Anti-inflammatory coumarins from Paramignya trimera

Context: Paramignya trimera (Oliv.) Burkill (Rutaceae) has been used to treat liver diseases and cancer. However, the anti-inflammatory effects of this medicinal plant and its components have not been elucidated.

Objective: This study investigated chemical constituents of the P. trimera stems and evaluated anti-inflammatory effects of isolated compounds.

Materials and methods: Cytotoxicity of isolated compounds (5–40?μM) toward BV2 cells was tested using 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) for 24?h. Inhibitory effects of isolated compounds (5-40?μM) on nitrite and PGE₂ concentrations were determined using Griess reaction and PGE₂ ELISA kit, respectively (pretreated with the compounds for 3?h and then stimulated for 18?h with LPS). Inhibitory effects of compounds (5-40?μM) on iNOS and COX-2 protein expression were evaluated by Western blot analysis (pretreated with the compounds for 3?h and then stimulated for 24?h with LPS).

Results: Seven coumarins were isolated and identified as: ostruthin (1), ninhvanin (2), 8-geranyl-7-hydroxycoumarin (3), 6-(6′,7′-dihydroxy-3′,7′-dimethylocta-2′-enyl)-7-hydroxycoumarin (4), 6-(7-hydroperoxy-3,7-dimethylocta-2,5-dienyl)-7-hydroxycoumarin (5), 6-(2-hydroxyethyl)-2,2-dimethyl-2H-1-benzopyran (6), and luvangetin (7). Compounds 1–4 and 7 inhibited NO and PGE₂ production in LPS-stimulated BV2 cells, with IC₅₀ values ranging from 9.8 to 46.8 and from 9.4 to 52.8?μM, respectively. Ostruthin (1) and ninhvanin (2) were shown to suppress LPS-induced iNOS and COX-2 protein expression.

Discussion and conclusion: The present study provides a scientific rationale for the use of P. trimera in the prevention and treatment of neuroinflammatory diseases. Ostruthin and ninhvanin might have potential therapeutic effects and should be considered for further development as new anti-neuroinflammatory agents.     

Chemical Constituents from the Leaves of Magnolia Denudata

Abstract

20 compounds were isolated from the leaves of Magnolia denudata including 16 lignans, which belong to 6 structural types. Except for (7R, 8S, 1′S) -δ^8′ - 1′, 4′ - dihydro - 5′- methoxy - 3, 4 -methylenedioxy - 4′ - oxo -7.O.2′, 8.1′ - neolignan (6), magliflonenone (9), 2,5′ - diene-2′, 8′- epoxy - 5′ - methoxy - 8 - methyl - 4′ - oxo - 3,4-methylenedioxy - spiro (5,5) - undecane (10), veraguensin (16) and β-sitosterol (20), the other 15 compounds were obtained from this species for the first time. The absolute configurations of 3 compounds (1,4,10) were determined by CD spectroscopy for the first time. The anti-inflammatory activities of compounds 1, 2 and 16 were assessed and 2 was shown to have significant inhibition effect on mice hind-paw edema induced by carrageenan.     

Phenolic compounds from the aqueous extract of Acacia catechu

Two new phenolic compounds, 5-hydroxy-2-[2-(4-hydroxyphenyl) acetyl]-3-methoxylbenzoic acid (1) and (2S,3S)-3,7,8,3′,4′-pentahydroxyflavane (2), were obtained from the aqueous extract of Acacia catechu, along with four known compounds identified as rhamnetin (3), 4-hydroxyphenyl ethanol (4), 3,3′,5,5′,7-pentahydroxyflavane (5), and fisetinidol (6). Their structures were determined on the basis of spectroscopic analysis. Free radical-scavenging activities of the new compounds were evaluated.     

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.     

Phenylpropanoids from Podocarpium podocarpum

Abstract

Context: Podocarpium podocarpum (DC.) Yang et Huang (Leguminoseae) is a very important Podocarpium species with significant anti-inflammatory, analgesic and anti-pyretic activities, which has not yet been subjected to adequate phytochemical investigation.

Objective: To isolate and identify bioactive compounds from P. podocarpum.

