Advances in indole alkaloids from traditional Chinese medicine of Uncariae Ramulus Cum Uncis documented in Chinese Pharmacopoeia / 中国中药杂志

Uncaria genus( Rubiaceae) contains 34 species all over the world,of which 11 species and one variant are present in China. Five species,namely U. rhynchophylla,U. macrophylla,U. hirsuta,U. sinensis and U. sessilifructus,are documented in Chinese Pharmacopoeia as the raw materials of Uncariae Ramulus Cum Uncis. Indole alkaloids are the characteristic constituents of Uncaria plants,in addition to triterpenes,lignans and flavones. This paper reviews the progress of indole alkaloids and their distribution within the five Uncaria species documented in Chinese Pharmacopoeia for better understanding the active constituents of Uncariae Ramulus Cum Uncis.

Bioassay-guided isolation of saikosaponins with agonistic activity on 5-hydroxytryptamine 2C receptor from Bupleurum chinense and their potential use for the treatment of obesity / 中国天然药物

5-Hydroxytryptamine 2C (5-HT) receptor is one of the major targets of anti-obesity agents, due to its role in regulation of appetite. In the present study, the 70% EtOH extract of the roots of Bupleurum chinense was revealed to have agonistic activity on 5-HT receptor, and the subsequent bioassay-guided isolation led to identification of several saikosaponins as the active constituents with 5-HT receptor agonistic activity in vitro and anti-obesity activity in vivo. The new compound, 22-oxosaikosaponin d (1), was determined by extensive spectroscopic analyses (HR-ESI-MS, IR, and 1D and 2D NMR). The primary structure-activity relationship study suggested that the intramolecular ether bond between C-13 and C-28 and the number of sugars at C-3 position were closely related to the 5-HT receptor agonistic activity. Saikosaponin a (3), the main saponin in B. chinense, showed obviously agonistic activity on 5-HT receptor with an EC value of 21.08 ± 0.33 μmol·Lin vitro and could reduce food intake by 39.1% and 69.2%, and weight gain by 13.6% and 16.4%, respectively, at 3.0 and 6.0 mg·kgin vivo. This investigation provided valuable information for the potential use of B. chinense as anti-obesity agent.

Chemical structure and bioactivity of cis-5'-oxopropylnicotine / 中国中药杂志

In this paper, the chemical constituents and bioactivities of leaves of Nicotiana tabacum were investigated. Six compounds were isolated by means of various chromatographic techniques (silica gel, Sephadex LH-20, MCI GEL CHP-20P and HPLC), and their structures were elucidated as cis-5'-(2-oxopropyl)-nicotine (1), 3-O-(9, 12, 15-octadecatrienoyl)-glyceryl-β-D-galactppyranoside (2), (l'R, 2R, 5S, 10R)-2-(1', 2'-dihydroxy-l'-methylethyl)-6, 10-dimethylspiro [4, 5] dec-6-en-8-one (3), (l'S, 2R, 5S, l0R)-2-(1', 2'-dihydroxy-l'-methylethyl)-6, 10-dimethylspiro [4, 5] dec-6-en-8-one (4),2, 3-dihydroxypropyl-β-D-galactoside (5) and phenylethyl β-D-glucopyranoside (6) by extensive spectroscopic analyses (UV, IR, MS, 1D- and 2D-NMR). Among them, compound 1 is a new alkaloid, and compounds 2-6 are isolated for the first time from N. tabacum. Compounds 1 and 2 were assayed for agitating activities on transient receptor potential vanilloid 1 (TRPV1), melatonin receptor 1 and 2 (MT1 and MT2), 1 showed agitating rate of 55.41% (1.53mmol•L⁻¹) on MT2 and 2 possessed agitating rate of 128.11% (0.59 mmol•L⁻¹) and 52.00% (0.73mmol•L⁻¹) on TRPV1 and MT1, respectively.

