Showing papers in "Chemical & Pharmaceutical Bulletin in 1986"
TL;DR: The 70% MeOH extract of Ganoderma lucidum had an inhibitory effect on angiotensin converting enzyme activity, and from this extract, five new triterpenes, named ganoderal A, ganoderols A and B, and ganodes K and S, were isolated.
Abstract: The 70% MeOH extract of Ganoderma lucidum had an inhibitory effect on angiotensin converting enzyme activity, and from this extract, five new triterpenes, named ganoderal A, ganoderols A and B, and ganoderic acids K and S, were isolated. Their structures were determined on the basis of spectral evidence.
210 citations
140 citations
TL;DR: Although indomethacin remained as a glass for 2 years at room temperature, pulverized glassy indometHacin was found to crystallize, and the rate of crystallization was determined by the X-ray diffraction method and followed first-order kinetics.
Abstract: Glassy indomethacin was prepared by cooling the melt, and the glassy state was confirmed by the jump of heat capacity and the anomalous endothermic park (heat capacity maximum) in the differential scanning calorimetry (DSC) curve. The influences of the cooling rate of the melt and the heating rate of the glass formed on the glass transition temperature (Tg) were examined, and the apparent activation energy of glass transition was calculated to be 212.5kJ/mol. The relaxation process below Tg was traced in terms of the area under the anomalous endothermic park of the DSC curve and the rate of relaxation during annealing was found to reach the maximum at about 303 K. The rate of dissolution of glassy indomethacin was far greater than that of crystalline indomethacin. Although indomethacin remained as a glass for 2 years at room temperature, pulverized glassy indomethacin was found to crystallize, and the rate of crystallization was determined by the X-ray diffraction method. The degree of crystallization was determined by Hermans' method, and was found to reach a maximum of 60% after 2 months. The process of crystallization followed first-order kinetics.
117 citations
TL;DR: The structures of punicalin and punicalagin, isolated from the bark of Punica granatum L. (pomegranate), have been revised to 4, 6-(S, S)-gallagyl-D-glucose (1) and 2, 3-(S)-hexahydroxy-diphenoyl-4, 6-S,S)-gallagon-Dglucoses (2), respectively, on the basis of chemical and spectroscopic evidence as mentioned in this paper.
Abstract: The structures of punicalin and punicalagin, isolated from the bark of Punica granatum L. (pomegranate), have been revised to 4, 6-(S, S)-gallagyl-D-glucose (1) and 2, 3-(S)-hexahydroxy-diphenoyl-4, 6-(S, S)-gallagyl-D-glucose (2), respectively, on the basis of chemical and spectroscopic evidence. In addition, a new hydrolyzable tannin, 2-O-galloyl-4, 6-(S, S)-gallagyl-D-glucose (3) was isolated from the same plant source, and characterized.
112 citations
TL;DR: In this article, pairs of enantiomers of nine aldoses were separated on gas-liquid chromatography equipped with an SE-30 capillary column as trimethylsilyl ethers after conversion of the aldosing to methyl 2-(polyhydroxyalkyl)-thiazolidine-(4R)-carboxylates using the reaction with L-cysteine methyl ester.
Abstract: Pairs of enantiomers of nine aldoses were separated on gas-liquid chromatography equipped with an SE-30 capillary column as trimethylsilyl ethers after conversion of the aldoses to methyl 2-(polyhydroxyalkyl)-thiazolidine-(4R)-carboxylates using the reaction with L-cysteine methyl ester.
105 citations
103 citations
TL;DR: The effect of grinding in an agate centrifugal ball mill at 200 rpm on the physicochemical properties of indomethacin (IMC) polymorphs was studied by means of X-ray diffraction analysis, infrared spectroscopy and differential scanning calorimetry.
