Antibacterial carbazole alkaloids from Clausena harmandiana twigs

Three new carbazole alkaloids, harmandianamines A-C (1-3), together with fifteen known compounds (4-18) were isolated from the twigs of Clausena harmandiana. The structures were elucidated by spectroscopic methods, including UV, IR, NMR, and MS. The antibacterial activity against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphylococcus aureus TISTR 1466 and methicillin-resistant S. aureus (MRSA) SK1 of some isolated compounds was also evaluated. Compound 6 exhibited significant antibacterial activity against MRSA SK1 with an MIC value of 0.25 μg/mL which higher than that of standard drug, vancomycin (MIC value=1 μg/mL) whereas compounds 14 and 5 showed strong activity with MIC values of 4 and 8 μg/mL, respectively. Only compound 14 showed strong antibacterial activity against S. aureus TISTR 1466 with an MIC value of 4 μg/mL.     

Anti-inflammatory and analgesic potential of a novel steroidal derivative from Bryophyllum pinnatum

A new steroidal derivative, urs Stigmast-4, 20 (21), 23-trien-3-one and other four compounds were isolated from the leaves of Bryophyllum pinnatum. The structure of this new steroid was elucidated and established by standard spectroscopic methods. Carrageenan induced paw edema model was used for anti-inflammatory and acetic acid induced model used for analgesic activity. This new steroidal compound was found to be active in reducing inflammation (% inhibition 87.29 and 84.45 respectively) when compared with diclofenac. Further, it showed 75.72% protection in analgesic activity in acetic acid induced writhing test in mice. In conclusion the % inhibition against carrageenan induced rat paw edema and % protection against acetic acid induced writhings showed by new compound revealed that the anti-inflammatory and analgesic activity of aqueous extract B. pinnatum are mainly due to the presence of this steroidal compound.     

Kujigamberol, a new dinorlabdane diterpenoid isolated from 85million years old Kuji amber using a biotechnological assay

A new compound, 15,20-dinor-5,7,9-labdatriene-18-ol (1), named kujigamberol, was isolated from amber, fossilized tree resin from the Kuji area in Japan, has been dated as being 85 million years old (late Cretaceous). Kujigamberol was identified using the hypersensitive mutant yeast (zds1? erg3? pdr1? pdr3?) with respect to Ca²⁺-signal transduction. The structure was elucidated on the basis of spectroscopic analysis including 1D NMR, 2D NMR and HR-EI-MS. It was different from known diterpenoids with a similar activity isolated from Baltic amber (agathic acid 15-monomethyl ester (2), dehydroabietic acid (3) and pimaric acid (4)). Kujigamberol showed glycogen synthase kinase-3β (GSK-3β) inhibition activity involving the growth restored activity against the mutant yeast and was cytotoxic to HL60 cells (IC₅₀ = 19.6 μM).     

Labdane-type diterpenes and flavones from Dodonaea viscosa

A new labdane diterpenoid, 2,18-dihydroxylabda-7,13(E)-dien-15-oic acid (1), together with two known labdane diterpenes (3, 4), a new flavone, 5,7-dihydroxy-3,6,4'-trimethoxy-3'-(4-hydroxy-3-methyl-but-2-enyl)flavone (2) with three known flavones (5-7) were isolated from the aerial parts of Dodonaea viscosa. Their structures were determined by extensive analysis of spectroscopic data (1D and 2D NMR, MS) and by comparison with literature data. The anti-inflammatory activity of five compounds (1-5) was evaluated with a flow cytometry TNF-α secretion assay on human THP-1 cell line.     

