Terpenic and phenolic glycosides from leaves of Breynia officinalis HEMSL

From the leaves of Breynia officinalis, collected on Okinawa Island, six terpenic glucosides and six phenolic glycosides were isolated. Two of the terpenic glucosides were found to be known, and they were identified as turpinionoside B and betulalbuside A. The structures of the remaining terpenic glucosides were elucidated to be megastigmane glucosides, named breyniaionosides A-D, using spectroscopic analyses. The absolute structure of breyniaionoside D was determined using the modifed Mosher's method. The absolute structure of the known compound betulalbuside A was determined for the first time in this study. Six phenolic glycosides were found to be arbutin and its derivatives. Two known compounds were found to be robustaside A and eximine. New compounds were named isorobustaside A, and breyniosides A and B, and their structures were elucidated from spectroscopic evidence.     

New lignan glycosides from Cissus quadrangularis stems

Phytochemical investigation of Cissus quadrangularis stems led to the isolation of one new phenolic glycoside (1) and two new lignan glycosides (7 &; 8) along with twelve known compounds (2–6 &; 9–15). Their chemical structures were determined on the basis of extensive spectroscopic analysis using 1D, 2D NMR, and mass spectrometric analysis. Among the known compounds, 4–6, 9 and 12 were isolated for the first time from the genus Cissus whereas compounds 10, 11 and 13 for the first time from this plant.     

New phenolic glycosides from the seeds of Cucurbita moschata

Five new phenolic glycosides, cucurbitosides A-E (1-5), were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as 2-(4-hydroxy)phenylethanol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1), 2-(4-hydroxyphenyl)ethanol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2), 4-hydroxybenzyl alcohol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (3), 4-hydroxybenzyl alcohol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (4) and 4-hydroxyphenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (5) on the basis of spectroscopic analysis and chemical evidence.     

New flavonoid glycosides from the leaves of Solidago altissima

Two new flavonoid glycosides kaempferol 3-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (1), and quercetin 3-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (2), together with six known flavonoid glycosides were isolated from the leaves of Solidago altissima L. grown in Kochi of Japan. The structure elucidation of the isolated compounds was performed by acid hydrolysis and spectroscopic methods including UV, IR, ESI-MS, 1D- and 2D-NMR experiments.     

New oleanene glycosides from the leaves of Acanthopanax japonicus

The structures of 6 new oleanene glycosides (1--6) isolated from the leaves of Acanthopanax japonicus FRANCH et. SAVART (Araliaceae) were elucidated by mass, 1D, and 2D NMR spectroscopy. The structures of 1--6 were established as 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester of 3beta,23-dihydroxy-olean-12-en-28,29-dioic acid, 3beta,30-dihydroxy-olean-12-en-23,28-dioic acid, 3beta,29-dihydroxy-olean-12-en-23,28-dioic acid (=dianic aicd), 3beta-dihydroxy-olean-12-en-23,28-dioic acid (=gypsogenic acid), 3beta,29-dihydroxy-23-oxo-olean-12-en-28-oic acid, and 3beta-hydroxy-23-oxo-olean-12-en-28,29-dioic acid, designated acanjaposide D (1), E (2), F (3), G (4), H (5), and I (6), respectively.     

New flavonol glycosides from the leaves of Caragana brachyantha

Two new flavonol glycosides, brachysides C and D, together with three known flavonol glycosides, were isolated from the leaves of Caragana brachyantha. The structures of brachysides C and D were elucidated on the basis of detailed spectroscopic analysis as quercetin 5-O-[α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside]-7-O-[α-l-rhamnopyranoside] and quercetin 5-O-[α-l-rhamnopyranosyl-(1 → 6)-β-d-glucopyranoside]-7-O-[α-l-rhamnopyranoside]-4′-O-[α-l-rhamnopyranoside], respectively. The presence of flavonol tetra- and triglycosides bearing a sugar moiety at position 5 was the first report from this genus Caragana.     

