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1.
Article in English | WPRIM | ID: wpr-781235

ABSTRACT

Two new folate-derived analogues, named uncarophyllofolic acids A (1) and B (2), respectively, were isolated from the Uncaria rhynchophylla hook bearing stem (Gouteng in Chinese). The distinct stereochemical structures of 1 and 2 were determined by spectroscopic data analysis in combination with acidic hydrolysis and Marfey's derivatization, along with comparison of their specific rotation and Cotton effect (CE) data with those of the biogenetically related known derivatives as well as theoretical calculations of electronic circular dichroism (ECD) spectra. A plausible biosynthetic pathway of 1 and 2, associating to folate metabolism and the previously reported orychophragines A-C from Orychophragmus violaceus, is discussed.

2.
Acta Pharmaceutica Sinica ; (12): 1075-1081, 2019.
Article in Chinese | WPRIM | ID: wpr-780184

ABSTRACT

Five alkaloids were isolated from a decoction of Uncaria rhynchophylla by a combination of various chromatographic techniques, including macroporous adsorbent resin, MCI resin, silica gel, Sephadex LH-20, and reversed phase HPLC. Their structures were characterized by comprehensive analyses of spectroscopic data as monoterpene indole alkaloids (+)-(7R)-3-oxo-7-hydroxy-3,7-seco-dihydrorhynchohylline (1), (+)-(7S)-3-oxo-7-hydroxy-3,7-seco-dihydrorhyncho-hylline (2), (+)-(7R)-3-oxo-7-hydroxy-3,7-seco-rhynchohylline (3) and (+)-(7S)-3-oxo-7-hydroxy-3,7-seco-rhynchohylline (4), and a β-carboline alkaloid 1,2,3,4-tetrahydro-1-oxo-β-carboline (5). Among them, 1 and 2 are new compounds, 3 and 4 are new natural products that were semi-synthesized from isorhynchohylline with incorrect specific rotations, and 5 is isolated for the first time from the genus Uncaria.

3.
Article in Chinese | WPRIM | ID: wpr-256046

ABSTRACT

Twenty five known aromatic glycosides (1-25) and three known sesquiterpene glycosides (26-28) have been isolated from the twigs of Litsea cubeba by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis (MS, IR, 1D and 2D NMR) as (7S,8R)-dehydrodiconiferyl alcohol 4,9'-di-O-β-D-glucopyranoside(1),(7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(2), (7S,8R)-urolignoside(3), (7R,8S)-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside(4), saposide B(5), lanicepside A(6), matairesinol-4-O-β-D-glucopyranoside (7), tyraxjaponoside B(8), (+)-lyoniresinol-9'-O-β-D-glucopyranoside (9), alaschanisoside A (10), syringin (11), psoralenoside (12), isopsoralenoside (13), scopolin(14), 2,6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside (15), 3-hydroxy-4,5-dimethoxyphenyl-β-D-glucopyranoside (16), 2-(3,4-dihydroxyphenyl)ethyl-β-D-glucopyrnoside (17), 2-(4-dihydroxyphenyl)ethyl-β-D-glucopyranoside (18), (+)-catechin-7-O-β-D-glucopyranoside (19), 3'-O-methylepicatechin-7-O-β-D-glucopyranoside (20), kaempferitrin (21), quercetin-3-O-α-L-rhamnopyranside (22), kaempferol-3-O-β-D-glucopyranoside (23), kaempferol 3-O-β-D-glucopyranosyl(1→2)-O-β-D-galactopyr anoside-7-O-α-L-rhamnopyranoside (24), quercetin 3-O-α-L-rhamnopyranosyl(1→6)-O-β-D-glucopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-glucopyranoside (25), staphylionoside D(26), vomifoliol 9-O-β-D-glucopyranoside (27), dihydrovomifoliol-O-β-D-glucopyranoside (28). Compounds 1-21 and 24-28 were obtained from this genus for the first time.