Study of anti-inflammatory,analgesic and antipyretic activities of seeds of Hyoscyamus niger and isolation of a new coumarinolignan

A chemical and biological validation of the traditional use of Hyoscyamus niger seeds as anti-inflammatory drug has been established. The methanolic extract of seeds of H. niger (MHN) was evaluated for its analgesic, anti-inflammatory and antipyretic activities in experimental animal models at different doses. MHN produced significant increase in hot plate reaction time, while decreasing writhing response in a dose-dependent manner indicating its analgesic activity. It was also effective in both acute and chronic inflammation evaluated through carrageenin-induced paw oedema and cotton pellet granuloma methods. In addition to its analgesic and anti-inflammatory activity, it also exhibited antipyretic activity in yeast-induced pyrexia model. Furthermore, the bioactive MHN under chemical investigation showed the presence of coumarinolignans as major chemical constituent and yielded a new coumarinolignan, cleomiscosin A methyl ether (1) along with four known coumarinolignans, cleomiscosin A (2), cleomiscosin B (3), cleomiscosin A-9′-acetate (4) and cleomiscosin B-9′-acetate (5). The structure elucidation of 1 was done by spectroscopic data interpretation and comparative HPLC analysis. Cleomiscosin A, but not its isomer cleomiscosin B, reduced dry and wet weight of cotton pellet granuloma in mice. This suggests that cleomiscosin A is an important constituent of MHN responsible for anti-inflammatory activity.     

Phenylpropionic acid derivates from the bark of Cerbera manghas

Two new phenylpropionic acid derivates, cerberic acids A (1) and B (2), were isolated from the bark of Cerbera manghas. Their structures were established on the basis of spectroscopic methods including IR, ESI-FT-ICR-MS, 1D and 2D NMR. Primary bioassays showed that compound 1 possessed weak cytotoxic activity against HepG2, MCF-7, and HeLa cell lines with IC₅₀ values of 44.7, 52.3, 48.7 μg/ml, respectively.     

Two new triterpenoids from the roots of Actinidia chinensis

Two new triterpenoids (1, 2), together with one flavonoid glycoside and thirteen known triterpenoids were isolated from the roots of Actinidia chinensis Planch (Actinidiaceae). The structures of the new constituents were elucidated as 12α-chloro-2α, 3β, 13β, 23-tetrahydroxyolean-28-oic acid-13-lactone (1), 2α, 3α, 19α, 23, 24-pentahydroxyurs-12-en-28-oic acid (2). Structure elucidation was accomplished by 1D, 2D NMR spectra (HMQC, HMBC, ¹H-¹H COSY, TOCSY, and NOESY) and mass spectrometry (ESIMS). Moreover, two known triterpenoids showed positive cytotoxic activity against LOVO and HepG2 cell lines.     

Triterpenoids of Euphorbia kansuensis Proch

Phytochemical investigation of the ethanol extract of Euphorbia kansuensis Proch. led to the isolation of three new triterpenoids, along with ten known compounds. Their structures were established by extensive 1D and 2D NMR, as well as other spectrum analysis. Biological activities of the three new compounds against Hela cell, Hep-G2 cell, C. albicans ATCC10231 cell and SC5314 cell were evaluated. They showed strong anti-tumor and moderate anti-inflammatory activities with MIC values ranging from 13 to 25μg/ml and from 30 to 128μg/ml.     

Chemical constituents of Kigelia pinnata twigs and their GLUT4 translocation modulatory effect in skeletal muscle cells

Phytochemical investigation of the ethanolic extract of twigs of Kigelia pinnata DC. afforded one new iridoid 7-hydroxy eucommiol (1), and nine known compounds (2-10). The structure of compounds was elucidated by extensive spectroscopic methods, including 1D, 2D NMR experiments and MS analysis. All these compounds were evaluated for GLUT4 translocation modulatory effect in skeletal muscle cells. Four of the tested compounds 1, 5, 6 and 7 showed significant stimulation of GLUT4 translocation to cell surface in skeletal muscle cells without any adverse effect on cell viability. Effect of these four compounds was concentration-dependent and comparable to standard drug rosiglitazone. These findings indicate that constituents of K. pinnata may provide leads for the therapeutics for insulin resistance and diabetes.     

Two new bisindole alkaloids from the seeds of Strychnos nux-vomica

The reinvestigation of Strychnos nux-vomica resulted in the isolation of two colorless monoquaternary bisindole alkaloids from the seeds. The structures of the two new compounds named 4-N-hydroxymethyl strychnidin-17-acetic acid (1) and 10, 11-dimethoxy-4-N-hydroxymethyl strychnidin-17-acetic acid (2), were defined by detailed spectral analyses, especially ¹H NMR, ¹³C NMR, DEPT, HSQC, ¹H NMR–¹H NMR, NOESY, HMBC and TOF-MS.     

