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Introduction: There is a paucity of information on the frequency of Chlamydia trachomatis -induced reactive arthritis (ReA) and undifferentiated spondyloarthropathy (uSpA) in India. In this study, arthritic patients suffering from ReA, uSpA, and rheumatoid arthritis (RA) were screened to investigate the presence of C. trachomatis infection in the synovial fluid (SF) or serum by molecular and non-molecular methods. Methodology: A total of 76 arthritic patients with ReA (n = 16) and uSpA (n = 22) composed the study group while those with RA (n = 38) served as controls. The detection of C. trachomatis DNA was done by semi-nested PCR (snPCR) and nested PCR (nPCR) targeting two different genes of C. trachomatis , namely major outer membrane protein and plasmid, respectively. The presence of serum or SF immunoglobulin IgG and IgA antibodies against C. trachomatis was studied by commercial enzyme-linked immunosorbent assay kits. Results: The SF from 9 of 38 (23.6%) patients (5 with ReA and 4 with uSpA) was positive for at least one C. trachomatis DNA by snPCR or nPCR in comparison to RA (1/38 [2.6%]; p value < 0.05). There was no correlation between the snPCR or nPCR and the serological results of patients with ReA or uSpA. Conclusions: As molecular diagnostic techniques established intra-articular C. trachomatis infection among this group of seronegative spondyloarthropathies in India, these findings should be viewed with concern, and snPCR or nPCR should be considered for a more reliable diagnosis.

Chlamydia trachomatis-induced genitourinary Reactive Arthritis (ReA) can serve as good model for host-pathogen interaction. However, due to poor antigen presentation, cell-mediated immunity does not contribute as anticipated. Present study aims to evaluate protective role of anti-C. trachomatis antibodies vis-a-vis inflammatory chlamydial Major Outer Membrane Protein (MOMP). Prospective study was undertaken in 30 patients with genitourinary ReA. 30 Rheumatoid Arthritis (RA) and 30 osteoarthritis patients constituted controls. Subjects found to be PCR-positive for C. trachomatis were investigated for presence of MOMP in Synovial Fluid (SF) by fluorescence assay while anti-C. trachomatis IgA/IgM antibodies were estimated in SF/venous blood by ELISA. C. trachomatis MOMP was evident by the presence of elementary bodies in SF of 9 ReA PCR-positive patients (30%; p

The incorporation of tryptamine, dopamine, N-deacetylisoipecoside, N-deacetylipecoside into alangimarckine, deoxytubulosine and ankorine and of strictosidine and vincoside into alangimarckine and deoxytubulosine in young Alangium lamarckii Thw. (Alangiaceae) has been studied and specific utilisation of N-deacetylisoipecoside demonstrated. Parallel experiments with nordeoxytubulosine and deoxytubulosine suggested that O-methylation precedes condensation of protoemetine with tryptamine and further the reduction of ethylene side chain takes place before condensation. Hydroxylation at C-8 in the trans-quinolizidine moiety is the terminal step in the biosynthesis of alangimarckine.

Chlamydia trachomatis ( C. trachomatis )-induced reactive arthritis (ReA)/undifferentiated spondyloarthropathy (uSpA) are unrecognised/underestimated entities, and clinicians often fail to recognise them. In India, our group was the first to report intra-articular C. trachomatis infection in patients with ReA/uSpA having genitourinary symptoms.1 Males were predominant (78%) and majority of patients presented with an oligoarthritic profile (80%), enthesitis (11%) and human leukocyte antigen (HLA) B27 (40%); however, none reported ocular infection. Despite this observation, it is also very likely that C. trachomatis -induced ReA/uSpA is underdiagnosed in women. Intra-articular C. trachomatis …

