12,20-Epoxypregnane Glycosides from the Roots of Oxypetalum caeruleum.

The MeOH extract from dried roots of Oxypetalum caeruleum (Apocynaceae, formerly known as Asclepiadaceae) plants yielded twenty new pregnane glycosides, some of which had a new 12,20-epoxy type aglycone. The structures of these compounds were established using NMR, MS spectroscopic analysis and chemical evidence.

Mosquito Larvicidal Activity of Compounds from Unripe Fruit Peel of Avocado (Persea americana Mill.).

Mosquitoes are important vectors responsible for spreading a number of diseases affecting both humans and animals. Many diseases as dengue, chikungunya, yellow fever, malaria, filariasis and Japanese encephalitis are spread by mosquitoes. There are many reports of plant extracts and their active constituents showing anti-mosquito activities as larvicidal, pupicidal, ovicidal and adulticidal activities. Persea americana Mill. (Lauraceae), known as avocado, has been reported to show many pharmacological and antimicrobial activities. In this communication, the mosquito larvicidal activities of the three-active constituents, avocadene, avocadyne and avocadenol-A, from the methanolic extract of the unripe fruit peel are presented. The three mosquito species studied were Aedes aegypti, Culex quinquefasciatus and Anopheles stephensi. All three compounds showed the highest larvicidal activity against An. stephensi, LC50 values being 2.80ppm for avocadene, 2.33ppm for avocadyne and 2.07ppm for avocadenol-A. Avocadene showed larvicidal activity of 3.73ppm against Ae. aegypti and 5.96ppm against Cx. quinquefasciatus. The LC50 value of avocadyne was 5.35ppm against Ae. aegypti and 3.98ppm against Cx. quinquefasciatus. Similarly, avocadenol-A showed 6.56ppm against Ae. aegypti and 2.35ppm against Cx. quinquefasciatus. The active constituents were isolated by bioactivity-guided fractionation by silica gel column chromatography and RP HPLC. The compounds were identified by physical and spectroscopic data and compared with literature values already reported.

C21 Steroidal Glycosides from the Roots of Oxypetalum caeruleum.

The MeOH extract from dried roots of Oxypetalum caeruleum (Apocynaceae) plants yielded seventeen new pregnane glycosides, some of which had the acylated-ramanone or -isoramanone type aglycone. The structures of these compounds were established using NMR, MS spectroscopic analysis and chemical evidence.

Chukranoids A-I, isopimarane diterpenoids from Chukrasia velutina.

Bioactivity guided separation of Chukrasia velutina root methanolic extract led to the isolation of nine new isopimarane diterpenoids, chukranoids A-I (1-9). The absolute configuration was then assigned by comparing the experimental CD spectra and the calculated CD spectra. Chukranoids A-I (1-9) showed moderate antimalarial activity against Plasmodium falciparum 3D7 strain. It seems that conjugate system in the isopimarane skeleton may influence their antimalarial activity.

Walsogynes H-O from Walsura chrysogyne.

Eight new limonoids, walsogynes H-O (1-8) were isolated from the barks of Walsura chrysogyne, and their structures were determined on the basis of the 1D and 2D NMR data. Walsogynes H-M (1-6) and O (8) were concluded to be 11,12-seco limonoids with a dodecahydro-1H-naphtho[1,8-bc:3,4-c']difuran skeleton, and walsogyne N (7) to be 11,12-seco limonoid sharing a unique dodecahydronaphtho[1,8-bc:5,4-b'c']difuran skeleton. Walsogynes H-O (1-8) exhibited potent antimalarial activity against Plasmodium falciparum 3D7 strain with IC50 value of 2.5, 2.6, 1.6, 2.5, 1.5, 2.6, 2.1, and 1.1 µM, respectively.

Tetracyclic Triterpenoids, Steroids and Lignanes from the Aerial Parts of Oxypetalum caeruleum.

The MeOH extract from dried aerial parts of Oxypetalum caeruleum (Apocynaceae) plants yielded seventeen compounds, including four new tetracyclic triterpenoids, one pregnane glycoside, two lignane glycosides, and ten known compounds. The structures of the new compounds were established using NMR, MS spectroscopic analysis and chemical evidence.

Triterpenoids from Walsura trichostemon.