Materials and methods: Ethanol extract of the whole plant of P. podocarpum was subjected to repeated column chromatography. Chemical structures of the compounds were identified by 1D, 2D-NMR spectra and MS data. Human cervical carcinoma (HeLa) and pancreatic carcinoma (PANC-1) cell lines were employed to evaluate the in vitro cytotoxic activity of the isolated constituents at six concentrations (0.001, 0.01, 0.1, 1.0, 10.0, 100.0?μg/ml).

Results: A new phenylpropanoid glycoside, podocarioside A (1), together with four known compounds, (E)-3-(4-hydroxy-3-propoxyphenyl) acrylic acid (2), schizandrin (3), dehydrodiconiferyl alcohol (4) and dihydrodehydrodiconiferyl alcohol (5), were isolated from P. podocarpum. Compounds 1, 3 and 4 showed moderate cytotoxic against HeLa cells with IC₅₀ values of 38.62, 8.64 and 5.85?μg/mL, respectively, while none exhibited toxicity against PANC-1 cells.

Discussion and conclusion: This is the first report on the isolation and identification of bioactive compounds from P. podocarpum. In vitro cytotoxic assay of the isolated constituents establishes the potential of those components as antitumor agents.     

Chemical constituents of the Annona glabra fruit and their cytotoxic activity

Abstract

Context: Traditional Chinese medicines have attracted increasing interest as potential sources of novel drugs with a wide range of biological and pharmacological activities. Annona glabra Linn (Annonaceae) is used in traditional medicine as an anticancer drug. Phytochemical investigation of this plant led to the isolation of acetogenins, ent-kauranes, peptides, and alkaloids. In addition, compounds exhibited anticancer, anti-HIV-reserve, and antimalaria.

Objective: Isolation, structure determination, and cytotoxic activity evaluation of compounds from the methanol extract from A. glabra fruits.

Materials and methods: Using chromatographic methods to isolate compounds from the A. glabra methanol extract. The cytotoxic activity of compounds was evaluated by a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay. In addition, compounds which showed significant cytotoxic activity were chosen for further study apoptosis characteristics.

Results: One new, (2E,4E,1′R,3′S,5′R,6′S)-dihydrophaseic acid 1,3′-di-O-β-d-glucopyranoside, and eight known compounds, (2E,4E,1′R,3′S,5′R,6′S)-dihydrophaseic acid 3′-O-β-d-glucopyranoside (2), icariside D₂ (3), icariside D₂ 6′-O-β-d-xylopyranoside (4), 3,4-dimethoxyphenyl O-β-d-glucopyranoside (5), 3,4-dihydroxybenzoic acid (6), blumenol A (7), cucumegastigmane I (8), and icariside B₁ (9), were isolated from the fruits of A. glabra. Icariside D₂ (3) was found to show significant cytotoxic activity on the HL-60 cell line with the IC₅₀ value of 9.0?±?1.0?µM and did not show cytotoxic activity on the Hel-299 normal cell line. The further test indicated that compound 3 induced apoptosis via alteration of expression of apoptosis-related proteins and decreased phosphorylation of AKT in HL-60 cells.

Discussion and conclusion: The results suggested that the constituents from A. glabra may contain effective compounds which can be used as anticancer agents.     

Anti-inflammatory constituents from Perovskia atriplicifolia

Abstract

Context: Perovskia atriplicifolia Benth (Labiantae) has long been used as a traditional herbal medicine for anti-inflammation in Pakistan; this prompted us to isolate anti-inflammatory compounds from this plant.

Objective: The objective of this study was to isolate and characterize the anti-inflammatory principles from Perovskia atriplicifolia.

Materials and methods: The CHCl₃-soluble fraction of the methanol extract of the whole plant on column chromatography yielded compounds 1–6. The anti-inflammatory potential of the compounds 1–6 was evaluated by Leukotriene C4 (LTC₄) Release Assay which was performed according to the established protocol. LTC₄ in the supernatant of each well was measured using an ELISA kit (Cayman Chemical Co., Ann Arbor, MI).

