C-glycosyl Flavones Research Articles

Identification of the phenolic components of chrysanthemum flower ( Chrysanthemum morifolium Ramat)

A standardised profiling method based on liquid chromatography with diode array and electrospray ionisation/mass spectrometry (LC–DAD–ESI/MS) was used to identify 46 flavonoids and 17 caffeic acid derivatives in the aqueous methanol extract of Flos chrysanthemum ( Chrysanthemum morifolium Ramat) (Compositae), an important Chinese herb. Fifteen caffeoylquinic acids and 15 flavonoids were positively identified and the remaining compounds were provisionally identified. The detected phenolics were present at concentrations greater than 0.001% of the dry plant material. Many of these phenolics have been reported to have human health benefits. Twenty-five compounds, including C-glycosylated flavones and aliphatic acid-containing caffeoylquinic acids, are reported for the first time in chrysanthemum flower, and this comprehensive analysis of the phenolic components of herb Flos chrysanthemum will be helpful for the quality control of this herb and its products, and to understand the usage and function.

Computational evaluation of Isoorientin (C-glycosyl flavone) on PPAR-gamma receptors and HMG-CoA reductase using MOE 2008.10

Peroxisome proliferators-activated receptor-gamma (PPAR-gamma) plays an essential role in lipid and glucose homeostasis. Numerous studies and comprehensive reviews have documented various naturally derived ligands as PPAR-γ a potential source of novel anti-diabetic compounds from plants and herbs [1]. Isoorientin, a C-glycosyl flavone, has been isolated as an antidiabetic and antihyperlipidemic agent from aerial parts of Gentiana ollivieri Griseb. [2]. The objective of this study is to find out, the relation between these receptors and ligand. We used docking property and site finder and electrostatic map tools of molecular operating environment (MOE) 2008.10 computer programme from Chemical computing group. Protein structures were taken from Protein Data Bank PDB and operated with Protonate 3D and minimized. Ligands were designed by LigX.

Computational evaluation of Isoorientin (C-glycosyl flavone) on PPAR-gamma receptors and HMG- CoA reductase using MOE 2008.10

Peroxisome proliferators-activated receptor-gamma (PPAR-gamma) plays an essential role in lipid and glucose homeostasis. Numerous studies and comprehensive reviews have documented various naturally derived ligands as PPAR-γ a potential source of novel anti-diabetic compounds from plants and herbs [1]. Isoorientin, a C-glycosyl flavone, has been isolated as a antidiabetic and antihyperlipidemic agent from aerial parts of Gentiana ollivieri Griseb. [2]. The objective of this study is to find out, the relation between these receptors and ligand. We used docking property and site finder and electrostatic map tools of molecular operating environment (MOE) 2008.10 computer programme from Chemical computing group. Protein structures were taken from Protein Data Bank PDB and operated with Protonate 3D and minimized. Ligands were designed by LigX. Results shown that, E score1: -16.0501 and E refine: -32.3072 for Isoorientin-PPAR gamma docking study, E score1: -9.8957 E refine: -17.2581 for Isoorientin-HMG-CoA docking study. Data obtained from experiments demonstrated that isoorientin can be candidate as a good multi-target drug template.

Robustness of QTLs across germplasm pools using a model quantitative trait

Knowledge of the inheritance of C-glycosyl flavone synthesis in maize (Zea mays L.) silk tissues has been acquired through detailed genetic studies involving primarily germplasm from the Corn Belt Dent race. To test the robustness of this genetic knowledge, we examined C-glycosyl flavone synthesis in a genetically distinct germplasm pool, popcorn. C-glycosyl flavone profiles and levels and the involvement of three specific genes/quantitative trait loci (p, pr1, and sm1) in C-glycosyl flavone synthesis were examined in popcorn germplasm representing at least two races and various diverse geographic regions. Twenty-four inbred lines and 23 hybrids involving these inbred lines and inbred line R17 were characterized for their flavone profiles and levels in silk tissues. Two F2 mapping populations were constructed to examine the involvement of p, pr1, and sm1 on C-glycosyl flavone synthesis. C-glycosyl flavone levels threefold higher than previously reported in Corn Dent Belt materials and a novel class of compounds were discovered. The gene action of sm1 was different, the functional p allele was not always dominant, and pr1 did not affect mays in synthesis. Based on this rather simplistic "model" quantitative trait, it appears that caution should be exercised when attempting to apply quantitative trait locus knowledge accumulated in one germplasm base to a germplasm base that is known to be distinctly unique.

