Flavonoid glycosides from the aerial parts of Curcuma comosa

Four new flavonoid glycosides, curcucomosides A–D (1–4), three known flavonoid glycosides, 5–7, and four known diarylheptanoids, 8–11, were isolated from the ethanol extract of the aerial parts of Curcuma comosa. The structures of the new compounds were established as rhamnazin 3-O-α-l-arabinopyranoside (1), rhamnocitrin 3-O-α-l-arabinopyranoside (2), rhamnazin 3-O-α-l-rhamnopyranosyl-(1→2)-O-α-l-arabinopyranoside (3), and rhamnocitrin 3-O-α-l-rhamnopyranosyl-(1→2)-O-α-l-arabinopyranoside (4) by spectroscopic analysis and chemical reactions whereas those of the known compounds were identified by spectral comparison with those of the reported values.     

Saponins from Astragalus hareftae (NAB.) SIRJ.

Four cycloartane- (hareftosides A–D) and oleanane-type triterpenoids (hareftoside E) were isolated from Astragalus hareftae along with fifteen known compounds. Structures of the compounds were established as 3,6-di-O-β-d-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane (1), 3,6,24-tri-O-β-d-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane (2), 3-O-β-d-xylopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),25(S)-epoxycycloartane (3), 16-O-β-d-glucopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), 3-O-[β-d-xylopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucuronopyranosyl]-soyasapogenol B (5) by the extensive use of 1D- and 2D-NMR experiments along with ESI-MS and HR-MS analyses.     

Alkenylresorcinols and cytotoxic activity of the constituents isolated from Labisia pumila

Phytochemical investigation on the leaves of Labisia pumila (Myrsinaceae), an important medicinal herb in Malaysia, has led to the isolation of 1-O-methyl-6-acetoxy-5-(pentadec-10Z-enyl)resorcinol (1), labisiaquinone A (2) and labisiaquinone B (3). Along with these, 16 known compounds including 1-O-methyl-6-acetoxy-5-pentadecylresorcinol (4), 5-(pentadec-10Z-enyl)resorcinol (5), 5-(pentadecyl)resorcinol (6), (−)-loliolide (7), stigmasterol (8), 4-hydroxyphenylethylamine (9), 3,4,5-trihydroxybenzoic acid (10), 3,4-dihydroxybenzoic acid (11), (+)-catechin (12), (−)-epicatechin (13), kaempferol-3-O-α-rhamnopyranosyl-7-O-β-glycopyranoside (14), kaempferol-4′-O-β-glycopyranoside (15), quercetin-3-O-α-rhamnopyranoside (16), kaempferol-3-O-α-rhamnopyranoside (17), (9Z,12Z)-octadeca-9,12-dienoic acid (18) and stigmasterol-3-O-β-glycopyranoside (19) were also isolated. The structures of these compounds were established on the basis of 1D and 2D NMR spectroscopy techniques (¹H, ¹³C, COSY, HSQC, NOESY and HMBC experiments), mass spectrometry and chemical derivatization. Among the constituents tested 1 and 4 exhibited strongest cytotoxic activity against the PC3, HCT116 and MCF-7 cell lines (IC₅₀ values ⩽10 μM), and they showed selectivity towards the first two-cell lines relative to the last one.     

Phytochemical and chemotaxonomic study of Pulsatilla cernua (Thunb.) Bercht. ex J. Presl

Twenty-two compounds were isolated from the 70% EtOH–H₂O extract of Pulsatilla cernua (Thunb.) Bercht. ex J. Presl roots, and their structures were determined based on ¹H NMR, ¹³C NMR and MS spectroscopic data, including (+)-pinoresinol (1), matairesinol (2), 4-ethoxycinnamic acid (3), p-hydroxy ethyl cinnamate (4), 3-(4′-methoxyphenyl)-2(E)-propenoic acid (5), methyl 4-hydroxycinnamate (6), radicol (7), cryptomeridiol (8), fraxinellone (9), diolmycin B2 (10), hederagonic acid (11), hederagenin (12), oleanolic acid (13), 3-O-α-L-arabinopyranosyl-oleanolic acid (14), hederagenin 3-O-α-L-arabinopyranoside (15), 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] oleanolic acid (16), hederasaponin B (17), kizutasaponin K₁₂ (18), patrinia saponin H3 (19), hederacholichiside F (20), cernuoside A (21) and cernuoside B (22). Eight compounds (3–10) were isolated and identified from the genus Pulsatilla for the first time.     

