Studies on the constituents of Swertia japonica Makino II. On the structures of new glycosides

Two new secoiridoid glycosides, swertiajaposide A (1) and swertiajaposide B (2), a new unsaturated alco-hol glycoside, 3-butenyl 6'-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (3), and a new lignan glycoside, 7R,7'R,8S,8'S-(+)-neo-olivil-4-O-beta-D-glucopyranoside (4), were isolated together with six known compounds from the whole plants of Swertia japonica Makino. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.     

Saracoside: a new lignan glycoside from Saraca indica, a potential inhibitor of DNA topoisomerase IB

Chemical investigation of the stem bark of Saraca indica has resulted in the isolation of a new lignan glycoside, saracoside, along with four known lignan glycosides lyoniside, icariside E3, (+)5'-methoxyisolarciresinol-9'-O-beta-D-glucopyranoside and nudiposide, and a phenolic glucopyranoside, 3,4,5-trimethoxyphenyl-beta-D-glucopyranoside, which has been isolated for the first time from this species. The isolated lignan glycosides exhibit potent DNA topoisomerase IB inhibitory activity.     

Caffeoyl, coumaroyl, galloyl, and hexahydroxydiphenoyl glucoses from Balanophora japonica.

Eighteen new and sixteen known acyl glucoses having caffeoyl, coumaroyl, galloyl, and hexahydroxydiphenoyl groups were isolated from a medicinal parasitic plant, Balanophora japonica. Their structures were determined by spectroscopic and chemical methods. Caffeoyl ellagitannins, which have been rarely found in nature, were major phenolic constituents of this plant, and this is the first report of the isolation of ellagitannins from Balanophoraceae.     

New cardenolide and acylated lignan glycosides from the aerial parts of Asclepias curassavica

Three new cardenolide glycosides and six new acylated lignan glycosides were obtained along with nineteen known compounds from the aerial parts of Asclepias curassavica L. (Asclepiadaceae). The structure of each compound was determined based on interpretations of NMR and MS measurements and chemical evidence.     

A new lignan from Balanophora abbreviata and inhibition of lipopolysaccharide (LPS)-induced inducible nitric oxide synthase (iNOS) expression

Six lignans including a new lignan (1), beta-sitosterol glucopyranoside and phenylpropanoids were isolated from the whole plants of Balanophora abbreviata Bl. (Balanophoraceae). Their structures were determined by NMR, MS analysis and other spectroscopic methods. Lignans (1, 2 and 4) showed potent inhibitory activities on the lipopolysaccharide (LPS)-induced inducible nitric oxide synthase (iNOS) expression in RAW 264.7 cells.     

Larrealignans A and B, novel lignan glycosides from the aerial parts of Larrea tridentata

Two new lignan glycosides, named larrealignans A (1) and B (2), and a known lignan (3) were isolated from the aerial parts of Larrea tridentata (Zygophyllaceae). The structures of 1 and 2 were determined on the basis of spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds (1-3) and aglycones (1a, 2a) of 1 and 2 were evaluated for their cytotoxic activities against HL-60 human leukemia cells.     

Rhyncosides A-F, phenolic constituents from the Chinese mangrove plant Bruguiera sexangula var. rhynchopetala

Chemical investigation on the stem of a Chinese mangrove plant Bruguiera sexangula var. rhynchopetala (Rhizophoraceae) resulted in the isolation and characterization of four new phenolic glycosides rhyncosides A-D (1-4), and two new lignan derivatives namely rhyncosides E-F (5-6), along with twelve known phenolic constituents. Their structures were determined by extensive spectroscopic data analyses.     

Chemical constituents from the leaves of Manglietia phuthoensis and their effects on osteoblastic MC3T3-E1 cells

Two new phenyl glycosides, mangliesides A and B (1, 2), a new ionol glycoside, manglieside C (3), two new lignan glycosides, mangliesides D and E (4, 5), were isolated from the leaves of Manglietia phuthoensis, along with two known lignans, 3-methoxymagnolol (6) and obovatol (7). Their structures were established by means of 1D and 2D NMR, electrospray ionization (ESI)-MS and HR-ESI-MS experiments. Among them, compounds 2 and 5 significantly (p<0.05) increased the growth and differentiation of osteoblastic MC3T3-E1 cells in vitro.     

