Cytotoxic constituents from the skin of the toad Bufo bufo gargarizans

To study the chemical composition of the skin of Bufo bufo gargarizans, various chromatographic methods were used in the isolation procedures and the structures of isolated compounds were determined based on NMR and MS analysis. As a result, two new compounds were isolated from its ethanolic extract and characterized as N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N-methylurea (1) and 19-oxocinobufotalin 3-adipoylarginine ester (2), together with 11 known compounds. Isolated bufadienolides showed significant inhibition effect against human hepatocellular carcinoma cell line SMMC-7721 in vitro.     

Adlumiceine methyl ester,a new alkaloid from Fumaria vaillantii

A new alkaloid, adlumiceine methyl ester (1), together with two known alkaloids, parfumine (2) and N-methylhydrastine methyl ester (3), was isolated from aerial parts of Fumaria vaillantii. The structures of compounds were determined by 1D/2D NMR and MS data. All three compounds were tested for cytotoxic activity against PC3 and MCF7 cell lines using Alamar blue assay. The tested compounds showed no significant cytotoxic activity (IC₅₀>50 μM) against PC3 and MCF7 cell lines.     

A new sesquiterpene lactone glycoside and a new quinic acid methyl ester from Patrinia villosa

A new sesquiterpene lactone glycoside (1) and a new quinic acid methyl ester (2) were isolated from Patrinia villosa, together with another two known compounds chlorogenic acid n-butyl ester (3), 3, 4-di-O-caffeoylquinic acid methyl ester (4). Their structures were established using 1D/2D-NMR spectroscopy, mass spectrometry, and comparing with spectroscopic data reported in the literature.     

New dianthramide and cinnamic ester glucosides from the roots of Aconitum carmichaelii

Four new compounds N-salicyl-3-hydroxyanthranilic acid methyl ester (1), N-(2′-dehydroxysalicyl)-3-hydroxyanthranilic acid methyl ester (2), methyl-4-β-D-allopyranosyl-ferulate (3), and methyl-4-β-D-gulopyranosyl-cinnamate (4), along with six known compounds (5–10), were isolated from the roots of Aconitum carmichelii Debx. Their structures were elucidated on the basis of spectral data analysis, including 1D, 2D-NMR, and HR-ESI-MS. Compounds 1 and 2 showed the inhibition of nitric oxide (NO) production with IC₅₀ values of 9.13 and 19.94 μM, respectively.     

One new triterpene ester from Nepeta suavis

One new tetracyclic triterpene ester (1) has been isolated from the chloroform-soluble portion of the whole plant of Nepeta suavis along with two known compounds, namely artemetin (2) and jaceidin (3). The structures of the isolated compounds were assigned on the basis of their ¹H and ¹³C NMR spectra including two-dimensional NMR techniques such as COSY, HMQC, and HMBC experiments and comparison with the literature data.     

Tenuifoliose Q,a new oligosaccharide ester from the root of Polygala tenuifolia willd.

From the cortexes of Polygala tenuifolia Willd., a new oligosaccharide ester, tenuifoliose Q (1), was isolated together with three known compounds. The structure of 1 was elucidated by spectroscopic and physiochemical analysis as an oligosaccharide esterified with acetic, benzoic and p-hydroxycinnamoyl acid.     

Two new triterpenoid saponins from Ilex cornuta

Two new triterpenoid saponins (1 and 2) were isolated from the stems of Ilex cornuta, along with two known triterpenoids (3 and 4). The structures of compounds 1 and 2 were determined as ursane-12,19-diene-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (1), 3α,23α-dihydroxy-olean-9(11),12-diene-28-oic acid 28-O-β-d-glucopyranosyl ester (2), on the basis of hydrolysis and spectral evidence, including 1D and 2D NMR and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) analyses. Protective effects of compounds 1–4 were tested against H₂O₂-induced H9c2 cardiomyocyte injury, and the data showed that all these compounds had no cell-protective effect.     

Structural elucidation of fritillahupehin from bulbs of fritillaria hupehensis Hsiao et K.C. Hsia

A novel diterpenoid ester, fritillahupehin (1) and three known fatty acids, palmitic acid (2), lignoceric acid (3) and azelaric acid (4), have been isolated from the bulbs of Fritillaria hupehensis Hsiao et K.C. Hsia. The structure of fritillahupehin has been established to be ent-kauran-16β-yl lignocerate by means of spectroscopic and chemical evidence. Compounds 2–4 were isolated from Fritillaria sp. for the first time.     