The phytochemical analysis and antioxidant activity assessment of orange peel (Citrus sinensis) cultivated in Greece–Crete indicates a new commercial source of hesperidin

The flavonoid content of several methanolic extract fractions of Navel orange peel (flavedo and albedo of Citrus sinensis) cultivated in Crete (Greece) was first analysed phytochemically and then assessed for its antioxidant activity in vitro. The chemical structures of the constituents fractionated were originally determined by comparing their retention times and the obtained UV spectral data with the available bibliographic data and further verified by detailed LC-DAD-MS (ESI+) analysis. The main flavonoid groups found within the fractions examined were polymethoxylated flavones, O-glycosylated flavones, C-glycosylated flavones, O-glycosylated flavonols, O-glycosylated flavanones and phenolic acids along with their ester derivatives. In addition, the quantitative HPLC analysis confirmed that hesperidin is the major flavonoid glycoside found in the orange peel. Interestingly enough, its quantity at 48 mg/g of dry peel permits the commercial use of orange peel as a source for the production of hesperidin. The antioxidant activity of the orange peel methanolic extract fractions was evaluated by applying two complementary methodologies, DPPH(*) assay and the Co(II)/EDTA-induced luminol chemiluminescence approach. Overall, the results have shown that orange peel methanolic extracts possess moderate antioxidant activity as compared with the activity seen in tests where the corresponding aglycones, diosmetin and hesperetin were assessed in different ratios.

HPLC-PDA-MS and NMR Characterization of C-Glycosyl Flavones in a Hydroalcoholic Extract of Citrus aurantifolia Leaves with Antiplatelet Activity

A hydroalcoholic extract of lime ( Citrus aurantifolia) leaves has been developed in Cuba to be used as a nutritional supplement and phytomedicine in the form of tincture (TLL). A HPLC-PDA-ESI/MS/MS method has been used for the comprehensive analysis of C-glycosyl flavones in TLL. Six C-glycosyl flavones were characterized and, to confirm the proposed structures and to elucidate the nature of the sugar units, a preparative procedure was applied, and isolated compounds were characterized by NMR. Apigenin-6,8-di-C-beta-D-glucopyranoside (vicenin II) (1), diosmetin-6,8-di- C-beta- d-glucopyranoside (2), apigenin-8-C-beta-D-glucopyranoside (vitexin) (3), apigenin-8-C-[alpha-L-arabinopyranosyl-(1-->6)]-O-beta-D-glucopyranoside (4), apigenin-6-C-[alpha-l-arabinopyranosyl-(1-->6)]-O-beta-D-glucopyranoside (5). and apigenin-6-C-beta-D-glucopyranoside (isovitexin) (6) were identified in TLL and quantified by HPLC-PDA. Compounds 4 and 5 were two new arabinosyl derivatives of vitexin and isovitexin. Inhibitor effect of TLL on platelet aggregation induced by physiological agonists of platelets was evaluated in human plasma. TLL inhibited significantly ADP and epinephrine-induced platelet aggregation in a concentration-dependent manner (IC 50=0.40 and 0.32 mg/mL, respectively).

Antioxidant C-glycosyl flavones from the leaves of Sasa kurilensis var . gigantea

C-glycosyl flavones, kurilensin A ( 1) and B ( 2), together with two known compounds, tricin-4′- O-β- d-glucopyranoside ( 3) and tricin-5- O-β- d-glucopyranoside ( 4), were isolated from hot-water extracts of the leaves of Sasa kurilensis. The structure of the compounds was determined by spectroscopic analyses including 1D, 2D NMR and MS. The absolute configuration of sugar moieties in 1 and 2 was determined by chiral HPLC analyses of the benzoyl derivatives of acid hydrolysis. Compounds 1 and 2 exhibited higher radical scavenging activity than ascorbic acid in the 1,1-diphenyl-2-pycrylhydrazyl (DPPH) assay system.