New cholestane glycosides from the leaves of Cordyline terminalis

Four new cholestane glycosides (1-4) were isolated from the leaves of Cordyline terminalis (Agavaceae). The structures of the new compounds were determined on the basis of spectroscopic analysis and a few chemical transformations followed by chromatographic and spectroscopic analyses.     

New phenolic compounds from the leaves of Artocarpus heterophyllus

One new 2-arylbenzofuran derivative, artocarstilbene B(1), one new benzaldehyde derivative,(E)-3,5-dihydroxy-4-(3-methylbut-1-enyl)benzaldehyde(2), as well as 18 known compounds(3–20) were obtained from the leaves of Artocarpus heterophyllus. Their structures were elucidated on the basis of extensive spectroscopic techniques including 2D NMR and HR-ESIMS. Many compounds exhibited moderate to weak inhibitory activity against the proliferation of the PC-3, NCI-H460, and A549 cancer cell lines.     

Triterpene glycosides from the stems of Akebia quinata

The stems of Akebia quinata have been analyzed for their triterpene glycoside constituents, resulting in the isolation of six new triterpene glycosides, along with 19 known ones. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were deter-mined to be 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]olean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucuronopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid O-alpha-L-rhamnopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid, and 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid, respectively. The main triterpene glycosides contained in the stems of A. quinata were found to have two sugar units at C-3 and C-28 of the aglycone in this study, whereas those of Akebia trifoliate were reported to possess one sugar unit at C-28 of the aglycone. It may be possible to distinguish between A. quinata and A. trifoliate chemically by comparing their triterpene glycoside constituents.     

Studies on the constituents of Lonicera species. XVII. New iridoid glycosides of the stems and leaves of Lonicera japonica THUNB

Four new iridoid glycosides, named L-phenylalaninosecologanin (1), 7-O-(4-beta-D-glucopyranosyloxy-3-methoxybenzoyl)secologanolic acid (2), 6'-O-(7alpha-hydroxyswerosyloxy)loganin (3) and (Z)-aldosecologanin (5), were isolated, together with a known one, newly named (E)-aldosecologanin (4), from the stems and leaves of Lonicera japonica. Their structures were established on the basis of chemical and spectral data.     

New Clerodane Diterpenoids from Casearia membranacea

Bioassay‐guided fractionation of an AcOEt extract of Casearia membranacea resulted in the isolation of six new clerodane diterpenes, caseamembrins G–L ( 1 – 6 ). The structures of the new compounds, including their relative configurations, were established by an extensive study of their spectral data, especially 2D NMR. The cytotoxic activities of the isolated diterpenes against human oral epidermoid (KB), cervical epitheloid (Hela), and liver (Hep59T/VGH) carcinoma cell lines were investigated.     

Iridoid and phenolic glycosides from the roots of Prismatomeris connata

A new phenolic glycoside, 1-O-[beta-D-glucopyranoyl-(1-->6)-beta-D-glucopyranosyl]-3,4,5-trimethoxyphenol, named prismaconnatoside (1), together with one known phenolic glycoside (2) and four aspruloside type iridoid glycosides (3-6) were isolated from the roots of Prismatomeris connata. Their structures were determined by spectroscopic and spectrometric methods. Based on the results, along with those from other studies, iridoids were suggested to be chemical markers to distinguish between P. connata and P. tetrandra, two species that are confused in traditional Chinese medicine.     

Antioxidative phenylethanoid and phenolic glycosides from Picrorhiza scrophulariiflora

One new phenylenthanoid glycoside, scroside D (2), was isolated from the roots of Picrorhiza scrophulariiflora (Scrophulariaceae), together with nine known phenylethanoid and phenolic glycosides: 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside (1), 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-beta-D-glucopyranosyl (1-->3)-beta-D-glucopyranoside (3), scroside B (4), hemiphroside A (5), plantainoside D (6), scroside A (7), androsin (8), piceoside (9), and 6-O-feruloyl-beta-D-glucopyranoside (10). The structures of these compounds were elucidated using spectroscopic methods. The antioxidative activities of these isolated compounds were evaluated based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. Compounds 1, 2, and 6 showed potent antioxidative effects as those of ascorbic acid and the structure-activity relationship is discussed.     