Chemical structure of cyperotundic acid from rhizomes of Cyperus rotundus / 中国中药杂志

Thirteen compounds were isolated from the ethyl acetate extract of the rhizomes of Cyperus rotundus(Xiangfu) by means of various chromatographic techniques(silica gel, Al2O3, Sephadex LH-20, MCI GEL CHP-20P and HPLC), and their structures were identified as cyperotundic acid(1),(4S, 5E, 10R)-7-oxo-trinoreudesm-5-en-4β-ol(2), 4-hydroxy-4, 7-dimethyl-1-tetralone(3), taraxerone(4), dammaradienyl acetate(5), zeorin(6), sarmentine(7), guineensine(8), pellitorine(9), caprolactam(10), liriodendrin(11), 3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2,6-dimethoxyphenoxy]propyl-β-D-glucopyranoside(12)and 1-(3, 4-methylenedioxyphenyl)-1E-tetradecene(13) by extensive spectroscopic analyses(IR, MS, 1D-and 2D-NMR). Compound 1 was a new rearranged sesquiterpene and named as cyperotundic acid, which did not obey the isoprene rule.Compounds 2-13 were obtained from the genus Cyperus for the first time.

Chemical constituents of Swertia delavayi and their anti-hepatitis B virus activity / 中国中药杂志

Fifteen known compounds were isolated from Swertia delavayi by silica gel, Sephadex LH-20 and Rp-18 column chromatographies. Based on extensive spectroscopic analysis (MS, 1H, 13C-NMR), their structures were identified aserythrocentaurin (1), erythrocentaurindimethylacetal (2), sweroside (3), swertiamarin (4), gentiopicroside (5), swertiakoside A (6), 2'-O-acetylswertiamarin (7), 4'-O-[(Z) -coumaroyl] swertiamarin (8), 1,5,8-trihydroxy-3-methoxyxanthone (9), 8-O-β-D-glucopyranosyl-1-hydroxy-2,3, 5-trimethoxyxanthone (10), 8-O-[β-D-xyl- opyranosyl-(1 --> 6)-β-D-glucopyranosyl]-7,8-dihydroxy-3-methoxyxanthone (11), isovitexin (12), β-sitosterol (13), daucosterol (14), and oleanolic acid (15). Among them, ten ones (14, 7-11, 13) were obtained from S. delavayi for the first time. The isolates were evaluated for their anti-HBV activities in HepG 2. 2. 15 cell line in vitro. The results showed that compound 1, 2, 6, 7, 9 and 12 exhibited significant inhibitory activity on HBV DNA replication with IC50 values from 0.05 to 1.46 mmol x L(-1).

Chemical constituents of Swertia patens / 中国中药杂志

Chemical constituents of Swertia patens. The whole plant of air-dried Swertia patens was extracted with 90% EtOH. The water extract was suspended in H₂O and extracted with petroleum ether, EtOAc and n-BuOH, successively. The compounds were isola- ted and purified by column chromatography from the EtOAc fraction, and identified based on spectral analyses (MS, ¹H-NMR, ¹³C- NMR). Eighteen compounds were isolated and elucidated as 3, 4-dihydro-1H,6H,8H-naptho [1,2-c:4,5-c', d'dipyrano-1, 8-dione (1), angelone (2), gentiogenal (3), erythricin (4), erythrocentaurin (5), gentianine (6), swertiakoside B (7), swertiamarin (8), 2'-O-actylswertiamarin (9), amarogentin (10), 1, 3, 5-trihydroxyxanthone (11), 1, 3-dihydroxy-5-methoxyxanthone (12), 1-hydroxy- 2, 3, 5-trimethoxyxanthone (13), gentiocrucine (14), 3-hydroxyphenylketone (15), n-hexacosyl ester 4-hydroxy-trans-cinnamate (16), n-hexacosyl ester 4-hydroxy-cis-cinnamate (17), and cholest-4-en-3-one (18). Compounds 1-7, 9-18 were obtained from S. patens for the first time.