A new sesquiterpene ester from the fruits of Celastrus orbiculatus

From the fruits of Celastrus orbiculatus Thunb., a new dihydroagarofuran sesquiterpene ester named 6α,13β-diacetoxy-1β,8β,9β-tribenzoyloxy-β-dihydroagarofuran (1) has been isolated, along with three known compounds: 1β,6α,8β-triacetoxy-9α-benzoyloxy-β-agarofuran (2), 1β,6α-diacetoxy-9α-benzoyloxy-β-dihydroagarofuran (3) and β-sitostrol (4). The structure of 1 was elucidated on the basis of spectroscopic methods.     

Two flavonoid glycosides and a phenylpropanoid glucose ester from the leaves of Sterculia foetida

Two new flavonoid glycosides, hypolaetin 4′-methyl ether 8-O-β-d-glucuronide 2″-sulfate (1) and hypolaetin 4′-methyl ether 3′-O-β-d-glucoside (2), and a new phenylpropanoid glucose ester, 1,6-diferuloyl glucose (3), were isolated from the leaves of Sterculia foetida L. Their structures were elucidated by spectroscopic analysis and chemical evidence.     

Colebroside A,A New Diglucoside of Fatty Acid Ester of Glycerin from Clerodendrum colebrookianum

Abstract

Colebroside A (1), a new diglucoside of fatty acid ester of glycerin, was isolated from the aerial parts of Clerodendrum colebrookianum Walp., along with nine known compounds (2–10). Their structures were elucidated by spectroscopic and chemical methods. Compounds 2, 3, 4, 5, 7, 8, 9 and 10 have been obtained from this plant for the first time.     

Tropane alkaloids from <Emphasis Type="Italic">Erythroxylum emarginatum</Emphasis>

A tropane alkaloid, anhydroecgonine methyl ester N-oxide (2), was isolated for the first time as a naturally occurring compound, with anhydroecgonine methyl ester (1) from the bark of Erythroxylum emarginatum. Compound 1 was also isolated from the twigs. Their structures were elucidated mainly by spectroscopic methods.     

群海绵Agelas sp.的化学成分研究

目的 研究海绵Agelas sp.的化学成分。方法 运用乙醇提取、硅胶、Sephadex-LH₂₀色谱柱、HPLC等多种方法进行分离和纯化,根据理化性质和波谱数据进行结构鉴定。结果 分离得到9个化合物,经结构鉴定分别为4,5-二溴吡咯-2-甲酰胺（1）、4,5-二溴吡咯-2-甲酸（2）、4,5-二溴吡咯-2-甲酸甲酯（3）、N-（4,5-二溴-2-吡咯甲酰基）甘氨酸甲酯（4）、1-（4,5-二溴-2-吡咯甲酰胺基）丙酸甲酯（5）、1-（4,5-二溴-2-吡咯甲酰胺基）丙酸乙酯（6）、异吲哚-1,3-二酮（7）、2（3H）-苯并噻唑酮（8）和manzacidin C（9）。结论 化合物4~9为首次从该属海绵中分离得到,其中化合物4~6为新天然产物。     

Antimicrobial phenolic derivatives from<Emphasis Type="Italic">Dendranthema zawadskii</Emphasis> var.<Emphasis Type="Italic">latilobum</Emphasis> kitamura (Asteraceae)

A phytochemical study on the root ofDendranthema zawadskii var.latilobum Kitamura, using a series of silica gel column chromatography and reversed phase C-18 HPLC chromatography, led to the isolation of (1S, 2S)-1, 2, 3-trihydroxy-1-(3, 4-methylenedioxyphenyl)propane (1), 4-methoxycinnamic acid (2), acacetin (3) and caffeic acid methyl ester (4). The structures of these compounds were determined using spectroscopic analyses (UV, IR, HRTOFMS and NMR), with comparison of their spectral data with previously reported values. Compound1 was isolated for the first time, with compounds2 and4 from this plant reported for the first time. The antibacterial and antifungal activities of the isolated compounds were measured using the disc diffusion method. Also, their cytotoxicities against the cancer cell lines, A549, B16F1 and SK-Mel-2, and brine shrimp lethalities were evaluated.     

Three new compounds from the stem bark of Juglans mandshurica

Three new compounds, 3,6-dihydroxy-4,5-dimethoxy-1,8-naphalic anhydride (1), 3,4,5,6-tetrahydroxy-1,8-naphalic anhydride (2), and methyl (7E,9E)-6,11-dioxononadeca-7,9-dienoate (3), were isolated from the stem bark of Juglans mandshurica. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, HR-TOF-MS, and by comparison with the literature data.     