Rheumatoid arthritis (RA) is a chronic, autoimmune, systemic and inflammatory rheumatic disease that leads to inflammation of the joints and surrounding tissues. Identification of novel protein(s) associated with severity of RA is a prerequisite for better understanding of pathogenesis of this disease that may also have potential to serve as novel biomarkers in the diagnosis of RA. Present study was undertaken to compare the amount of autoantigens and autoantibodies in the plasma of RA patients in comparison to healthy controls. Plasma samples were collected from the patients suffering from RA, Osteoarthritis (OA), Systemic lupus erythematosus (SLE) and healthy volunteers. The screening of plasma proteins were carried out using 2-dimensional gel electrophoresis followed by identification of differentially expressed protein by MALDI-TOF MS/MS. Among several differentially expressed proteins, transthyretin (TTR) has been identified as one of the protein that showed significantly up regulated expression in the plasma of RA patients. The results were further validated by Western blot analysis and ELISA. In comparison to OA synovium, an exclusive significantly high expression of TTR in RA has been validated through IHC, Western blotting and IEM studies. Most importantly, the increase in expression of TTR with the progression of severity of RA condition has been observed. The autoantibodies against TTR present in the RA plasma were identified using immunoprecipitation-Western methods. The significant production of autoantibodies was validated by ELISA and Western blot analysis using recombinant pure protein of TTR. Hence, these novel observations on increase in TTR expression with the increase in severity of RA conditions and significant production of autoantibodies against TTR clearly suggest that a systematic studies on the role TTR in the pathogenesis of RA is immediately required and TTR may be used as a serum diagnostic marker together with other biochemical parameters and clinical symptoms for RA screening and diagnosis.

The furanose ring in 4,6-bis(methylthio)-2-(2,3-anhydro-1-deoxy-β-D-allofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine, C 13 H 16 N 4 O 4 S 2 , is almost planar with the epoxide ring in an exo orientation.

Diels-Alder reaction of citral dienol acetate 3 with in-situ generated p-benzoquinones from 4 (a-d) furnished cycloadducts 5 (a-d) in quantitative yields. Brief exposure of 5b towards activated silica gel furnished acyl migrated product 6a in quantitative yield.

The cycloaddition reaction of D-glucose based dienes 1 (b,c) with in-situ generated 2-methoxycarbonyl-p-benzoquinone 2 furnished cycloadducts 3 (a, b) with excellent stereo-and regiochemical control. The cyclo-adduct 3b on further transformations furnished fuctionalised decalin 7c in quantitative yield.

The cycloaddition reaction/conjugate addition reaction is effectively controlled by a suitable combination of vinylketene dithioacetals 1 ( a – c ) and in situ generated p -benzoquinones 2 ( a – c ). The reaction of 1c with 2b provided cycloaddition product 3c , while the reaction of 1a with 2b yielded a conjugate addition product 4b in good yield.

The reductive elimination-amination of 2(a, b) in the presence of amines 3 (a, b) under ultrasound irradiation provides pyrrolidines 5 (a,b,g,h) in excellent yield.

Central Drug Research Institute, Lucknow-226 001, Uttar Pradesh, India Manuscript received 18 May 2011, accepted 25 May 2011

The synthesis of a series of 4-amino/hydroxy-6-substituted-12-(2′,2′-diethoxyethyl)-1H/2H-pyrazolo[3,4-d]pyrimidines by alkylation of substituted pyrazolo[3,4-d]pyrimidines has been described, and their antiallergic activity evaluated in mice. The 2 most active compounds 4b and 5b were also tested in the rat. The most active compound 4b showed non-significant antihistaminic or antiserotoninergic activity.

Steric control offered by the 3-substituents in D-xylofuranosyl- and D-glucofuranosyl sugars has been exploited for the regioselective N-2-glycosylation of 4,6-bis(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (1), to generate key intermediates suitable for later transformations to pyrazolo[3,4-d]pyrimidine nucleosides.

The incorporation of labelled racemic 2′-aminoreticuline 2 into racemic 12-aminotetrahydropalmatine 6, 12-aminocanadine 8, 12-aminopalmatine 10 and 12-aminoberberine 11 has been studied in Cocculus laurifolius DC (Menispermaceae) and specific incorporation of 2 into 6, 8, 10 and 11 demonstrated. Further, it has been shown that 2 is not metabolized by the plants to form tetrahydropalmatine 5, palmatine 9 and berberine 12.

Reaction of 2-ethylthioadenine (1) with protected ribose (2) in the presence of stannic chloride gave 2-ethylthioadenosine (4). Oxidation of 5 with potassium permanganate yielded the corresponding sulfone (6) which furnished spongosine (7) after treatment with sodium methoxide. Similarly, reactions of 7-amino-5-ethylthio-1,2,3-triazolo[4,5-d]pyrimidine (8) with the ribose (2) gave 8-azaspongosine (13). The compounds (4) and 7 demonstrated potent antiaggregatory effects both in human platelet-rich plasma and whole blood, whereas, the aza analog (13) showed no inhibitory activity on platelet aggregation. Both (4) and (7) inhibit platelet aggregation in the presence of adenosine deaminase, whereas, adenosine is non-inhibitory, suggesting that analogs (4) and (7) are poor substrates for adenosine deaminase.

