Biomedical subjects
Publications and source records attributed to S Arihara.
Two new steroid derivatives, (22E,24R)-3alpha-ureido-ergosta-4,6,8(14),22-tetraene (1) and (22E,24R)-5alpha,8alpha-epidioxyergosta-6,9,22-triene-3beta-ol 3-O-beta-D-glucopyranoside (2) were isolated from the fruit bodies of Chlorophyllum molybdites (Agaricaceae). The structures were established by spectroscopic and chemical methods. These compounds exhibited cytotoxicity against Kato III cells.
A new benzofuran glycoside, masutakeside I (1) and a new C10 acetylenic acid, masutakic acid A (2) were isolated from the fruiting bodies of the fungus Laetiporus sulphureus var. miniatus. Their structures were established by spectroscopic and chemical methods. The known compounds 3-6 were also obtained and identified as egonol, demethoxyegonol, egonol glucoside and egonol gentiobioside. Some of these compounds exhibited cytotoxicity against Kato III cells.
Two novel steroids, polasterol A (1) and polasterol B sulfate (2), along with two known compounds, 22(E),24-isopropylcholesta-5, 22-dien-3 beta-ol (3) and halistanol sulfate (4), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1 and 2 were determined as 3 beta-hydroxy-24-isopropylcholesta-5, 22(E)-dien-7-one and 24xi-isopropenylcholesta-22(Z), 28(29)-diene-2 beta,3 alpha,6 alpha-triyl trisodium sulfate on the basis of spectroscopic investigations and a chemical conversion.
Four cycloartane triterpenes, cyclopassifloic acids A (1), B (2), C (3), and D (4), and six related saponins, cyclopassiflosides I (5), II (6), III (7), IV (8), V (9), and VI (10), were isolated from the leaves and stems of Passiflora edulis, and their structures were elucidated on the base of extensive NMR experiments and chemical methods. Cyclopassifloic acids A-D were assigned as 22(R), 24(S)-1alpha,3beta,22,24,31-pentahydroxy-24-methylcycloartan -28-oic acid; 24(S)-1alpha,3beta,24, 31-tetrahydroxy-24-methylcycloartan-28-oic acid; 20(S),24(S)-1alpha, 3beta,21,24,31-pentahydroxy-24-methylcycloartan-28-oic acid; and 22(R)-1alpha,3beta,22-trihydroxy-24-oxocycloartan-28-oic acid, respectively. Cyclopassiflosides I-VI, in turn, were established as the 28-O-beta-D-glucopyranosides of cyclopassifloic acids A-D. Finally, cyclopassiflosides III and V were demonstrated as the 28, 31-bis-O-beta-D-glucopyranosides of cyclopassifloic acids B and C, respectively. Also obtained in this investigation were the known compounds passiflorin (11) and passifloric acid (12).
Three cycloartane triterpenes, cyclopassifloic acids E (1), F (2), and G (3), and their saponins, cyclopassiflosides VII (4), VIII (5), IX (6), X (7), and XI (8), were isolated from the leaf and stem parts of Passiflora edulis. The structures of 1-8 were elucidated on the basis of extensive NMR experiments and by chemical methods.
Two novel steroids with a cyclopropane ring at C-25 and C-26, 7-oxopetrosterol (1) and 7alpha-hydroxypetrosterol (2), along with two known compounds, petrosterol (3) and 23,24-dihydrocalysterol (4), have been isolated from the Japanese marine sponge Strongylophora corticata. The structures of 1 and 2 were determined as 26, 27-cyclo-24,27-dimethyl-3beta-hydroxycholest-5-en-7-one and 26, 27-cyclo-24,27-dimethylcholest-5-en-3beta,7alpha-diol on the basis of spectroscopic investigations.
Four new oleanane-type triterpene glycosides, madlongisides A-D (1-4), were isolated from the seeds of Madhuca longifolia, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds mimusopside A, Mi-saponins A, B, and C, and 3-O-beta-D-glucopyranosyl protobassic acid.
Oligosaccharides A, B, and C (1-3, respectively) were isolated from the stem of Hoya carnosa. Their structures were established by NMR and chemical methods. Compounds 1 and 2 were 6-deoxy-3-O-methyl-beta-allopyranosyl(1-->4)-beta-cymaropyranosyl( 1-- >4)-beta-cymaropyranosyl(1-->4)-beta-cymaronic acid delta-lactone and 6-deoxy-3-O-methyl-beta-allopyranosyl(1-->4)-beta-oleandropyranosyl++ +(1 -->4)-beta-cymaropyranosyl(1-->4)-beta-cymaronic acid delta-lactone, respectively. Compound 3 was the sodium salt of 2.
Two new polyhydroxylated sterols, dendronesterols A (1) and B (2), have been isolated from the octocoral Dendronephthya gigantea. The structures of 1 and 2 were proposed on the basis of extensive NMR experiments. Compound 2 was found to be weakly cytotoxic toward L1210 cells.
The stem of Stephanotis floribunda afforded a new cyclic pentapeptide stephanotic acid (1), possessing a novel 6-(leucin-3'-yl) tryptophan skeleton. The structure of 1 was assigned on the basis of extensive NMR experiments and a chemical reaction and shown to be closely related to the bicyclic octapeptide moroidin (3), a toxin from Laportea moroides.
