Records of Natural Products Articles

A new phenolic glycoside named salicyltomenside (1), with five similar compounds, salicyltremuloidin (2), tremuloidin (3), isograndidentatin A (4), siebolside B (5), and salicin (6) were isolated from Populus tomentosa Carr. Additionally, salicyltremuloidin (2) was obtained from the plant for the first time. Structure of the new compound was determined using spectroscopic methods including ESI-MS and 1D- and 2D-NMR. Others were elucidated through 1H and 13C NMR spectra and comparison with literature data. Notably, salicyltomenside (1) and salicyltremuloidin (2) were structural isomers.

Some species of Euphorbia have been used as medicinal plants to treat wounds, and skin diseases, around the world. The solvents n-hexane, ethyl acetate, and methanol were used successively to prepare extracts of the aerial parts of E. characias subsp. wulfenii, E. helioscopia, E. macroclada, E. seguieriana subsp. seguieriana, and E. virgata. Linear incision, circular excision wound models and the hydroxyproline assay method were used to assess the wound-healing activity. The inhibition of the increase in capillary permeability induced by acetic acid was used to assay the anti-inflammatory activity. The methanol extract of the aerial parts of E. characias subsp. wulfenii showed statistically significant wound-healing activity with 43.03% tensile strength for the linear incision wound model and a 65.24% reduction in the area of the wound by day 10 for the circular excision model. The tissue treated with this extract was found to contain 35.47 µg/mg of hydroxyproline. The methanol extract of E. characias subsp. wulfenii inhibited inflammation induced by acetic acid with a value of 34.74%. The results showed that the aerial parts of E. characias subsp. wulfenii possess wound-healing and anti-inflammatory activities on different models.

 One new C18-diterpenoid alkaloid, along with four known diterpenoid alkaloids have been isolated from the roots of Aconitum sinomontanum.  Their structures were established as sinomontanine I (1), delcosine (2), lepenine (3), napelline (4), and kirinine B (5) by extensive spectroscopic techniques and chemical methods.The immunosuppressive effects of compounds 1–4 were evaluated in vitro through ConA-induced or LPS-induced splenocyte proliferation, with IC50 values of 8.909 μM, 1.515 μM，5.078 μM, and 1.167 μM (ConA-induced)，or 3.661 μM, 4.417 μM, 5.129 μM, and 1.830 μM (LPS-induced), and compounds 1–4 showed a significant cytotoxic effect with CC50 values of 447.5 μM, 702.2 μM, 310.6 μM and 794.1 μM, respectively. The CC50/IC50 value of 2 and 3 suggested that these compounds were potential immunosuppressive agents for the treatment of autoimmune diseases characterized by arthritis, such as rheumatoid arthritis..

The objective in this study is to isolate and characterize volatile compounds of Lavandula stoechas L. subsp. stoechas rooted with micropropagation techniques and grown under suitable in vitro conditions. Microdistillation procedure was applied on aerial parts of this plant. The volatile compounds were characterized by GC-FID and GC-MS systems, simultaneously. Based on results, twenty-two compounds were identified. Major volatile compounds included camphor (38.5%), bornyl acetate (10.6%), α-fenchone (8.9%), 1,8-cineole (4.3%), α-pinene (4.0%), linalool (3.5%), viridiflorol (3.8%) myrtenal (2.7%), geranyl acetate (2.1%). These results were positively related with data published regarding the plant growing wild.

Phytochemical investigation on pathogenic fungus Cylindrocarpon destructans isolated form Meconopsisgrandis plant led to the isolation of two new isochromene derivatives namely, 6,8-dimethoxy-3-methyl-3,4-dihydrobenzoisochromene-4,9,10-triol (1) and 3,5,6-trihydroxy-4-methylbenzoisochromene-9,11-dione (2) along with four known compounds (3-6). The structures of these compounds were elucidated by 1D and 2D NMR and mass spectroscopic data analysis. The isolated compounds were evaluated for cytotoxic activity. The compounds 1-4 showed good inhibition against the growth of cell lines MCF-7 and PC-3. Compounds 5-6 showed minimum inhibitory effect of cancerous cell lines growth.

A new acylated benzyl alcohol glucoside, benzyl alcohol 3',6'-di-O-galloyl-b-glucopyranoside (1), together with a known analogue, 6'-O-galloyl-b-glucopyranoside (2)  and a cyanogenic glucoside, 6‵-O-galloylprunasin (3) were isolated from the leaves of Syzygium austroyunnanense. Their structures were characterized based on the spectroscopic methods and comparison with literature. This is the first phytochemical study on Syzygium austroyunnanense.

