Anti-tobacco Mosaic Virus Research Articles

Neolignans from Flower Buds of Magnolia fargesii and their Antitobacco Mosaic Virus Activities

Neolignans from Flower Buds of Magnolia fargesii and their Antitobacco Mosaic Virus Activities

Antiviral Chromones from the Stem of Cassia siamea

Seven new chromones, siamchromones A-G (1-7), and 12 known chromones (8-19) were isolated from the stems of Cassia siamea. Compounds 1-19 were evaluated for their antitobacco mosaic virus (anti-TMV) and anti-HIV-1 activities. Compound 6 showed antitobacco mosaic virus (anti-TMV) activity with an inhibition rate of 35.3% and IC50 value of 31.2 μM, which is higher than that of the positive control, ningnamycin. Compounds 1, 10, 13, and 16 showed anti-TMV activities with inhibition rates above 10%. Compounds 4, 6, 13, and 19 showed anti-HIV-1 activities with therapeutic index values above 50.

Design, Synthesis, and Anti-tobacco Mosaic Virus (TMV) Activity of Phenanthroindolizidines and Their Analogues

On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of phenanthroindolizidines and their analogues 3-20 were designed, targeting tobacco mosaic virus (TMV) RNA, synthesized, and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds displayed good anti-TMV activity, and some of them exhibited higher antiviral activity than that of commercial Ningnanmycin (perhaps the most successful registered antiplant viral agent). Especially, (S)-deoxytylophorinine (5) with excellent anti-TMV activity (inactivation activity, 59.8%/500 μg mL(-1) and 40.3%/100 μg mL(-1); curative activity, 65.1%/500 μg mL(-1) and 43.7%/100 μg mL(-1); and protection activity, 70.2%/500 μg mL(-1) and 51.3%/100 μg mL(-1)) emerged as a potential inhibitor of the plant virus. Compound 20 exhibited a strong in vivo protection effect against TMV at 100 μg mL(-1), which indicated that phenanthroindolizidine analogues with a seven-membered D ring have a new and interesting structural scaffold and have great potential for further development as tobacco protection agents.

Phenolic Compounds from Arundina graminifolia and Their Anti-Tobacco Mosaic Virus Activity

Key Laboratory of Tobacco Chemistry of Yunnan Province, Yunnan Academy of Tobacco Science, Kunming 650106, P. R. ChinaReceived February 6, 2012, Accepted April 2, 2012Key Words : Arundina gramnifolia , Phenolic compounds, Anti-tobacco mosaic virus activityArundina gramnifolia belongs to Orchidaceae family. It isa terrestrial plant extends from India, Nepal, Thailand,Malaysia, Singapore, South China to Indonesia and acrossthe Pacific Islands. The genus is considered to possessactivities of detoxification, antiarthritis and abirritation andis used as antidote and demulcent.

Rapid Synthesis and Antiviral Activity of (Quinazolin-4-Ylamino)Methyl-Phosphonates Through Microwave Irradiation

This study describes the simple synthesis of new (quinazolin-4-ylamino) methylphosphonates via microwave irradiation. Substituted-2-aminobenzonitrile reacted with 1,1-dimethoxy-N,N-dimethylmethanamine at a reflux condition to obtain N′-(substituted-2-cyanophenyl)-N,N-dimethylformamidine (1). The subsequent reaction of this intermediate product with α-aminophosphonate (2) in a solution containing glacial acetic acid in 2-propanol through microwave irradiation resulted in the formation of (quinazolin-4-ylamino)methyl-phosphonate derivatives 3a to 3x, which were unequivocally characterized by the spectral data and elemental analysis. The influence of the reaction conditions on the yield of 3a was investigated to optimize the synthetic conditions. The relative optimal conditions for the synthesis of 3a include a 1:1 molar ratio of N′-(2-cyanophenyl)-N,N-dimethylformamidine to diethyl amino(phenyl)methylphosphonate and a 4:1 volume ratio of isopropanol to HOAc in the solvent mixture, at a reaction temperature of 150 °C, with a microwave power of 100 W and a corresponding pressure of 150 psi for 20 min in the microwave synthesizer. The yield of 3a was approximately 79%, whereas those of 3b to 3x were approximately 77% to 86%. Some of the synthesized compounds displayed weak to good anti-Tobacco mosaic virus (TMV) activity.

The Limonoids and Their Antitobacco Mosaic Virus (TMV) Activities from Munronia unifoliolata Oliv.

