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Two new iridoid glycosides, callicoside E (1) and callicoside F (2), were isolated from the leaves of Callicarpa nudiflora. Their structures were established by one- and two-dimensional NMR spectroscopy and mass spectrometry. In an in vitro bioassay, compounds 1 and 2 showed an pronounced hepatoprotective activity against d-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

Two new noroleanane-type triterpenoid saponins, 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-L-fucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranoside (1) and 3β,20α,24-trihydroxy-29-norolean-12-en-28-oic acid 24-O-β-D-glucopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucopyranoside (2) were isolated from the stems of Stauntonia chinensis DC., together with three known compounds, brachyantheraoside B2 (3), eupteleasaponin Ⅷ (4) and fargoside B (5). Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of compounds 1 and 2 were evaluated against five human tumor cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780). Compounds 1 and 2 showed moderate cytotoxic activities toward the tested cell lines with IC50 values ranging from 12.71 to 32.04 μM.

Background Platelet activation and subsequent accumulation at sites of vascular injury perform a central role in thrombus formation, which is believed to be the trigger of several cardiovascular diseases, such as atherosclerosis, myocardial infarction and strokes. In this sense, the search for agents that are capable of blocking platelets aggregation has important implications for these diseases. Callicarpa nudiflora (C. nudiflora) Hook is a traditional Chinese medicine herb for eliminating stasis to subdue swelling and hemostasis. Our previous study found several compounds extracted from this herb, including 1, 6-di-O-caffeoyl-β-D-glucopyranoside (CGP), showed inhibitory effects on adenosine diphosphate (ADP) induced platelet aggregation. Purpose The aim of current study is confirmation of the anti-platelet effects and elucidation of the probable mechanisms. Methods The experiments were performed on platelet rich plasma freshly isolated from SD rat. ADP, U46619 or arachidonic acid (AA) induced platelet aggregation assay were performed to evaluate the anti-platelet properties of CGP. Activated αIIbβ3 integrin abundance, serotonin (5-HT) secretion, thromboxane A2 (TXA2) synthesis was determined to assess the effects of CGP on platelet activation. Furthermore, RhoA and PI3K/Akt/GSK3β signal transduction were analyzed by Western Blotting assay. In addition, radiolabelled ligand binding assay was involved to evaluate the ability of CGP binding to thromboxane prostanoid (TP) and P2Y12 receptors. Results CGP inhibited platelet aggregation induced by ADP, U46619 and arachidonic acid (AA), significantly. Furthermore, it is also found that LGP exhibited obvious inhibitory effects on αIIbβ3 integrin activation, serotonin (5-HT) secretion from granule and thromboxane A2 (TXA2) synthesis. Next, we found that CGP suppressed RhoA and PI3K/Akt/GSK3β signal transduction. Data from radiolabelled ligand binding assay showed that CGP displayed apparent competing effects on TP and P2Y12 receptors. Conclusion Collectively, the data presented here demonstrated that CGP, a natural compound from Callicarpa nudiflora Hook, inhibited the development of platelet aggregation and amplification of platelet activation. These inhibitory effects may be associated with its dual-receptor inhibition on P2Y12 and TP receptors.

Two new iridoid glycosides, callicoside C (1) and callicoside D (2), together with three known compounds (3–5), were isolated from the leaves of Callicarpa nudiflora. Their structures were established by 1D and 2D NMR spectroscopy and mass spectrometry. In an in vitro bioassay, compound 1 showed pronounced hepatoprotective activity against d-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

Two new norneolignans, (7

Two new iridoid glycosides, callicoside E (

Cloperastine hydrochloride, a piperidine derivative, is a drug substance with a central antitussive effect and widely used in cough treatment; and its impurities have not been reported. Herein we isolated and identified five impurities (named as impurity A, B, C, D and E) in cloperastine hydrochloride bulk drug and developed a quantitative HPLC method. First, impurity A, B, C were enriched by ODS column chromatography and isolated by semi-preparative HPLC, at the same time, impurity D was purified by ODS column chromatography. Then, impurity E was enriched by strong acid degradation and purified by semi-preparative HPLC. At last, their structures were characterized by a variety of spectral data (MS, 1H NMR, 13C NMR, HSQC, HMBC and 1H-1H COSY). Impurity A was confirmed as 1-[2-(diphenylmethoxy)ethyl]piperidine, which having one less chloro-substituent compared with cloperastine. Impurity B was confirmed as 1-[2-[(2-chlorophenyl)(phenyl)methoxy]ethyl]piperidine, which was the isomer of cloperastine with 2-chloro-substituent. Impurity C was confirmed as 1-[2-[(3-chlorophenyl)(phenyl)methoxy]ethyl]piperidine, which was the isomer of cloperastine with 3-chloro-substituent. Impurity D was confirmed as (4-chlorophenyl)(phenyl)methanone, which was the raw material for the synthesis of cloperastine. Impurity E was confirmed as (4-chlorophenyl)(phenyl)methanol, which was an intermediate in the synthesis of cloperastine, and it was also a hydrolysate of cloperastine. Finally, the developed method was validated in terms of specificity, linearity, sensitivity, precision and accuracy.