Abstract: The effect of grinding in an agate centrifugal ball mill at 200 rpm on the physicochemical properties of indomethacin (IMC) polymorphs was studied by means of X-ray diffraction analysis, infrared spectroscopy and differential scanning calorimetry. The α and γ forms (metastable and stable forms) of IMC were ground at 4°C ant at 30±0.5°C, and the degree of crystallinity (Xc) of the ground products was measured by the X-ray diffractional internal standard method.The Xc of the γ form ground at 4°C decreased with increasing grinding time, and was 0% after 4 h, that is, the γ form had been converted to a noncrystalline solid. After grinding for 1 h at 30°C, about 45% of γ form of IMC was converted to noncrystalline solid, while the product ground for 10 h was transformed to the α form.The Xc of the α form ground for 2 h at 4°C was 0%, that is, the αform had been converted to a noncrystalline solid within 2 h at 4°C. The Xc of the α form ground at 30°C decreased with increasing grinding time and the value after 10 h was about 60%.The solubility in distilled water at 35°C of the γ form ground for 10 h at 4°C was about 60% larger than that of the intact γ form. The solubilities of the γ form gournd for 10 h at 30°C, the α form gound for 10 h at 4°C and the α form gound for 10 h at 30°C were all the same, 0.94 mg/100 ml, which is equal to that of the α form at 35°C.
102 citations
TL;DR: A chemical examination of the leaves of Terminalia catappa L. (Combretaceae) has led to the isolation and characterization of four new hydrolyzable tannins named terflavins A (1) and B (2), tergallagin (3) and tercatain (4).
Abstract: A chemical examination of the leaves of Terminalia catappa L. (Combretaceae) has led to the isolation and characterization of four new hydrolyzable tannins named terflavins A (1) and B (2), tergallagin (3) and tercatain (4), together with eight known tannins : punicalin (5), punicalagin (6), chebulagic acid (7), geraniin (8), granatin B (9), 1-desgalloyleugeniin (10), corilagin (11) and 2, 3-[(S)-4, 4', 5, 5', 6, 6'-hexahydroxydiphenoyl]-D-glucose (12). Terflavins A (1) and B (2) possess novel structures in which a flavogallonyl (triphenyl) ester group is single bonded to the glucopyranose ring, and are presumed to be biosynthetic precursors of punicalagin (6) and punicalin (5), respectively, while tergallagin (3), which contains a gallagyl (tetraphenyl) group and a unique tergalloyl ester group attached to the glucose moiety, seems to be formed biosynthetically from punicalagin (6).
100 citations
TL;DR: In this paper, a chemical examination of the bark of Cinnamomum cassia has led to the isolation of three flavan-3-ol glucosides (1-3) and three oligomeric procyanidins (4-6) named cinnamtannins A2-A4, together with (-)-epicatechin(7), procyclanidin B-2 (8), B-5 (9) and C-1 (11), and a doubly-linked proanthocyanidin (10
Abstract: A chemical examination of the bark of Cinnamomum cassia( ?? ?? ?? ?? : Lauraceae) has led to the isolation of three flavan-3-ol glucosides (1-3) and three oligomeric procyanidins (4-6) named cinnamtannins A2-A4, together with (-)-epicatechin(7), procyanidins B-2 (8), B-5 (9) and C-1 (11), and a doubly-linked proanthocyanidin (10). On the basis of chemical and spectroscopic evidence, compounds 1-3 were characterized as (-)-epicatechin 3-O-, 8-C- and 6-C-β-D-glucopyranosides, respectively, while compounds 4-6 were shown to be tetrameric, pentameric and hexameric procyanidins, respectively, consisting exclusively of (-)-epicatechin units linked linearly through C(4β)-C(8) bonds.
96 citations
TL;DR: The trapped amount of liposomes in the present expriments appeared to be insufficient for practical therapy, but a more powerful magnet may give better results.
Abstract: Liposomes containing ultrafine magnetite were prepared and their transport characteristics in a magnetic field were examined in vitro and in vivo. About 15μg of magnetite (Fe3O4) could be entrapped in the liposomes per μmol of lipid without impairing the liposomal encapsulation capacity for the aqueous marker (3H-inulin). In in vitro experiments, when 0.1 ml of liposome suspension (0.86μmol of lipids and 13.3μg of magnetite) was applied to a glass capillary at a flow rate of the medium of 0.17 ml/min, about 35% of the liposomes was found in the region of the applied magnetic field (4000 G).It became apparent that the ability of the magnetic field to hold the liposomes was influenced by the flow rate of the medium and the magnitude of the magnetic field. The viscosity of the medium and diameter of the capillary where the magnet is applied for fixation of the liposomes may also affect the holding capacity.In vivo experiments were carried out with rats having Yoshida sarcoma implanted in a foot pad. The liposomes were injected from the branch of the femoral artery without impairing normal blood flow in the tumor tissue. A very small amount of the liposomes, but significantly more than the control, was trapped at the tumor tissue.The trapped amount of liposomes in the present expriments appeared to be insufficient for practical therapy, but a more powerful magnet may give better results.