Chemical constituents of Lepidium meyenii / 中国中药杂志

To study the chemical constituents of Lepidium meyenii, the air-dried rhizome of L. meyenii was extracted with 70% EtOH. The extract was condensed to a small amount of volume and extracted with petroleum ether, EtOAc and n-BuOH, successively. The compounds were isolated and purified by column chromatography, and identified based on spectral analyses (1H-NMR, 13C-NMR, HRESIMS). Eighteen compounds were isolated from L. meyenii, including 7 alkaloids and 4 fatty acids and 7 other compounds. They were characterized as (3-hydroxybenzyl) carbamic acid(1), phenylmethanamine(2), N-benzylformamide (3), N-benzylacetamide (4), pyridin-4-ylmethanamine(5), n-(4-methoxybenzyl) aniline(6), uracil(7), succininc acid(8), decanedioic acid(9), n-hexa- decanoic acid methyl ester(10), heptanoic acid(11), solerole(12), pyromucic acid methyl ester(13), 5-hydroxymethyl-2-furancar- boxadehyde(14), 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde(15), 1,7-dihydroxy-2,3, 4-trimethoxyxanthone (16), 1,7-di- hydroxy-3,4- dimethoxy-xanthone(17), (+)-pinoresinol(18). Meanwhile, compounds 1-18 were obtained from L. neyenii for the first time.

Chemical constituents of Swertia kouitchensis Franch / 中国中药杂志

This study is to investigate the chemical constituents of Swertia kouitchensis. The whole plants of air-dried Swertia kouitchensis was extracted with 90% EtOH. The water extract was suspended in H2O and extracted with petroleum ether, EtOAc and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the EtOAc fraction, and their structures were identified based on spectral analyses (MS, 1H-NMR, 13C-NMR). Twenty-eight compounds were obtained, and characterized as erythrocentaurin (1), erythrocentaurin dimethylacetal (2), swertiamarin (3), vogeloside (4), 2'-O- actylswertiamarin (5), swertianoside D (6), gentiocrucines A-B (7-8), gentiocrucine (9), 1-hydroxy-3, 7, 8-trimethoxyxanthone (10), 1-hydroxy-3, 5, 6-trimethoxyxanthone (11), 3-epitaraxerol (12), erythrodiol 3-O-palmitate (13), (+) -syringaresinol (14), caffeic acid (15), trans-coniferyl aldehyde (16), trans-coniferyl alcohol (17), 3, 4-dihydroxybenzoic acid (18), 4-hydroxy-3-methoxybenzoic acid (19), 3, 4-dihydroxybenzoic aldehyde (20), 2, 3-dihydroxybenzoic acid (21), 4-hydroxybenzoic acid (22), 3-acetoxybenzoic acid (23), 3-hydroxybenzoic acid (24), 3-hydroxybenzoic alcohol (25), nicotinic acid (26), 2-furoic acid (27), and uracil (28). Compounds 1-4, 6-28 were obtained from S. kouitchensis for the first time.

Chemical constituents of Swertia angustifolia / 中国中药杂志

This present work is to study the chemical constituents of Swertia angustifolia. The whole plants of air-dried Swertia angustifolia was extracted with 90% EtOH. The water extract was suspended in H2O and extracted with petroleum ether, EtOAc and nBuOH, successively. The compounds were isolated and purified by column chromatography from the EtOAc fraction, and identified based on spectral analyses (MS, 1H-NMR, 13C-NMR). Fourteen compounds were isolated and characterized as 1, 8-dihydroxy-3, 7-dimethoxyxanthone (1), 1, 8-dihydroxy-3, 5, 7-trimethoxyxanthone (2), 7-hydroxy-3, 8-dimethoxyxanthone-1-O-β-D-glucopyranoside (3), 8-0-[β-D-xylopyranosyl-(1-6) -β-D-glucopyranosyl] -1, 7-dihydroxy-3-methoxyxanthone (4), (+) -syringaresinol (5), ferulic acid (6), trans-coniferyl aldehyde (7), sinapaldehyde (8), trans-coniferyl alcohol (9), 3, 4-dihydroxybenzoic acid (10), 2-hydroxybenzoic acid (11), isophthalic acid (12), 2-furoic acid (13), and 2-methyl-4(3H)-quinazolinone(14). Compounds 2-14 were obtained from this plant for the first time.