To study the chemical constituents of Stauntonia chinensis.The chemical constituents were isolated and purified by column chromatography on silica gel,ODS,Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of physicochemical properties and special analysis.Seven compounds were isolated from the leaves of Stauntonia chinensis,whose structures were elucidated as 3-O-β-D-glucopyranosyl-( 1 →3)-[β-D-xylopyranosyl-( 1 →2) ]-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-( 1 →4)-β-D-glucopyranosyl-( 1 →6)-β-D-glucopyranosyl]-3β-hydroxy-30-norolean-12,20( 29)-dien-28-oic acid( 1),3-[( O-β-D-glucopyranosyl-( 1→3)-[α-L-rhamnopyranosyl-( 1 →2) ]-α-L-arabinopyranosyl) oxy]-30-norolean-12,20( 29)-dien-28-oic acid O-β-D-glucopyranosyl-( 1 → 6)-β-D-glucopyranosyl ester( 2),3-O-β-D-[( α-L-xylopyranosyl-( 1 → 2)-O-α-L-arabinopyranosyl)oxy]-30-norolean-12-en-28-oic acid α-L-rhamnopyranosyl-( 1 → 4)-O-β-D-glucopyranosyl-( 1 → 6)-O-β-D-glucopyranosyl ester( 3), yemuoside YM27( 4), yemuoside YM21( 5),yemuoside YM10( 6) and yemuoside YM7( 7).Compounds 1 ~ 3 are isolated from this plant for the first time.

Five new oleanane-type triterpenoid saponins, oleiferasaponins D1–D5 (1–5), were isolated from the defatted seeds of Camellia oleifera Abel. Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of compounds 1–5 were evaluated against five human tumor cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780). Compounds 1–2 exhibited cytotoxic activity against five human cancer cell lines, with IC50 values ranging from 3.31 to 10.23 μM. Compounds 3–5 showed moderate cytotoxic activities toward the tested cell lines.

Three new lignans, (1R,2R,5R,6R)-1-hydroxy-2-(3,4-methylenedioxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (1), (1R,2S,5R,6R)-1-hydroxy-2-(3,4-methylenedioxyphenyl)-6-(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (2), and (1R,2S,5R,6R)-1-hydroxy-2-(3,4-dihydroxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (3), were isolated from the leaves of Callicarpa nudiflora Hook. Their structures were elucidated on the basis of spectroscopic data and chemical methods. Compounds 1–3 exhibited antioxidant activities with EC50 values of 19.8, 18.5, and 8.3 μM, respectively.

Four new triterpenoid saponins, 2α,3α,19α,24-tetrahydroxyolean-12-en-28-oic-acid 28-O-β-D-glucopyranosyl ester (1), 2α,3α,19α,23-tetrahydroxyolean-12-en-28-oic-acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-glu-copyranosyl ester (2), 2α,3α,19α-trihydroxyolean-12-en-28-oic-acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl ester (3), 2α,3α,23,29-tetrahydroxyurs-12,19-dien-28-oic-acid 28-O-β-D-glucopyranosyl ester (4), together with three known compounds (5-7), were isolated from the leaves of Callicarpa nudiflora HOOK. Their structures were established by means of spectroscopic methods and chemical evidence. Hepatoprotective activities of the isolated compounds against D-galactosamine-induced toxicity have been tested. Among them, compounds 1-3 showed pronounced hepatoprotective activities against D-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

Two new flavan glycosides, (2S)-5,7,4'-trihydroxyflavan-7-O-β-D-glucopyranoside and (2S)-5,7,4'-trihydroxyflavan-5-O-β-D-glucopyranoside, and a new neolignan, (7S,8S)-3-methoxyl-3'-O-β-D-glucopyrannosyl-4':8,5':7-diepoxyneolignan-4,9'-diol, were isolated from the leaves of Liquidambar formosana Hance. Their structures were elucidated on the basis of spectroscopic data and chemical evidence.