New ellagitannin and galloyl esters of phenolic glycosides from sapwood of Quercus mongolica var. crispula (Japanese oak)

Two novel glycosides, 4,5-dimethoxy-3-hydroxyphenol 1-O-β-(6′-O-galloyl)-glucopyranoside (1) and (+)-2α-O-galloyl lyoniresinol 3α-O-β-d-xylopyranoside (2), as well as a novel ellagitannin named epiquisqualin B (3), were isolated from sapwood of Quercus mongolica var. crispula along with 19 known phenolic compounds. The structures of the novel compounds were elucidated on the basis of chemical and spectroscopic investigation. Compound 2 is the first example of a lignan galloyl ester, and 3 is the oxidation product of vescalagin, which is the major ellagitannin of this plant.     

Configurational assignments of C-nitromethyl-C-hydroxy branched-chain carbohydrate derivatives by use of a europium shift-reagent in 1 H-N.M.R. spectroscopy

Configurational assignments for the tertiary alcoholic centers of four branched-chain 3-C-nitromethylglycopyranosides, namely, methyl 2-benzamido-4,6-O-benzylidene-2-deoxy-3-C-nitromethyl-α-D-allopyranoside (1), benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-C-nitromethyl-α-D-glucopyranoside (4), benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-C-nitromethyl-α-D-allopyranoside (5), and methyl 4,6-O-benzylidene-3-C-nitromethyl-2-O-p-tolylsulfonyl-α-D-glucopyranoside (8), were made on the basis of the downfield chemical shifts of their identifiable protons per molar equivalent of added Eu(fod)₃, as compared with those of model compounds, of known configuration, having a close structural relationship. In some cases, the assignments were corroborated by the position of the acetyl resonances in the unshifted 60-MHz p.m.r. spectra of the corresponding O-acetyl derivatives.     

α-Glucosidase inhibitory effects of polyphenols from Geranium asphodeloides: Inhibition kinetics and mechanistic insights through in vitro and in silico studies

Some Geranium species have been used to treat diabetes. To evaluate the scientific basis of this ethnopharmacological use, we aimed to isolate potent α-glucosidase inhibitory metabolites of Geranium asphodeloides Burm. through in vitro bioactivity-guided fractionation. All the tested extracts showed high α-glucosidase inhibitory effect compared to acarbose. Among the tested extracts, the ethyl acetate subextract showed the highest activity with an IC₅₀ value of 0.85 ± 0.01 µM. A hydrolysable tannin, 1,2,4-tri-O-galloyl-β-d-glucopyranose (1), and five flavonoid glycosides, kaempferol-3-O-α-rhamnopyranoside (2), kaempferol-3-O-α-arabinofuranoside (3), quercetin-3-O-β-glucopyranoside (4), quercetin-3-O-α-rhamnopyranoside (5), and quercetin-3-O-α-rhamnofuranoside (6), were isolated from the ethyl acetate subextract. Their structures were identified by 1D- and 2D-NMR experiments. 1 exhibited the highest α-glucosidase inhibitory effect, approximately 61 times more potent than positive control, acarbose, with an IC₅₀ value of 0.95 ± 0.07 µM. Also, 2 was more potent than acarbose. An enzyme kinetics analysis revealed that compounds 2, 3 and 4 were competitive, whereas 1 and 6 uncompetitive inhibitors. Molecular docking studies were performed to get insights into inhibition mechanisms of the isolated compounds in the light of the enzyme kinetic studies using various binding sites of the enzyme model.     

Flavonoids and phenolic acids from the aerial parts of Alyssum alyssoides L. (Brassicaceae)

Two phenolic acids (1 and 2) and seven flavonoids (3–9) were isolated from the aerial parts of Alyssum alyssoides (Brassicaceae). All these compounds (1–9) were isolated from this particular species for the first time. Their structures were identified, on the basis of MS and NMR spectra as: p-hydroxy-benzoic acid (1), 3-methoxy-4-hydroxybenzoic acid (vanillic acid) (2), kaempferol 3-O-β-D-glucopyranoside (astragalin) (3), kaempferol 3-O-(6″-α-L-rhamnopyranosyl)-β-D-glucopyranoside (nicotiflorin) (4), quercetin 3-O-β-D-glucopyranoside (isoquercetin) (5), quercetin 3-O-β-D-galactopyranoside (hyperoside) (6), isorhamnetin 3-O-β-D-glucopyranoside (7), isorhamnetin 3-O-β-D-galactopyranoside (8) and isorhamnetin 3-O-(6″-α-L-rhamnopyranosyl)-β-D-glucopyranoside (narcissin) (9). The chemotaxonomic significance of these compounds was summarized.     