Five new limonoids, named munronoids K-O (1-5), together with three known limonoids were isolated from Munronia unifoliola Oliv. These limonoids were involved in the skeletons of evodulone, gedunin, and peieurianin types of limonoids, and their structures were established on the basis of spectroscopic data. Compound 5 featuring a γ-lactone ring instead of the β-substituted furan ring was found in the peieurianin type for the first time. The antitobacco mosaic virus (anti-TMV) activities of compounds 1-8 were also evaluated with half-leaf, enzyme-linked immunosorbent assay, and Western blot methods, and limonoids 1, 5, and 8 showed stronger anti-TMV treatment activities than the positive control ningnanmycin. Six compounds (1-5 and 8) exhibited infection inhibition activities against TMV.

Two New 4‐Hydroxyisoflavanes from the Root of Codonopsis cordifolioidea and Their Anti‐virus Activities

AbstractTwo new 4‐hydroxyisoflavanes, cordifoliflavanes A and B (1 and 2), were isolated from the roots of Codonopsis cordifolioidea. Their structures were elucidated by spectroscopic methods, including extensive 1D‐ and 2D‐NMR techniques. Compounds 1 and 2 were tested for their anti‐HIV‐1 activities and anti‐tobacco mosaic virus activities. The results showed that compounds 1 and 2 have modest anti‐HIV‐1 activities and anti‐tobacco mosaic virus activities, respectively.

Isoflavones from the roots and stems of Nicotiana Tabacum and their anti-tobacco mosaic virus activities

Two new isoflavones, 7-hydroxy-6,3′,4′,5′-tetramethoxy-isoflavone (1) and 6-hydroxy-7,3′,4′,5′-tetramethoxy-isoflavone (2), together with seven known isoflavones were isolated from the roots and stems of Nicotiana tabacum. Their structures were determined by means of HRESIMS, extensive 1D and 2D NMR spectroscopic studies and chemical evidences. The anti-tobacco mosaic virus (anti-TMV) activities of the isoflavones were also evaluated. The results reveal that compound 9 shows high anti-TMV activity, compound 2 shows moderate anti-TMV activity, and compounds 1, 3–8 show weak anti-TMV activities.

Chemical constituents from fruits of Harrisonia perforata

Eight limonoids ( 1– 8) including three A, B and D-seco-16-nor-type ones, 5,6-dehydrodesepoxyharperforin C2 ( 1), harrpernoid B ( 2), and its C-9S epimer, harrpernoid C ( 3), along with six known compounds ( 9– 14), were isolated from fruits of Harrisonia perforata. Extensive spectroscopic analysis was used to elucidate their structures and stereochemistries. Further confirmation of structures of 1 and 2 were obtained by single-crystal X-ray diffraction. Limonoids ( 1– 8) were evaluated for their anti-tobacco mosaic virus activity and in vitro cytotoxicity against A549 and HL60 cell lines; only compound 2 showed weak activity.

Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides

Starting from 4-chlorobenzoic acid, 10 new 5-(4-chlorophenyl)-N-substituted-N-1,3,4-thiadiazole-2-sulfonamide derivatives were synthesized in six-steps. Esterification of 4-chlorobenzoic acid with methanol and subsequent hydrazination, salt formation and cyclization afforded 5-(4-chlorophen-yl)-1,3,4-thiadiazole-2-thiol (5). Conversion of this intermediate into sulfonyl chloride 6, followed by nucleophilic attack of the amines gave the title sulfonamides 7a-7j whose structures were confirmed by NMR, IR and elemental analysis. The bioassay tests showed that compounds 7b and 7i possessed certain anti-tobacco mosaic virus activity.

Anti-Tobacco Mosaic Virus (TMV) Quassinoids from Brucea javanica (L.) Merr.

Two new quassinoids, javanicolide E (1) and javanicolide F (2), along with fifteen known C-20 quassinoids were isolated from the seeds of Brucea javanica (L.) Merr. The antitobacco mosaic virus (TMV) activity of these quassinoids was screened by the conventional half-leaf and leaf-disk method along with Western blot analysis. All of the seventeen quassinoids showed potent anti-TMV activity. Among them, eight compounds, brusatol (3), bruceine B (4), bruceoside B (5), yadanzioside I (6), yadanzioside L (7), bruceine D (8), yadanziolide A (9), and aglycone of yadanziolide D (17), showed strong antiviral activities, with IC(50) values in the range of 3.42-5.66 microM, and were much more effective than the positive control, ningnanmycin (IC(50) = 117.3 microM). The antiviral structure-activity relationships of quassinoids against TMV were also discussed.