Iridoid and acyclic monoterpene glycosides, kankanosides L, M, N, O, and P from Cistanche tubulosa

Three iridoid glycosides, kankanosides L, M, and N, and two acyclic monoterpene glycosides, kankanosides O and P, were isolated from fresh stems of Cistanche tubulosa (Orobanchaceae) together with eight iridoid glycosides, five acyclic monoterpene glycosides, three phenylpropanoid glycosides, and four lignan glycosides. Their structures were elucidated on the basis of chemical and physicochemical evidence.     

Hyaluronidase inhibitors from Keiskea japonica

An extract of Keiskea japonica MIQ. showed an inhibitory effect on hyaluronidase activity. From the extract, four new phenylpropanoids, two new maltol glycosides, two new monoterpene glycosides, and two new phenolic compounds were isolated together with 19 known compounds. Among these constituents, two phenylpropanoids and a flavone glucuronide were revealed as hyaluronidase inhibitors.     

Two New Lignan Glycosides from Saussurea laniceps

Two new lignan glycosides, lanicepsides A and B ( 1 and 2 ), along with the eight known compounds 3 – 6 , epipinoresinol, syringin, ethyl caffeate, and 5,6,7‐trihydroxy‐4′‐methoxyflavone, including sesquiterpene lactones, lignans, and a flavone, were isolated from the ethanol extract of Saussurea laniceps. Their structures were determined by spectroscopic methods especially 1D‐ and 2D‐NMR techniques.     

A new acylated flavonol glycoside from the leaves of Eriobotrya japonica

A new acylated flavonol glycoside was isolated from the leaves of Eriobotrya japonica along with two known flavonol glycosides. Their structures were determined by extensive spectroscopic investigation.     

Three New Lignan Derivatives from Lindera glauca (Siebold et Zucc.) Blume

Two new aryl‐tetralin lignan glycosides, linderanosides A and B ( 1 and 2 , resp.), and a new dihydrobenzofuran neolignan glycoside, linderanoside C ( 3 ), together with five known lignan derivatives ( 4 – 8 ) were isolated from the trunk of Lindera glauca. The structures of these new compounds were determined through spectroscopic analyses, including extensive 2D‐NMR data and acid hydrolysis. The absolute configurations of the compounds were clarified by circular dichroism (CD) spectroscopic studies. Compounds 1 – 8 were evaluated for their cytotoxicity against A549 (non‐small cell lung adenocarcinoma), SK‐OV‐3 (ovarian cancer cells), A498 (human kidney epithelial cells), and HCT‐15 (colon cancer cells) human tumor cell lines using sulforhodamine B assays in vitro.     

A New Lignan and Four New Lignan Glycosides from Mananthes patentiflora

A new lignan, 5‐hydroxyjusticidin A (= 9‐(1,3‐benzodioxol‐5‐yl)‐5‐hydroxy‐4,6,7‐trimethoxynaphtho[2,3‐c]furan‐1(3H)‐one; 1 ), and four new diphyllin‐type lignan glycosides, mananthosides C–F ( 2 – 5 ), containing glucosyl (Glc), arabinosyl (Ara), galactosyl (Gal), and/or apiosyl residues, have been isolated from Mananthes patentiflora, together with five known compounds. Their structures and configurations were elucidated by in‐depth 1D‐ and 2D‐NMR experiments, as well as MS analysis.     

Glycosides of Atractylodes japonica

From the water-soluble portion of the methanol extract of the fresh rhizome of Atractylodes japonica, five new sesquiterpenoid glycosides, including a compound having a secoguaiane skeleton, and a new aromatic compound glycoside were isolated together with ten known compounds. Their structures were clarified by spectral investigation.     

Three new glycosides from Sinopodophyllum emodi (Wall.) Ying.

Tow new aryltetralin-type lignan glycosides: methyl epipodophyllate 7'-O-beta-D-glucopyranoyl-(1-->6)-beta-D-glucopyranoside (1), 4-demethylepipodophyllotoxin 7'-O-beta-D-glucopyranoside (2), and a new phenyl ethanol glycoside: phenyl ethanol 4-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (3), along with three known compounds: junipetriolosides (4), 3,4-dihydroxy-phenyl ethanol (5), and 4-hydroxy-phenyl ethanol (6) were isolated and identified from the n-butanol extract of the roots and rhizomes of Sinopodophyllum emodi (Wall.) Ying. The structures of the above were established by means of spectral data and chemical methods.     

