Qiang,Wu, Hong-Ling,Peng, Tao,Yao, Xin-Sheng

, p. 1772 - 1775 (2012)

Houttuynoids A-E (1-5), a new type of flavonoid with houttuynin tethered to hyperoside, and their presumed biosynthetic precursor hyperoside (6) were isolated from the whole plant of Houttuynia cordata. Their structures were elucidated by analysis of 1D and 2D NMR. A hypothetical biogenetic pathway for houttuynoids A-E was proposed. Compounds 1-5 exhibited potent anti-HSV (herpes simplex viruses) activity.

Effect of magnesium cations on the activity and stability of β-galactosidases


, p. 1156 - 1159 (2007)

It was shown that the presence of magnesium cations in the reaction mixture increases, approximately twofold, the activity of bacterial Escherichia coli and yeast Kluyveromyces lactis β-galactosidases but does not affect the activity of bovine liver and f

Desmettianosides A and B, bisdesmosidic furostanol saponins with molluscicidal activity from Yucca desmettiana

Diab, Yasser,Ioannou, Efstathia,Emam, Ahmed,Vagias, Constantinos,Roussis, Vassilios

, p. 686 - 690 (2012)

Bioactivity-guided separation of the aqueous methanolic extract of Yucca desmettiana leaves, which in a preliminary screening exhibited significant molluscicidal activity, led to the isolation and structure elucidation of two new steroidal saponins (1 and 2). The structures of desmettianosides A and B, identified as bisdesmosidic furostanol glycosides with six and five sugar units, respectively, were established by detailed spectroscopic analyses of their NMR and MS data. Compounds 1 and 2 exhibited high molluscicidal activity against Biomphalaria alexandrina snails with LC100 values of 6 and 11 mg/L, respectively.

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4'-deoxy-4'-fluoro-Thomsen-Friedenreich epitope

Johannes, Manuel,Reindl, Maximilian,Gerlitzki, Bastian,Schmitt, Edgar,Hoffmann-R?der, Anja

, p. 155 - 161 (2015)

The development of selective anticancer vaccines that provide enhanced protection against tumor recurrence and metastasis has been the subject of intense research in the scientific community. The tumor-associated glycoprotein MUC1 represents a well-established target for cancer immunotherapy and has been used for the construction of various synthetic vaccine candidates. However, many of these vaccine prototypes suffer from an inherent low immunogenicity and are susceptible to rapid in vivo degradation. To overcome these drawbacks, novel fluorinated MUC1 glycopeptide-BSA/TTox conjugate vaccines have been prepared. Immunization of mice with the 4'F-TF-MUC1-TTox conjugate resulted in strong immune responses overriding the natural tolerance against MUC1 and producing selective IgG antibodies that are cross-reactive with native MUC1 epitopes on MCF-7 human cancer cells.

β-Galactosidase transferase activity in ice and use of vinyl-β-D-galactoside as donor


, p. 2017 - 2023 (1997)

The ability of vinyl-β-D-galactoside as a donor in transglycosylation reactions catalysed by the β-glycosidase from Aspergillus oryzae using allylic alcohol and methyl-α-galactoside as acceptors is tested. A kinetic study made in comparison with another donor, the 2-nitrophenyl-β-D-galactoside, shows that the use of the latter leads at room temperature to better yields than those obtained from the former. A reverse situation is observed in ice at -7°C, conditions in which the yield for transglycosylation can be enhanced from 59% to 82% with methyl-α-galactoside as an acceptor.

New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)

Tchoukoua, Abdou,Tabopda, Turibio Kuiate,Usukhbayar, Narandulam,Kimura, Ken-ichi,Kwon, Eunsang,Momma, Hiroyuki,Koseki, Takuya,Shiono, Yoshihito,Ngadjui, Bonaventure Tchaleu

, p. 2261 - 2267 (2017)

Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1–4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR data and HR-ESI-MS analyses. At concentrations of 100 μM of each compounds, none of the tested compounds caused a significant growth reduction against HL60 cells.


Akhmedzhanova, V.