A new protopanaxadiol-type ginsenoside, 6-O-β-d-glucopyranosyl-20-O-β-d-glucopyranosyl-20(S)-protopanaxadiol-3-one (1), along with three known compounds, was isolated from the roots of Panax notoginseng. Their structures were determined based on some pieces of spectroscopic and chemical evidence. Compound 1 exhibited cytotoxic activity against five human cancer cell lines, with IC50 values ranging from 5.4 to 8.6 μg/ml.

Two new triterpenoids, 2α,3α,19α,23-tetrahydroxyurs-12,20(30)-dien-28-oic acid (1) and 2α,3α,19α-trihydroxyurs-12-en-28-oic acid-28-O-β-D-xylopyranosyl (1→2)-β-D-glucopyranoside (2), and a new acylated flavone glycoside, luteolin 3'-O-(6″-E-caffeoyl)-β-D-glucopyranoside (3), together with three known compounds (4-6), were isolated from the leaves of Callicarpa nudiflora Hook. Their structures were elucidated on the basis of spectroscopic data and chemical methods. Anti-platelet aggregation activities of these compounds were evaluated in vitro. Compounds 1 and 2 showed inhibitory effects on ADP-induced platelet aggregation with EC50 values of 9.48 μM and 25.31 μM, respectively.

Nine new triterpenoid saponins named longicarposides A–I ( 1 – 9 ), together with three known saponins ( 10 – 12 ), were isolated from the stems of Gordonia longicarpa . The structures of the saponins were elucidated by a combination of 1D and 2D NMR techniques, mass spectrometry, and chemical methods. They were characterized to be oleanane-type saponins with sugar moieties linked to C-3 of the aglycone. Cytotoxic activities of these saponins were evaluated against five human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780) by using the MTT in vitro assay. Compounds 5, 7, 8, 10 , and 11 exhibited potent cytotoxic activity with IC 50 values of 1.42–8.42 µM, while 6, 9 , and 12 showed selective cytotoxic activity toward the tested cell lines.

Eleven oleanane-type triterpenoid glycosides, named gordonsaponins A−K, were isolated from the stems of Gordonia kwangsiensis . Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of all eleven were evaluated against five human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780), with only one having activity against all tested cell lines, with IC 50 values ranging from 0.1 to 2.41 μM.

To study the chemical constituents of Callicarpa nudiflora.The chemical constituents were isolated and purified by column chromatography on silica gel, ODS, Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of physicochemical properties and special analysis.Eleven compounds were isolated from the leaves of Callicarpa nudiflora, whose structures were elucidated as 2α,3α-dihydroxyurs-12-en-28-oic acid (1), isorhamnetin (2), 2α,3β,19α-trihydroxyurs-12-en-28-oic acid(3), 2α,3α,19α,23-tetrahydroxyurs-12-en-28-oic acid(4), 2α,3α,19α-trihyhydroxy-olean-12-en-28-O-α-D-glucopyranoside (5), benzyl-4'-hydroxy-benzoyl-3'-O-β-D-glucopyranoside(6) (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol(7), philonotisflavone(8), 1, 6-di-O-caffeoyl-β-D-glucopyranoside (9), luteolin-4'-O-(6"-E-caffeoyl)-β-D-glucopyranoside (10), and (6S, 9R)-roseoside(11).All compounds are isolated from this plant for the first time.

To study the chemical constituents of stem of Camellia oleifera.The chemical constituents were isolated and purified by column chromatography on silica gel, ODS, Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of physicochemical properties and special analysis.Seven compounds were isolated from the stem of Camellia oleifera, whose structures were elucidated as (-) -pinoresinol (1), (-) -medioresinol (2), skullcapflavone II (3), betulinic acid (4), ursolic acid (5), 3-O-β-D-glucopyranosyl- (1 --2) -β-D-xylopyransoyl-(1 --3) -[β-D-glucopyranosyl- (1 --2)] -β-D-glucuronopyranosyl-22α-angeloyloxyolean-12-ene-15α,16α,28-triol (6) and oleanolic acid (7).Compounds 1 - 6 are isolated from this plant for the first time, and compounds 1 - 3 are isolated from this genus for the first time.

