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A phytochemical investigation on the flesh fruits of atemoya led to the isolation of seven new kaurane type diterpenoids, (4S*,5S*,8S*,9R*,10S*,13R*,16R*)-16-hydro-18-nor-kauran-4,17-diol (1), (4S*,5S*,8S*,9R*,10S*,13R*,16S*)-18-nor-kauran-4,16,17-triol (2), (4S*,5S*,8S*,9R*,10S*,13R*,16S*)-17-acetoxy-18-nor-kauran-4,16-diol (3), (4S*,5S*,8S*,9R*,10S*,13R*,16R*)-18-nor-kauran-4,16,17-triol (4), (4S*,5S*,8S*,9R*,10S*,13R*,16S*)-17-acetoxy-16-hydro-18-nor-kauran-4-ol (5), (4R*,5S*,8S*,9R*,10S*,13R*,16S*)-16,17-dihydroxy-19-nor-kauran-4-hydroperoxide (6), and (4R*,5S*,8S*,9R*,10S*,13R*,16S*)-kauran-16,19-diol (7) along with 26 known ent-kaurane compounds. Their structures are determined on the basis of spectroscopic data and optical rotation. Compounds 1-5 were new 18-nor-kauran-4-ol type diterpenoids, which are very rarely obtained from natural sources.

Alkaline hydrolysis of crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae) yielded a new glycosidic acid, muricatic acid D; three known glycosidic acids, namely, muricatic acids A, B, and C; and three known organic acids, namely, isobutyric, 2S-methylbutyric, and 2S-methyl-3S-hydroxybutyric acid. Two new genuine resin glycosides with macrolactone structures (jalapins), muricatins X and XI, were also isolated from the fraction. Their structures were determined using spectroscopic data and chemical evidence.

Four hexaglycosides of methyl 3S,12S-dihydroxyhexadecanoate (1-4) were provided after treatment of the crude convolvulin fraction from Rhizoma Jalapae Braziliensis (the root of Ipomoea operculata (GOMES) MART., Convolvulaceae) with indium(III) chloride in methanol. The structures of 1-4 were elucidated on the basis of spectroscopic and chemical methods. Their sugar moieties were partially acylated with organic acids including (3S,9R)-3,6:6,9-diepoxydecanoic (exogonic) acid, (E)-2-methylbut-2-enoic (tiglic) acid, and isovaleric acid.

A new resin glycoside, named muricatin IX (1), was isolated from the seeds of Ipomoea muricata (L.) JACQ. (Convolvulaceae). The structure of 1 was determined on the basis of spectroscopic data as well as chemical evidence. Compound 1 is the first representative of resin glycosides in which an organic acid connects the sugar moiety and the aglycone moiety to form macrocyclic ester ring.

Four new resin glycosides, named calysolins XIV (1), XV (2), XVI (3), and XVII (4) were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM.. et SCHULT. (Convolvulaceae). Their structures were determined based on spectroscopic and chemical evidence, and consisted of two different types: those (1) with a macrolactone structure and those (2-4) with a non-macrolactone structure. Their sugar moieties were partially acylated by specific organic acids, including tiglic, 2S-methylbutyric, and 2S,3S-nilic acids. Additionally, evaluation of the antiviral activity of 1-4 revealed effects against the herpes simplex virus type 1.

Four new acylated glycosidic acid methyl esters were isolated after treatment of the crude ether-insoluble resin glycoside (convolvulin) fraction obtained from the seeds of Quamoclit pennata BOJER (Convolvulaceae) with indium(III) chloride in methanol. Their structures were elucidated on the basis of spectroscopic data and chemical conversions.

Four new resin glycosides having macrolactone structures (jalapins), named calysolins X (1)-XIII (4), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The sugar moieties of 1-4 were partially acylated by some organic acids, including tiglic acid, 2S-methylbutyric acid, and 2S,3S-nilic acid. Additionally, the antiviral activity of 1-4 toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.