94 citations
TL;DR: Hydrolyzable tannins from crude drugs were examined for inhibitory activity against glucosyltransferase from a cariogenic bacterium, Streptococcus mutans, and penta- and hexagalloylglucose were the most potent, being inhibitory at a concentration of 10-3M.
Abstract: Hydrolyzable tannins from crude drugs were examined for inhibitory activity against glucosyltransferase from a cariogenic bacterium, Streptococcus mutans. Pentagalloylglucose showed a strong inhibitory effect, whereas ellagitannins stimulated the glucan synthesis in 10% ethanol. All the gallotannins were more potent than chlorhexidine gluconate in an aqueous reaction mixture. Among them, penta- and hexagalloylglucose were the most potent, being inhibitory at a concentration of 10-3M. The inhibitory character of gallotannins depended on the number of galloyl residues.
TL;DR: This fluorometric method was sensitive enough to measure the amount of aliphatic aldehydes, including 4-hydroxynonenal, generated by microsomal peroxidation in rat liver.
Abstract: A fluorometric method for the determination of aliphatic aldehydes using 1, 3-cyclohexanedione reagent and high-performance liquid chromatography (HPLC) was developed.Straight-chain aldehydes of C3-C10 were reacted with 1, 3-cyclohexanedione at 60°C for 1 h and the fluorescent decahydroacridine derivatives2, 3) formed were determined by HPLC on an ODS column. The calibration curves for the aldehydes were linear in the range of 0-10 ng and the relative standard deviation at the 5 ng level was about 2.3%.This method was sensitive enough to measure the amount of aliphatic aldehydes, including 4-hydroxynonenal, generated by microsomal peroxidation in rat liver.
TL;DR: The structures of azinomycins A and B, new antitumor antibiotics produced by a strain of Streptomyces, were determined on the basis of their spectral and chemical properties.
Abstract: The structures of azinomycins A and B, new antitumor antibiotics produced by a strain of Streptomyces, were determined on the basis of their spectral and chemical properties. The structures of three related metabolites coproduced with these antibiotics were also determined.
TL;DR: In this article, a chemical examination of the bark of Punica granatum L. (Punicaceae) has led to the isolation of five new ellagitannins, punicacorteins A, B, C and D, and punigluconin, together with the known ellagITannins casuariin (6) and casuarinin (7).
Abstract: A chemical examination of the bark of Punica granatum L. (Punicaceae) has led to the isolation of five new ellagitannins, punicacorteins A, B, C and D, and punigluconin, together with the known ellagitannins, casuariin (6) and casuarinin (7). Based on chemical and spectroscopic evidence, the structures of punicacorteins A, B, C and D were established as novel C-glycosideic ellagitannins, the former two possessing a unique tetraphenyl (gallagyl) ester group (1 and 2), and the latter two containing a galloyl group in place of the gallagyl group (3 and 4), while punigluconin was characterized as 2, 3-di-O-galloyl-4, 6-(S)-hexahydroxydiphenoylgluconic acid (5).
TL;DR: Antitumor glucan (grifolan LE) was purified from LELFD by diethylaminoethyl-Sephadex A-25 chromatography and ethanol precipitation and showed antitumor activity against sarcoma 180 cells in ICR mice.
Abstract: Chemical characterization of the extracts, and purification and structural characterization of an antitumor glucan obtained from liquid-cultured mycelium of Grifola frondosa are described in this paper. The mycelium (13 g dry weight/1 culture) was extracted successively with hot water (LMHW, 14.9 g/100 g mycelium), cold alkali (LMCA, 6.3 g/100 g mycelium), and hot alkali (LMHA, 4.5 g/100 g mycelium). Each extract was dialyzed and then the polysaccharide fraction was precipitated with ethanol. Another portion of the mycelium was incubated with a buffer composed of glucose (5.0%) and citric acid, pH 4.5, for 3 d and the supernatant was obtained (LELFD, 50 g/100 g mycelium). The brothe was dialyzed and the nondialyzable fraction was precipitated with ethanol (LLFD, 1.3 g/1 culture). All of the above fractions were composed of glucose as the major carbohydrate. Except for LMHW, all fractions showed antitumor activity against sarcoma 180 cells in ICR mice. The activity was the strongest in the LELFD fraction. Antitumor glucan (grifolan LE) was purified from LELFD by diethylaminoethyl-Sephadex A-25 chromatography and ethanol precipitation. Grifolan LE gave Mr of more than 5×106 (8 M urea/0.2 N NaOH), [α]D -6°--9° (c=0.1%; 0.3 N NaOH), and showed metachromasy coupled with Congo red. By carbon-13 nuclear magnetic resonance spectra and methylationanalyses, grifolan LE was found to be a branched β-1, 3-glucan containing a branch at C-6 of every three main chain glucosyl units.