Studies on the constituents of Japanese mistletoes from different host trees, and their antimicrobial and hypotensive properties

The chemical constituents of Japanese mistletoes, Taxillus yadoriki Danser, Taxillus kaempferi Danser, and Korthalsella japonica Engler, epiphyting to different host trees were compared, and the antimicrobial and hypotensive properties of some isolated flavonoids were examined. Two known flavonoid glycosides, hyperin and quercitrin, were isolated from Taxillus yadoriki Danser, together with fatty acids, phytosterol, and phytosterol-glucoside. There was remarkable variation of contents of quercitrin among the plants on different host trees. From Taxillus kaempferi Danser, fatty acids, phytosterol, phytosterol-glucoside, quercetin, avicularin, and taxillusin were isolated, and quercitrin and hyperin were also identified. There was no remarkable variation of compositions of flavonoid glycosides among the plants on different host trees. A known flavone glycoside, chrysoeriol-4'-O-glucoside, was isolated from Korthalsella japonica Engler, together with fatty acids, phytosterol, oleanolic acid, and phytosterol-glucoside. Chrysoeriol-4'-O-glucoside is contained in this plant irrespective of the host trees.     

A new lignan glycoside and phenylethanoid glycosides from Strobilanthes cusia BREMEK

The root of Strobilanthes cusia BREMEK. (Acanthaceae), popularly known as Da-Ching-Yeh, has been commonly used in traditional Chinese medicine. It is used to treat influenza, epidemic cerebrospinal meningitis, encephalitis B, viral pneumonia, mumps, and severe acute respiratory syndrome (SARS). In this study, we found a new lignan glycoside (6) and two new phenylethanoid glycosides (7, 8) together with five known compounds as chemical constituents of Strobilanthes cusia root. Some samples were examined for anti-herpes simplex virus type-1 (HSV-1) activity. Among the tested samples, lupeol showed anti-HSV-1 activity (EC(50): 11.7 microM) and showed 100% inhibition of virus plaque formation at 58.7 microM.     

Furofuranic glycosylated lignans: a gas-phase ion chemistry investigation by tandem mass spectrometry

Alkali metal cation adducts, [M+Alk](+), and [M-H](-) ions of four known glycosylated furofuran lignans, (+)-pinoresinol 4-O-beta-D-glucopyranoside, (+)-phylliroside, (+)-8-hydroxypinoresinol 4-O-beta-D-glucopyranoside, and (+)-8-hydroxypinoresinol 8-O-beta-D-glucopyranoside, recently isolated from Carex distachya, were generated by electrospray ionization and allowed to undergo collisionally activated dissociation (CAD) in a quadrupole ion trap (QIT) and in a triple quadrupole (TQ) mass spectrometer. CAD mass spectra of [M+Na](+) and [M+Li](+) adducts revealed the presence of structurally diagnostic product ions. CAD mass spectra of deprotonated glycosylated furofuran lignans showed the typical neutral loss of 162 Da when the glucose residue was bound to a phenolic oxygen atom. When glycosylation occurred at an alcoholic oxygen, as for (+)-8-hydroxypinoresinol 8-O-beta-D-glucopyranoside, a neutral loss of 180 Da represented the main fragmentation pathway. Selective hydrogen/deuterium (H/D) exchange of all the acidic hydrogen atoms of furofuran glycosides, performed by introducing lignan glycosides in D(2)O/CH(3)OD solutions, were employed to obtain information on the nature of the product ions generated during TQ/CAD processes. Energy-resolved TQ/CAD mass spectra of deprotonated lignan glycosides and their deprotonated aglycones were used in a qualitative way to infer information on the integrated energetic picture of CAD fragmentations and to investigate the mechanism of the predominant dissociation/isomerization processes. On the basis of the hypothesized fragmentation mechanisms, gas-phase features of the furofuran ring were derived. The presence of an OH substituent in the C8 position decreased the electron density in the adjacent C8' position, modifying the fragmentation pathway.     

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.