Five new resin glycosides having macrolactone structures (jalapins), named calysolins V-IX (1-5), were isolated from the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae). Their structures were determined on the basis of spectroscopic data as well as chemical evidence. The isolated compounds could be classified into two macrolactone types-one having a 22-membered ring (1-4) and the other with a 27-membered ring (5). The sugar moieties of 1-5 were found to exist in partially acylated forms comprising 2S-methylbutyric acid and tiglic acid. Compounds 4 and 5 are the first representatives of the calysolic acid C as the component glycosidic acid. Additionally, the antiviral activity of 1-5, together with calysolins I-IV and soldanelline B, which are previously isolated jalapins from this plant, toward herpes simplex virus type 1 was evaluated. All the compounds showed antiviral activity.

Three new acylated methyl glycosides and two new acylated glycosidic acid methyl esters were isolated after treatment of the crude ether-insoluble resin glycoside (convolvulin) fraction from seeds of Quamoclit pennata BOJER (Convolvulaceae) with indium(III) chloride in methanol. Their structures were elucidated on the basis of spectroscopic data and chemical conversions.

Treatment of the ether-insoluble resin glycoside (convolvulin) fraction from seeds of Quamoclit pennata (Convolvulaceae) with indium(III) chloride in methanol provided three oligoglycosides of hydroxy fatty acid (glycosidic acid) methyl esters and two methyl glycosides, which were partially acylated by a glycosidic acid, 7S-hydroxydecanoic acid 7-O-β-D-quinovopyranoside (quamoclinic acid B) and/or two organic acids, (E)-2-methylbut-2-enoic (tiglic) acid and/or 3R-hydroxy-2R-methylbutyric (nilic) acid. Their structures were elucidated on the basis of spectroscopic data and chemical conversions.

Five new norlanostane-type triterpenoid glycosides were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae). Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.

An oxidative methyl esterification of aldehydes was effectively achieved. The trivalent indium reagent, indium(III) triflate, was revealed to accelerate the reactions in many cases. Aromatic aldehydes with various substituents were subjected to this method, and each produced the corresponding methyl esters in good to excellent yields within a relatively short reaction time.

Three new resin glycosides, quamoclins V (1), VI (2), and VII (3) and a new tetrahydropyran derivative, quamopyran (4), were isolated from the seeds of Quamoclit pennata BOJER (Convolvulaceae). The chemical structures of these compounds were determined primarily on the basis of spectroscopic data. The carboxyl group of the aglycone, 11S-convolvulinolic acid, of 1 and 2 was linked intermoleculary with a hydroxy group of the sugar moiety to form a macrocyclic ester structure, as in already known jalapins, and 3 was an acylated glycosidic acid methyl ester. All of the sugar moieties of 1-3 were acylated by one 2S-methylbutyric acid. Compound 4 was a diketone having a tetrahydropyran ring.

Two new norlanostane-type triterpenoid glycosides and a new phenylpropanoid glycoside were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae), along with two known alkaloids. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.

Three new norlanostane-type triterpene glycosides, scillanostasides A, B, and C, and two new lanostane-type triterpene glycosides, scillanostasides D and E, were isolated from the bulbs of Scilla scilloides Druce (Liliaceae) along with one known norlanostane-type triterpene heptaglycoside, scillascilloside G-1. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.

Garlicnin A (1), a new stable, sulfur-containing compound isolated from a fraction of the acetone extracts of Allium sativum L. garlic bulbs, showed the potential to suppress tumor cell proliferation by inhibiting the polarization of M2 alternatively activated macrophages, and its structure was characterized as 3,4-dimethyl-5-(4,5-dithia-1E,7-octadiene)-tetrahydrothiophene-2-sulfoxide-S-oxide, on the basis of the results of spectroscopic analysis results.

Three new 15-hydroxy-trinor type (1-3), a new tetranor type (4), and two new 3,15,23,24-tetrahydroxy-16-oxo type cycloartane glycosides (5, 6) were isolated from the rhizome of Cimicifuga heracleifolia KOMAROV. Their structures were determined by the use of the 2D-NMR techniques and chemical evidence.

Four new iridoid glucosides were isolated from the whole plant of Ajuga reptans L. (Labiatae) along with four known iridoid glucosides, one known diterpenoid glycoside, one known aliphatic alcohol glycoside, and three known ecdysteroids. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. The diterpenoid glycoside exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and H₂O₂ scavenging activities.