Seven new triterpenoids from the aerial parts of Ilex cornuta and protective effects against H2O2-induced myocardial cell injury

Seven new triterpenoids (1–7), together with two known ones (8–9), were isolated from the aerial parts ofIlex cornuta. The leaves of I. cornuta are the major source of “Kudingcha”, a popular herbal tea consumed in China and other countries. The structures of compounds 1–7 were determined as 20-epi-urs-12,18-dien-28-oic acid 3β-O-α-l-arabinopyranoside (1), 20-epi-urs-12,18-dien-28-oic acid 2′-O-acetyl-3β-O-α-l-arabinopyranoside (2), 20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (3), 3β,23-dihydroxy-20-epi-urs-12,18-dien-28-oic acid (4), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-α-l-arabinopyranoside (5), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronic acid (6), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (7), on the basis of spectroscopic analyses (IR, ESI–MS, HR-ESI–MS, 1D and 2D NMR) and chemical reactions. Protective effects against H₂O₂-induced H9c2 cardiomyocyte injury were tested in vitro for compounds 1–9, and the data showed that compound 4 had significant cell-protective effect. Compounds 1-9 did not show significant DPPH radical scavenging activity.     

Two new guaiane sesquiterpenes from Datura metel L. with anti-inflammatory activity

Chemical investigation of an acidic methanol extract of the whole plants of Datura metel resulted in the isolation of two new guainane sesquiterpenes, 1β,5α,7β-guaiane-4β,10α,11-triol (1) and 1α,5α,7α-11-guaiene-2α,3β,4α,10α,13-pentaol (2), along with eight known compounds: pterodontriol B (3), disciferitriol (4), scopolamine (5), kaempferol 3-O-β-d-glucosyl(1 → 2)-β-d-galactoside 7-O-β-d-glucoside (6), kaempferol 3-O-β-glucopyranosyl(1 → 2)-β-glucopyranoside-7-O-α-rhamnopyranoside (7), pinoresinol 4′′-O-β-d-glucopyranoside (8), (7R,8S,7′S,8′R)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxy-lignan-4-O-β-d-glucopyranoside (9), and (7S,8R,7′S,8′S)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4-O-β-d-glucopyranoside (10). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. Compounds 2-4 and 6-10 were shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells.     

Phenolic compounds and rare polyhydroxylated triterpenoid saponins from Eryngium yuccifolium

Phytochemical investigation on the whole plant of Eryngium yuccifolium resulted in the isolation and identification of three phenolic compounds (1-3) and 12 polyhydroxylated triterpenoid saponins, named eryngiosides A-L (4-15), together with four known compounds kaempferol-3-O-(2,6-di-O-trans-p-coumaroyl)-β-d-glucopyranoside (16), caffeic acid (17), 21β-angeloyloxy-3β-[β-d-glucopyranosyl-(1→2)]-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyloxyolean-12-ene-15α,16α,22α,28-tetrol (18), and saniculasaponin III (19). This study reports the isolation of these compounds and their structural elucidation by extensive spectroscopic analyses and chemical degradation.     

Sesquiterpenoids and flavonoids from Pteris multifida Poir.

Phytochemical research of Pteris multifida Poir. led to the isolation of fifteen compounds, including six flavonoids (1–6) and nine sesquiterpenoids (7–15). Their structures were characterized by NMR, MS, ORD and CD data. Compounds kaempferol 3-O-α-L-rhamnoside-7-O-β-D-glucoside (1), myricetin 3-O-β-D-glucoside (2), kaempferol 3-O-β-D-glucoside (4), luteolin-7-O-β-D-rutinoside (5), quercetin-3-O-α-L-rhamnopyranoside (6), (2S,3S)-12-hydroxypterosin Q (7), (2S,3S)-pterosin Q (8), 2-hydroxypterosin C (9) and (2S)-12-hydroxypterosin A (10) were first isolated from P. multifida, and compounds 1–2 and 10 were first isolated from the family Pteridaceae. Furthermore, the chemotaxonomic significance of the isolates was discussed.     

New triterpene saponins from Phryna ortegioides

Four new and three known oleanane-type saponins have been isolated from the methanolic extract of Phryna ortegioides, a monotypic and endemic taxon of Caryophyllaceae.The structures of the new compounds were determined as gypsogenic acid 28-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (2), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-]-β-d-glucopyranosyl ester (3), 3-O-α-l-arabinofuranosyl-16α-hydroxyolean-12-en-23,28-dioic acid-28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (4). Their structures were established by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. Noteworthy, none of isolated compounds possesses as aglycone moiety gypsogenin, considered a marker of Caryophyllaceae family.The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. Only compound 6 showed a weak activity against A375 and DeFew cell lines with IC₅₀ values of 77 and 52 μM, respectively. None of the other tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number.     