Anti-HBV activities of Streblus asper and constituents of its roots

The extracts from leaves, heartwood, barks and roots of the Streblus asper were investigated for anti-HBV activities, separately. The results suggested that the MeOH extracts of the heartwood, barks, and roots exhibited good anti-HBV activities. Further investigations displayed that ethyl acetate and n-butanol soluble parts of their MeOH extracts showed more significant anti-HBV activities. Moreover, a new lignan, together with 11 known compounds, was isolated from n-butanol-soluble part of MeOH extract of the roots of S. asper. The structures were elucidated by spectroscopic methods, including 1D NMR ((1)H NMR, (13)C NMR), 2D NMR (HMQC, HMBC) and HR-EI-MS experiments. Compounds 1-3 were evaluated for their anti-HBV activities. Honokiol showed significant anti-HBV activity with IC(50) values of 3.14μM and 4.74μM for HBsAg and HBeAg with no cytotoxicity respectively, while lamivudine (3TC, positive control) exhibited weak anti-HBV activity with IC(50) values of 11.81μM and 25.80μM for HBsAg and HBeAg respectively.     

A new dilactone from the seeds of Gaultheria yunnanensis

Gaultheriadiolide (1), a new compound, together with the known dauosterol (2), ginkgetin (3), myricetin (4), 6-ethyl-5-hydroxy-2,7-dimethoxy-1,4-naphthoquinone (5), ursolic acid (6), methyl salicylate 2-O-β-d-xylosyl(1→6)β-d-glucopyranoside (7), and methyl salicylate 2-O-β-d-glucopyranoside (8) were isolated from Gaultheria yunnanensis. The structure was elucidated on the basic of spectral analysis, especially 1D and 2D NMR. Primary bioassays showed that compound 1 had medium cytotoxic activity against HEp-2 and HepG2 Cells, with IC₅₀ of 23.337 μM and 29.4497 μM, respectively.     

Theacrine,a purine alkaloid with anti-inflammatory and analgesic activities

The anti-inflammatory and analgesic effects of theacrine (1, 3, 7, 9-tetramethyluric acid), a purine alkaloid which is abundantly present in Camellia kucha, were investigated. Xylene-induced ear edema, acetic acid-induced vascular permeability and λ-carrageenan-induced paw edema were used to investigate anti-inflammatory activity, and acetic acid-induced writhing and hot-plate tests were used to determine analgesic effect. Oral administration of theacrine (8–32 mg/kg) induced dose-related anti-inflammatory and analgesic effects. On the other hand, oral caffeine administration (8–32 mg/kg) did not show an inhibitory effect on the inhibition of inflammatory response or cause analgesia. Additionally, the result of the acute toxicity test showed that the LD₅₀ of theacrine was 810.6 mg/kg (769.5–858.0 mg/kg). The data obtained suggest theacrine possessed analgesic and anti-inflammatory activities.     

Anti-inflammatory,cyclooxygenase (COX)-2, COX-1 inhibitory and antioxidant effects of Dysophylla stellata Benth.

The n-hexane and ethyl acetate extracts of whole plants of Dysophylla stellata significantly inhibited edema when applied topically at doses of 0.5 and 1 mg/ear in TPA-induced ear edema assay in mice. Further, both the extracts were evaluated for COX-1 and COX-2 inhibitory activities and showed 85.42 and 57.38%; and 71.79 and 89.27% inhibition at 50 µg/ml, respectively. Chromones (1 and 2) present in these extracts could be responsible for their COX-1 and COX-2 inhibitory and anti-inflammatory activities. The ethyl acetate extract showed antioxidant activity in DPPH and ABTS radical scavenging assay where as n-hexane extract found to be inactive.     

New coumarin glycosides from the leaves of Diospyros crassiflora (Hiern)

Two new 5-methylcoumarin glycosides named diosfeboside A (1) and B (2) and five known compounds namely kaempferol 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside (3), ursolic acid (4), betulinic acid (5), stigmasterol (6) and stigmasterol 3-O-β-d-glucopyranoside (7) were isolated from the leaves of Diospyros crassiflora (Hiern). Their structures were established through interpretation of 1 and 2D NMR, mass spectra analysis and comparison with reported data. In vitro cytotoxic activity of the new compounds against human carcinoma cell lines (HL-60, Bel-7402, BGC-823, and KB) was evaluated and no cytotoxicity was observed for each of them.     