Bioactivity guided separation of Walsura trichostemon stem methanolic extract led to the isolation of four new dammarane (1-4) and two new apotirucallane triterpenoids (5-6), together with one limonoid (7), 11,25-dideacetyltrichostemonate, 12ß, 20S, 24R-trihydroxydammar-25-en-3-one and 12ß, 20S, 25-trihydroxydammar-23-en-3-one. Compounds 1-7 showed in vitro inhibitory activity on the proliferation of A549, human lung adenocarcinoma cell line.

Leishmanicidal phenolic compounds derived from Dalbergia cultrata.

Leishmaniasis is a protozoan tropical infection that is estimated to be more than 0.3 million new cases occur annually worldwide. A novel phenolic compound, cultratin A (1), was isolated as a leishmanicidal constituent from the timber of Dalbergia cultrata, along with three known neoflavanoids (2, 3, 4), two benzofurans (5, 6), and two phenolic compounds (7, 8). Their structures were determined using spectral methods. Among them, a new compound (1) and 4-(S)-methoxydalbergione (2) showed effective leishmanicidal activities (IC50: 2.0 and 2.6 µM, respectively), while compound 8 showed moderate activity (IC50: 11 µM). The cytotoxicity of compounds 1 and 2 was also weaker than that of the other compounds.

Effect of monoterpene ester from Blumea axillaris (Lam.) DC and its acetyl derivative against plant pathogenic fungi and their in silico molecular docking.

The present study was aimed to isolate active constituents from Blumea axillaris (Lam.) DC (Asteraceae) against phytopathogenic fungi. Bioactivity guided fractionation of the successive n-hexane, chloroform and methanol extract led to the isolation of the monoterpene ester (4 R,5S)-4-hydroxy-7-tigloyloxycarvotanacetone (1). The compound 1 was converted into acetyl derivative (2). The acetyl derivative (2) and the parent compound 1 were tested again phytopathogenic fungi by using mycelial inhibition and minimal inhibitory concentration values were found out by the broth microdilution method. The acetyl derivative (2) showed the highest antifungal activity against Rhizoctonia solani and Aspergillus niger. Based upon in vitro results, compound 1 was tested against Fusarium oxyporum (wilting disease) and compound 2 was tested against R. solani (leaf blight disease) in vivo using the foliar spray method. Both compounds had no phytotoxicity and also in silico docking study showed that both compounds were binding similarly as commercial fungicide carbendazim.

Antihyperlipidemic effect of iridoid glycoside deacetylasperulosidic acid isolated from the seeds of Spermacoce hispida L. - A traditional antiobesity herb.

ETHNOBOTANICAL RELEVANCE: The interest on herbal health supplements for obesity is increasing globally. Our previous ethnobotanical survey in Tiruvallur district, Tamil Nadu, India indicated the use of Spermacoce hispida L. seeds for the treatment of obesity. AIM OF THE STUDY: This study was aimed to validate the traditional claim and to identify the antihyperlipidemic principle in the seeds of Spermacoce hispida using bioassay guided fractionation method. METHODS: Bioassay monitored fractionation of the aqueous extract from Spermacoce hispida seeds was carried out using triton WR 1339 induced hyperlipidemic animals. It yielded deacetylasperulosidic acid (DAA) as the active ingredient. Pharmacokinetic properties of DAA were predicted using DataWarrior and SwissADME tools. In vitro antiobesity and antihyperlipidemic effects of DAA were evaluated in 3T3L1 preadipocytes and HepG2 cells, respectively. The chronic antihyperlipidemic efficacy of DAA was evaluated in high fat diet fed rats. RESULTS: DAA did not show any mutagenic and tumorigenic properties. It bound with PPARα with comparable ligand efficiency as fenofibrate. The treatment with DAA significantly lowered the proliferation of matured adipocytes, but not preadipocytes. The treatment of steatotic HepG2 cells with DAA significantly decreased the LDH leakage by 43.03% (P < 0.05) at 50 µM concentration. In triton WR 1339 induced hyperlipidemic animals, the treatment with 50 mg/kg dose significantly lowered the TC, TG and LDL-c levels by 40.27, 46.00 and 63.65% respectively. In HFD fed animals, the treatment at 10 mg/kg decreased BMI and AC/TC ratio without altering SRBG. It also improved serum lipid, transaminases and phosphatases levels of HFD fed animals. The treatment lowered adipocyte hypertrophy and steatosis of hepatocytes. CONCLUSION: This preliminary report supported the traditional use of Spermacoce hispida for the treatment of obesity. Further detailed investigations on the long term safety, efficacy and molecular mode of action of Spermacoce hispida and DAA will throw more light on their usefulness for the management of obesity.