Results: The bioassay-guided phytochemical investigation of the CHCl₃ soluble fraction of the methanol extract of Perovskia atriplicifolia furnished six compounds, abrotanone (1), abrotandiol (2), (+)-pinoresinol (3), (+)-syringaresinol (4), (+)-lariciresinol (5), and (+)-taxiresinol (6). The compounds (1–6) were evaluated for their inhibitory activities on LTC₄ release. Among the tested compounds, (+)-taxiresinol (6) exhibited the most potent inhibition of LTC₄ release with an IC₅₀ value of 3.4?±?0.09?µM followed by compounds 4, 5, 3, and 2 with an IC₅₀ value ranging from 7.9?±?0.04 to 17.2?±?0.07?µM. Abrotanone (1) showed the lowest inhibition of LTC₄ release with an IC₅₀ value of 35.1?±?0.05?µM (the positive control, zileuton, 0.77?±?0.05?µM).

Conclusion: Compounds 1–6 were found to possess inhibitory activity and seem to have potential therapeutic effect on inflammatory diseases.     

Nigrosporanenes C and D,two new cyclohexene derivatives from the enphytic fungus Nigrospora oryzae S4

Abstract

Two new cyclohexene derivatives, nigrosporanenes C and D (1 and 2), together with three known compounds (3-5), were isolated from the culture of an endophyte Nigrospora oryzae S4. Their structures were characterized by a combination of detailed spectroscopic analysis and comparison of their NMR data with those reported in the literature. All compounds were tested for anti-phytopathogenic activity, however, none of them showed activity at a concentration of 20 μM.     

Antiprotozoal Activity Against Plasmodium falciparum. and Trypanosoma cruzi. of Xanthones Isolated from Chrysochlamys tenuis.

Abstract

One new prenylated xanthone, 1,5-dihydroxy-3-methoxy-4-isoprenylxanthone (1), along with four previously known prenylated xanthones, ananixanthone (2), 1,3,7-trihydroxy-2,4-diisoprenylaxnthone (3), 8-desoxygartanin (4), and toxyloxanthone A (5), have been isolated from Chrysochlamys tenuis. (Hammel) (Clusiaceae). Compound 1 showed moderate activity (31 ± 9 µM) against a chloroquine-resistant strain of Plasmodium falciparum., and compounds 3 and 5 showed the highest antimalarial potency, IC₅₀ = 20 ± 2 and 16 ± 4 µM, respectively. Evaluated against Trypanosoma cruzi., compound 1 presented negligible activity, but compounds 2, 3, and 4 showed mild antitrypanosomal activity with IC₅₀ values of 23 ± 4, 21 ± 5, and 24 ± 3 µM, respectively. All structures were elucidated by NMR spectroscopy in combination with UV, IR, and MS spectral data.     

The α-amylase and α-glucosidase inhibitory activities of the dichloromethane extracts and constituents of Ferulago bracteata roots

Context: Ferulago (Apiaceae) species have been used since ancient times for the treatment of intestinal worms, hemorrhoids, and as a tonic, digestive, aphrodisiac, or sedative, as well as in salads or as a spice due to their special odors.

Objectives: This study reports the α-amylase and α-glucosidase inhibitory activities of dichloromethane extract and bioactive compounds isolated from Ferulago bracteata Boiss. &; Hausskn. roots.

Materials and methods: The isolated compounds obtained from dichloromethane extract of Ferulago bracteata roots through bioassay-guided fractionation and isolation process were evaluated for their in vitro α-amylase and α-glucosidase inhibitory activities at 5000–400?µg/mL concentrations. Compound structures were elucidated by detailed analyses (NMR and MS).

Results: A new coumarin, peucedanol-2′-benzoate (1), along with nine known ones, osthole (2), imperatorin (3), bergapten (4), prantschimgin (5), grandivitinol (6), suberosin (7), xanthotoxin (8), felamidin (9), umbelliferone (10), and a sterol mixture consisted of stigmasterol (11), β-sitosterol (12) was isolated from the roots of F. bracteata. Felamidin and suberosin showed significant α-glucosidase inhibitory activity (IC₅₀ 0.42 and 0.89?mg/mL, respectively) when compared to the reference standard acarbose (IC₅₀ 4.95?mg/mL). However, none of the tested extracts were found to be active on α-amylase inhibition.

Discussion and conclusions: The present study demonstrated that among the compounds isolated from CH₂Cl₂ fraction of F. bracteata roots, coumarins were determined as the main chemical constituents of this fraction. This is the first report on isolation and characterization of the bioactive compounds from root extracts of F. bracteata and on their α-amylase and α-glucosidase inhibitory activities.     