Chemical constituents from ethyl acetate extract of flower of Albizia julibrissin / 中国中药杂志

The ethyl acetate extract of the flower of Albizia julibrissin was isolated and purified by silica gel, Sephadex LH-20 and MCI GEL CHP-20P column chromatography to yield 29 compounds. Their structures were elucidated as 8-hydroxy-2, 6-dimethyl-2E, 6Z-octadienoic acid (1), 8-O-formyl-2, 6-dimethyl-2E, 6Z-octadienoic acid (la), 8-hydroxy-2, 6-dimethyl-2E, 6E-octadienoic acid (2), 8-O-formyl-2, 6-dimethyl-2E, 6E-octadienoic acid (2a), (2E, 6S)-2, 6-dimethyl-6-O-beta-D-xylpyranosyloxy-2, 7-menthia-folic acid (3), clovan-2beta, 9alpha-diol (4), 2beta-O-formyl-clovan-9alpha-ol (4a), 2beta, 9alpha-O-diformyl-clovan (4b), vomifoliol (5), (6S, 9R)-roseoside (6), vanillin (7), 4-O-ethylgallic acid (8), 3-ethoxy4-hydroxy-benzoic acid (9), p-hydroxybenzaldehyde (10), gallic acid (11), protocatechoic acid (12), stearic acid (13), palmitic acid (14), 2, 3-dihydroxypropyl hexadecanoate (15), linoleic acid (16), scopoletin (17), indole-3-carboxaldehyde (18), 2-furoic acid (19), 5-(hydroxymethyl)-2-furaldehyde (20), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 22-dien-3beta-ol (21), (22E, 24R)-5alpha, 8alpha-epidioxy-ergosta-6, 9, 22-trien-3beta-ol (22), (+)-lariciresinol 9'-stearate (23), formononetin (24) and uridine (25). Compounds 1a, 2a, 4a and 4b were new artifacts from the separation process, and others were obtained from A. julibrissin for the first time.

Chemical structure of capsicuoside A from fruits of Capsicum annuum / 中国中药杂志

Five compounds were isolated from Capsicum annuum by means of various chromatographic techniques (silica gel, Sephadex LH-20, MCI GEL CHP-20P and HPLC), and their structures were determined as luteolin-7-O-[2"-O-(5"-O-sinapoyl)-beta-D-apiofuranosyl]-beta-D-glucopyranoside (1), uridine (2), adenosine (3), 7-hydroxy-6-methoxy cinnamic acid ethyl ester (4) and 7-hydroxy cinnamic acid ethyl ester (5) by extensive spectroscopic analyses (UV, IR, MS, 1D- and 2D-NMR). Among them, compound 1 is a new flavone glycoside named as capsicuoside A, and cmpounds 2-5 are isolated for the first time from the fruits of C. annuum.

Simultaneous determination of five constituents in eight Qingyedan species derived from Swertia plants by HPLC / 中国中药杂志

<p><b>OBJECTIVE</b>To develop an HPLC method for simultaneous determination of swertiamarin, gentiopicroside, sweroside, mangiferin, erythrocentaurin, and to detect these five constituents in eight Qingyedans derived from Swertia mileensis, S. cincta, S. patens, S. punicea, S. delavayi, S. nervosa, S. macrosperma and S. yunnanensis.</p><p><b>METHOD</b>The separation was carried out on a Thermo BDS Hypersil C18 (4. 6 mm x 250 mm, 5 microm) column eluted with mobile phase of water containing 0. 1% phosphoric acid and methanol (B) in gradient program (0-10 min, 18%-20% B; 10-30 min, 20%-35% B; 30-35 min, 35%-60% B). The column temperature was 32 degrees C , and the detection wavelength was set at 250, 260, 225 nm. The flow rate was 0. 7 mL . min-1 from 0 to 30 min, and be increased to 1. 0 mL . min-1 in 35 min.</p><p><b>RESULT</b>The five compounds were well separated. The linear response ranges of swertiamarin, gentiopicroside, sweroside, mangiferin, erythrocentaurin were 0. 072-13. 39, 0. 1204. 518, 0. 060-5. 050, 0. 025-1. 518, and 0. 031-0. 210 microg, respectively. The mean recoveries of five compounds were 97.03% -102. 7% (RSD 1. 8% -6.2% ). There are swertiamarin, gentiopicroside and sweroside in most samples, and mangiferin in half samples. But erythrocentaurin was only detected in a few samples. The contents of five compounds were different in different samples. The contents of swertiamarin in S. mileensis, S. patens, S. yunnanensis and S. delavayi are up to 34. 47-118.05 mg . g-1, the contents of gentiopicroside are up to 25. 91 mg . g-1 in S. cincta. In S. puncea all contents of swertiamarin, gentiopicroside, sweroside and mangiferin are higher, especially the content of sweroside. There are Xiao-Qingyedans and Da-Qingyedans called in markets, and they can be identified by the contents of swertiamarin, gentiopicroside and sweroside. S. punicea can be identified by the content of sweroside, and the ratio gentiopicroside/total content can be used for identification of S. cincta from other seven Qingyedan species.</p><p><b>CONCLUSION</b>The method was certified to be accurate and reliable and can be used for identification and quality evaluation of traditional Chinese medicine Qingyedan derived from Swertia species.</p>