4.
Article in Chinese | WPRIM | ID: wpr-250413

ABSTRACT

Two new phenylpropanoids(1 and 2), together with thirteen known compounds(3-15), have been isolated from the root of Paeonia lactiflora by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis(MS,IR,1D and 2D NMR)as(+)-(7R,8R)-1-guaiacyl-1,2-propanediolacetonide(1),(-)-(7R,8S)-1-guaiacyl-1,2-propanediolacetonide(2),O-senecioyllomatin(3),O-angeloyllomatin(4),(+)-cis-3'-senecioyloxy-4'-angeloyloxy-3',4'-dihydroseselin(5),columbianadin(6), benzyl 2,5-dihydroxybenzoate(7),3,6-dimethyl-5-hydroxyBenzo-furan(8),(S)-evofolin-A(9),2,3-dihydroxy-4-methoxyacetophenone(10), 2,5-dihydroxy-4-methoxyacetophenone(11), 2,5-dihydroxy-4-methyl acetophenone(12),ethyl 4-hydroxybenzoate(13), vanillic acid(14),and 4-hydroxy-3-methoxybenzaldehyde(15).Compounds 1 and 2 were new compounds,and compounds 3-9 were obtained from the genus Paeonia for the first time.

5.
Acta Pharmaceutica Sinica ; (12): 616-2016.
Article in Chinese | WPRIM | ID: wpr-779213

ABSTRACT

Sixteen lignanoids were isolated from an aqueous extract of the commonly used Chinese traditional medicine Dangshen, the dried roots of Codonopsis pilosula, by using a combination of various chromatographic techniques, including silica gel, macroporous adsorbent resin, MCI resin, sephadex LH-20, and reversed phase semi-preparative HPLC. On the basis of spectral data analysis, their structures were elucidated and identified as (-)-(7R, 7'R, 8R, 8'S)-4, 4'-dihydroxy-3, 3', 5, 5', 7-pentamethoxy-2, 7'-cyclolignane (1), (-)-(7R, 8S)-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranosyl-(1"'→2")-β-D-glucopyranoside (2), (-)-(7R, 8S)-dihydrodehydrodiconiferyl alcohol (3), (+)-(7S, 8R)-dehydrodiconiferyl alcohol (4), (+)-balanophonin (5), (+)-demethoxypinoresinol (6), (+)-pinoresinol (7), (+)-epipinoresinol (8), (-)-syringaresinol (9), (-)-medioresinol (10), (-)-lariciresinol (11), (-)-secoisolariciresinol (12), (-)-ent-isolariciresinol (13), (+)-(7S, 8S)-3-methoxy-3', 7-expoxy-8, 4'-neolignan-4, 9, 9'-triol (14), (+)-(7S, 8R)-3', 4-dihydroxy-3-methoxy-8, 4'-neolignan (15), and (-)-(7R, 8R)-3', 4-dihydroxy-3-methoxy-8, 4'-neolignan (16). All these compounds were isolated from C. pilosula for the first time, while compound 1 is a new natural product of 2, 7'-cyclolignan and 2 is a new 4', 7-epoxy-8, 3'-neolignan diglucoside. Compound 12 showed activity against Fe2+-cysteine induced rat liver microsomal lipid peroxidation with an inhibition ratio of (63.4±8.3)% at 1×10-5 mol·L-1.

6.
Acta Pharmaceutica Sinica ; (12): 411-2016.
Article in Chinese | WPRIM | ID: wpr-779185

ABSTRACT

From an ethanol extract of Euphorbia micractina roots, sixteen terpenoids were isolated by a combination of various chromatographic techniques, including column chromatography over macroporous resin, silica gel, and Sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as loliolide myristate (1), 24-methylenetirucall-8-en-3β,11α-diol-7-one (2), loliolide (3), 3β-hydroxy-5α,6α-epoxy-7-megastigmen-9-one (4), jolkinol A (5), jolkinol D (6), latilagascene F (7), helioscopinolide A (8), helioscopinolide B (9), 3-O-acetylhelioscopinolide B (10), helioscopinolide D (11), helioscopinolide E (12), (+)-11-acetoxyatis-16-en-3,14-dione (13), erythrodiol (14), uvaol (15) and betulin (16). All of the compounds were obtained from this plant for the first time, in which 1 and 2 are new compounds.