TL;DR: Microencapsulation of ketoprofen using Eudragit RS, which is a copolymer synthesized from acrylic and methacrylic acid esters with a low content of quaternary ammonium groups, was investigated, and good reproducibility in microcapsule preparation was observed.
Abstract: Microencapsulation of ketoprofen using Eudragit RS, which is a copolymer synthesized from acrylic and methacrylic acid esters with a low content of quaternary ammonium groups, was investigated. The preparation is based on dispersion of acetone containing the drug in liquid paraffin. Aluminium tristearate was used as an additive for the preparation of microcapsules. Good reproducibility in microcapsule preparation was observed. The microcapsules obtained were uniform and free-flowing particles. The dissolution rates of ketoprofen from these microcapsules were considerably decreased as compared with that from ketoprofen powder.
TL;DR: In this paper, the kinds of linear pentaamines with various combinations of 3 or 4 methylene chain intervals were synthesized, leading to symmetrical and unsymmetrical pentaamine.
Abstract: The kinds of linear pentaamines with various combinations of 3 or 4 methylene chain intervals were synthesized. The methods were tentatively classified into two, leading to symmetrical and unsymmetrical pentaamines, all of which were prepared by successive alkylation of secondary amino derivatives of benzylamine with N-(3-bromopropyl or 4-bromobutyl)phthalimide in the presence of KF-Celite, coupled with the purification of the phthaloyl compounds by silica gel column chromatography. Protecting benzyl and phthaloyl groups were removed by usual methods. The carbon-13 unclear magnetic resonance (13C-NMR) spectra of the ten pentaamines were recorded in D2O as fully protonated forms, and a comparative analysis of their spectra allowed the complete assignment of all 13C chemical shifts.
TL;DR: The ether-soluble fraction of MeOH extract from the leaves of Cryptomeria japonica D. DON showed an anti-inflammatory effect when topically applied to rats and an inhibitory effect on histamine-induced ileum contraction.
Abstract: The ether-soluble fraction of MeOH extract from the leaves of Cryptomeria japonica D. DON showed an anti-inflammatory effect when topically applied to rats and an inhibitory effect on histamine-induced ileum contraction. The active component was isolated and identified as ciscommunic acid (1). Two new diterpenoids were also isolated along with two known compounds and were determined to be imbricataloic acid dimethyl acetal (5) and (E)-13-hydroxylabda-8 (17), 11, 14-trien-19-oic acid, obtained as the methyl ester (6m), by chemical and spectroscopic methods.
TL;DR: In this paper, sixteen triterpene acids were isolated from the gills of Ganoderma lucidum (Polyporaceae) along with five known triterpenes.
Abstract: Sixteen new triterpene acids isolated as the methyl esters from the gills of Ganoderma lucidum (Polyporaceae) along with five known triterpenes. The structures of seven new compounds among them, ganoderic acids C2, E, I, and K, compounds B8 and B9 and lucidenic acid F, were elucidated. Detailed analyses of their proton and carbon-13 nuclear magnetic resonance (1H- and 13C-NMR) spectra were also done by application of two-dimensional NMR techniques.
TL;DR: Results suggest that the primary binding site of NY-S is located in the fragment C region of the HSA molecule, which is markedly hydrophobic and contains the single tryptophan residue.
