Identification of anti-inflammatory components in Sinomenii Caulis based on spectrum-effect relationship and chemometric methods.

The present study aimed to identify the anti-inflammatory components in Sinomenii Caulis (SC) based on spectrum-effect relationship and chemometric methods. A phytochemical investigation of SC extract was performed firstly and afforded eleven potential bioactive compounds. The HPLC fingerprints of 19 batches of SC samples were evaluated by the chemometric methods such as similarity analysis (SA) and hierarchical clustering analysis (HCA). The anti-inflammatory effects of these samples were determined by inhibition of Nitric Oxide (NO) production. Partial least squares regression (PLSR) and artificial neural network (ANN) were used to explore the spectrum-effect relationship of SC. The results indicated that there was a close correlation between chemical fingerprint and anti-inflammatory activity of SC, and peaks 8, 9, 12, 13, 14, 16, 19 and 22 might be potential anti-inflammatory compounds in SC. The verification experiments by testing individual compounds and a combination of them indicated that sinomenine (P8), magnoflorine (P13), menisperine (P16) and stepharanine (P19) were the major anti-inflammatory compounds in SC. Collectively, the present study established the spectrum-effect relationship mode of SC and discovered the anti-inflammatory compounds in SC, which could be used for exploration of bioactive components and quality control of herbal medicines.

Neo-clerodane diterpenes and phytoecdysteroids from Ajuga decumbens Thunb. and evaluation of their effects on cytotoxic, superoxide anion generation and elastase release in vitro.

Five novel compounds, including four neoclerodane diterpenoids, named ajugacumbins KN (1-4) along with a phytoecdysterone, named ajugacetalsterone E (5), were isolated from the whole herbs of Ajuga decumbens (Labiatae). Their structures were elucidated on the basis of detailed spectroscopic analysis including IR, HRESIMS, CD, 1D and 2D NMR spectroscopic experiments. Compounds 1-5 were evaluated for their cytotoxic activities and the effects on superoxide anion generation and elastase release in FMLP/CB-induced human neutrophils.

Cytotoxic limonoids from the root bark of Dictamnus angustifolius.

Three novel limonoids, dictangustone G (1), dictangustone H (2), and dictangustone I (3) were isolated from the root bark of Dictamnus angustifolius. Their structures were elucidated on the basis of detailed spectroscopic analysis including UV, IR, HRESIMS, 1D and 2D NMR spectroscopic experiments. Compounds 1-3 were evaluated for their cytotoxic activities using Hela, A549, MCF7, and LN229 cell lines.

Chemical constituents from Agrimonia pilosa Ledeb. and their chemotaxonomic significance.

Phytochemical investigation of the ethanol extract from the whole plant of Agrimonia pilosa led to the isolation of 31 compounds, including 16 flavonoids (1-16), 5 triterpenes (17-21), 1 isocoumarin (22), 5 phenolic acids (23-27), 1 ceramide (28), 2 agrimols (29-30) and 1 fatty acid (31). Their structures were determined by various spectroscopic analyses. Compounds 5, 7 and 20 were firstly isolated from the genus Agrimonia, and compounds 6, 10-11, 15, 26, 28 and 31 were isolated from the family Rosaceae for the first time. Moreover, the chemotaxonomic significance of these compounds was summarised.

Comparative analysis of volatile oils in the stems and roots of Ephedra sinica via GC-MS-based plant metabolomics.

With a great difference in therapeutic effects of Mahuang (MH, the stems of Ephedra sinica) and Mahuanggen (MHG, the roots of Ephedra sinica), chemical differences between MH and MHG should be investigated. In the present study, gas chromatography-mass spectrometry (GC-MS)-based plant metabolomics was employed to compare volatile oil profiles of MH and MHG. The antioxidant activities of volatile oils from MH and MHG were also compared. 32 differential chemical markers were identified according to the variable importance in the projection (VIP) value of orthogonal partial least squares discriminant analysis (OPLS-DA) and P value of Mann-Whitney test. Among them, chemical markers of tetramethylpyrazine (TMP) and α-terpineol were quantified. Their contents were much higher in most MH samples compared with MHG. The antioxidant assay demonstrated that MH had significantly higher free radical-scavenging activity than MHG. Although MH and MHG derived from the same medicinal plant, there was much difference in their volatile oil profiles. MH samples had significantly higher content of two reported pharmacologically important chemical markers of TMP and α-terpineol, which may account for their different antioxidant activities.

