Two new iridoid glycosides from Callicarpa nudiflora.

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.[Formula: see text].

Cytotoxic triterpenoid saponins from the defatted seeds of Camellia oleifera Abel.

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.

Two new iridoid glycosides from the leaves of Callicarpa nudiflora.

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.

Hepatoprotective iridoid glucosides from Callicarpa nudiflora.

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.

[Chemical Constituents from Stauntonia chinensis].

Objective: To study the chemical constituents of Stauntonia chinensis. Methods: 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. Results: Seven compounds were isolated from the leaves of Stauntonia chinensis,whose structures were elucidated as 3-O-ß-D-glucopyranosyl-( 1 →3)-[ß-D-xylopyranosyl-( 1 →2) ]-α-L-arabinopyranosyl-28-O-[α-L-rhamnopyranosyl-( 1 →4)-ß-D-glucopyranosyl-( 1 →6)-ß-D-glucopyranosyl]-3ß-hydroxy-30-norolean-12,20( 29)-dien-28-oic acid( 1),3-[( O-ß-D-glucopyranosyl-( 1→3)-[α-L-rhamnopyranosyl-( 1 →2) ]-α-L-arabinopyranosyl) oxy]-30-norolean-12,20( 29)-dien-28-oic acid O-ß-D-glucopyranosyl-( 1 → 6)-ß-D-glucopyranosyl ester( 2),3-O-ß-D-[( α-L-xylopyranosyl-( 1 → 2)-O-α-L-arabinopyranosyl)oxy]-30-norolean-12-en-28-oic acid α-L-rhamnopyranosyl-( 1 → 4)-O-ß-D-glucopyranosyl-( 1 → 6)-O-ß-D-glucopyranosyl ester( 3), yemuoside YM27( 4), yemuoside YM21( 5),yemuoside YM10( 6) and yemuoside YM7( 7). Conclusion: Compounds 1 ~ 3 are isolated from this plant for the first time.

Two new triterpenoids from Callicarpa kwangtungensis.

Two new triterpenoids, 2α,3ß,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.

Four New Triterpenoids from Callicarpa kwangtungensis.

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

[n-Butyl Alcohol-soluble Chemical Constituents of Psidium guajava Leaves].

OBJECTIVE: To study the chemical constituents of the leaves of Psidium guajava. METHODS: 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. RESULTS: 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-ß-D-glucopyranosyl-benzophenone (3), casuarictin (4),2,6-dihydroxy-3,5-dimethyl-4-O-(6"-O-galloyl-ß-D-glucopyranosyl)-benzophenone(5), globulusin A(6), and kaempferol-3-O-ß-D-(6"-galloyl) galactopyranoside (7). CONCLUSION: Compounds 3 and 5 ~ 7 are isolated from this plant for the first time.

[Chemical Constituents from Camellia oleifera Stem].

OBJECTIVE: To study the chemical constituents of stem of Camellia oleifera. METHODS: 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. RESULTS: 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-ß-D-glucopyranosyl- (1 --> 2) -ß-D-xylopyransoyl-(1 --> 3) -[ß-D-glucopyranosyl- (1 --> 2)] -ß-D-glucuronopyranosyl-22α-angeloyloxyolean-12-ene-15α,16α,28-triol (6) and oleanolic acid (7). CONCLUSION: 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.

[Chemical Constituents from Callicarpa nudiflora].

OBJECTIVE: To study the chemical constituents of Callicarpa nudiflora. METHODS: 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. RESULTS: 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,3ß,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-ß-D-glucopyranoside(6) (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol(7), philonotisflavone(8), 1, 6-di-O-caffeoyl-ß-D-glucopyranoside (9), luteolin-4'-O-(6"-E-caffeoyl)-ß-D-glucopyranoside (10), and (6S, 9R)-roseoside(11). CONCLUSION: All compounds are isolated from this plant for the first time.

Hepatoprotective triterpenoid saponins from Callicarpa nudiflora.