, p. 601 - 602 (1986)


The phenolic acids from Oplopanax elatus Nakai stems and their potential photo-damage prevention activity

Han, Yu,Cheng, Dongsheng,Hao, Mimi,Yan, Jiejing,Ruan, Jingya,Han, Lifeng,Zhang, Yi,Wang, Tao

, p. 39 - 48 (2022)

25 phenolic acids, including four new isolates, eurylophenosides A–D (1–4) and 21 known ones (5–25) were isolated and identified from the stems of Oplopanax elatus Nakai. Among the known compounds 5–9, 11–13, 16, 18–25 were isolated from the genus for the first time; 17 was first obtained from the plant; and the NMR data of 22 was reported here first. Meanwhile, the UVB-induced photodamage model of HaCaT cells was used to study the prevent-photodamage abilities of compounds 1–2, 4–8, 11–13 and 15–25 with a nontoxic concentration at 50?μM. Moreover, a dose-dependent experiment was conducted for active compounds at the concentration of 10, 25, and 50?μM, respectively. Consequently, pretreatment with compounds 1, 16, 17, 19, 20, 22, 24 and 25 could suppress the cell viability decreasing induced by UVB irradiation in a concentration-dependent manner. These results indicated that phenolic acids were one kind of material basis with prevent-photodamage activity of O. elatus. Graphic abstract: [Figure not available: see fulltext.].

Synthesis of oligosaccharide phosphates: fragments of the biosynthetic intermediates of Salmonella O-specific polysaccharides.


, p. 141 - 146 (1980)


Kaempferol and its glycosides from Equisetum silvaticum L. from the khanty-mansi autonomous area

Bonacheva,Botirov, E. Kh.

, p. 777 - 780 (2014)

Three flavonoids were isolated from the aerial part of the wood horsetail (Equisetum silvaticum L.); two of them were found for the first time. The compounds were identified as kaempferol, kaempferol 3-O-β-D-galactopyranosyl-7-O-α-L-rhamnopyranoside and kaempferol 3-O-rutinosyl-7-O-L-rhamnopyranoside on the basis of the chemical transformations and IR, UV, 1H-NMR and mass spectra.


Narayanan, Venkateswaran,Nagarajan, Natesan Shanmugan

, p. 2364 - 2365 (1988)

Key Word Index-Dalbergia spinosa; Leguminosae; leaves; prunetin 4'-O-β-D-galactoside; 7-methyltectorigenin 4'-O-β-D-galactoside; stem-bark; known isoflavones.Abstract-The chemical examination of the leaves and steam-bark of Dalbergia spinosa has yielded, in addition to a number of known isoflavones, two new isoflavone galactosides, prunetin 4'-O-β-D-galactoside and 7-methyltectorigenin 4'-O-β-D-galactoside.

Antifungal saponins from bulbs of garlic, Allium sativum L. var. Voghiera

Lanzotti, Virginia,Barile, Elisa,Antignani, Vincenzo,Bonanomi, Giuliano,Scala, Felice

, p. 126 - 134 (2012)

A bioassay-guided phytochemical analysis of the polar extract from the bulbs of garlic, Allium sativum L., var. Voghiera, typical of Voghiera, Ferrara (Italy), allowed the isolation of ten furostanol saponins; voghieroside A1/A2 and voghieroside B1/B2, based on the rare agapanthagenin aglycone; voghieroside C1/C2, based on agigenin aglycone; and voghieroside D1/D2 and E1/E2, based on gitogenin aglycone. In addition, we found two known spirostanol saponins, agigenin 3-O-trisaccharide and gitogenin 3-O-tetrasaccharide. The chemical structures of the isolated compounds were established through a combination of extensive nuclear magnetic resonance, mass spectrometry and chemical analyses. High concentrations of two eugenol diglycosides were also found for the first time in Allium spp. The isolated compounds were evaluated for their antimicrobial activity towards two fungal species, the air-borne pathogen Botrytis cinerea and the antagonistic fungus Trichoderma harzianum.