Antimicrobial activities of some Thai traditional medical longevity formulations from plants and antibacterial compounds from Ficus foveolata

Context: Medicinal plants involved in traditional Thai longevity formulations are potential sources of antimicrobial compounds.

Objective: To evaluate the antimicrobial activities of some extracts from medicinal plants used in traditional Thai longevity formulations against some oral pathogens, including Streptococcus pyogenes, Streptococcus mitis, Streptococcus mutans, and Candida albicans. An extract that possessed the strongest antimicrobial activity was fractionated to isolate and identify the active compounds.

Materials and methods: Methanol and ethyl acetate extracts of 25 medicinal plants used as Thai longevity formulations were evaluated for their antimicrobial activity using disc diffusion (5?mg/disc) and broth microdilution (1.2–2500?µg/mL) methods. The ethyl acetate extract of Ficus foveolata Wall. (Moraceae) stems that exhibited the strongest antibacterial activity was fractionated to isolate the active compounds by an antibacterial assay-guided isolation process.

Results and discussion: The ethyl acetate extract of F. foveolata showed the strongest antibacterial activity with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of 19.5–39.0 and 39.0–156.2?µg/mL, respectively. On the basis of an antibacterial assay-guided isolation, seven antibacterial compounds, including 2,6-dimethoxy-1,4-benzoquinone (1), syringaldehyde (2), sinapaldehyde (3), coniferaldehyde (4), 3β-hydroxystigmast-5-en-7-one (5), umbelliferone (6), and scopoletin (7), were purified. Among these isolated compounds, 2,6-dimethoxy-1,4-benzoquinone (1) exhibited the strongest antibacterial activities against S. pyogenes, S. mitis, and S. mutans with MIC values of 7.8, 7.8, and 15.6?µg/mL, and MBC values of 7.8, 7.8, and 31.2?µg/mL, respectively. In addition, this is the first report of these antibacterial compounds in the stems of F. foveolata.     

2H-Pyranone and isocoumarin derivatives isolated from the plant pathogenic fungus Leptosphaena maculans

Abstract

Two new 2H-pyranones and two new isocoumarin derivatives, maculanslines A-D (1–4), together with seven known compounds (5–11), were isolated from the plant pathogenic fungus Leptosphaena maculans. Their planar structures and absolute configuration were elucidated by comprehensive spectroscopic techniques including high-resolution electrospray ionization mass spectrum, 1D and 2D nuclear magnetic resonance, as well as electronic circular dichroism. All 11 compounds were tested for their inhibitory activity against α-glucosidase. Compound 1 showed moderate inhibitory activity against α-glucosidase with IC₅₀ of 74.35 μM.     

Antitussive,expectorant, and anti-inflammatory activities of four caffeoylquinic acids isolated from Tussilago farfara

Context: The flower bud of Tussilago farfara L. (Compositae) (FTF) is one of the traditional Chinese medicinal herbs used to treat cough, phlegm, bronchitic, and asthmatic conditions.

Objective: The objective of this study is to isolate four caffeoylquinic acids from the ethyl acetate extract (EtE) of FTF and to evaluate their antitussive, expectorant, and anti-inflammatory activities.

Materials and methods: The structures of compounds 1–4 isolated from EtE were determined by spectral analysis. Mice were orally treated with these compounds and their mixture (in a ratio of 5:28:41:26 as in EtE) at doses of 10 and 20?mg/kg once daily for 3 d. The antitussive and expectorant activities were evaluated separately with the ammonia liquor-induced model and the phenol red secretion model. The anti-inflammation activity was evaluated using leukocyte count in the bronchoalveolar lavage fluid after ammonia liquor-induced acute airway inflammation.

Results: The four compounds were identified as chlorogenic acid (1), 3,5-dicaffeoylquinic acid (2), 3,4-dicaffeoylquinic acid (3), and 4,5-dicaffeoylquinic acid (4). All compounds, especially compound 4 (58.0% inhibition in cough frequency), showed a significant antitussive effect. However, the mixture was the most effective to inhibit the cough frequency by 61.7%. All compounds also showed a significant expectorant effect, while compound 2 was the most potent to enhance the phenol red secretion by 35.7%. All compounds significantly alleviated inflammation, but compound 4 showed the strongest effect to inhibit the leukocytosis by 49.7%.