Abstract: The location of Site I on the human serum albumin (HSA) molecule was investigated.Naphthol yellow- S (NY-S) was used as a representative ligand for Site I, since the bilirubin-displacing effect of NY-S was similar to that of Site I drugs such as warfarin and phenylbutazone.NY-S was bound to HSA with at least three classes of binding sites. The binding parameters of the primary class were one binding site (n1=1) and a binding constant (K1) of >107M-1, and the complex at equimolar ratio of dye to albumin exhibited metachromasy. The intrinsic fluorescence intensity, attributed to the single tryptophan residue (position 214), decreased significantly in this complex. Fragments A and C (residues 299-585 and 124-298, respectively, in the amino acid sequence of HSA) obtained by cyanogen bromide cleavage of HSA showed NY-S-binding ability.The binding of NY-S to fragment A or C aused the same metachromasy as seen with NY-S-HSA complex. Fragment C is markedly hydrophobic and contains the single tryptophan residue. The binding of NY-S to HSA was diminished by the chemical modification of lysine residues with pyridoxal 5'-phosphate (PLP). Further, lysine residues modified by PLP existed in fragment C.These results suggest that the primary binding site of NY-S, which corresponds to Site I, is located in the fragment C region of the HSA molecule.
TL;DR: The structure of ganoderic acid T was determined by the spectral data and X-ray analysis, and the structures of the other compounds were elucidated on the basis of their spectral data as discussed by the authors.
Abstract: New lanostane-type triterpenoids, ganoderic acids T, S and R were isolated from the cultured mycelia of Ganoderma lucidum. The structure of ganoderic acid T was determined by the spectral data and X-ray analysis, and the structures of the other compounds were elucidated on the basis of their spectral data.
TL;DR: From a comparison of the antitumor activities of 7 products derived by oxidizing RA-V with 2, 3-dichloro-5, 6-dicyano-p-benzoquinone and 6 native cyclic hexapeptides isolated from R. cordifolia, it is surmised that the active site in the RA-series is present at the α-side of RA molecules.
Abstract: New antitumor cyclic hexapeptides RA-IV, RA-III, RA-II and RA-I were isolated as minor constituents of Rubia cordifolia. Their structures were elucidated by means of various instrumental and chemical analyses. From a comparison of the antitumor activities of 7 products derived by oxidizing RA-V with 2, 3-dichloro-5, 6-dicyano-p-benzoquinone and 6 native cyclic hexapeptides isolated from R. cordifolia, it is surmised that the active site in the RA-series is present at the α-side of RA molecules.
TL;DR: In this article, a chemical examination of high-quality commercial rhubarb (Choukichio :?????? ) has led to the isolation and characterization of eight flavan-3-ol glucosides and three proanthocyanidin glucoside, together with several known compounds.
Abstract: A chemical examination of high-quality commercial rhubarb (Choukichio : ?? ?? ?? ) has led to the isolation and characterization of eight flavan-3-ol glucosides and three proanthocyanidin glucosides, together with several known compounds, i.e., (+)-catechin 5-O-β-D-glucopyranoside (1), (+)-catechin 7-O-β-D-glucopyranoside (2), procyanidin B-2 8-C-β-D-glucopyranoside (3) and procyanidin B-2 6-C-β-D-glucopyranoside (4). On the basis of chemical and spectroscopic evidence, the former compounds were characterized as (+)-catechin 3'-O-β-D-glucopyranoside (5), (+)-catechin 4'-O-β-D-glucopyranoside (6), (+)-catechin 7, 3'-di-O-β-D-glucopyranoside (7), (+)-catechin 5, 3'-di-O-β-D-glucopyranoside (8), (+)-catechin 3', 4'-di-O-β-D-glucopyranoside (9), (+)-catechin 5, 4'-di-O-β-D-glucopyranoside (10), (+)-catechin 8-C-β-D-glucopyranoside (11), (+)-catechin 6-C-β-D-glucopyranoside (12), procyanidin B-3 7-O-β-D-glucopyranoside (13), procyanidin B-1 8-C-β-D-glucopyranoside (14) and procyanidin B-1 6-C-β-D-glucopyranoside (15).
TL;DR: The utility of four urethane type N-protecting groups, benzyloxy carbonyl (Z), p-nitro-benzyloxycarbonyl [Z(NO2)], trichloroethoxycarboyl (Troc) and tert-butoxycarbONYl (Boc) groups, was tested in the ruthenium tetroxide (RuO4) oxidation of N-protected L-proline esters as discussed by the authors.