Bacillus circulans β-galactosidase catalyses the synthesis of N-acetyl-lactosamine in a hydro-organic medium via a steady-state ordered Bi Bi reaction mechanism

Bridiau, Nicolas,Maugard, Thierry

, p. 24 - 31 (2012)

Starting from a galactosyl donor, the β-galactosidase from Bacillus circulans (Lactoles L3; BcβGal) catalyses the transgalactosylation of N-acetyl-d-glucosamine (GlcNAc) in hydro-organic media, leading to the synthesis of N-acetyl-lactosamine (LacNAc). The aim of this study was to determine the kinetic properties of LacNAc synthesis and sought to highlight the effect of the organic solvent on the enzyme kinetic parameters. Analyses of enzyme kinetics were performed in aqueous solutions and water/tert-butanol mixtures. A steady-state ordered Bi Bi mechanism was characterised for the transgalactosylation of GlcNAc catalysed by BcβGal in water/tert-butanol (70:30, v/v) mixtures, starting from o-nitrophenyl-β-d- galactopyranoside (oNPG) as a galactosyl donor. Moreover, tert-butanol was shown to have various effects on the kinetic parameters of the total transformation of oNPG and lactose catalysed by BcβGal, which led us to liken this solvent to a noncompetitive inhibitor towards the former and a competitive inhibitor towards the latter.

Flavonoid characterization and in vitro antioxidant activity of Aconitum anthora L. (Ranunculaceae)

Mariani, Cristina,Braca, Alessandra,Vitalini, Sara,De Tommasi, Nunziatina,Visioli, Francesco,Fico, Gelsomina

, p. 1220 - 1226 (2008)

In this paper, we report studies on morphological, phytochemical, and biological aspects of a population belonging to Aconitum anthora L. Two compounds, quercetin 3-O-((β-d-glucopyranosyl-(1→3)-(4-O-(E-p-coumaroyl))-α-l -rhamnopyranosyl-(1→6)-β-d-galactopyranoside))-7-O-α-l-r hamnopyranoside (1) and kaempferol 3-O-((β-d-glucopyranosyl-(1→3)-(4-O-(E-p-coumaroyl))-α-l -rhamnopyranosyl-(1→6)-β-d-galactopyranoside))-7-O-α-l-r hamnopyranoside (2), together with two known flavonol glycosides (3-4) were isolated and identified from A. anthora. The antioxidant activity of the four identified flavonoids was screened by three in vitro tests.

A new flavonol glycoside from the seeds of Nigella glandulifera

Liu, Yu-Ming,Liu, Qing-Hua,Chen, Bao-Quan

, p. 1334 - 1338 (2011)

A new flavonol glycoside, kaempferol 3-O-α-L-rhamnopyranosyl (1→6)-O-[β-D-glucopyranosyl (1→2)-O-β-D-galactopyranosyl (1→2)]-O- β-D-glucopyranoside (1), together with a known compound, kaempferol 3-O-β-D-glucopyranosyl (1→2)-O-β-D-galactopyranosyl (1→2)-O-β-Dglucopyranoside (2) was isolated from the seeds of Nigella glandulifera. Their structures were elucidated on the basis of spectral analysis, including ESI-MS, ESI-MS/MS, HR-ESI-MS, DQF-COSY, TOCSY, HSQC and HMBC techniques.


, p. 762 (1966)

Structure elucidation of secondary metabolites isolated from the leaves of Ixora undulate and their inhibitory activity toward advanced glycation end-products formation

Sugimoto, Sachiko,Wanas, Amira Samir,Mizuta, Tsutomu,Matsunami, Katsuyoshi,Kamel, Mohamed Salah,Otsuka, Hideaki

, p. 189 - 195 (2014)

Three aromatic glycosides (1-3), two sulfur and nitrogen-containing compound glucosides (4, 5), and one flavonoid glycoside (6) were isolated from the leaves of Ixora undulata. Their structures were established by extensive 1D, 2D NMR, and HRESIMS experim

New Steroidal Saponins from the Leaves of Yucca elephantipes

Zhang, Ying,Yang, Chong-Ren,Zhang, Ying-Jun

, p. 1807 - 1813 (2013)

Two new spirostanol saponins, namely elephanosides G and H (1 and 2, resp.) were isolated from the leaves of Yucca elephantipes (Agavaceae), together with the two known furostanol saponins 3 and 4 and the six known flavonoid O- and C-glycosides 5-10. The