Further knowledge on barley ( Hordeum vulgare L.) leaves O-glycosyl- C-glycosyl flavones by liquid chromatography-UV diode-array detection-electrospray ionisation mass spectrometry

Thirty-seven flavonoids and a hydroxycynnamic acid have been characterized in barley leaves ( Hordeum vulgare L.) by liquid chromatography-UV diode-array coupled to ion trap mass spectrometry with electrospray ionisation interface (negative mode). Their structures have been determined by the study of the ion mass fragmentation which characterizes C-glycosyl flavones and O-glycosyl- C-glycosyl flavones, and differentiates di- O-glycosyl flavones from O-diglycosyl-flavones. The majority of them are described for the first time in barley. Saponarin (isovitexin-7- O-glucoside), lutonarin (isoorientin-7- O-glucoside) and isoscoparin-7- O-glucoside derivatives constitute the major part of the detected compounds. Some acylated derivatives are also described, namely, 7- O-[6-acyl]-glucoside and -7- O-[6-acyl]-glc-4′-glucoside of isovitexin, isoorientin and isoscoparin.

Resistance to <I>Spodoptera frugiperda</I> (Lepidoptera: Noctuidae) and <I>Euxesta stigmatias</I> (Diptera: Ulidiidae) in Sweet Corn Derived from Exogenous and Endogenous Genetic Systems

Field trials using Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae) and Euxesta stigmatias Loew (Diptera: Ulidiidae) were conducted to evaluate resistance and potential damage interactions between these two primary corn, Zea mays L., pests against Lepidoptera-resistant corn varieties derived from both endogenous and exogenous sources. The endogenous source of resistance was maysin, a C-glycosyl flavone produced in high concentrations in varieties 'Zapalote Chico 2451' and 'Zapalote Chico sh2'. The exogenous resistance source was the Bacillus thuringiensis (Bt)11 gene that expresses Cry1A(b) insecticidal protein found in 'Attribute GSS-0966'. Damage by the two pests was compared among these resistant varieties and the susceptible 'Primetime'. Single-species tests determined that the Zapalote Chico varieties and GSS-0966 effectively reduced S. frugiperda larval damage compared with Primetime. E. stigmatias larval damage was less in the Zapalote Chico varieties than the other varieties in single-species tests. E. stigmatias damage was greater on S. frugiperda-infested versus S. frugiperda-excluded ears. Ears with S. frugiperda damage to husk, silk and kernels had greater E. stigmatias damage than ears with less S. frugiperda damage. Reversed phase high-performance liquid chromatography analysis of nonpollinated corn silk collected from field plots determined that isoorientin, maysin, and apimaysin plus 3'-methoxymaysin concentrations followed the order Zapalote Chico sh2 > Zapalote Chico 2451 > Attribute GSS-0966 = Primetime. Chlorogenic acid concentrations were greatest in Zapalote Chico 2451. The two high maysin Zapalote Chico varieties did as well against fall armyworm as the Bt-enhanced GSS-0966, and they outperformed GSS-0966 against E. stigmatias.

Characterization of C-glycosyl flavones O-glycosylated by liquid chromatography–tandem mass spectrometry

Fifty three O-glycosyl- C-glycosyl flavones with O-glycosylation on phenolic hydroxyl or on the C-glycosyl residue or combination of both forms have been studied by liquid chromatography-UV diode array detection-electrospray ionisation mass spectrometry ion trap in the negative mode. The study of the relative abundance of the main ions from the MS preferential fragmentation on –MS2 and/or –MS3 events allows the differentiation of the position of the O-glycosylation, either on phenolic hydroxyl or on the sugar moiety of C-glycosylation. In addition, it is possible to discriminate between O-glycosylation at 2″ and at 6″ positions. The occurrence of an abundant ion Y 0 − ([( M − H ) -132/-146/-162] −, mono- O-pentosyl/rhamnosyl/hexosyl- C-glycosyl derivatives) after –MS2 fragmentation characterizes the O-glycosylation on phenolic hydroxyls. The preferential fragmentation leading to a relevant Z 1 − ( [Y 1 -18] −) fragment is characteristic of 2″- O-glycosyl- C-glycosyl derivatives. The 6″- O-glycosyl- C-glycosyl derivatives are characterized by 0,2 X 0 − , which is generated by a global loss of the sugar moiety from the O-glycosylation at 6″ and the glycosidic fraction that involves the carbons 6″-3″ of the C-glycosyl residue ( [( M − H ) -162-120] − , in the case of 6″- O-hexosyl- C-hexosyl derivatives). Regarding the combined O-glycosylated compounds (both on phenolic hydroxyl and on sugar moiety at C-glycosylation), the main fragmentation on –MS2 events produces a Y 0 − characterizing the O-glycosylation on the phenolic hydroxyl, and the – MS3[( M − H ) → Y 0 ] − fragmentation of the O-glycosylation on the C-glycosyl residue.

