Two new steroidal derivatives from the fruit body of Chlorophyllum molybdites.

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 benzofuran glycoside and an acetylenic acid from the fungus Laetiporus sulphureus var. miniatus.

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.

New cycloartane triterpenoids from Passiflora edulis.

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 new 26,27-cyclosterols from the marine sponge Strongylophora corticata.

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.

Five lanostane triterpenoids and three saponins from the fruit body of Laetiporus versisporus.

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 cycloartane triterpenoids and six related saponins from Passiflora edulis.

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).

New 24-isopropylcholesterol and 24-isopropenylcholesterol sulfate from the marine sponge Epipolasis species.

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.

Antisweet natural products. XV. Structures of Jegosaponins A-D from Styrax japonica Sieb. et Zucc.

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.

Polyhydroxylated sterols from the octocoral Dendronephthya gigantea.

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.

Stephanotic acid, a novel cyclic pentapeptide from the stem of Stephanotis floribunda.

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.

Oligosaccharides from Hoya carnosa.

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.

New oleanene triterpenoid saponins from Madhuca longifolia.

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.

Pregnane glycosides, gymnepregosides G-Q from the roots of Gymnema alternifolium.

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.

New lanostanoid glycosides from the fruit body of laetiporus versisporus

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.

A new bromopyrrole alkaloid and the optical resolution of the racemate from the marine sponge homaxinella sp

A new bromopyrrole alkaloid (1) along with (+/-)-2 and (+/-)-longamide (3) has been isolated from the Japanese marine sponge Homaxinella sp. The structures of the compounds were proposed on the basis of spectroscopic data. The optical resolution of (+/-)-2 by chiral HPLC was successful and afforded the two enantiomers, (+)-2 and (-)-2.

Peroxypolasol and mugipolasol: two novel diterpenes from the marine sponge epipolasis sp

Two novel diterpenes, peroxypolasol (1) and mugipolasol (2), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1 and 2 were determined on the basis of spectroscopic data. Compound 1 is a diterpene with a peroxide ring in the side chain, and 2 is an unusual six/five-membered ring diterpene with an ethyl unit at C-2.

Isolation and absolute structures of enantiomeric 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol 1-O-glucosides from the bark of Hovenia trichocarpa.

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.

Pregnane glycosides, gymnepregosides A-F from the roots of Gymnema alternifolium.

The structural elucidation of six new related polyoxypregnane glycosides, gymnepregosides A (1), B (2), C (3), D (4), E (5) and F (6), together with two known compounds, from the roots of Gymnema alternifolium (Asclepiadaceae) was achieved through on a detailed study of 1H- and 13C-NMR spectral data and chemical means. The results obtained for new compounds, 1-6, show that they are (20S)-pregn-6-ene-3 beta,5 alpha,8 beta,12 beta,14 beta,17 beta,20-heptaol or sarcostin 3-O-glycosides, and all the sugars at C-3 are beta(1-->4)-linked. Some of them possessed benzoyl, cinnamoyl and tigloyl residues as the ester linkages located at C-12 and/or C-20 of the aglycon.

Polasols A-C, three new diterpenes from the marine sponge Epipolasis sp.

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.

Hovetrichosides C-G, five new glycosides of two auronols, two neolignans, and a phenylpropanoid from the bark of Hovenia trichocarea.

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.