Flavonol glycosides and steroidal saponins from the leaves of Cestrum nocturnum and their cytotoxicity

Mimaki, Yoshihiro,Watanabe, Kazuki,Ando, Yuka,Sakuma, Chiseko,Sashida, Yutaka,Furuya, Shigenori,Sakagami, Hiroshi

, p. 17 - 22 (2001)

Phytochemical analysis of the leaves of Cestrum nocturnum (Solanaceae) resulted in the isolation of two new flavonol glycosides (1, 2) and seven steroidal saponins (3-9), including four new ones (4, 6, 7, and 9). The structures of the new compounds were d



, p. 465 (1981)


Two new flavonol glycosides from Polygala sibirica L. Var megalopha Fr.

Huang, Yan-Jie,Zhou, Ling-Yun,Wang, Jun-Min,Li, Qiang,Geng, Yuan-Yuan,Liu, Hai-Yang,Hua, Yan,McPhee, Derek J.

, p. 21494 - 21500 (2015)

Two new flavonol glycosides, named polygalin H (1) and polygalin I (2), as well as the known compound polygalin D (3), were isolated from the whole plant of Polygala sibirica L. var megalopha Fr. Their structures were elucidated on the basis of spectroscopic data analysis. These flavonol glycosides exhibited strong inhibitory activities against xanthine oxidase in vitro. Their half-maximal inhibitory concentrations (IC50) were calculated, which were 9.48, 8.31, 16.00 μM, respectively.

Antiproliferative steroidal glycosides from Digitalis ciliata

Perrone, Angela,Capasso, Anna,Festa, Michela,Kemertelidze, Ether,Pizza, Cosimo,Skhirtladze, Alexandre,Piacente, Sonia

, p. 554 - 562 (2012)

Two new compounds, a furostanol glycoside (1) and a pregnane glycoside (4), along with eight known compounds, belonging to the classes of spirostane (2,3), pregnane (5-7) and cardenolide (8-10) glycosides, were isolated from the seeds of Digitalis ciliata. Their structures were elucidated by 1D and 2D-NMR experiments as well as ESI-MS analysis. For the first time pregnane glycosides of the diginigenin series have been isolated from D. ciliata. The cytotoxic effects of compounds 1-10 on cell viability of several cancer cell lines, namely human breast cancer (MCF-7), human glioblastoma (T98G), human lung adenocarcinoma (A549), human colon carcinoma (HT-29), and human prostate cancer (PC-3) cell lines were evaluated. Compounds 1, 4, 7 and 8 showed antiproliferative effects against MCF-7, HT-29 and A549 cancer cells with IC50 values ranging from 8.3 to 20 μM. The effects of compounds 1-10 on cell proliferation were evaluated on these three cancer cell lines by cell cycle analysis of DNA content using flow cytometry. Compounds 7, 8 and 10 induced significant changes in G2/M cell cycle phase of all analyzed cells. The obtained results indicate that compounds 7, 8 and 10 are cytostatic compounds effective in reducing cell proliferation by inducing accumulation of the cells in the G2/M phase of the cell cycle.

Probing the Neuraminidase Activity of Influenza Virus Using a Cytolysin A Protein Nanopore

Kwak, Dong-Kyu,Kim, Jin-Sik,Lee, Mi-Kyung,Ryu, Kyoung-Seok,Chi, Seung-Wook

, p. 14303 - 14308 (2020)

Neuraminidase (NA), one of the major surface glycoproteins of influenza A virus (IAV), is an important diagnostic biomarker and antiviral therapeutic target. Cytolysin A (ClyA) is a nanopore sensor with an internal constriction of 3.3 nm, enabling the detection of protein conformations at the single-molecule level. In this study, a nanopore-based approach is developed for analysis of the enzymatic activity of NA, which facilitates rapid and highly sensitive diagnosis of IAV. Current blockade analysis of the d-glucose/d-galactose-binding protein (GBP) trapped within a type I ClyA-AS (ClyA mutant) nanopore reveals that galactose cleaved from sialyl-galactose by NA of the influenza virus can be detected in real time and at the single-molecule level. Our results show that this nanopore sensor can quantitatively measure the activity of NA with 40-80-fold higher sensitivity than those previously reported. Furthermore, the inhibition of NA is monitored using small-molecule antiviral drugs, such as zanamivir. Taken together, our results reveal that the ClyA protein nanopore can be a valuable platform for the rapid and sensitive point-of-care diagnosis of influenza and for drug screening against the NA target.