7.
Article in Chinese | WPRIM | ID: wpr-237684

ABSTRACT

From an aqueous extract of Lonicera japonica flower buds, sixteen compounds were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as 6'-O-acetylvogeloside (1), 6'-O-acetylsecoxyloganin (2), dichlorogelignate (3), guanosinyl-(3' --> 5')-adenosine monophosphate(GpA,4) , 5'-O-methyladenosine (5), 2'-O-methyladenosine (6), adenosine (7), syringin (8), methyl 4-O-β-D-glucopyranosyl caffeate (9), (-)-dihydrophaseic acid 4'-O-β-D-glucopyranoside (10), ketologanin (11), 7α-morroniside (12), 7β-morroniside (13), kingiside (14), cryptochlorogenic acid methyl ester (15), and 6-hydroxymethyl-3-pyridinol (16). All the compounds were obtained from this plant for the first time, compounds 1 and 2 are new compounds, 3 and 5 are new natural products, and 4 is the first example of dinucleoside monophosphate isolated from a plant extract.


Subject(s)
Chromatography, High Pressure Liquid , Drugs, Chinese Herbal , Chemistry , Flowers , Chemistry , Lonicera , Chemistry , Mass Spectrometry , Molecular Structure
8.
Article in Chinese | WPRIM | ID: wpr-305342

ABSTRACT

A new aporphine alkaloid (1), together with five known analogues (2-6), has been isolated from the branch of Litsea greenmaniana by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis ( MS, IR, 1D and 2D NMR) as 2,9-dihydroxy-1,10-dimethoxy-4,5-dihydro-7-oxoaporphine (1), laurotetanine (2), N-methyllaurotetanine (3), isodomesticine (4), isocorydine (5), and norisocorydine (6). Compound 1 was a new compound, and compounds 2-6 were obtained from this plant for the first time.


Subject(s)
Alkaloids , Chemistry , Aporphines , Chemistry , Drugs, Chinese Herbal , Chemistry , Litsea , Chemistry , Molecular Structure , Spectrometry, Mass, Electrospray Ionization
9.
Article in Chinese | WPRIM | ID: wpr-350672

ABSTRACT

A new compound (1), together with ten known compounds (2-11), have been isolated from the branch of Litsea greenmaniana by using various chromatographic techniques. Their structures were identified by spectroscopic data analysis as N-trans-3, 4-methylenecinnamoyl-3-methoxytyramine (1), N-trans-feruloyltyramine (2), N-cis-feruloyltyramine (3), (+)-sesamin (4), (+)-pinoresinol(5), cinnamophilin (6), dihydrodehydrodiconiferyl alcohol (7), benzoic acid (8), 4-hydroxy ethylbenzoate (9), p-hydroxybenzaldehyde(10), and 4-hydroxy-3-methoxy-benzyl alcohol (11). Compound 1 was a new compound, and compounds 2-11 were obtained from this plant for the first time.


Subject(s)
Drugs, Chinese Herbal , Chemistry , Litsea , Chemistry , Mass Spectrometry , Molecular Structure
10.
Acta Pharmaceutica Sinica ; (12): 428-431, 2011.
Article in Chinese | WPRIM | ID: wpr-348938

ABSTRACT

In order to find the anti-virus constituents of Alternanthera philoxeroides (Mart.) Griseb, the investigation was carried out. The paper reported the five triterpenoid saponins isolated from n-BuOH fraction: 3-O-beta-D-glucopyranosyl (1-->3)-O-[beta-D-glucopyranosyl-oleanolic acid]-28-O-beta-D-glucuronopyranoside (1), oleanolic acid-3-O-beta-D-glucuronopyranoside (calenduloside E, 2), oleanolic acid-3-O-beta-D-glucopyranosyl-28-Obeta-D-glucopyranosyl ester (chikusetsusaponin-IVa, 3), 3-O-(6'-O-butyl-beta-D-glucuronopyranosyl)-oleanolic acid-28-O-beta-D-glucopyranosyl ester (4) and hederagenin-3-O-beta-D-glucuronopyranoside (HN-sapoins K, 5). 1 is a new compound, saponins 4 and 5 were isolated from the plant for the first time.


Subject(s)
Amaranthaceae , Chemistry , Antiviral Agents , Chemistry , Pharmacology , Hep G2 Cells , Hepatitis B virus , Humans , Molecular Structure , Oleanolic Acid , Chemistry , Pharmacology , Plants, Medicinal , Chemistry , Saponins , Chemistry , Pharmacology , Triterpenes , Chemistry , Pharmacology
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