Abstract:
:Ginsenoside Rb1 is an important saponin of ginseng(s); however, Rb1, with 3-O- and 20-O-sugar moieties, has low bioavailability. Here, we report the derivatization of ginsenoside Rb1 to completely generate six types of highly bioactive minor ginsenoside Rg3 and its derivatives by FeCl3 catalysis, the reaction conditions are similar to enzymatic reaction conditions. In FeCl3 catalysis, the only 20-O-sugar-moiety of ginsenoside Rb1 was decomposed into the minor ginsenosides Rk1 and Rg5 with newly produced C-20 ethylene bands; but also hydrolyzed into 20(S)-Rg3 and 20(R)-Rg3; subsequently the C-24(25) ethylene bands of 20(S)-Rg3 and 20(R)-Rg3 were hydrated to 20(S)-25-OH-Rg3 and 20(R)-25-OH-Rg3. After separation of reaction mixture from 34 g ginsenoside-Rb1 by silica-gel-column, the 3.3 g sample I of TLC top-band consisting of Rg5 and Rk1, 8.7 g sample II of TLC middle-band consisting of 20(S)-Rg3 and 20(R)-Rg3, 3.5 g sample III of TLC bottom-band consisting of unknown product-I and -II including 20(S)-25-OH-Rg3, were obtained. The sample III consisting of unknown product-I and -II was purified by crystallization, and identified to 20(S)-25-OH-Rg3 and 20(R)-25-OH-Rg3 by HPLC-Evaporative Light Scattering Detector (ELSD) and NMR. Therefore, six types of minor-ginsenosides Rk1, Rg5, 20(S)-Rg3, 20(R)-Rg3, 20(S)-25-OH-Rg3 and 20(R)-25-OH-Rg3 were successfully prepared from ginsenoside Rb1 by FeCl3 catalysis. FeCl3 has low toxicity and is inexpensive, and the reaction conditions are similar to enzymatic reaction conditions; thus, this method is applicable to the development of ginseng-based drugs.
journal_name
Chem Pharm Bull (Tokyo)journal_title
Chemical & pharmaceutical bulletinauthors
Yu H,Wang Y,Liu C,Yang J,Xu L,Li G,Song J,Jin Fdoi
10.1248/cpb.c18-00426subject
Has Abstractpub_date
2018-01-01 00:00:00pages
901-906issue
9eissn
0009-2363issn
1347-5223journal_volume
66pub_type
杂志文章abstract::A new monomethylated ganglioside, DSG-A (3), was obtained, together with four known gangliosides, compounds (1, 2, 4, 5), from the lipid fraction of the chloroform/methanol extract of the ovary of the sea urchin Diadema setosum. The structures of the new ganglioside was determined on the basis of chemical and spectros...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.734
更新日期:2008-05-01 00:00:00
abstract::A pentacosapeptide corresponding to the entire amino acid sequence of Neurospora crassa metallothionein and several related cysteine-containing peptides were synthesized by the conventional solution method and their heavy metal-binding properties were examined. The Cu2+- or Cu+-binding properties of the various peptid...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.2322
更新日期:1989-09-01 00:00:00
abstract::In order to understand the relation between the electronic structure of neurotransmitters and the brain, a model of the brain based on absolute hardness (eta) and absolute electronegativity (chi) is described. It was found that the coordinate r(chi, eta) of electronic structures of neurotransmitters obtained using the...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.517
更新日期:2004-05-01 00:00:00
abstract::The regioselective intramolecular 1,3-dipolar cycloaddition of the phenylsulfonylallene-nitrone derivatives has been developed. This reaction showed that the distal double bond of the allene exclusively reacted with the nitrone group to produce the bicyclic isoxazolidine derivatives regardless of the substitution patt...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.60.381
更新日期:2012-01-01 00:00:00
abstract::Optically active structural isomers (1b-f and dst-1b-f) of 3',4'-di-(O)-(-)-camphanoyl-(+)-khellactone (DCK) were synthesized and their anti-human immunodeficiency virus (HIV) activity was investigated. The value of the sensitivity index (SI) of 1b was greater than that of DCK. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.59.1075
更新日期:2011-01-01 00:00:00
abstract::Caragana tibetica KOM. (Fabaceae) is a medicinal plant that has been traditionally used in western part of China. In the course of our screening study on antioxidant activity of medicinal plants, the 70% acetone extract of the stems of C. tibetica was found to have a potent superoxide anion scavenging activity. Tibeti...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.53.1204
更新日期:2005-09-01 00:00:00
abstract::Two new clerodane-type diterpenoids trivially named as ballotenic acid (1) and ballodiolic acid (2) have been isolated from Ballota limbata along with three the known compounds; beta-amyrin, oleanolic acid, and beta-sitosterol. The structure elucidation of the new compounds was based primarily on two-dimensional (2D)-...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.52.441
更新日期:2004-04-01 00:00:00