Enantioseparation and plant virucidal bioactivity of new quinazoline derivatives with α-aminophosphonate moiety

Enantiomers of some new quinazoline derivatives bearing α-aminophosphonate moiety were separated under normal-phase conditions on two immobilized polysaccharide-based chiral stationary phases (Chiralpak IA and Chiralpak IC). The role of two chiral stationary phases (CSPs), polar modifier and column temperature on retention time and separation factor was studied. Apparent thermodynamic parameters were deduced from Van’t Hoff plots and plausible mechanism of chiral recognition has been discussed. The semi-preparative separation of some compounds was executed successfully in n-hexane/isopropyl alcohol (IPA) on the Chiralpak IA column. The preliminary bioassay showed that both the enantiomers of the investigated series of compounds possessed similar anti-tobacco mosaic virus (TMV) activities.

Synthesis and bioactivities of 1,3,2‐benzodiazaphosphorin‐2‐carboxamide 2‐oxides containing α‐aminophosphonate groups

AbstractIn order to search for novel antitumor and antiviral agents with high activity and low toxicity, a series of 1‐ethoxycarbonylmethyl‐3‐ethyl‐1,2,3,4‐tetrahydro‐4‐oxo‐1,3,2‐benzodiazaphosphorin‐2‐carboxamide 2‐oxides containing α‐aminophosphonate groups have been designed and synthesized by a convenient one‐pot procedure in good yields. The structures of products were confirmed by 1H NMR, 31P NMR, IR spectra, and elemental analyses. The bioassay results showed that some of them possess excellent anti–tobacco mosaic virus activities and exhibit higher inhibitory effects compared with that of the contrast drug 2,4‐dioxyhexahydro‐1,3,5‐triazine. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:97–101, 2001

A convenient synthesis of N‐t‐butyl‐N′‐aminocarbonyl‐N‐(substituted)benzoyl‐hydrazine containing α‐aminoalkylphosphonate groups in a one‐pot procedure

AbstractA variety of novel N‐t‐butyl‐N′‐aminocarbonyl‐N‐(substituted)benzoylhydrazines containing α‐aminoalkylphosphonate groups were synthesized. Treatment of α‐aminoalkylphosphonates with triphosgene yielded α‐isocyanatoalkylphosphonates, and subsequent addition with N‐t‐butyl‐N‐substituted benzoylhydrazines provided the title compounds in a one‐pot procedure with good yields. The triphosgene‐mediated reaction for the synthesis of α‐isocyanatoalkylphosphonates enjoys a number of advantages: the reaction is carried out under mild condition in good yield, triphosgene is relatively safe to handle because of its low vapor pressure and high stability, and the experimental procedure is simple. This method can be applicable to the synthesis of other α‐isocyanatoalkyl‐phosphonates and urylenediphosphonates. The structures of all of the products and by‐products were confirmed by 1H NMR, 31P NMR, IR and mass spectroscopy, and elemental analysis. We also found that some of the compounds possess potential antitobacco mosaic virus (TMV) activities and anticancer activities. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:68–72, 2001

Reduced virus infectivity inN. tabacum secreting a TMV-specific full-size antibody

We developed a new concept of controlling plant virus infection based on the expression and secretion of full-size antibodies in plants. The neotope-specific anti-Tobacco Mosaic Virus (anti-TMV) antibody mAb24 has a high affinity towards epitopes present only on the surface of intact tobacco mosaic virions. The infectivity of the virus is inhibited almost completely if TMV is adsorbedin vitro at ratios as low as 300 antibody molecules per virion prior to inoculation. Cloned full-size cDNAs of mAb24 heavy and light chains were integrated into the plant expression vector pSS in tandem array and used for transformation ofNicotiana tabacum. The resulting transgenic tobacco plants expressed heavy- and light-chains of mAb24 which were assembled into functional antibodies and exported to the intercellular space. TMV specificity and affinity of the plant-produced antibody (mAb24-P) was not altered when compared to the original murine mAb24. F1 progenies segregated 3:1 with respect to antibody secretion and showed up to two-fold higher expression levels compared to the F0 plants. Upon infection with TMV F1 plants producing mAb24-P showed a reduction of necrotic lesion numbers which is correlated with the amount of antibody produced in transgenic plants.

Induction of anti-tobacco mosaic virus antibodies in mice by rabbit antiidiotypic antibodies.

Conventional rabbit antiidiotypic antibodies were raised against a private rabbit anti-tobacco mosaic virus (TMV) idiotype. These rabbit antiidiotypic antibodies were covalently coupled to lipopolysaccharide and then injected into BALB/c mice. As compared with controls, these mice, which have never seen the antigen, synthesized anti-TMV antibodies that are strongly idiotypically cross-reactive with the starting rabbit idiotype. Monoclonal anti-TMV antibodies were prepared from these mice. Furthermore, xenogeneic or syngeneic antiidiotypic antibodies, raised against these monoclonal anti-TMV antibodies, recognized specifically the rabbit idiotype. Rabbit antiidiotypic antibodies alone can induce the same effects, but the concentration of anti-TMV antibodies is lower.