Two new iridoid glucosides, callicoside A (1) and callicoside B (2), were isolated from the leaves of Callicarpa nudiflora. Their structures were elucidated by means of spectroscopic methods and chemical evidences. In an in vitro bioassay, compound 1 showed pronounced hepatoprotective activity against D-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

To study the chemical constituents of the leaves of Psidium guajava.The chemical constituents were isolated by column chromatography on silica gel, Sephadex LH-20 and MPLC. Their chemical structures were elucidated on the basis of special analysis.Seven compounds were isolated from n-butyl alcohol fraction, whose structures were elucidated as morin-3-O-α-L-arabopyranoside (1), morin-3-O-α-L-iyxopyranoside (2), 2,6-dihydroxy-4-O-β-D-glucopyranosyl-benzophenone (3), casuarictin (4),2,6-dihydroxy-3,5-dimethyl-4-O-(6"-O-galloyl-β-D-glucopyranosyl)-benzophenone(5), globulusin A(6), and kaempferol-3-O-β-D-(6"-galloyl) galactopyranoside (7).Compounds 3 and 5 ~ 7 are isolated from this plant for the first time.

To study the chemical constituents of the leaves of Liquidambarformosana.The chemical constituents were isolated and purified by column chromatography on silicagel, Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of physicochemical properties and special analysis.Eight compounds were isolated from the leaves of Liquidambar formosana, whose structures were elucidated as gallic acid (1), p-hydroxy-benzoic acid (2), 3-methoxy-4-hydroxy-benzoic acid (3), 3,5-dihydroxy-4-methoxy-benzoic acid (4) kaempferol (5), 3,4-dihydroxy-benzoic acid (6), 3,4-dihydroxy-5-methoxy-benzoic acid (7) and 3β,23,29-trihydroxy-olean-12-en-28-oic acid-β-D-glucopyranosyl ester (8).Compounds 1-8 are isolated from the leaves of Liquidambar formosana for the first time.

To study the ethyl acetate-soluble chemical constituents of Callicarpa kwangtungensis.The chemical constituents were isolated by column chromatography on silica gel, Sephadex LH-20 and MPLC. Their chemical structures were elucidated on the basis of special analysis.Seven compounds were isolated from ethyl acetate part, whose structures were elucidated as caffeic acid(1),2α,3α, 19α-trihyhydroxy-urs-12-en-28-O-β-D-glucopyranoside (2),2α,3, 19α-trihyhydroxy-olean-12-en-28-O-β-D-glucopyranoside (3), 2α, 3α, 19α-trihyhydroxy-olean-12-en-28-O-β-D-glucopyranoside (4), ferulic acid (5), 2α, 3β, 19α-trihyhydroxy-urs-12-en-28-O-β-D-glucopyranoside(6), and ( + )-isolariciresinol-9-O-β-D-glucopyranoside(7).All these compounds are isolated from this plant for the first time.

Four new triterpenoids which were identifed as 2α,3β,6β,19α-tetrahydroxy- oleanolic acid 28-O-β-D-glucopyranoside (1), 2-O-β-D-glucopyranosyloxy-3α,19α-di-hydroxyoleanolic acid (2), 2-O-β-D-glucopyranosyloxy-3α,19α-dihydroxyursolic acid (3), 2α,3α,6β,19α-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (4), were isolated from the aerial parts of Callicarpa kwangtungensis together with three known triterpenoids identified as 2α,3β,21β-trihydroxyursolic acid 28-O-β-D-glucopyranoside (5), 2α,3α,19α,23-tetrahydroxyoleanolic acid 28-O-β-D-glucopyranoside (6), 2α,3α,19α,23-tetrahydroxyursolic acid 28-O-β-D-glucopyranoside (7). Their structures were elucidated by the combination of mass spectrometry (MS), one and two-dimensional NMR experiments.

Three new labdane-type diterpene glycosides, 15,18-di-O-β-d-glucopyranosyl-13(E)-ent-labda-7(8),13(14)-diene-3β,15,18-triol (1), 15,18-di-O-β-d-glucopyranosyl-13(E)-ent-labda-8(9),13(14)-diene-3β,15,18-triol (2), and 15-O-β-d-apiofuranosyl-(1→2)-β-d-glucopyranosyl-18-O-β-d-glucopyranosyl-13(E)-ent-labda-8(9),13(14)-diene-3β,15,18-triol (3), were isolated from the fruits of Rubus chingii. Their structures were elucidated on the basis of spectroscopic data and chemical methods. The cytotoxic activities of compounds 1-3 were evaluated against five human tumor cell lines (HCT-8, BGC-823, A549, and A2780). Compounds 3 showed cytotoxic activity against A549 with an IC50 value of 2.32μM.