A new labdane-type diterpenoid glucoside and two new labdane-type diterpenoids were isolated from the fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with 14 known compounds comprising seven labdane-type diterpenoids, one halimane-type diterpenoid, two oleanane-type triterpenoids, two ursane-type triterpenoids, one aromadendrane-type sesquiterpenoid, and one flavonoid. Their structures were characterized on the basis of spectroscopic data as well as chemical evidence. Furthermore, the antioxidative activities of the flavonoid were evaluated using five different analyses.

Alkaline hydrolysis of the crude resin glycoside fraction of the leaves, stems, and roots of Calystegia soldanella ROEM. et SCHULT. (Convolvulaceae) gave four new glycosidic acids, named calysolic acids A, B, C, and D, along with one known glycosidic acid, soldanellic acid B, and three organic acids, 2S-methylbutyric, tiglic, and 2S,3S-nilic acids. The structures of the new glycosidic acids were characterized on the basis of spectroscopic data and chemical evidence.

A new dolabellane diterpene glycoside, named squoside A, and three new cycloartane glycosides, named squarrosides V, VI, and VII, have been isolated from the dried aerial parts of Thalictrum squarrosum (Ranunculaceae). Their structures were determined by two dimensional (2D) NMR spectroscopic analysis and chemical evidence.

Four new ent-kaurane diterpenoids (16R)-ent-kauran-17,19-diol (1), (16R)-17-hydroxy-ent-kauran-19-oic acid (2), (16S)-17-hydroxy-ent-kauran-19-oic acid (3), and (16R)-17-dimethoxy-ent-kauran-19-oic acid (4) have been isolated from the fresh fruits of Annona cherimola together with eight known compounds. Their structures are determined on the basis of spectroscopic data and optical rotation.

Three new labdane-type diterpenoids, viteagnusins F, G, and H, were isolated from the hexane extract of fruit (chasteberry) of Vitex agnus-castus L. (Verbenaceae) along with seven known compounds including four labdane-type diterpenoids, one norlabdane-type diterpenoid, one aromadendrane-type sesquiterpenoid, and one flavonoid. The chemical structures of the three new labdane-type diterpenoids were determined on the basis of spectroscopic data as well as chemical evidence.

Novel Cucurbitane-type glycosides, 5beta,19beta-epoxy-29-nor-3,11-dioxo-cucurbit-24-ene-27-oic acid 27-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1) and 19,29-nor-3,11-dioxo-cucurbit-4,24-diene-27-oic acid 27-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (2) were isolated from the roots of Siraitia grosvenori SWINGLE.

Besides 12 known glycosides, five new steroidal glycosides have been isolated from the stems of Solanum sodomaeum L. (Solanaceae). The chemical structures of these five glycosides were determined on the basis of spectroscopic data as well as chemical evidence, and the structure of one known steroidal glycoside was corrected.

A new characteristic steroidal glycoside of the 23S,26R-hydroxylated spirostanol-type named indioside F was isolated from the fruit of Solanum indicum, along with indioside A and protodioscin. On the basis of spectroscopic analysis, the structure of indioside F was found to be 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranosyl (beta-chacotriosyl) (22R,23S,25R,26R)-spirost-5-ene-3beta,23,26-triol.

Two new guaiane-type sesquiterpene (1, 2), 2 new phenylpropanoid derivatives (3, 4), and 5-oxo-11-hydroxy-8(Z)-undecenoic acid 11-O-glucoside (5), together with 17 known compounds have been isolated from the whole plants of Youngia japonica (L.) Dc., which have been known to be used as folk medicines to treat people suffering from atopy. The guaiane-type sesquiterpene, grosheimin (17) exhibited strong antiallergic and antioxidant activities.

Four acyclic diterpene glycosides were extracted from Habanero, the fruits of Capsicum chinense JACQ., which is known as one of the hottest peppers in existence. Two of these glycosides were identified as capsianoside XIII and capsianoside XV. The other two were new ones and were characterized as 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 17,19-dihydroxy-6E,10E,14Z-(3S)-geranyllinalool 17-O-beta-D-glucopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside and 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 6E,10E,14Z-(3S)-17-hydroxy-geranyllinalool 17-O-[3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 6'E,10'E,14'Z-(3'S)-13'R,19'-dihydroxy-geranyllinalool-16'-oyl (16'-->2)-[alpha-L-rhamnopyranosyl-(1-->3)]-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->6)]-beta-D-glucopyranoside.