Discussion and conclusion: The caffeoylquinic acids and their mixture, exhibiting significant antitussive, expectorant, and anti-inflammatory effects, could be considered as the main effective ingredients of FTF, and they may act in a collective and synergistic way.     

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.     

Bioassay-guided isolation and evaluation of antimicrobial compounds from Ixora megalophylla against some oral pathogens

Context Ixora megalophylla Chamch. (Rubiaceae) is a new plant species recently found in southern Thailand. Ethyl acetate extracts of its leaves and stems showed antimicrobial activities.

Objectives To isolate and identify the antimicrobial compounds from I. megalophylla leaves and stems.

Materials and methods The dried leaves (1.7?kg) and stems (3.5?kg) were consecutively extracted with petroleum ether (5?L?×?4), ethyl acetate (5?L?×?3) and ethanol (5?L?×?4) under reflux conditions. The ethyl acetate extract was subjected to an antimicrobial assay guided isolation with Candida albicans and Streptococcus mutans. Compounds 1–10 were identified by ¹H NMR, ¹³C NMR and EI-MS. Minimal lethal concentration (MLC) against C. albicans and Streptococcus spp. was determined using a broth microdilution method for 48 and 24?h, respectively.

Results and discussion On the basis of the antimicrobial assay guided isolation, 10 known compounds, including vanillic acid (1), syringic acid (2), 4-hydroxy benzaldehyde (3), scopoletin (4), loliolide (5), syringaldehyde (6), sinapaldehyde (7), coniferaldehyde (8), syringaresinol (9) and 2,2′-dithiodipyridine (10), were identified. Compounds 1–5 were purified from the ethyl acetate extract of the leaves, while 6–9 and 10 were from the ethyl acetate and ethanol extracts of the stems, respectively. Among these isolates, 10 showed the strongest antibacterial activities against S. mutans and Streptococcus mitis, with minimum inhibitory concentrations (MICs) of 2–4?μg/mL, and MLC of 4?μg/mL, as well as having a weak antifungal activity against C. albicans (MIC of 125?μg/mL). This is the first report of the antimicrobial activities of 10.     

A microbial model of mammalian metabolism: biotransformation of 4,5-dimethoxyl-canthin-6-one using Cunninghamella blakesleeana CGMCC 3.970

1.?A filamentous fungus, Cunninghamella blakesleeana CGMCC 3.970, was applied as a microbial system to mimic mammalian metabolism of 4,5-dimethoxyl-canthin-6-one (1). Compound 1 belongs to canthin-6-one type alkaloids, which is a major bioactive constituent of a traditional Chinese medicine (the stems of Picrasma quassioides).

2.?After 72?h of incubation in potato dextrose broth, 1 was metabolized to seven metabolites as follows: 4-methoxyl-5-hydroxyl-canthin-6-one (M1), 4-hydroxyl-5-methoxyl-canthin-6-one (M2), canthin-6-one (M3), canthin-6-one N-oxide (M4), 10-hydroxyl-4,5-dimethoxyl-canthin-6-one (M5), 1-methoxycarbonl-β-carboline (M6), and 4-methoxyl-5-O-β-D-glucopyranosyl-canthin-6-one (M7).

3.?The structures of metabolites were determined using spectroscopic analyses, chemical methods, and comparison of NMR data with those of known compounds. Among them, M7 was a new compound.

4.?The metabolic pathways of 1 were proposed, and the metabolic processes involved phase I (O-demethylation, dehydroxylation, demethoxylation, N-oxidation, hydroxylation, and oxidative ring cleavage) and phase II (glycosylation) reactions.

5.?This was the first research on microbial transformation of canthin-6-one alkaloid, which could be a useful microbial model for producing the mammalian phase I and phase II metabolites of canthin-6-one alkaloids.

6.?1, M1?M5, and M7 are canthin-6-one alkaloids, whereas M6 belongs to β-carboline type alkaloids. The strain of Cunninghamella blakesleeana can supply an approach to transform canthin-6-one type alkaloids into β-carboline type alkaloids.     