Chemical constituents of Halenia elliptica / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Halenia elliptica.</p><p><b>METHOD</b>The air-dried whole plants of Halenia elliptica were extracted with 90% EtOH. The EtOH extract was condensed to a small amount of volume and extracted with petroleum ether, EtOAc and n-BuOH, successively. The compounds were isolated and purified by column chromatography from the EtOAc fraction, and identified based on spectral analyses (MS, 1H-NMR, 13C-NMR).</p><p><b>RESULT</b>12 compounds were isolated from H. elliptica, and characterized as 8-hydroxy-2-methylchromone (1), 5-methoxy-2-methylchromone (2), 7-epi-vogeloside (3), coniferl aldehyde (4), sinapaldehyde (5), norbellidifolin (6), 1-hydroxyl-2,3,4,6-tetramethoxyxanthone (7), 1-hydroxyl-2,3,4,7-tetramethoxyxanthone (8), 1-hydroxyl-2,3,5-trimethoxyxanthone (9), together with azelaic acid, beta-sitosterol, and oleanolic acid.</p><p><b>CONCLUSION</b>Compounds 1, 2 were new natural compounds and compounds 3-6, 10 were obtained from H. elliptica for the first time and compound 6 showed inhibitory activities against HBsAg and HBeAg secretion with IC50 value of 0.77 and < 0.62 mmol x L(-1), respectively.</p>

Chemical constituents of Swertia hispidicalyx / 中国中药杂志

<p><b>OBJECTIVE</b>To study the chemical constituents of Swertia hispidicalyx.</p><p><b>METHOD</b>The EtOAc part of S. hispidicalyx was chromatographied by various column chromatography methods, and the isolates were identified based on spectroscopic analyses (MS, 1H-and 13C-NMR).</p><p><b>RESULT</b>Eleven compounds were isolated from S. hispidicalyx and characterized as 1,3,5,8-tetrahydroxyxanthone (1), 1,5,8-trihydroxy-3-methoxyxanthone (2), gentiolactone (3), swertiamarin (4), 3,4-dihydro-1H,6H,8H-naphtho [1, 2-c:4, 5-c', d'] dipyrano-1,8-dione (5), (+)-syringaresinol (6), trans-coniferyl aldehyde (7), maslinic acid (8), oleanolic acid (9), daucosterol (10), and -sitosterol (11).</p><p><b>CONCLUSION</b>Compounds 1-11 were obtained from S. hispidicalyx for the first time.</p>

New isoprenylated flavonoid from Morus alba / 中国中药杂志

Sanggenol P (1), a new isoprenylated flavonoid, together with nine known ones, cyclomorusin (2), morusin (3), mulberrofuran G (4), sanggenol A (5), sanggenol L (6), sanggenol N (7), cyclomulberrin (8), cyclocommunol (9) and ursolic acid (10) was isolated from Morus alba L. Sanggenol P (1) was characterized based on extensive IR, UV, 1D and 2D NMR spectroscopic analysis. Compounds 5, 6, 7 and 9 were obtained from this plant for the first time.