Abstract: The utility of four urethane type N-protecting groups, benzyloxycarbonyl (Z), p-nitro-benzyloxycarbonyl [Z(NO2)], trichloroethoxycarboyl (Troc) and tert-butoxycarbonyl (Boc) groups, was tested in the ruthenium tetroxide (RuO4) oxidation of N-protected L-proline esters. Three groups, but not the Z group, which was decomposed by RuO4, were found to be stable during the oxidation and afforded high yields of the corresponding L-pyroglutamic acid esters. Removal of the protecting groups from the oxidation products was carried out successfully in the usual manner to give N-unsubstituted (NH-type) L-pyroglutamic acid derivatives without racemization. The first transformation of L-proline into L-pyroglutamic acid and its derivatives has been accomplished.
TL;DR: Glycyrrhizin and carbenoxolon sodium showed no detectable inhibition of either enzyme at less than 10-4 M, and disodium salt of olean-12-ene-3β, 30-diol 3β,30-di-O-hemiphthalate inhibited 5-lipoxygenase most strongly.
Abstract: Glycyrrhetinic acid and fifteen derivatives of glycyrrhetinic acid including glycyrrhizin were examined to determine whether they inhibit the lipoxygenase and the cyclooxygenase activities of cloned mastocytoma cells. These compounds were more effective in inhibiting the lipoxygenase than the cyclooxygenase. Of these compounds, the disodium salt of olean-12-ene-3β, 30-diol 3β, 30-di-O-hemiphthalate inhibited 5-lipoxygenase most strongly (ID50, 5.8×10-6 M), whereas the half-inhibition dose for the cyclooxygenase was 5.6×10-5 M. Glycyrrhetinic acid, the aglycone of glycyrrhizin, slightly inhibited the lipoxygenase and the cyclooxygenase at a concentration of 10-4 M but had little effect at 10-5 M. Glycyrrhizin and carbenoxolon sodium showed no detectable inhibition of either enzyme at less than 10-4 M.
TL;DR: A number of lignans, including those isolated from Arctium lappa (Compositae), were subjected to Ca2+ antagonist assay and tranchelogenin had a potent and long-lasting antihypertensive effect on spontaneously hypertensive rats.
Abstract: A number of lignans, including those isolated from Arctium lappa (Compositae), were subjected to Ca2+ antagonist assay. The most potent activity occurred in trachelogenin, the calculated Ic50 and pA2 of which were 1.1×10-6 M and 6.60 respectively. Tranchelogenin had a potent and long-lasting antihypertensive effect on spontaneously hypertensive rats.
TL;DR: The methanolic extract of the aril of Myristica fragrans HOUTT had anti-plaque action against a cariogenic becterium, Streptococcus mutans and dehydrodi isoeugenol and 5'-methoxydehydrodiisoeugenols were identified as the major antibacterial principles.
Abstract: The methanolic extract of the aril of Myristica fragrans HOUTT. (mace) had anti-plaque action against a cariogenic becterium, Streptococcus mutans. Through fractionation of the extract followed by microbial assay by using the tube dilution technique, dehydrodiisoeugenol (1) and 5'-methoxydehydrodiisoeugenol (2) were identified as the major antibacterial principles. Both compounds completely inhibited the bacterial growth at a concentration of 12.5 μg/ml. During this experiment, threo-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propan-1-ol methyl ether (6) and guaiacin (8) were isolated for the first time from mace.
TL;DR: An antitumor glucan (SSG) was isolated from the culture filtrate of Sclerotinia sclerotiorum IFO 9395 by sequential use of ethanol precipitation, ion exchange chromatography on diethyl-aminoethyl-Sephadex A-25, and precipitation with ammonium sulfate and showed potent antitumors activity against the solid form of sarcoma 180 in ICR mice.
Abstract: An antitumor glucan (SSG) was isolated from the culture filtrate of Sclerotinia sclerotiorum IFO 9395 by sequential use of ethanol precipitation, ion exchange chromatography on diethyl-aminoethyl-Sephadex A-25, and precipitation with ammonium sulfate. From the results of methylation analysis and carbon-13 nuclear magnetic resonance spectroscopy, SSG was concluded to be a β-1, 3-D-glucan branched at position 6 of every two 3-substituted β-glucosyl units. SSG formed a complex with congo red in dilute alkali solution, and showed potent antitumor activity against the solid form of sarcoma 180 in ICR mice.