Two new triterpenoids, 2α,3β,16α,19α,23-pentahydroxyolean-12-en-28-oic acid (1) and 2α,3α,11α,21α,23-pentahydroxyurs-12-en-28-oic acid (2), were isolated from the aerial parts of Callicarpa kwangtungensis. Their structures were elucidated by 1D and 2D analyses, as well as MS and IR spectra.

A new benzophenone glycoside, 2,6-dihydroxy-4-O-β- d -glucopyranosylbenzophenone (1), was isolated from the leaves of guajava L. Its structure was elucidated by spectral and chemical methods. 1 showed significant activities to secretion of NO in mouse peritoneal macrophages in 10 μmol/L.

To study the chemical constituents of the leaf of Salix matsudana.The chemical constituents were isolated by column chromatography on silica gel, Sephadex LH-20 and MPLC. Their structures were elucidated on the basis of spectral analysis.Eight compounds were isolated and their structures were identified as beta-Sitosterol(1),5,7-Dihydroxychromone-7-O-beta-D-glucopyranoside(2), (2S)-Helichrysin A(3), (2R)-Helichrysin A(4), Luteolin-7-O-beta-D-glucoside(5), Salicin(6), Apigenin-7-O-beta-D-glucopyranside(7), Lutelion-3'-methylether-7-O-f-D-glucopyranside(8).Compounds 1-4 are isolated from this plant for the first time.

Four new triterpenoid saponins, 2α,3α,19α,24-tetrahydroxyolean-12-en-28-oic-acid 28-O-β-D-glucopyranosyl ester (1), 2α,3α,19α,23-tetrahydroxyolean-12-en-28-oic-acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-glu-copyranosyl ester (2), 2α,3α,19α-trihydroxyolean-12-en-28-oic-acid 28-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl ester (3), 2α,3α,23,29-tetrahydroxyurs-12,19-dien-28-oic-acid 28-O-β-D-glucopyranosyl ester (4), together with three known compounds (5-7), were isolated from the leaves of Callicarpa nudiflora HOOK. Their structures were established by means of spectroscopic methods and chemical evidence. Hepatoprotective activities of the isolated compounds against D-galactosamine-induced toxicity have been tested. Among them, compounds 1-3 showed pronounced hepatoprotective activities against D-galactosamine-induced toxicity in WB-F344 rat hepatic epithelial stem-like cells.

A new tetrahydrophenanthrene named henryin A (1) was isolated from the leaves of Chloranthus henryi. Its structure was determined to be (S)-4,6,9-trimethyl-5,6,7,8-tetrahydrophenanthrene-1,2-diol on the basis of IR, MS, 1D and 2D NMR spectral.

A new regioisomer of andrographolide, 17-hydro-9-dehydro-andrographolide (1), and five new sulfates of andrographolide (2–6) were isolated from Xiyanping, a China licensed anti-inflammatory drug derived from andrographolide through sulfation reaction. Their chemical structures were elucidated by spectroscopic and chemical methods. The inhibition effects of these compounds on angiogenesis were evaluated by rat aortic ring assay. Compounds 1 and 3 exhibited strong inhibitory activities on vascular endothelial cell tube formation in rat aorta ring at the concentration of 1 μM. Compounds 4 and 5 showed moderate suppression on angiogenesis at 10 μM.

Eight new oleanane-type triterpenoid glycosides, gordonosides I-P (1-8), and two new phenolic glycosides (9 and 10) were isolated from the stems of Gordonia chrysandra. Their structures were elucidated by spectroscopic and chemical methods. In an in vitro bioassay, compound 1 showed a strong inhibitory effect on nitric oxide production in LPS-activated macrophages with an IC50 value of 0.14 μM.

Three novel sesquiterpenoid-based meroterpenoids of psidials A−C (1−3) have been isolated from the leaves of Psidium guajava L. Their complete structures were elucidated by spectral and chemical me...

A new tetrahydrophenanthrene named henryin A (1) was isolated from the leaves of Chloranthus henryi. Its structure was determined to be (S)-4,6,9-trimethyl-5,6,7,8-tetrahydrophenanthrene-1,2-diol on the basis of IR, MS, 1D and 2D NMR spectral.

Three novel sesquiterpenoid-based meroterpenoids of psidials A-C (1-3) have been isolated from the leaves of Psidium guajava L. Their complete structures were elucidated by spectral and chemical methods, and that of 1 was confirmed by single-crystal X-ray diffraction analysis. Psidial B (2) and C (3) represented the new skeleton of the 3,5-diformylbenzyl phloroglucinol-coupled sesquiterpenoid. A possible biosynthetic pathway for 2-3 was postulated. 2-3 showed activity to enzyme PTP1B in 10 microM.