Polythosides A and B, two new triterpenoid saponins from the roots of Acacia polyacantha Willd. (Mimosaceae)

Tchoukoua, Abdou,Tomfeun Nganou, Sandrine Carole,Dabole, Bernard,Yoshida, Jun,Ito, Yoshiaki,Ngadjui, Bonaventure Tchaleu,Shiono, Yoshihito

, p. 190 - 195 (2021/05/03)

Two new oleanane-type triterpene saponins, named polythosides A and B (1 and 2), together with a known compound, silphioside E (3), were isolated from the roots of Acacia polyacantha. Their structures were elucidated by analysis of 1D and 2D-NMR experiments, and mass spectrometry (HR-ESITOF-MS) as oleanolic acid 3-O-β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranoside (1), 3-O-[β-D-galactopyranosyl-(1→2)-β-D-xylopyranosyl-(1→6)-[β-D-xylopyranosyl-(1→4)]-[β-D-xylopyranosyl-(1→2)]-β-D-galactopyranosyl] oleanolic acid-28-O-β-D-glucopyranosyl ester (2) and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (3). The cytotoxic effect of isolated saponins was evaluated on the H4IIE rat hepatoma cell line. The results show that none of the compounds (assayed at 100 μM) showed cytotoxicity against H4IIE cells.

Identification of potential anti-inflammatory and melanoma cytotoxic compounds from Aegiceras corniculatum

Vinh, Le Ba,Phong, Nguyen Viet,Ali, Irshad,Dan, Gao,Koh, Young Sang,Anh, Hoang Le Tuan,Van Anh, Do Thi,Yang, Seo Young,Kim, Young Ho

, p. 2020 - 2027 (2020/09/01)

Many chemicals found in mangroves reportedly exhibit potent anticancer, antibacterial, anti-inflammatory, antioxidant, and antitumor properties. Several of such compounds include feature unique structures and display interesting pharmacological effects. Few medicinal mangrove plants from Vietnam have been characterized with regard to their chemical constituents. Aegiceras corniculatum (L.) Blanco is a mangrove shrub that exhibits activity against various types of cancer. To identify new secondary metabolites and determine the source(s) of biological activity in Vietnamese medicinal mangrove plants, the chemical constituents of A. corniculatum were isolated, and their structures were appropriately established using common spectroscopic methods (1D and 2D-NMR, IR, HR-ESI-MS), and by producing derivatives by chemical reactions. Complementarily, it is worth noting, that the anti-inflammatory effects of the isolated compounds were investigated by measuring the production of pro-inflammatory cytokines IL-12 p40, IL-6, and TNF-α in lipopolysaccharide-stimulated bone marrow-derived dendritic cells; in this sense, the target compounds 2 and 3 were potent inhibitors of cytokines TNF-α, IL-6, and IL-12 p40, indicating promising anti-inflammatory effects. Furthermore, compounds 1 and 4 strongly promoted apoptosis of B16F10 melanoma cells. It is convenient to highlight, that the obtained results suggest that saponins from A. corniculatum could be potential candidates for treating cancer and inflammatory illnesses.

Cycloartane and oleanane glycosides from the tubers of Eranthis cilicica

Watanabe, Kazuki,Mimaki, Yoshihiro,Fukaya, Haruhiko,Matsuo, Yukiko

, (2019/01/14)

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1-11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

Process route upstream and downstream products

Process route

4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside

4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside



cytidine 5'-monophosphate-N-acetylneuraminic acid

cytidine 5'-monophosphate-N-acetylneuraminic acid



Conditions Yield
With Na3PO4 buffer; sodium acetate; carboxymethyl-dodecyl-dimethyl-ammonium betaine; sodium chloride; calcium chloride; multistep reaction : 1) bacterial neuraminidase (V. cholera), bovine serum albumin, 2) β-D-galactosidase; colorimetric assay method for determination of linkage specificity of bacterial and viral neuraminidases; other neuraminidases;