Quantitative trait loci for maysin synthesis in maize (Zea mays L.) lines selected for high silk maysin content

Maysin is a naturally occurring C-glycosyl flavone found in maize (Zea mays L.) silk tissue that confers resistance to corn earworm (Helicoverpa zea, Boddie). Recently, two new maize populations were derived for high silk maysin. The two populations were named the exotic populations of maize (EPM) and the southern inbreds of maize (SIM). Quantitative trait locus (QTL) analysis was employed to determine which loci were responsible for elevated maysin levels in inbred lines derived from the EPM and SIM populations. The candidate genes consistent with QTL position included the p (pericarp color), c2 (colorless2), whp1 (white pollen1) and in1 (intensifier1) loci. The role of these loci in controlling high maysin levels in silks was tested by expression analysis and use of the loci as genetic markers onto the QTL populations. These studies support p, c2 and whp1, but not in1, as loci controlling maysin. Through this study, we determined that the p locus regulates whp1 transcription and that increased maysin in these inbred lines was primarily due to alleles at both structural and regulatory loci promoting increased flux through the flavone pathway by increasing chalcone synthase activity.

Association analysis of candidate genes for maysin and chlorogenic acid accumulation in maize silks

Two compounds, the C-glycosyl flavone maysin and the phenylpropanoid product chlorogenic acid (CGA), have been implicated in corn earworm (Helicoverpa zea Boddie) resistance in maize (Zea mays L.). Previous quantitative trait locus (QTL) analyses identified the pericarp color (p) locus, which encodes a transcription factor, as the major QTL for maysin and CGA. QTL analysis has also implicated the dihydroflavanol reductase (DFR; E.C. no. 1.1.1.219) locus anthocyaninless1 (a1) and the duplicate chalcone synthase (CHS; E.C. no. 2.3.1.74) loci colorless2 (c2) and white pollen1 (whp1) as genes underlying QTL for maysin and/or CGA synthesis. Epistatic interactions between p and a1 and between p and c2 were also defined. CHS catalyzes the first step in the flavonoid pathway and represents one of the first enzyme steps following the branch off the general phenylpropanoid pathway towards CGA synthesis. In maize, the reduction of dihydroflavanol to leucoanthocyanin by DFR immediately follows the pathway branch leading to C-glycosyl flavone production. The detection of QTLs for maysin and CGA concentration at loci encoding enzyme steps following the pathway branch points implicates alterations in the flow of biochemical intermediates as the biological basis of the QTL effects. To examine if sequence variation among alleles of a1, c2, and whp1 affect maysin and CGA synthesis in maize silks, we performed an association analysis. Because the p locus has often been a major QTL for maysin and CGA and has exhibited epistatic interactions with a1, c2, and whp1, association analysis was conditioned on the p genotype. A highly significant association of two sequence polymorphisms in the promoter of a1 with maysin synthesis was demonstrated. Additional conditioning on the genotype of the significant a1 polymorphism allowed the detection of a significant polymorphism within the whp1 promoter. Our analyses demonstrate that conditioning for epistatic factors greatly increases the power of association testing.

Analysis of antioxidant compounds in sweet orange peel by HPLC–diode array detection–electrospray ionization mass spectrometry

HPLC-diode array detection-electrospray ionization mass spectrometry was used to determine qualitatively and quantitatively the flavonoid content of several fractions and residues of extracts of Greek navel sweet orange peel (Citrus sinensis) from the region of southern Greece (Leonidi-Tripoli). The main groups of flavonoids found according to HPLC retention times, spectral data and literature references were polymethoxylated flavones, C-glycosylated flavones, O-glycosylated flavones, O-glycosylated flavanones, flavonols and phenolic acids and their derivatives. The ethyl acetate fraction which has been shown in previous work to possess the best radical scavenging activity among the others was found to contain C-glycosylated flavones, polymethoxylated flavones, O-glycosylated flavones, O-glycosylated flavanones, two phenolic acid derivatives and two unknown compounds, all in low concentrations. The group of C-glycosylated flavones was reported for the first time in the peel of Navel sweet orange. The C-glycosylated flavones found according to their spectral characteristics and literature were 6-C-beta-glucosyldiosmin, 6,8-di-C-glucopyranosylapigenin, 6,8-di-C-beta-glucosyldiosmin and two unknown. The results suggest that the ethyl acetate fraction of navel Citrus sinensis peel consists of significant antioxidant compounds and can be used as a food additive of natural origin or a pharmaceutical supplement using as a source of peel the byproducts of the orange juice industry.