From the fresh fruits of Strrax japonica Sieb. et Zucc., four new triterpenoid glycosides, named jegosaponins A-D (1-4), were isolated. Their structures were determined on the basis of spectroscopic data and chemical evidence. Compounds 1-4 are 3-O-tetraglycosides of barringtogenol C having an acetyl and a tigloyl or a (2Z)-hexenoyl groups at C-21, 22 and 28. The acylated saponins, 1-4, all showed antisweet activity.
Five lanostane triterpenes, named versisponic acids A-E and three lanostanoid glycosides, laetiposides E-G, were isolated from the fruit bodies of Laetiporus versisporus. Their structures were established by extensive NMR experiments and chemical methods.
Four new lanostanoid glycosides, 3beta, 7alpha-dihydroxy-24-methylene-lanost-8-en-21-oic acid 7-O-beta-D-glucopyranoside (1), 3beta,7alpha-dihydroxy-lanost-8, 24-dien-21-oic acid 7-O-beta-D-glucopyranoside (2), 7alpha-hydroxy-3-keto-lanost-8,24-dien-21-oic acid 7-O-beta-D-glucopyranoside (3), and 7alpha-hydroxy-3-keto-24-methylene-lanost-8-en-21-oic acid 7-O-beta-D-glucopyranoside (4) were isolated from the fruit bodies of Laetiporus versisporus. Compounds 1-4 were named laetiposides A-D, respectively. Their structures were established by extensive NMR experiments and chemical methods.
The structural elucidation of eleven new related polyoxypregnane glycosides, gymnepregosides G (1), H (2), I (3), J (4), K (5), L (6), M (7), N (8), O (9), P (10) and Q (11), from the roots of Gymnema alternifolium (Asclepiadaceae) was achieved by a detailed study of 1H- and 13C-NMR spectral data and chemical means. The results obtained for new compounds, 1-11, show that they are (20S)-pregn-6-ene-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptaol 3-O-glycosides, and all the sugars at C-3 are beta(i-->4)-linked. Some of them possess benzoyl, (E)- and (Z)-cin-namoyl, and tigloyl residues as the ester linkages located at C-12 and/or C-20 of the aglycone.
Two 2-hydroxy-2-benzylcoumaranone glycosides, 2,4, 6-trihydroxy-2-[(4'-hydroxyphenyl) methyl]-3(2H)-benzofuranone-4-yl-beta-D-glucopyranoside (maesopsin 4-O-glucoside) (1) and 2,4,6-trihydroxy-2-[(4'-hydroxyphenyl) methyl]-3(2H)-benzofuranone-4-yl-beta-D-glucopyranosido-4'-y l-alpha-L -rhamnopyranoside (maesopsin 4-O-glucosido 4'-O-rhamnoside) (2), two neolignan glycosides, 2R-(E)-2, 3-dihydro-2-(4'-hydroxy-3'-methoxylphenyl)-5-(3"-hydroxy-1"-pro pen yl) -7-methoxy-3-benzofuranmethanol-4'-yl-beta-D-glucopyranosyl-(1-->3 )-[ beta-D-glucopyranosyl-(l-->2)]-beta-d-glucopyranoside (3) and (threo) 1-(4'-hydroxy-3'-methoxy)-2-(4"-hydroxymethyl-2", 6"-dimethoxyphenoxy)-propane-1,3-diol-4'-yl-beta-d-glucopynosid e (4), and a phenylpropanoid glycoside, 3-methoxy-5-(2'-propenyl)-1, 2-benzenediol-1-yl-beta-D-apiofuranosyl-(1-->6)-beta-D- glucopyransodie (5) were isolated from the bark of Hovenia trichocarea. Compounds 1-5 were named hovetricosides C-G, respectively, and their structures were established by extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds acanthoside B, kelampayoside A, shashenoside I, and 3,4, 5-trimethoxyphenol-1-O-beta-D-xylopyranosyl-(1-->6)-beta-D- glucopyranoside.
Four new oleanane-type triterpene glycosides, proceraosides A-D (1-4), were isolated from the seeds of Albizia procera. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and a monoterpenic carboxylic acid linked to a monoterpene quinovoside as the acyl moiety at C-21. The common oligosaccharide moiety linked to C-28 in 1-3 was determined as alpha-l-arabino- furanosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-rhamnopyranosy l- (1-->2)-beta-D-glucopyranosyl ester. These compounds differed in the C-3-linked sugar unit or in the configuration of C-6' of the inner monoterpene moiety in the C-21-linked acyl unit. Compound 4 was established as the 16-deoxy analogue of 1.
Three new diterpenes, polasols A-C (1-3), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1-3 were assigned primarily by 2D NMR methods.
Two 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol 1-O-glucosides, hovetrichosides A (1) and B (2), were isolated from the bark of Hovenia trichocarpa. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1 and 2 were (1R), (2S)-1-(4-hydroxy-3-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-1, 3-propanediol 1-O-beta-D-glucopyranoside and (1S), (2R)-1-(4-hydroxy-3-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-1, 3-propanediol 1-O-beta-D-glucopyranoside, respectively.