This study was designed to investigate the antioxidative and anti-inflammatory effects of the extract of Ribes mandshuricum (Maxim.) Kom. leaves. Seven major flavonoids (rutin, hyperoside, isoquercetin, trifolin, astragalin, quercetin and kaempferol ) were successfully prepared from the Ribes mandshuricum leaves by MAE-DES methods followed by X-5 macroporous resin. Then, the antioxidant activities of Ribes mandshuricum leaves flavonoids were evaluated by DPPH, ABTS and FRAP assays. We revealed that the Ribes mandshuricum leaves flavonoids had the antioxidant abilities. Finally, it was discovered that Ribes mandshuricum leaves flavonoids could effectively inhibit the NO production and increase the IL-10 cytokines production in LPS-induced RAW 264.7 cells. It suggested that the Ribes mandshuricum leaves flavonoids had the potential anti-inflammatory effects. Therefore, the major flavonoids of Ribes mandshuricum leaves have potential use as functional food or cosmetics to delay senescence, guard health and prevent chronic disease.

In this study the antioxidant and anticholinesterase activities of the crude ethanol extract, as well as the dichloromethane and water extracts obtained from partitioning of the crude ethanol extract, of the plant Salvia cassia Samuelss ex. Rech. Fil, were determined. The extracts were screened for their total phenolic and flavonoid contents. The dichloromethane extract, which showed higher inhibition of lipid peroxidation, higher metal chelating capacity and also a higher flavonoid content than the other extracts was analyzed for its constituents. GC-MS analysis resulted in the identification of a total of 30 long chain hydrocarbons. A series of b-amyrin fatty acid esters, a triterpene acid oleanolic acid, a diterpenoid manoyloxide, and two flavonoids apigenin 7, 4′-dimethyl ether and salvigenin were isolated by open column chromatography. Their structures were identified based on NMR and mass spectrometric techniques. The isolated compounds were also tested for their anticholinesterase activities. The triterpenoids as well as the water extract exhibited promising anticholinesterase activity.

 A new aporphine alkaloid, named Litsine A, along with two known ones were isolated from the root barks of Litsea glutinosa. The new structure was determined by various spectroscopic techniques including 1D(1H-, 13C-NMR), 2D-NMR(HMBC, HSQC, COSY and ROESY) and high resolution electrospray ionization mass spectrometry (HR-ESI-MS), where as the structures of the known compounds were elucidated through 1D-NMR, mass spectrometric analysis and compared with the reported data in literature. The effects of these compounds on glucose uptake in C2C12 myotubes were evaluated at the concentration

Spiranthera odoratissima A. St. Hil. (Rutaceae), a plant grown in midwestern Brazil, has been used for treating rheumatism, infection and abdominal pain. This research aims to investigate chemical constituents of essential oils from S. odoratissima A. St. Hil. leaves and flowers. Essential oils were obtained by hydrodistillation and fully characterized by gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Results of the essential oil from S. odoratissima A. St. Hil. leaves showed that it has 28 volatile compounds which represent 93.8% of the oil. Its major compounds were b-caryophyllene (23.8%), bicyclogermacrene (10.8%), δ-cadinene (7.1%), germacrene D (5.9%), a-copaene (5.5%) and b-elemene (5.3%). Results of the essential oil from S. odoratissima A. St. Hil. flowers showed that it has 29 volatile compounds which represent 94.4% of the oil. Its main constituents were b-caryophyllene (14.1%), spathulenol (8.1%), g-cadinene (7.2%), α-cadinol (6.6%), a-copaene (6.4%), τ-muurolol (6.3%), δ-cadinene (5.8%), b-elemene (5.4%) and alloaromadendrene (5.2%). In this research, chemical constituents of the essential oil from S. odoratissima A. St. Hil. flowers were investigated for the first time.

In this work, we investigated the chemical constituents of hydrodistillation essential oil from the aerial parts of Artemisia frigida Willd. All together 14 components were identified by GC-MS. Moreover, we tested the fumigant and contact activities of the essential oil and its five major individual compounds (terpinen-4-ol, verbenone, camphene, α-terpineol and α-terpinyl acetate) against Liposcelis bostrychophila, Lasioderma serricorne and Tribolium castaneum. In fumigant toxicity tests, α-terpineol possessed the strongest activity (LC50 = 3.27 mg/L air) against L. serricorne. Terpinen-4-ol exhibited the strongest activity (LC50 = 0.08 and 3.74 mg/L air respectively) against L. bostrychophila and T. castaneum. As for contact toxicity, terpinen-4-ol and α-terpinyl acetate exhibited fair toxicity against L. bostrychophila (LD50 = 33.10 and 31.80 µg/cm2 respectively) and L. serricorne (LD50 = 8.62 and 8.87 µg/adult respectively), and camphene possessed the strongest activity (LD50 = 5.13 µg/adult) against T. castaneum. The results indicated that A. frigida essential oil and its individual compounds had the potential to be developed as natural fumigants and insecticides for control of these three stored-product insects.