Characterization and quantitation of antioxidant constituents of sweet pepper (Capsicum annuum L.).

Sweet peppers (Capsicum annuum L.) cv. Vergasa have been studied at four maturity stages (immature green, green, immature red, and red). The individual phenolics (hydroxycinnamic acids and flavonoids), vitamin C (ascorbic acid and dehydroascorbic acid), and individual carotenoids were characterized and quantified. Five hydroxycinnamic derivatives and 23 flavonoids were characterized and quantified from the pericarp of sweet pepper by high-performance liquid chromatography-diode array detection-electrospray ionization-mass spectrometry. Identification was carried out by their UV spectra, chromatographic comparisons with authentic markers, identification of hydrolysis products, and tandem mass spectrometry analysis. Hydroxycinnamic derivatives, O-glycosides of quercetin, luteolin, and chrysoeriol, and a large number of C-glycosyl flavones have been characterized. Some of these compounds were found for the first time in nature. Clear differences in the individual and total phenolic content were detected between the different maturity stages. Immature green pepper had a very high phenolic content while green, immature red, and red ripe peppers showed a 4-5-fold reduction. Ascorbic acid was the main form of vitamin C, and its content increased as the pepper reached maturity. The red ripe stage had a relevant impact on the carotenoids content. Thus, immature green peppers showed the highest content of polyphenols, while red ripe fruits had the highest content of vitamin C and provitamin A.

Approach to the study of C-glycosyl flavones by ion trap HPLC-PAD-ESI/MS/MS: application to seeds of quince (Cydonia oblonga).

Ion trap HPLC-PAD-ESI/MS/MS has been used to study C-glycosyl flavones in quince seeds. Comparative analysis of the ions [(M-H)-60]-, [(M-H)-90]- and [(M-H)-120]- from 6-C- and 8-C-glycosyl flavone isomers, together with their respective retention times, allowed deductions to be made about the nature of the sugar units and the positions of C-glycosylation. Vicenin-2 (6,8-di-C-glucosyl apigenin), lucenin-2 (6,8-di-C-glucosyl luteolin), stellarin-2 (6,8-di-C-glucosyl chrysoeriol), isoschaftoside (6-C-arabinosyl-8-C-glucosyl apigenin), schaftoside (6-C-glucosyl-8-C-arabinosyl apigenin), 6-C-pentosyl-8-C-glucosyl chrysoeriol and 6-C-glucosyl-8-C-pentosyl chrysoeriol were identified in quince seed.

The genetic basis of C-glycosyl flavone B-ring modification in maize (Zea mays L.) silks.

Resistance to corn earworm (CEW) (Helicoverpa zea Boddie) has been attributed to high concentrations of C-glycosyl flavones and chlorogenic acid in maize (Zea mays L.) silks. The most common C-glycosyl flavones isolated from maize silks are maysin, apimaysin, and methoxymaysin, which are distinguished by their B-ring substitutions. For a better understanding of the genetic mechanisms underlying the synthesis of these compounds, we conducted a quantitative trait locus (QTL) study with two populations: (Tx501 x NC7A)F2 and (Tx501 x Mp708)F2. For chlorogenic acid, maysin, and methoxymaysin concentration, the major QTL for both populations was located on chromosome 4 near umc1963. For apimaysin, the major QTL in both populations was located at the position of the pr1 locus on chromosome 5. The QTL alleles on chromosome 4 that increased the synthesis of methoxymaysin significantly decreased the synthesis of maysin and chlorogenic acid. This decrease in maysin concentration was four-fold greater than the increase in methoxymaysin. Our results indicate that the QTL on chromosome 4, responsible for the increase in methoxymaysin synthesis, alters the dynamics of both the phenylpropanoid and flavonoid pathways.

A maize QTL for silk maysin levels contains duplicated Myb-homologous genes which jointly regulate flavone biosynthesis.