abstract::The effect of propranolol (PPL), phenoxybenzamine (PBZ) or bicuculline (BCL) on the diazepam (DZP)-induced changes of pineal melatonin synthesis in male rats was examined in vivo and in vitro. Administration of PBZ did not affect the inhibitory action of DZP on pineal melatonin synthesis in vivo. A single injection of...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.39.2677
更新日期:1991-10-01 00:00:00
abstract::A new flavonol triglycoside, isorhamnetin 3-O-beta-D-xylopyranosyl-(1"-->3)-alpha-L-rhamnopyranosyl-(1'''-->6")-beta-D-galactopyranoside, has been isolated from the leaves of Hammada scoparia together with two known compounds, isorhamnetin 3-O-beta-D-apiofuranosyl-(1'''-->2")[alpha-L-rhamnopyranosyl-(1"-->6")]-beta-D-...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.50.1268
更新日期:2002-09-01 00:00:00
abstract::The effect of regucalcin, a calcium-binding protein isolated from rat liver cytosol, on cytosolic Ca2+/calmodulin-dependent protein kinase activity was investigated. The increase in cytosolic Ca2+/calmodulin-dependent protein kinase activity with passage of incubation time was clearly prevented by the presence of regu...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.38.2216
更新日期:1990-08-01 00:00:00
abstract::6-Amino-6-deoxyfumagillol (5) was synthesized by reductive amination of 6-oxo-6-deoxyfumagillol (4), which was obtained by oxidation of fumagillol (2). The reduction proceeded stereoselectively by the equatorial attack of hydride and 5 was found to have the same stereochemistry as that of 2. Several derivatives of 5 w...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.575
更新日期:1992-03-01 00:00:00
abstract::A novel Fourier transform infrared (FT-IR) microspectroscopy equipped with a micro hot stage (thermal FT-IR microscopic system) was used to quickly study the phase transformation of acetaminophen polymorphs by a one-step process. Acetaminophen was sealed in KBr disc on the first and second heating processes under this...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.50.153
更新日期:2002-02-01 00:00:00
abstract::The manufacture of highly drug-loaded fine globular granules eventually applied for orally disintegrating tablets has been investigated using a unique multi-functional rotor processor with acetaminophen, which was used as a model drug substance. Experimental design and statistical analysis were used to evaluate potent...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c14-00687
更新日期:2015-01-01 00:00:00
abstract::The pharmacokinetics of [6]-gingerol were investigated in rats with acute renal failure induced by bilateral nephrectomy, or those with acute hepatic failure induced by a single oral administration of carbon tetrachloride (CCl4), to clarify the contribution of the kidney and liver to the elimination process of [6]-gin...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.40.1295
更新日期:1992-05-01 00:00:00
abstract::Five new components, named multiforisins A, B, C, D, and E, with immunosuppressive activity were isolated from an Ascomycete, Gelasinospora multiforis. Multiforisin A, the main immunosuppressive principle of this fungus, was deduced to be 5-formyl-3-(hydroxymethyl)-4-methoxy-6-(1E-propenyl)-alpha-pyrone. Multiforisins...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.43.547
更新日期:1995-04-01 00:00:00
abstract::Pyrrole-2,5-dicarboxylates were rapidly and selectively reduced to the corresponding mono-alcohol using 3 eq of diisobutylaluminum hydride at 0°C. Pyrrole-2,4-dicarboxylate showed the same reactivity; however, the selectivity decreased with pyrrole-3,4-dicarboxylate. When the nitrogen atom of the pyrrole-2,5-dicarboxy...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c16-00122
更新日期:2016-01-01 00:00:00
abstract::A reaction of methyl (4R,5R)-4,5-epoxy-2(E)-hexenoate 1 with N-benzylmethylamine gave a diastereomerically pure methyl (4R,5R)-4,5-epoxy-(3S)-N-benzylmethylamino hexanoate 6 and methyl (4S,5R)-4-N-benzyl-methylamino-5-hydroxy-2(E)-hexenoate 7. The former was chemoenzymatically converted to (-)-osmundalactone 11, which...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.849
更新日期:2001-07-01 00:00:00
abstract::A new isoflavone, 4'-gamma,gamma-dimethylallyloxy-5,7,2',5'-tetramethoxyisoflavone, brandisianin A (1), was isolated from the leaves of Millettia brandisiana, along with one synthetically known isoflavone, 7,4'-di-O-prenylgenistein (2) and twelve known compounds. The structures were elucidated on the basis of extensiv...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.835
更新日期:2008-06-01 00:00:00
abstract::The alkylation of 2-phenyl-4-quinolones was investigated and showed that the N-alkylation versus O-alkylation is highly dependent on whether C-5 is hydroxylated or not. N-Alkylation is favoured by the presence of a 5-hydroxyl group. The synthetic and the NMR structural studies are reported. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.1352