Diels-Alder reaction of citral dienol acetate 3 with in-situ generated p-benzoquinones from 4 (a-d) furnished cycloadducts 5 (a-d) in quantitative yields. Brief exposure of 5b towards activated silica gel furnished acyl migrated product 6a in quantitative yield.

The furanose ring in 4,6-bis(methylthio)-2-(2,3-anhydro-1-deoxy-β-D-allofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine, C 13 H 16 N 4 O 4 S 2 , is almost planar with the epoxide ring in an exo orientation.

A fraction showing in vitro and in vivo antiviral activity was isolated from the green alga Ulva fasciata found in the Indian Ocean off the West coast of India. The structure of its major component was established to be N-palmitoyl-2-amino-1,3,4,5-tetrahydroxyoctadecane on the basis of spectral studies.

In - situ generated 2-substituted- p -benzoquinones from 3 ( b – d ) showed dual reactivity towards substituted glucofuranodienes 1 ( a – c ) and 2 ( a – c ). The cycloaddition showed complete stereo- and regiochemical control.

Steric control offered by the 3-substituents in D-xylofuranosyl- and D-glucofuranosyl sugars has been exploited for the regioselective N-2-glycosylation of 4,6-bis(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (1), to generate key intermediates suitable for later transformations to pyrazolo[3,4-d]pyrimidine nucleosides.

The reaction of allylic alcohols (4–7) with sodium hydroxide, carbon disulfide and methyl iodide followed by heteroclaisen rearrangement over neutral alumina furnished (18–21) in 70–90% isolated yield.

The reaction of hemiketals (1–6) with sodium hydroxide and methyl iodide in the presence of TBAI as a catalyst furnished methoxy hemiketals (7–10) in more than 90% yield.

Central Drug Research Institute, Lucknow-226 001, India E-mail :Root@cdrilk.Sirnetd.ernet.in Fax : 91-0522-223405/223938 The structure and stereochemistry of biologically active alkaloids isolated from Croton sparsiflorus, Cocculus laurifolius, C. pendulus, Corydalis meifolia and Stephania glabra were established. Biosynthetic studies were carried out on proaporphine and dihydroproaporphgne alkaloids, crotsparine and crotsparinine, and abnormal aporphine alkaloid sparsiflorine; abnor­mal Erythrina alkaloid isococculidine; morphinan-dienone alkaloid sebiferine; quaternary aporphine bases magnoflorine and laurifoline; bisbenzylisoquinoline alkaloids, pendulin, cocsulinin, (±)-hayatin, (S,R)-hayatidin, (R,R)-isochondrodendrine and (R,R)-bebeerine; biphenylbisbenzylisoquinoline alkaloids tiliacorine, tiliacorinine and tiliageine; aporphine-1-benzylisoquinoline alkaloid thalicarpine; aporphine alkaloid glaucine; and Ipecac-ß-carboline alkaloid tubulosine. Synthesis of (+)-ophicarpinone, crotsparine, sparsiflorine, tetrahydroprotoberberine alkaloids, (1) scoulerine, (1)-tetrahydropalmatine and their bromo de­rivatives and biogenetic type synthesis of phenanthroindolizidine alkaloid, tylophorine, seco-phenanthroindolizidine alkaloid, septicin, antofine and alkaloid C, are presented.

From the aerial parts of Nepeta eriostachiya two rare ursane triterpenoids, 2α,3α-dihydroxyurs-12-en-28-oic acid and 2α,3β-dihydroxyurs-12-en-28-oic acid, together with a new triterpene, nepetoic acid identified as 2α-methoxy-3β-hydroxyurs-12-en-28-oic acid were isolated as their methyl esters. Their structures were established by chemical and spectroscopic means.

Central Drug Research Institute, Lucknow-226 001 Chemistry Department, Lucknow University, Lucknow-226 007 Manuscript received 12 June 1998 The incorporation of 2'-bromodidehydro[N-14CH3]reticulinium iodide (1) into (±)-12-bromotetrahydropalmatine (4), (+)-12- bromotetrahydropalmatine (9) and (—)-12-bromotetrahydropalmatine (7) in Cocculus laurifolius DC (Menispermaceae) has been studied and stereospecific reduction of 1 into (+)-9 and (—)-7 and (1)44), 12-bromotetrahydropalmatines demonstrated.

The reaction of 2,3-dihydrofuran (1), dihydropyran (2) and indole (8) with acyloxysulfonium salt (3) and Methyl amine furnished vinyl sulfides 6, 7 and 10 respectively in very good yields.