Three new steroidal glycosides, named solaviasides A, B, and C, have been isolated from the fruits of Solanum viarum DUNAL (syn. S. khasianum var. chatterjeeanum, Solanaceae), along with seven known ones. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence.

Two new halimane-type diterpenoids, viteagnusins A and B, and three new labdane-type diterpenoids, viteagnusins C, D, and E, were isolated from the fruit of Vitex agnus-castus L. (Chasteberry, Verbenaceae) along with two known diterpenoids. Their chemical structures were determined on the basis of spectroscopic data.

Two new cycloartane glycosides, named aquilegiosides K and L, have been isolated from the dried underground parts of Aquilegia vulgaris. Their structures were determined by two dimensional (2D) NMR spectroscopic analysis and chemical evidence.

A new pregnane glycoside, 3-O-beta-lycotetraosyl 5alpha-pregna-3beta,26beta-diol-20-one was isolated from overripe tomato, the fruit of Lycopersicon esculentum MILL.

Two new C(28) steroidal glycosides, tuboanosides A (1) and B (2), were isolated from the fruit of Tubocapsicum anomalum MAKINO. Their chemical structures were elucidated on the basis of spectroscopic and X-ray diffraction analysis of the p-bromobenzoyl derivative (4) of tuboanosigenin (3), the sapogenol derivative of these two glycosides. Tuboanosides have the structural peculiarity of an unusual side chain carrying an unusual linkage with a C-21 bound to C-25 on the lactone ring.

Two new labdane diterpene glycosides, named aquosides A and B, and a new megastigmane glycoside, named aquoside C, have been isolated from the air-dried aerial parts of Aquilegia hybrida together with three known compounds comprising a phenolic glycoside and two flavone C-glycosides. Their structures were determined on the basis of spectroscopic data and chemical evidence.

Conversion of the spirosolane-type glycoside, esculeoside A, a major component contained in the ripe tomato Lycopersicon esculentum fruits, into a solanocapsine-type sapogenol, esculeogenin B-2, (5alpha,22S,23R,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, and esculeogenin B-1, (5alpha,22R,23S,25S)-22,26-epimino-16beta,23-epoxy-3beta,23,27-trihydroxycholestane, which are rare naturally occurring compounds was attained by acid hydrolysis with 2 N HCl in dioxane and water (1 : 1).

Previously, we reported an interesting reaction by which esculeogenin A [(5alpha,22S,23S,25S)-3beta,23,27-trihydroxyspirosolane], a sapogenol of tomato-saponin, esculeoside A, was easily converted into a pregnane derivative, 5alpha-pregn-16-en-3beta-ol-20-one, merely by refluxing with pyridine and water. Its chemical mechanism including air oxidation is here described.

A new homostilbene, named scillabene A (2), and two new homoisoflavones, named scillavones A (3) and B (4), were isolated from the bulbs of Scilla scilloides DRUCE (Liliaceae) along with 13 known compounds comprising a homostilbene, seven homoisoflavones, a xanthone, a lignan, and three nortriterpenes. The structures of 2-4 were characterized as 3,5,4'-trihydroxy-3'-methoxy-4-methyl-trans-stilbene, (3R)-5,7,2'-trihydroxy-3',4'-dimethoxyspiro{2H-1-benzopyran-7'-bicyclo[4,2,0]octa[1,3,5]-trien}-4-one and (3S)-3-(3,4-dihydroxybenzyl)-5-hydroxy-6,7-dimethoxychroman-4-one, respectively, on the basis of spectroscopic data and X-ray crystallographic analysis.

Three new steroid glycosides named trikamsterosides C, D and E were isolated from the underground parts of Trillium kamtschaticum PALL. (Liliaceae) along with two known 18-norspirostanol glycosides trillenosides A and B. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence.