A New Bicoumarin from Stellera Chamaejasme L

Abstract

Thirteen compounds were isolated from roots of Stellera chamaejasme L. (Thymelaeaceae). They are β-sitosterol (2), simplexin (3), pimelea factor P2 (4), daucosterol (5), (+)-3-hydroxy-1,5-diphenyl-1-pentanone (6), 4-ethoxy-benzoic acid (7), 2,4,6-Trimethoxy-benzoic acid (8), (+)-afzelechin (9), fumaric acid (10), N,N-dimethyl-L-aspartic acid (11), umbelliferone (12), daphniretin (13) and a novel bicoumarin named bicoumastechamin (1). Among the known compounds, 7, 8, 9, 10 and 11 were first isolated from this plant, and 6 was first isolated from the natural resources. Their structures have been elucidated on the basis of spectral data. In vitro bioassays showed that 4 inhibited cancer cell growth, 13 exhibited immunomodulatory activity, and 6 exhibited both immunomodulatory and anti-tumor activity.     

Two new compounds from Atractylodes macrocephala with neuroprotective activity

In the present study, two new compounds, together with six known compounds, were isolated from rhizome of Atractylodes macrocephala Koidz by a series of silica gel, ODS column chromatography, and preparative HPLC. Their structures were characterized as atractylenolide II (1), atractylenolide I (2), biepiasterolid (3), isoatractylenolide I (4), atractylenolide III (5), 3β-acetoxyl atractylenolide I (6), (4E,6E,12E)-tetradeca-4,6,12-triene-8,10-diyne-13,14-triol (7), (3S,4E,6E,12E)-1-acetoxy-tetradeca-4,6,12-triene-8,10-diyne-3,14-diol (8) on the basis of 1D, 2D NMR, and circular dichroism analyses. Among them, compounds 6 and 8 were novel compounds. In addition, their neuroprotective activity against MPP⁺-induced SH-SY5Y cells was evaluated by MTT colorimetry. The results showed that all these compounds have definite protective effect on MPP⁺-induced SH-SY5Y cells.     

Two new phenolic compounds and antitumor activities of asparinin A from Asparagus officinalis

Two new phenolic acid compounds, asparoffin C (1) and asparoffin D (2), together with four known compounds, asparenyol (3), gobicusin B (4), 1-methoxy-2-hydroxy-4-[5-(4-hydroxyphenoxy)-3-penten-1-ynyl] phenol (5), and asparinin A (6), have been isolated from the stems of Asparagus officinalis. The structures were established by extensive spectroscopic methods (MS and 1D and 2D NMR). Compound 6 has obvious antitumor activities both in vitro and in vivo.     

New flavonoid from Patrinia villosa

Context: Patrinia villosa (Thunb.) Juss (Valerianaceae) is an important ancient herbal medicine widely used for inflammation, wound healing, and abdominal pain. But little is known of the phytochemical constituents of this herbal plant.

Objective: The objective of this study is to isolate and identify the bioactive components from P. villosa.

Materials and methods: A 70% EtOH extract of P. villosa was subjected to normal-phase silica, ODS silica gel column chromatography, and semi-preparative HPLC chromatography after partitioned successively with light petroleum, dichloromethane and n-BuOH. Chemical structures of the compounds were elucidated by spectroscopic methods including UV, 1D-NMR, 2D-NMR, HR-ESI-MS, and CD spectra. The cytotoxic activity of the new component was determined with the SMMC-7721 cell line using the MTT method after incubation for 48?h.

Results: A new flavonoid named patriniaflavanone A (1) along with four known compounds was isolated from P. villosa. The four known compounds were identified as luteolin 7-O-glucuronide-6″-methyl ester (2), p-hydroxyphenylacetic acid methyl ester (3), trans-caffeic acid (4), and trans-caffeic acid methylate (5) by comparison of their spectral data with the reported data. The IC₅₀ value of patriniaflavanone A (1) on SMMC-7721 was 61.27?μM.

Discussion and conclusion: This is the first report on the isolation and identification of patriniaflavanone A (1), and compounds 2–5 were isolated for the first time from the title plant. Patriniaflavanone A (1) exhibited moderate cytotoxic activity.