Conditions Yield
With β-D-galactosidase; water; at 30 ℃; pH 5.5; relative rate of hydrolysis;
With sodium azide; 4-morpholineethanesulfonic acid; antibody Ab21; sodium chloride; at 37 ℃; Rate constant; Michaelis constant;
With dihydroxy-methyl-borane; water; In various solvent(s); at 25 ℃; Rate constant; pH=11;
With β-galactosidase Grade VIII from Escherichia coli; sodium chloride; magnesium chloride; In phosphate buffer; at 25 ℃; pH=7.0; Further Variations:; Solvents; D2O; addition of isopropyl β-D-thiogalactopyranoside; Enzyme kinetics; Enzymatic reaction;
With β-galactosidase from Xanthomonas manihotis; In phosphate buffer; at 37 ℃; pH=6.0; Further Variations:; pH-values; Reagents; Kinetics;
With citrate buffer; phosphate buffer; soybean β-glucosidase; at 40 ℃; pH=5.0; Further Variations:; Reagents; Enzyme kinetics;
With β-galactosidase (EC from Aspergillus oriza; In phosphate buffer; at 37 ℃; pH=4.5; Further Variations:; pH-values; Enzyme kinetics;
With β-galactosidase from Penicillium sp; In acetate buffer; at 37 ℃; pH=5.0; Further Variations:; pH-values; Kinetics;
4-nitrophenyl α-D-galactoside

4-nitrophenyl α-D-galactoside



Conditions Yield
With α-galactosidase; at 25 ℃; for 0.0833333h; Rate constant;
With α-D-galactosidase; water; at 30 ℃; pH 5.5; relative rate of hydrolysis;
With α-D-galactosidase; sodium acetate; at 37 ℃; Rate constant; pH 5.6; enzymatic hydrolysis of natural and synthetic carbohydrate substrates; initial rate of hydrolysis; formation of Michaelis (enzyme-substrte) complex; Km; kinetic parameters as a function of pH; transglycosylation reactions;
With dihydroxy-methyl-borane; water; In various solvent(s); at 25 ℃; Rate constant; pH=11;
With α-galactosidase of Mortierella vinacea; In phosphate buffer; at 40 ℃; pH=5.9; Enzyme kinetics; Enzymatic reaction;
With citrate buffer; phosphate buffer; soybean β-glucosidase; at 40 ℃; pH=5.0; Enzyme kinetics;
With (6AR,6DR)-6A,6D-di-C-cyano-β-cyclodextrin; In phosphate buffer; at 59 ℃; pH=7.4; Further Variations:; Reagents; Kinetics;
With (6AR)-6A-C-formyl-6A-O-methyl-β-cyclodextrin; water; In aq. phosphate buffer; at 59 ℃; pH=8; Reagent/catalyst; Kinetics;






Conditions Yield
With trifluoroacetic acid; at 95 ℃; Kinetics;
methyl O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-β-D-galactopyranoside

methyl O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-β-D-galactopyranoside



methyl beta-D-galactopyranoside

methyl beta-D-galactopyranoside

Conditions Yield
With Streptomyces sp. exo-β-(1 -> 3)-D-galactanase SGalase1 cloned into E. coli and expressed; water; at 37 ℃; for 0.166667h; pH=3.8; aq. sodium acetate buffer; Reflux;
methyl O-β-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-Dgalactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-β-D-galactopyranoside

methyl O-β-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-O-β-Dgalactopyranosyl-(1<*>3)-O-β-D-galactopyranosyl-(1<*>3)-β-D-galactopyranoside



methyl beta-D-galactopyranoside

methyl beta-D-galactopyranoside

Conditions Yield
With Streptomyces sp. exo-β-(1 -> 3)-D-galactanase SGalase1 cloned into E. coli and expressed; water; at 37 ℃; for 0.166667h; pH=3.8; aq. sodium acetate buffer; Reflux;
Conditions Yield
With sodium tetrahydroborate; hydrazine; sodium nitrite; Product distribution; with or without hydrazinium sulfate: investigation of the hydrazinolysis-nitrous-deamination procedure; steric influence of the 3-O-substitution; mechanism is proposed;

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