Three new 15,16-seco-cycloartane glycosides, which were constructed by a C-C bond cleavage in the D ring, have been isolated from Cimicifuga Rhizome for the first time. Their structures were determined by the use of 2D NMR techniques and chemical evidence.

Three new monoterpenoids, called genipacetal, genipamide, and genipaol, were isolated from the fruit of Genipa americana L. (Rubiaceae), along with the four known iridoids genipin, gardendiol, deacetyl asperulosidic acid methyl ester, and shanzhiside. Their chemical structures were determined on the basis of spectroscopic data.

Two new steroid glycosides, named trikamsterosides A and B, and a new sesquiterpenoid glycoside named trikamsesuquiside A were isolated from the underground parts of Trillium kamtschaticum PALL. along with 18 known compounds comprising 12 steroids, one sesquiterpenoid glycoside, one phenylpropanoid, one flavonoid glycoside, and three phenylpropanoid sucrose esters. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence. Among them, one phenylpropanoid sucrose ester showed almost the same radical-scavenging effect on 1,1-diphenyl-2-picrylhydrazyl as that of alpha-tocopherol.

Four new triterpene glycosides, named nigellosides A, B, C, and D, were from the air-dried aerial parts of Nigella damascena L. (Ranunculaceae), and the structures were elucidated on the basis of spectroscopic data including 2D NMR spectra and chemical evidence. Their chemical structures have been characterized as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl gypsogenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl gypsogenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl hederagenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, and 3-O-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyl hederagenin 28-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester.

Three new C(28) steroidal glycosides, isotubocaposides A (1), B (2), and C (3), were isolated from the fruits of Tubocapsicum anomalum MAKINO. Their chemical structures were elucidated on the basis of spectroscopic and X-ray diffraction analysis of p-bromobenzoyl derivative (5) of isotubocaposigenin (4), the sapogenol derivative of these three glycosides. Isotubocaposides have the structural peculiarity of an unusual side chain carrying a C-21 bound to C-24 on the lactone ring.

Two new 15-deoxycimigenol-type (1, 2) and three new 24-epi-cimigenol-type glycosides (3-5) were isolated from Cimicifuga Rhizome, and the structures were elucidated on the basis of spectroscopic data including 2D NMR spectra and chemical evidence. The two new 15-deoxycimigenol-type glycosides were the first cimigenol-type glycosides lacking a hydroxyl group at C-15.

Two new steroidal alkaloid glycosides, esculeosides C and D, have been isolated from the ripe fruit of Cherry tomato [Lycopersicon esculentum var. cerasiforme (DUNAL) ALEF.], along with three known steroidal alkaloid glycosides, esculeoside A, esculeoiside B, and lycoperoside G. Their chemical structures were determined on the basis of spectroscopic data.

A new steroidal glycoside has been isolated from the underground parts of Solanum sodomaeum L., along with seven known steroidal glycosides. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence, and the structure of one known pregnane type glycoside was corrected. In addition, their antiproliferative activity against human promyelocytic leukemia (HL-60) cells was investigated, and five compounds exhibited stronger activity than cisplatin.

Two new 15,16-seco-cycloartane glycosides (1, 2) were isolated from Cimicifuga Rhizome. Their structures were determined by spectroscopic analysis.

Two new tetranor-cycloartane glycosides (1, 2) were isolated from Cimicifuga Rhizome. Their structures were determined by spectroscopic analysis. These compounds suggested the existence of a biogenetic pathway into C-23 lactone-type cycloartane glycosides.

By using beta-cyclodextrin-inclusion as a unique technique, an efficient separation of pharmacologically active phenolic compounds from Brazilian propolis was achieved to provide one new compound, 3-(3-hydroxy-3-methyl-butyl)-5-prenyl-4-hydroxycinnamic acid, together with two common cinnamic acid derivatives, artepillin C and capillartemisin A, and two known flavanols, aromadendrin and 3,5,7-trihydroxy-4'-methoxyflavanol.

Four new cycloartane glycosides, named aquilegiosides G-J, were isolated from the dried aerial parts of Aquilegia vulgaris. Their structures were determined by spectroscopic analysis and chemical evidence.