Pyrrole alkaloids from Bolbostemma Paniculatum

Three pyrrole alkaloids were isolated from Bolbostemma paniculatum. Their structures were elucidated as 4-(2-formyl-5-methoxymethylpyrrol-1-yl)butyric acid methyl ester (1), 2-(2-formyl-5-methoxymethylpyrrol-1-yl)-3-phenylpropionic acid methyl ester (2) and α-methyl pyrrole ketone (3) by spectroscopic techniques. Among them, 1 and 2 are new compounds.     

Isolation of major phenolics from Launaea spinosa and their protective effect on HepG2 cells damaged with t-BHP

Context: Some Launaea species (Asteraceae) are used traditionally to treat liver oxidative stress.

Objective: The present study investigates the protective effects of isolated compounds from Launaea spinosa Sch. Bip. (Asteraceae) against oxidative stress on t-BHP-induced HepG2 cells.

Materials and methods: Major phenolic content from flowering aerial parts of L. spinosa was isolated and identified. The protective effects of isolated compounds (10 and 20?μM) against oxidative stress induced by tert-butyl hydroperoxide (t-BHP) in HepG2 cells were investigated through the measurement of aspartate aminotransferase (AST), alanine transaminase (ALT), and superoxide dismutase (SOD) levels.

Results: A new phenolic compound identified as 2,3-diferulyl R,R-(+) methyl tartrate (6), in addition to five known metabolites, esculetin (1), esculetin-7-O-d-glucoside (cichoriin) (2), fertaric acid (3), acacetin-7-O-d-glucoside (4), and acacetin-7-O-d-glucuronic acid (5), were isolated. Oxidant-induced damage by 200?μM t-BHP in HepG2 cells was inhibited by compounds 1, 4, and 5 (10 and 20?μM), or quercetin (10?μM; positive control). The protective effects of compounds 1, 4, and 5 were associated with decreasing in AST, ALT, and SOD levels. Compound 4 (20?μM) decreased the AST level from 128.5?±?13.9 to 7.9 ±1.8?U/mL. Meanwhile, compound 1 (20?μM) decreased ALT activity from 20.3?±?7.0 to 7.6?±?2.4?U/mL, while compound 5 decreased SOD levels from 41.6?±?9.0 to 28.3?±?3.4?mU/mg.

Conclusion: The major phenolic compounds isolated from L. spinosa displayed a significant cytoprotective effect against oxidative stress, leading to maintenance of the normal redox status of the cell.     

A novel oligosaccharide ester from Syringa pubescens

Pubescenside A (1), a novel oligosaccharide ester, has been isolated from the flowers of Syringa pubescens, together with five known compounds d-mannitol (2), meso-inositol (3), hydrostytosol (4), glucose (5), and sucrose (6). The structure of 1 was elucidated as 1-O-[β-d-glucopyranosyl-(1–6)-β-d-galactopyranosyl-(1–1)-β-d-galactopyranosyl-6]-4,4-dimethylpelargonicate by chemical and spectroscopic means. The water extract of the flowers and leaves of S. pubescens showed cytotoxicity against L2215 cell line (IC₅₀ = 78 μg/ml).     

Phenolic compounds from the twigs and leaves of Tara (Caesalpinia spinosa)

Two new homoisoflavans, 4′-hydroxy-7-methoxy-3-benzyl-2H-chromene (1) and 3,4-cis-di-O-3-hydroxy-7-methoxy-3-(4-hydroxybenzyl)-4-ethoxychroman (2), one new coumarin, 7-methoxy-3-(4-hydroxybenzyl)coumarin (4), together with seven known phenolic compounds, bonducellin (3), anemarcoumarin A (5), (+)-syringaresinol (6), curuilignan D (7), scopoletin (8), and p-hydroxybenzaldehyde (9), were isolated from Tara (Caesalpinia spinosa Kuntze). The structures of the new compounds were characterized from their 1D and 2D NMR spectral data. All the compounds were isolated from this plant for the first time.     

Sinapic acid derivatives from the seeds of Raphanus nussatirus L.

A new disulfide glycoside, raphthioglucoside (1), and a new sinapic acid derivative, sinapic acid 5-hydroxymethylfurfural ester (2), together with sinapic acid (3) have been isolated from the seeds of Raphanus nussatirus L. The structures of compounds 1-3 were determined based on chemical analysis and spectroscopic methods (UV, 1D and 2D NMR, HRFABMS, HREIMS and elemental analysis).