Reinereins A and B, new onocerane triterpenoids from Reinwardtiodendron cinereum.

Bioactivity guided separation of Reinwardtiodendron cinereum barks methanol extract led to the isolation of two new onocerane triterpenoids, reinereins A and B (1 and 2), together with three known onocerane triterpenoids. Their structures were elucidated on the basis of NMR spectroscopic data. In vitro cytotoxic activities of the isolated compounds against several type of cancer cells were evaluated.

An immunochromatographic assay for rapid etection of salvinorin A.

We developed an immunochromatographic assay (ICA) that enables rapid analysis of salvinorin A (Sal A) in Salvia divinorum within 10 min. The result shows that no Sal A in other samples of Lamiaceae plants was detected, but it could recognize Sal A among other substances in complex samples. The main advantage of the ICA is its high performance in combination with low cost, simplicity, and speed. Our newly developed combined ICA/indirect competitive ELISA(icELISA) system enables analysis of large numbers of samples over short periods of time without cumbersome pretreatments in complex mixtures. This method can complement other instrumental analyses for salvinorins, and could be used to deter S. divinorum abuse.

Degradation rates and products of fluticasone propionate in alkaline solutions.

The apparent degradation rate constant of fluticasone propionate (FLT) in 0.1 M NaOH:methanol=1:1 at 37 °C was previously reported to be 0.169±0.003 h-1, and four degradation products (products 1-4) were observed in the solution. The aims of the present study were to assess the degradation rates of FLT in other alkaline solutions and clarify the chemical structures of the four degradation products in order to obtain basic data for designing an enema for inflammatory bowel disease. The apparent degradation rate constants in 0.05 M NaOH and 0.1 M NaOH:CH3CN=1:1 were 0.472±0.013 h-1 and 0.154±0.000 h-1 (n=3), respectively. The chemical structures of products 1-4 in 0.1 M NaOH:methanol=1:1 were revealed by nuclear magnetic resonance (NMR) and mass spectrometry data. The chemical structure of products 2 was that the 17-position of the thioester moiety of FLT was substituted by a carboxylic acid. The degradation product in 0.1 M NaOH:CH3CN=1:1 was found to be product 2 based on 1H NMR data. The degradation product in 0.05 M NaOH was considered to be product 2 based on the retention time of HPLC. These results are useful for detecting the degradation products of FLT by enzymes of the intestinal bacterial flora in the large intestine after dosing FLT as an enema.

Degradation rates and products of fluticasone propionate in alkaline solutions / 药物分析学报

The apparent degradation rate constant of fluticasone propionate (FLT) in 0.1 M NaOH:methanol=1:1 at 37 ℃ was previously reported to be 0.169 ± 0.003 h?1, and four degradation products (products 1–4) were observed in the solution. The aims of the present study were to assess the degradation rates of FLT in other alkaline solutions and clarify the chemical structures of the four degradation products in order to obtain basic data for designing an enema for inflammatory bowel disease. The apparent degradation rate constants in 0.05 M NaOH and 0.1 M NaOH:CH3CN=1:1 were 0.472 ± 0.013 h?1 and 0.154 ± 0.000 h?1 (n=3), respectively. The chemical structures of products 1–4 in 0.1 M NaOH:methanol=1:1 were revealed by nuclear magnetic resonance (NMR) and mass spectrometry data. The chemical structure of products 2 was that the 17-position of the thioester moiety of FLT was substituted by a carboxylic acid. The degradation product in 0.1 M NaOH:CH3CN=1:1 was found to be product 2 based on 1H NMR data. The degradation product in 0.05 M NaOH was considered to be product 2 based on the retention time of HPLC. These results are useful for detecting the degradation products of FLT by enzymes of the intestinal bacterial flora in the large intestine after dosing FLT as an enema.