Four new triterpenoid saponins, 2α,3α,19α,24-tetrahydroxyolean-12-en-28-oic-acid 28-O-ß-D-glucopyranosyl ester (1), 2α,3α,19α,23-tetrahydroxyolean-12-en-28-oic-acid 28-O-ß-D-xylopyranosyl-(1→2)-ß-D-glu-copyranosyl ester (2), 2α,3α,19α-trihydroxyolean-12-en-28-oic-acid 28-O-ß-D-xylopyranosyl-(1→2)-ß-D-glucopyranosyl ester (3), 2α,3α,23,29-tetrahydroxyurs-12,19-dien-28-oic-acid 28-O-ß-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.

[Ethyl acetate-soluble chemical constituents from Callicarpa kwangtungensis].

OBJECTIVE: To study the ethyl acetate-soluble chemical constituents of Callicarpa kwangtungensis. METHODS: 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. RESULTS: 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-ß-D-glucopyranoside (2),2α,3, 19α-trihyhydroxy-olean-12-en-28-O-ß-D-glucopyranoside (3), 2α, 3α, 19α-trihyhydroxy-olean-12-en-28-O-ß-D-glucopyranoside (4), ferulic acid (5), 2α, 3ß, 19α-trihyhydroxy-urs-12-en-28-O-ß-D-glucopyranoside(6), and ( + )-isolariciresinol-9-O-ß-D-glucopyranoside(7). CONCLUSION: All these compounds are isolated from this plant for the first time.

[Chemical Constituents from Leaves of Liquidambar formosana].

OBJECTIVE: To study the chemical constituents of the leaves of Liquidambarformosana. METHODS: 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. RESULTS: 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 3ß,23,29-trihydroxy-olean-12-en-28-oic acid-ß-D-glucopyranosyl ester (8). CONCLUSION: Compounds 1-8 are isolated from the leaves of Liquidambar formosana for the first time.

Potential anti-angiogenic sulfates of andrographolide.

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.

A new protopanaxadiol-type ginsenoside from the roots of Panax notoginseng.

A new protopanaxadiol-type ginsenoside, 6-O-ß-d-glucopyranosyl-20-O-ß-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.

Three new compounds from the leaves of Liquidambar formosana.

Two new flavan glycosides, (2S)-5,7,4'-trihydroxyflavan-7-O-ß-D-glucopyranoside and (2S)-5,7,4'-trihydroxyflavan-5-O-ß-D-glucopyranoside, and a new neolignan, (7S,8S)-3-methoxyl-3'-O-ß-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.

[Chemical constituents of Salix matsudana leaf].

OBJECTIVE: To study the chemical constituents of the leaf of Salix matsudana. METHODS: 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. RESULTS: 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). CONCLUSION: Compounds 1-4 are isolated from this plant for the first time.

Potential anti-inflammatory constituents of the stems of Gordonia chrysandra.

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.

Identification and quantification of five impurities in cloperastine hydrochloride.

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.

Two new norneolignans from Callicarpa kwangtungensis.

Two new norneolignans, (7S,8R)-3-methoxy-3',4,9-trihydroxy-4',7-epoxy-8,3'-neolignane-1'-carboxylic acid (1) and (7R,8R)-3-methoxyl-4,9-dihydroxy-3':7,4':8-diepoxyneolignan-1'-carboxylic acid methyl ester (2) were isolated from Callicarpa kwangtungensis, together with ten known compounds, genistin (3), daidzin (4), silybin A (5), isosilybin A (6), isosilybin B (7), p-hydroxybenzaldehyde (8), syringic acid (9), lanceolatin A (10), icariside C5 (11), and (3S,6E,10R)-10-ß-D-glucopyranosyloxy-3,11-dihydroxy-3,7,11-trimethyldodeca-1,6-diene (12). Compounds 1 and 2 were evaluated for their effects on the inhibition of nitric oxide (NO) production in lipopolysaccharide induced RAW264.7 cells. Compounds 1 and 2 exhibited inhibitory activity with IC50 values of 31.45 ± 0.38 and 40.72 ± 0.54 µM, respectively.