The maize p1 locus coincides with a major QTL (quantitative trait locus) determining levels of maysin, a C-glycosyl flavone that deters feeding by corn ear-worm. The p1 gene is tightly linked with a second gene, p2, and both genes encode similar Myb-domain proteins. We show here that maize cell cultures transformed with either the p1 or p2 genes expressed under a constitutive promoter accumulate transcripts for flavonoid biosynthetic genes, and synthesize phenylpropanoids and C-glycosyl flavones related to maysin. Additionally, maize plants that are deleted for the p1 gene have reduced maysin levels and moderate silk-browning reaction, whereas plants with a deletion of both p1 and p2 have non-detectable silk maysin and non-browning silks. We conclude that both p1 and p2 induce maysin biosynthesis in silk, although the two genes differ in their expression and pigmentation effects in other tissues. These results show that a QTL for flavone biosynthesis actually comprises two tightly linked genes with related functions.

Duplicate Loci as QTL

The C-glycosyl flavone maysin is an important component of corn earworm (Helicoverpa zea Boddie) (CEW) resistance in maize (Zea mays L.) silks. Chlorogenic acid (CGA), a product of the phenylpropanoid pathway, has also been implicated in CEW antibiosis. The transition from the 9-carbon phenylpropanoid to the 15-carbon flavonoid pathway represents a potentially important regulation point in C-glycosyl flavone biosynthesis. The enzyme chalcone synthase (CHS) catalyzes this reaction and is represented by a set of duplicate loci in maize, colorless2 (c2) and white pollenl (whpl ). Chromosomal regions of the maize genome have been identified as quantitative trait loci (QTL) for maysin synthesis that correspond to these two loci. Our objective was to investigate the role of CHS in flavone and CGA biosynthesis. We tested c2 and whpl as candidate loci using three related F 2 populations segregating for both structural and regulatory loci. Silks were harvested and analyzed from each population for flavonoid and phenylpropanoid content. Phenotypic data was combined with linkage maps generated for each population to conduct statistical and QTL analysis. Our results (i) support earlier findings of the requirement of a functional pericarp color1 (p1) allele for C-glycosyl fiavone biosynthesis, ( ii) demonstrate that variation at the c2 region on chromosome 4 influences both maysin and CGA levels in silks, (iii) reveal a dosage-dependent relationship between c2 and whpl in which the whp1 region acts cooperatively with functional c2 to increase flavones and partially compensates for nonfunctional c2, and (iv) demonstrate that mutations in c2 and whpl shunt intermediates from maysin synthesis to CGA. These results demonstrate that CHS function is a regulatory focal point of substrate flow between the flavone and phenylpropanoid pathways.

The biological basis of epistasis between quantitative trait loci for flavone and 3-deoxyanthocyanin synthesis in maize (Zea maysL.)

A major weakness in our understanding of the genetic basis of complex traits has been that of defining the extent and biological basis of epistasis. Our research group has been studying the genetic control of the accumulation of maysin, a C-glycosyl flavone, in maize, Zea mays (L.), silks. Previously, we demonstrated the importance of the p1 locus as a QTL for maysin synthesis. The p1 locus often exhibits significant epistatic interactions with other loci. We developed a mapping population, (W23al x GT119)F2, specifically designed to test whether genes in an intersecting pathway might be detected as QTLs for maysin synthesis and result in epistatic interaction effects. The a1 gene is not required for the synthesis of flavones but is required for the synthesis of 3-deoxyanthocyanins, an intersecting pathway, in maize silks. The p1 locus (P < 0.0001) was a QTL for both flavones and 3-deoxyanthocyanins. The a1 locus was also highly significant (P < 0.0001) for both traits, as was the p1 x a1 epistatic interaction (P < 0.0001). Our results demonstrate that altering the flux of biochemical intermediates between pathways may be the biological basis of major QTL effects and epistatic interactions.

An Iridoid Gentiobioside, a Benzophenone Glucoside and Acylated Flavone C-Glycosides from Tripterospermum japonicum (SIEB. et ZUCC.) MAXIM.

From aerial parts of Tripterospermum japonicum, 6'-O-beta-D-glucopyranosylmorroniside, benzophenone glucoside, named triptephenoside and 2'''- and 4'''-O-acetyl-2''-O-alpha-L-rhamnopyranosylisovitexins were isolated, along with known iridoid and secoiridoid glucosides, and C-glycosyl flavones.