New heterocyclic compounds from Ranunculus ternatus Thunb.

Five new heterocyclic compounds, 5-α-d-fructofuranosylmethyl-furfural (1), 5-β-d-fructofuranosylmethyl-furfural (2), 5-β-d-fructopyranosylmethyl-furfural (3), 4-(2-((2S-2,3-dihydroxypropoxy)methyl)-5-formyl-1H-pyrrol-1-yl)butanoic acid (4), and 3S,4S-4,5,8-trihydroxy-3-(prop-1-en-2-yl)isochroman-1-one (5), were obtained from the root of Ranunculus ternatus Thunb., which is a traditional Chinese anti-tuberculosis medicine. Their structures were elucidated by UV, IR, HRESIMS, NMR data, and the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Notably, compounds 1–3 are rarely occurring furfural fructosides in natural sources. These heterocyclic compounds could be further studied for the synthetic chemists and pharmacologists due to the source and structural properties.     

Bioactivity-guided isolation of cytotoxic sesquiterpenes of Rolandra fruticosa

Cytotoxicity-guided fractionation of a methanol extract of the leaves and twigs of Rolandra fruticosa using the HT-29 human colon cancer cell line led to the isolation of seven sesquiterpene lactones, including the hitherto unknown isorolandrolide, 13-methoxyisorolandrolide (1), and bourbonenolide, 2α,13-diacetoxy-4α-hydroxy-8α-isobutyroyloxybourbonen-12,6α-olide (2), as well as five known compounds, 13-acetoxyrolandrolide (3), 8-desacyl-13-acetoxyrolandrolide-8-O-tiglate (4), 2-epi-glaucolide E (5), 2α,13-diacetoxy-4α-hydroxy-8α-methacryloyloxybourbonen-12,6α-olide (6), and 2α,13-diacetoxy-4α-hydroxy-8α-tigloyloxybourbonen-12,6α-olide (7). The structures of the two sesquiterpenes were elucidated on the basis of spectroscopic methods. All isolates were evaluated for their cytotoxicity using the HT-29 cell line, and only 13-acetoxyrolandrolide (3) was found to possess a potent inhibitory effect against this cell line. Compounds 3, 5 and 6 were also tested in a NF-κB (p65) inhibition assay, and 3 was assessed in an in vivo hollow fiber assay.     

Three new D:A Friedo-oleanane triterpenes from the stem bark of Anacolosa poilanei and their cytotoxic activities

Three new D:A friedo-oleanane triterpenes, 3α-p-coumaroyl-D:A-friedo-oleanan-27-oic acid (1), 3α-(3,4-dihydroxycinnamoyl)-D:A-friedo-oleanan-27-oic acid (2), and 3α-(3,4-dihydroxycinnamoyl)-D:A-friedo-oleanan-27,15α-lactone (3) along with three known compounds, trichadenic acid A (4), trichadonic acid (5), and amentoflavone (6), were isolated from the stem barks of Anacolosa poilanei Gagnep. Their structures were established by spectral analysis, such as mass spectrometry, 1D-NMR, and 2D-NMR. Compound 1 exhibited cytotoxicity against LU-1, HepG2, MCF7, and KB cell lines. Compounds 2 and 3 were more active against KB and HepG2 compared to the LU-1 and MCF7 cells.     

Phenylethanoid glycosides from the leaves of Magnolia hodgsonii

Three new phenylethanoid glycosides, 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-d-allopyranoside (hodgsonialloside A, 1), 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-d-glucopyranosyl-(1 → 4)-β-d-allopyranoside (hodgsonialloside B, 2) and 2-(3-methoxy-4-hydroxyphenyl)ethyl 1-O-β-d-allopyranoside (hodgsonialloside C, 3) were isolated from the leaves of Magnolia hodgsonii in addition to six known compounds, tyrosol 4-O-β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranoside (4), kaempferol 3-O-neohesperidoside (5), kaempferol 3-O-rutinoside (6), kaempferol 3-O-α-l-rhamnopyranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside (7), (+)-syringaresinol O-β-d-glucopyranoside (8), and oblongionoside C (9). The structure elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D NMR experiments.     