Idiotypic studies of monoclonal anti-tobacco mosaic virus antibodies from one mouse

Monoclonal antibodies have been prepared from one BALB/c mouse immunized with tobacco mosaic virus. The monoclonal antibodies are distributed into three subgroups recognizing different epitopes on tobacco mosaic virus subunits. The idiotypic specificities of these monoclonal antibodies have been studied using syngeneic antiidiotypic sera. A sharing of idiotypic specificities has been observed between members of each subset. These idiotypes are not recurrent in BALB/c mice immunized with tobacco mosaic virus.

Estracellular polysaccharide formed by Pseudomonas hydrogenovora in autotrophic culture and its physiological activities.

Gram negative hydrogen bacterium Pseudomonas hydrogenovora was found to excrete an anthrone-H2SO4 positive viscous polysaccharide. About 12 g/liter of the polysaccharide was produced autotrophically on gaseous hydrogen at the stationary phase of growth. Biosynthesis of the polysaccharide occurred under nitrogen-deficient condition. Its elementary composition was C: 39.29%, H: 6.23%, O: 49.67%, N: 0.21% and ash 4.6%. The polysaccharide contained galactose, glucose, mannose and rhamnose as its main components. The polysaccharide had anti-tobacco mosaic virus and anti-tumor activities.

Idiotypic regulation of the immune system. Common idiotypic specificities between idiotypes and antibodies raised against anti-idiotypic antibodies in rabbits.

Anti-idiotypic antibodies (Ab2) were raised in allotype-matched rabbits against anti-carbohydrate or anti-tobacco mosaic virus antibodies (Ab1). Several Ab2 were purified and injected into a third series of rabbits III which synthesized antiantiidiotypic antibodies (Ab3). Antigen was then given for the first time in those rabbits who had synthesized Ab3. The specific antibody synthesized in rabbits III was called Ab1'. Anti-idiotypic antibodies were raised against purified Ab3 antibodies (Ab4). In most cases, Ab1' antibodies are sharing idiotypic specificities with Ab1. Ab3 did not react with antigen but shared idiotopes with Ab1 and Ab1' because Ab4 antibodies, which are anti-idiotypes to Ab3 do recognize specifically Ab1 and Ab1' antibodies belonging to the same chain of immunization. It seems therefore that Ab3 looks idiotypically like Ab1 and Ab4 displays the same behaviour as Ab2. A general view of the functioning of the immune system is presented.

The effect of tetranitromethane on the activity of anti-tobacco mosaic virus antibodies

FEBS LettersVolume 8, Issue 4 p. 229-231 Full-length articleFree Access The effect of tetranitromethane on the activity of anti-tobacco mosaic virus antibodies Claude Szpirer, Claude Szpirer Laboratoire de Physiologie Animale, Université Libre de Bruxelles, 1640 Rhode-St-Genèse, BelgiumSearch for more papers by this authorRaymond Jeener, Raymond Jeener Laboratoire de Physiologie Animale, Université Libre de Bruxelles, 1640 Rhode-St-Genèse, BelgiumSearch for more papers by this author Claude Szpirer, Claude Szpirer Laboratoire de Physiologie Animale, Université Libre de Bruxelles, 1640 Rhode-St-Genèse, BelgiumSearch for more papers by this authorRaymond Jeener, Raymond Jeener Laboratoire de Physiologie Animale, Université Libre de Bruxelles, 1640 Rhode-St-Genèse, BelgiumSearch for more papers by this author First published: June 08, 1970 https://doi.org/10.1016/0014-5793(70)80271-XCitations: 3AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL No abstract is available for this article. References 1 S.J. Singer, N.O. Thorpe, Proc. Natl. Acad. Sci. U.S., 60, (1968), 1371– 2 M. Sokolowsky, D. Harell, J.R. Riordan, Biochemistry, 8, (1969), 4740– 3 S. Fuchs, D. Givol, FEBS Letters, 2, (1968), 45– 4 M. Sokolowsky, J.R. Riordan, B.L. Vallee, Biochemistry, 5, (1966), 3582– 5 R.R. Porter, Biochem. J., 73, (1959), 119– Citing Literature Volume8, Issue4June 08, 1970Pages 229-231 ReferencesRelatedInformation