Two phenolic glycosides from Curculigo orchioides Gaertn

One new glycoside derivative from syringic acid and one new phenol glycoside, curculigoside E (1) and orchioside D (2), were isolated and characterized from the rootstock of Curculigo orchioides collected in the Nawalparasi District (Nepal). The structures of the new isolated compounds were elucidated by means of spectroscopic methods such as 1D, 2D NMR and MS.     

Two new chamigrane metabolites from fermentation broth of Steccherinum ochraceum

Two new chamigrane-type metabolites named steperoxides C (1) and D (2) were isolated from the basidiomycetes Steccherinum ochraceum. The structures of 1 and 2 were established on the basis of spectral methods (MS, IR, ID and 2D NMR experiments). Compounds 2 showed significant antimicrobial activity against Staphylococcus aureus at 10 and 5 μg/disk.     

Evaluation of analgesic, anti-inflammatory and hepatoprotective effects of lycorine from Sternbergia fisheriana (Herbert) Rupr

The present study reports the potential antinociceptive, anti-inflammatory and hepatoprotective activities of lycorine from Sternbergia fischeriana (Herbert) Rupr. (Amaryllidaceae). Lycorine was evaluated on mice by using acetic-acid induced writhing and tail-flick tests. Lycorine exhibited stronger inhibition than aspirin in acetic-acid induced abdominal stretching at 1.0 mg/kg dose. Lycorine also showed antinociceptive activity at 1.0 mg/kg dose in tail-flick test. The anti-inflammatory activity of lycorine was not found to be significant at dose of 0.5 mg/kg. However, at doses of 1.0 mg/kg and 1.5 mg/kg, i.p. showed a significant reduction with 53.45% and 36.42%, respectively in rat paw oedema induced by carrageenan against the reference anti-inflammatory drug indomethacin (3 mg/kg, i.p.) (95.70%). The ED₅₀ of lycorine was determined as 0.514 mg/kg. Hepatoprotective activity of lycorine on carbon tetrachloride (CCl₄) induced acute liver toxicity following biochemical parameters were also evaluated. Rats were treated with lycorine at doses of 1.0 mg/kg and 2.0 mg/kg, i.p. Results of biochemical tests were confirmed by histopathological examination. Lycorine exhibited significant hepatoprotective effect at dose of 2.0 mg/kg i.p. dose.     

Two new benzofuran derivatives with anti-inflammatory activity from Liriope spicata var. prolifera

Two new benzofuran derivatives, 2-(4′-hydroxybenzyl)-5,6-methylenedioxy-benzofuran () and 2-(4′-hydroxybenzoyl)-5,6-methylenedioxy-benzofuran (), along with 8 known compounds were isolated from 60% EtOH extract of the fibrous roots of Liriope spicata var. prolifera. Their structures were elucidated on the basis of extensive spectroscopic analysis. In an in vitro bioactive assay, the two new benzofuran derivatives showed anti-inflammatory activity. Compounds 1 and 2 exhibited significant inhibitory activity against neutrophil respiratory burst stimulated by phorbol 12-myristate 13-acetate (PMA) with IC₅₀ value of 4.15 ± 0.07 and 5.96 ± 0.37 μM, respectively.     

New isoflavonolignan with quinone reductase inducing activity from Alhagi pseudalhagi (M.B.)

Bioassay-directed separation of the chloroform extracts from the air-dried aerial part of Alhagi pseudalhagi (M.B.) led to the isolation of a new isoflavonolignan (1), together with five known isoflavones (2–6) (Fig. 1). Their structures were identified on the basis of spectral analysis of NMR, MS, IR, UV and CD spectral evidences. The quinone reductase (QR) inducing activities of the extracts and compound 1 were evaluated and the new isoflavonolignan (1) exhibited moderate quinone reductase (QR) inducing activity for hepa lclc7 cells.