New sterols and triterpenoids from four edible mushrooms.

Four edible mushrooms, Panellus serotinus, Lepista nuda, Tricholoma matsutake and Naematoloma sublateritium, have been investigated chemically. Two new sterols, 5alpha,9alpha-epidioxy-(22E)-ergosta-7,22-diene-3beta,6alpha-diol (1) and 5alpha,9alpha-epidioxy-(22E)-ergosta-7,22-diene-3beta,6beta-diol (2), have been isolated from Panellus serotinus. Compound 2 was also isolated from Lepista nuda. A new sterol, 3beta,5alpha,9alpha,14beta-tetrahydroxy-(22E)-ergosta-7,22-dien-6-one (3), and compound 2 have been isolated from Tricholoma matsutake. Three new triterpenoids, sublateriols A-C (4-6), have been isolated from Naematoloma sublateritium. The structures of the new compounds were elucidated on the basis of their spectral data.

Studies on the constituents of Catalpa species. VI. Monoterpene glycosides from the fallen leaves of Catalpa ovata G. Don.

Five new monoterpene glycosides, ovatolactone 7-O-(6'-O-p-hydroxybenzoyl)-beta-D-glucopyranoside, ovatic acid methyl ester 7-O-(6'-O-p-hydroxybenzoyl)-beta-D-glucopyranoside, 7-O-p-hydroxybenzoylovatol 1-O-(6'-O-p-hydroxybenzoyl)-beta-D-glucopyranoside, 6'-O-p-hydroxybenzoylcatalposide and (2E,6R)-2,6-dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside were isolated from the fallen leaves of Catalpa ovata G. Don. Their structures were determined by extensive spectroscopic studies and syntheses.

Secoiridoid glycosides from Gentiana scabra.

Two new secoiridoid glycosides, 4'-O-beta-D-glucopyranosylgentiopicroside (1) and 6'-O-beta-D-glucopyranosylgentiopicroside (2), have been isolated from the rhizomes and roots of Gentiana scabra together with three known compounds, olivieroside, 1-O-beta-D-glucopyranosylamplexine, and benzyl alcohol O-alpha-L-arabinopyranosyl (1 --> 6)-beta-D-glucopyranoside. The structures of 1 and 2 were elucidated using chemical and physicochemical (MS and NMR) studies.

Structures of new ceramides from the fruit bodies of Grifola frondosa.

Four new phytosphingosine-type ceramides, (2S,3S,4R)-2-[(2'R)-2'-hydroxydocosanoylamino]-1,3,4-octadecane triol (1), (2S,3S,4R)-2-[(2'R)-2'-hydroxytricosanoylamino]-1,3,4-octadecan etriol (2), (2S,3S,4R)-2-[(2'R)-2'-hydroxypentacosanoylamino]-1,3,4-octadec anetriol (3) and (2S,3S,4R)-2-[(2'R)-2'-hydroxyhexacosanoylamino]-1,3,4-octadeca netriol (4), have been isolated from the fruit bodies of Grifola frondosa. The structures of the new compounds were elucidated on the basis of their spectral data.

Studies of the constituents of Gardenia species. II. Terpenoids from Gardeniae Fructus.

Four new terpenoids, gardenate A (1), 2-hydroxyethyl gardenamide A (2), (1R,7R,8S,10R)-7,8,11-trihydroxyguai-4-en-3-one 8-O-beta-D-glucopyranoside (3) and Jasminoside F (4), were isolated from Gardeniae Fructus. Their structures were established on the basis of spectral analysis.

Sterol constituents from two edible mushrooms, Lentinula edodes and Tricholoma matsutake.

Two new sterols, (22E)-23-methylergosta-5,7,22-trien-beta-ol (1) and 5alpha,6alpha-epoxy-(22E)-ergosta-8,14,22-triene -3beta,7alpha-diol (2), have been isolated from two edible mushrooms, Lentinula edodes and Tricholoma matsutake, respectively, together with twelve known ones (3-14). The structures of the new compounds were elucidated on the basis of their spectral data.

Secoiridoid glycosides from the flower buds of Lonicera japonica.

Two secoiridoid glycosides, loniceracetalides A and B, were isolated in very small amounts, together with 10 known iridoid glycosides, from the flower buds of Lonicera japonica. The structures of loniceracetalides A and B were determined by spectroscopic analysis.

[Studies on the constituents of Ligustrum species. XIX. Structures of iridoid glucosides from the leaves of Ligustrum lucidum AIT].

Two new iridoid glucosides, named iso-8-epikingiside and 8-demethyl-7-ketologanin, were isolated together with 8-epikingiside, kingiside, ligustroside, 10-hydroxyligustroside, ligustaloside A and ligustaloside B from the leaves of Ligustrum lucidum AIT. (Oleaceae). The stereochemical structures of these new compounds were elucidated on the basis of spectroscopic evidence.