Degradation rates and products of fluticasone propionate in alkaline solutions / 药物分析学报

The apparent degradation rate constant of fluticasone propionate (FLT) in 0.1 M NaOH:methanol=1:1 at 37 ℃ was previously reported to be 0.169 ± 0.003 h?1, and four degradation products (products 1–4) were observed in the solution. The aims of the present study were to assess the degradation rates of FLT in other alkaline solutions and clarify the chemical structures of the four degradation products in order to obtain basic data for designing an enema for inflammatory bowel disease. The apparent degradation rate constants in 0.05 M NaOH and 0.1 M NaOH:CH3CN=1:1 were 0.472 ± 0.013 h?1 and 0.154 ± 0.000 h?1 (n=3), respectively. The chemical structures of products 1–4 in 0.1 M NaOH:methanol=1:1 were revealed by nuclear magnetic resonance (NMR) and mass spectrometry data. The chemical structure of products 2 was that the 17-position of the thioester moiety of FLT was substituted by a carboxylic acid. The degradation product in 0.1 M NaOH:CH3CN=1:1 was found to be product 2 based on 1H NMR data. The degradation product in 0.05 M NaOH was considered to be product 2 based on the retention time of HPLC. These results are useful for detecting the degradation products of FLT by enzymes of the intestinal bacterial flora in the large intestine after dosing FLT as an enema.

A new benzylisoquinoline alkaloid from Leontice altaica.

A new benzylisoquinoline alkaloid, lincangenine-4-ß-D-glucopyranoside (1), has been isolated from the roots of Leontice altaica, together with 5 known alkaloids. Its structure was elucidated on the basis of 1D and 2D NMR data, and chemical means.

Acyl flavonoids, biflavones, and flavonoids from Cephalotaxus harringtonia var. nana.

A methanol extract of the leaves of Cephalotaxus harringtonia var. nana and its ethyl acetate (EtOAc)-soluble fraction demonstrated strong antitumor activity against A549 and HT-29 cell lines. The EtOAc-soluble fraction was purified by column chromatography and high-performance liquid chromatography (HPLC) using a reverse-phase column to yield three novel acyl flavonoids and a biflavonoid, along with 15 other known compounds that included flavonoids, biflavonoids, and other phenolics. The structures of the new compounds were elucidated using spectral data from HR-MS and NMR, including two-dimensional NMR studies, as (2R,3R)-3-O-eicosanoyltaxifolin (1), (2R,3R)-3-O-docosanoyltaxifolin (2), (2R,3R)-3-O-tetracosanoyltaxifolin (3), and 6-methyl-4',7,7″-tri-O-methylamentoflavone (4). The isolated compounds, including the known compounds, were tested for possible antitumor activity; some of the biflavones were found to be active. The potent antitumor activity of the extract was attributed to Cephalotaxus alkaloids, such as homoharringtonine (20).

Transannular cyclization of (4S,5S)-germacrone-4,5-epoxide under basic conditions to yield eudesmane-type sesquiterpenes.

Transannular cyclizations of germacrone-4,5-epoxide under acidic and thermal conditions have been reported in our previous study. However, this process gave the different and interesting results under basic conditions. (4S,5S)-Germacrone-4,5-epoxide (1) was treated under basic conditions to yield four products (2-5). Compound 2 was an isomer of 1--(4S,5S,9Z)-4,5-epoxygermacra-7(11),9-dien-8-one--and the remaining three compounds (3-5) were eudesmane-type derivatives. Compounds 4 and 5 are new compounds. The structures of the new compounds were determined using high resolution (HR)-MS, one dimensional (1D)-NMR, 2D-NMR and circular dichroism (CD) spectroscopic data. Products 3-5 had the same carbon skeleton as that of eudesmane-type compounds; however, these compounds showed different arrangement of isoprene units to the natural eudesmane-type sesquiterpenes.

Chrotacumines G-J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity.

Four new chromone alkaloids, chrotacumines G-J (1-4), have been isolated from the barks of Dysoxylum acutangulum. Their structures and absolute configurations were elucidated on the basis of NMR and CD data. Chrotacumines G and J (1 and 4) showed osteoclast differentiation inhibitory activity in a dose dependent manner.

Mumic acids A-E: new diterpenoids from mumiyo.

Five new diterpenoids belonging to labdane and isopimarane skeletons, mumic acids A-E (1-5), have been isolated from mumiyo. Their structures and absolute configurations were elucidated on the basis of spectroscopic data and chemical derivatization.