Triterpene glycosides from red ginseng marc and their anti-inflammatory activities

Three new triterpene glycosides ursan-3β,19α,22β-triol-3-O-β-d-glucopyranosyl (2′→1″)-β-d-glucopyranoside (1), ursan-3α,11β-diol-3-O-α-d-glucopyranosyl-(6′→1″)-α-d-glucopyranosyl-(6″→1‴)-α-d-glucopyranosyl-(6‴→1‴′)-α-d-glucopyranoside (2) and lanost-5,24-dien-3β-ol-3-O-β-d-glucopyranosyl-(6′→1″)-β-d-glucopyranosyl-(6″→1‴)-β-d-glucopyranoside (3), together with one known compound were isolated and identified from the marc of red ginseng. Their structures were elucidated by spectroscopic data analysis. Compounds (1–3) were investigated for anti-inflammatory effects using the RAW 264.7 macrophage cell line. In the cell proliferation assay, lipopolysaccharide stimulation decreased cell proliferation of RAW 264.7 macrophage cells, but the suppression of cell proliferation was significantly protected by treatment with compounds 2 and 3. Compounds 2 and 3 had a suppressive effect on the production of nitric oxide (NO), and they inhibited mRNA expression of proinflammatory mediators such as inducible nitric oxide synthase, and cyclooxygenase-2, and proinflammatory cytokines such as two interleukins and tumor necrosis factor-α. These findings suggest that compounds 2 and 3 have potential anti-inflammatory activities.     

Sulphated polysaccharides of the grateloupiaceae family : Part VII. Investigation of the acetolysis products of a partially desulphated sample of the polysaccharide of pachymenia carnosa

Investigation of the acetolysis products of a partially desulphated sample of the polysaccharide isolated from Pachymenia carnosa led to the isolation and characterization of the following oligosaccharides: 3-O-α-D-galactopyranosyl-D-galactose (1), 4-O-β-D-galactopyranosyl-D-galactose (2), 3-O-(2-O-methyl-α-D-galactopyranosyl)-D-galactose (3), a 4-O-galactopyranosyl-2-O-methylgalactose (4), 3-O-α-D-galactopyranosyl-6-O-methyl-D-galactose (5), 4-O-β-D-galactopyranosyl-2-O-methyl-D-galactose (6), 2-O-methyl-4-O-(6-O-methyl-β-D-galactopyranosyl)-D-galactose (14), O-β-D-galactopyranosyl-(1→4)-O-α-D-galactopyranosyl-(1→3)-D-galactose (8), O-α-D-galactopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-galactose (9), O-β-D-galactopyranosyl-(1→4)-O-α-(2-O-methyl-D-galactopyranosyl)-(1→3)-D-galactose (11), O-α-(2-O-methyl-D-galactopyranosyl)-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-galactose (12), O-α-D-galactopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-2-O-methyl-D-galactose (13), O-α-(2-O-methyl-D-galactopyranosyl)-(1→3)-O-β-D-galactopyranosyl-(1→4)-2-O-methyl-D-galactose (16), and O-β-D-galactopyranosyl-(1→4)-O-α-D-galactopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-galactose (10). In addition, evidence was obtained for the presence of 4-O-(6-O-methyl-β-D-galactopyranosyl)-D-galactose (7) and O-β-D-galactopyranosyl-(1→4)-O-α-D-galactopyranosyl-(1→3)-6-O-methyl-D-galactose (15).     

C-glycosylflavone with rotational isomers from Vaccaria hispanica (Miller) Rauschert seeds

Five C-glycosylflavone were isolated from Vaccaria hispanica (Miller) Rauschert seeds. Their NMR spectra showed separate signals because of the existence of rotational isomers, which is an unusual phenomenon. The spectroscopic data revealed that compounds 1–5 were identified as apigenin 6-C-[α-l-arabinopyranosyl-(1′′′→2′′)-β-d-glucopyranosyl]-7-O-β-d-glucopyranoside (1), apigenin 6-C-[α-l-arabinopyranosyl-(1′′′→2′′)-β-d-glucopyranosyl]-7-O-(6′′′′-O-dihydroferuloyl)-β-d-glucopyranoside (2), apigenin 6-C-β-d-glucopyranosyl-7-O-(6′′′-O-dihydroferuloyl)-β-d-glucopyranoside (3) and isovitexin-2′′-O-arabinoside (4) and saponarin (5), respectively. The structure of ‘vaccarin’ was revised to apigenin 6-C-[α-l-arabinopyranosyl-(1′′′→2′′)-β-d-glucopyranosyl]-7-O-β-d-glucopyranoside and consequently 1 should be named ‘vaccarin’. Among the isolated compounds, 2 and 3 are new and named vaccarin E and vaccarin F, respectively.