Antioxidative phenols and phenolic glycosides from Curculigo orchioides

A new orcinol glucoside, orcinol-1-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (3), was isolated from the rhizomes of Curculigo orchioides GAERTN., together with seven known compounds: orcinol glucoside (1), orcinol-1-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (2), curculigoside (4), curculigoside B (5), curculigoside C (6), 2,6-dimethoxyl benzoic acid (7), and syringic acid (8). The structures of these compounds were elucidated using spectroscopic methods. The antioxidant activities of these isolated compounds were evaluated by colorimetric methods based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. All the compounds showed potent antioxidative activities and the structure-activity relationship is discussed.     

Novel lignans from the stems and leaves of Trachelospermum jasminoides

Two novel 5-methoxydibenzylhydroxybutyrolactone lignans named 5-methoxytracheloside and 5-methoxytrachelogenin were isolated from the stems and leaves of Trachelospermum jasminoides(Lindl.) Lem.,their structures were determined as(8S,8’S)-8’- hydroxy-3,3’,4,5-tetramethoxylignan-9,9’-olide-4’-O-β-D-glucopyranoside and(8S,8’S)-4’,8’-dihydroxy-3,3’.4,5-tertramethoxylignan -9,9’-olide by various spectroscopic analysis.5-Methoxytracheloside was a new compound and 5-methoxytrachelogenin was isolated from natural source for the first time.     

Two new phenolic glycosides from Viscum articulatum

Two new phenolic glycosides, 1-O-benzyl-[5-O-benzoyl-beta-D-apiofuranosyl (1-->2)]-beta-D-glucopyranoside (1), and 4;-hydroxy-7,3;-dimethoxyflavan-5-O- beta-D-gluco-pyranoside (2), together with nine known flavanones 3 - 11, have been isolated from the dried whole plants of Viscum articulatum.Their structures were identified by extensive spectral analysis, especially 2D NMR techniques. Compound 9 showed weak anti-HIV-1 activity.     

A new phenolic glycoside from the stems of Hydnocarpus hainanensis

A new phenolic glycoside (1) was isolated from the stems of Hydnocarpus hainanensis, along with 11 known compounds. The structures of all compounds were deduced using 1D, 2D NMR spectroscopic methods. The anti-oxidation activities of several compounds were also evaluated.     

Bioactive furanocoumarins from the stems and leaves of Clausena hainanensis

A new furanocoumarin, clauhainanin A (1), together with seven known furanocoumarins (2–8), were isolated from the stems and leaves of Clausena hainanensis. The structure of 1 was elucidated by extensive spectroscopic methods and the known compounds were identified by comparisons with data reported in the literature. All known compounds (2–8) were isolated from C. hainanensis for the first time. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1–8 exhibited significant inhibitory effects with IC₅₀ values ranging from 1.36 to 18.96 μM.     

Phenylpropanoid glycosides from the leaves of Paulownia coreana

Study on the water soluble fraction from the leaves of Paulownia coreana led to the isolation of verbascoside (1), isoverbascoside (2), campneoside II (3), and a new phenylpropanoid glycoside, (R,S)-7-hydroxy-7-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-rhamnopyranosyl(1 --> 3)-beta-d-(6-O-caffeoyl)-glucopyranoside (4). The structures of these compounds were established on the basis of spectroscopic evidence.     

Lupane glycosides from the leaves of Acanthopanax koreanum

Three new lupane-type saponins, acankoreosides F--H (1--3) were isolated from the methanol extract of the leaves of Acanthopanax koreanum NAKAI. The structures of these three saponins were established by chemical and spectroscopic analysis as 3alpha,30-dihydroxylup-20(29)-en-23,28-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (1), 3alpha,30-dihydroxylup-23-al-20(29)-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (2), and (20S) 3alpha-hydroxylup-23-al-28,29-dioic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester (3), respectively. The effects of the isolates (1-3) on the lipopolysaccharide-induced production of nitric oxide and prostaglandin E2 were evaluated in RAW 264.7 macrophages.