更新日期:2001-10-01 00:00:00
abstract::Chalcone (3) has been synthesized as a new chalcone derivative bearing benzofuran moiety at 1 position. Such chalcone was used as a model dielectrophile applied to react with some nucleophiles such as 5-amino pyrazoles, 5-amino-1,2,4-triazole, 2-aminobenzimidazole, and 6-uraciles under Michael reaction conditions and ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c15-00922
更新日期:2016-01-01 00:00:00
abstract::This paper describes practical and selective hydrogenation methodologies using heterogeneous palladium catalysts. Chemoselectivity develops dependent on the catalyst activity based on the characteristic of the supports, derived from structural components, functional groups, and/or morphologies. We especially focus on ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章,评审
doi:10.1248/cpb.c16-00153
更新日期:2017-01-01 00:00:00
abstract::We have developed a novel organometallic catalysis and applied it to drug discovery. Two new catalysts were found, ruthenium hydride with a nitrogen-containing heterocyclic carbene (A) and an organopalladium catalyst supported on a sulfur-terminated semiconductor, gallium arsenide (001) (B). Both catalysts are environ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章,评审
doi:10.1248/cpb.55.1099
更新日期:2007-08-01 00:00:00
abstract::Two sensitive and selective spectrofluorimetric and spectrophotometric stability-indicating methods have been developed for the determination of some non-steroidal anti-inflammatory oxicam derivatives namely lornoxicam (Lx), tenoxicam (Tx) and meloxicam (Mx) after their complete alkaline hydrolysis. The methods are ba...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.54.653
更新日期:2006-05-01 00:00:00
abstract::In the course of an exploratory investigation of antitumor-promoting catechins, 3-O-acyl-(+)-catechins of varying carbon lengths from C(4) to C(18) were assessed for inhibitory effects on the activation of the Epstein-Barr virus early antigen. Like 3-O-acyl-(-)-epigallocatechins, the (+)-catechin derivatives showed pr...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.51.1448
更新日期:2003-12-01 00:00:00
abstract::To estimate membrane potential in synaptosomes with the use of tetraphenylphosphonium (TPP+), an equation relating the amount of TPP+ accumulated in synaptosomes with membrane potential was derived from the following two assumptions. (1) TPP+ molecules were distributed into plasma membranes, mitochondria and cytosol o...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.37.3333
更新日期:1989-12-01 00:00:00
abstract::The adsorptive behavior of the anti-inflammatory drug meloxicam was studied by cyclic, differentia-pulse and square-wave voltammetry on a hanging mercury drop electrode (HMDE). The drug was accumulated at HMDE and a well-defined stripping peak current was obtained at -1.42 V vs. Ag/AgCl (saturated KCl) electrode in ac...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.49.1257
更新日期:2001-10-01 00:00:00
abstract::A new benzofuroquinoline derivative, 3,9-bis(N,N-dimethylcarbamoyloxy)-5H-benzofuro[3,2-c]quinoli ne-6-one (KCA-098), shows poor oral absorption due to practical insolubility in water. In this study, a co-grinding technique employing a water-soluble polymer was used for improvement of the dissolution rate of KCA-098. ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.47.1311
更新日期:1999-09-01 00:00:00
abstract::Oiling-out is a unique phenomenon that the liquid phase is separated into two parts during crystallization. The emergence of new liquid phase changes the environment where crystals nucleate and grow, we call "mother phase," because target material and impurities become distributed to each phase according to their own ...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c19-01015
更新日期:2020-01-01 00:00:00
abstract::A novel time-controlled system based on elementary osmotic pump tablet containing a drug-resin complexes (DRCs) core is presented. In the traditional osmotic pump tablets (OPTs), the lag time was always minimized. On the contrary, in the DRCs osmotic pump tablet (DRCOPT), the lag time was increased to achieve time-con...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.56.457
更新日期:2008-04-01 00:00:00
abstract::The tumor microenvironment is considered as one of the important targets for anticancer drug discovery. In particular, nutrient deficiency may be observed in tumor microenvironment; biakamides A-D (1-4) isolated from marine sponge Petrosaspongia sp. as growth inhibitors against cancer cells adapted to glucose-deprived...
journal_title:Chemical & pharmaceutical bulletin
pub_type: 杂志文章
doi:10.1248/cpb.c18-00587
更新日期:2019-03-01 00:00:00