Flavonoids and other constituents from Aletris spicata and their chemotaxonomic significance.

Eleven compounds, including four flavonoids [(2R,3R)-2,3-dihydro-3,5-dihydroxy-7,4'-dimethoxyflavone (1), 5-hydroxy-7,8,4'-trimethoxy-flavone (2), amentoflavone (10) and apigenin (11)], two penylpropanoids [sinapaldehyde (3) and 3-methoxy-4-hydroxy-cinnamic aldehyde (4)], three phenolic acids [4-hydroxyl-3,5-dimethoxy-benzaldehyde (5), 4-hydroxyacetophen-one (6) and p-hydroxybenzaldehyde (7)], one furan derivative [5-hydroxymethyl furfural (8)] and one steroid saponin [ß-sitosterol-3-O-ß-d-glucoside (9)], were isolated and identified from Aletris spicata. Among them, compounds 1-7, 9 and 10 were reported from the genus Aletris for the first time. Furthermore, seven of them (1-6, 10) were obtained from the family Liliaceae for the first time. Chemotaxonomy of the isolated compounds is discussed briefly.

A new quinoline alkaloid from the roots of Dictamnus angustifolius.

AIM: To investigate the quinoline alkaloids from the roots of Dictamnus angustifolius G.Don ex Sweet (Rutaceae). METHOD: The quinoline alkaloids were isolated by various column chromatographic methods and their structures were elucidated on the basis of spectral analysis. RESULTS: A new quinoline alkaloid, 5-methoxylrobustine (1), along with five known quinoline alkaloids were obtained, and their structures were identified as dictamnine (2), robustine (3), isopteleine (4), γ-fagarine (5), and skimmianine (6). Cytotoxicity testing of these alkaloids showed that all of them had weak cytotoxic activities against human breast cancer cells (MCF7). CONCLUSION: Compound 1 is a new quinoline alkaloid. Alkaloid 3 showed stronger anti-proliferation effect than the other alkaloids.

A new taxane diterpenoid from Taxus chinensis var. mairei.

Taxadiene (3), a new taxane diterpenoid with an unusual hydroxy substituting at C-17, and six known compounds including two taxane diterpenoids (1 and 2) and four flavonoids (4-7) were isolated from the whole seedling of the Taxus chinensis var. mairei. Among them, compound 7 was isolated from T. chinensis var. mairei for the first time. Structures of these compounds were elucidated on the basis of spectroscopic data and by comparison with reported literature data.

Caesappin A and B, two novel protosappanins from Caesalpinia sappan L.

Two novel protosappanins, named Caesappin A (1) and B (2), along with three known protosappanins were isolated from Caesalpinia sappan L. Caesappin A is a new type protosappanin with a seven-membered ring fusing an acetal-type section. Compound 4 was isolated from the genus Caesalpinia for the first time. The structures were elucidated on the basis of spectral analysis and the absolute configuration was determined by the ECD experiment coupled with calculated ECD spectra. Their cytotoxic activities were evaluated using MTT assay.

Degraded limonoids and quinoline alkaloids from Dictamnus angustifolius G. Don ex Sweet. and their anti-platelet aggregation activity.

A new degraded limonoid, named isodictamdiol A (1), two known degraded limonoids (2, 3) and a new nature product of quinoline alkaloid (4) along with five known quinoline alkaloids (5-9) were isolated from the root bark of Dictamnus angustifolius G. Don ex Sweet.. Certain useful NMR data were generalized to determine the structures of compounds 1 and 4. The structural elucidation of Compound 4 was first reported herein. Compounds 1-9 showed significant inhibitory effects on platelet aggregation induced by ADP at 250 µM, while Compound 4 showed potent anti-platelet aggregation activity.