Direct Synthesis of Thioethers from Carboxylates and Thiols Catalyzed by FeCl3.

A new and efficient method has been developed for the synthesis of thioethers from carboxylates and thiols. The reaction proceeds via a Fe(III)-catalyzed direct displacement of carboxylates from benzylic or allylic esters by heterocyclic thiols. Short reaction times, good to excellent yields of products, and few side reactions are the significant features of the new protocol.

Anti-cancer evaluation of carboxamides of furano-sesquiterpene carboxylic acids from the soft coral Sinularia kavarattiensis.

The chemical investigation of soft coral Sinularia kavarattiensis is described. It yielded furano-sesquiterpene carboxylic acids 1 and 2 and their methyl esters 3 and 4. Semi-synthesis of furano-sesquiterpene carboxylic acid 1 gave amide derivatives 5-12. Structures of all the compounds were established by IR, NMR and mass spectral analysis. Interestingly all compounds are selectively potent on leukemia cell line. All these compounds were screened for cytotoxic activity against five human cancer cell lines (leukemia, prostate, lung, breast and cervix). Among these compounds 9 and 10 showed promising activity against leukemia and prostate cancer cell lines.

Study on bioactive compounds from Streptomyces sp. ANU 6277.

An attempt was made to study the bioactive compounds from a terrestrial Streptomyces sp. ANU 6277 isolated from laterite soil. Four active fractions were recovered from the solvent extracts obtained from the culture broth of five day-old strain. Three bioactive compounds were purified and identified as 3-phenylpropionic acid, anthracene-9,10-quinone and 8-hydroxyquinoline. The components of the partially purified fourth active fraction were analyzed by gas chromatography-mass spectrometry and identified as benzyl alcohol, phenylethyl alcohol and 2H-1, 4-benzoxazin-3 (4H)-one. Four active fractions were screened for antimicrobial activity against Gram-positive and Gram-negative bacteria, and fungi including phytopathogenic, toxigenic and dermatophytic genera. Among these metabolites, 8-hydroxyquinoline exhibited strong antibacterial and antifungal activity as compared to 3-phenylpropionic acid and anthracene-9,10-quinone.

Correction to: Extraction and bioactive profile of the compounds produced by Rhodococcus sp. VLD-10.

[This corrects the article DOI: 10.1007/s13205-016-0576-6.].

Biological activity of phenylpropionic acid isolated from a terrestrial Streptomycetes.

The strain ANU 6277 was isolated from laterite soil and identified as Streptomyces sp. closely related to Streptomyces albidoflavus cluster by 16S rRNA analysis. The cultural, morphological and physiological characters of the strain were recorded. The strain exhibited resistance to chloramphenicol, penicillin and streptomycin. It had the ability to produce enzymes such as amylase and chitinase. A bioactive compound was isolated from the strain at stationary phase of culture and identified as 3-phenylpropionic acid (3-PPA) by FT-IR, EI-MS, 1H NMR and 13C NMR spectral studies. It exhibited antimicrobial activity against different bacteria like Bacillus cereus, B. subtilis, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Pseudomonas aeruginosa, P. flourescens, Staphylococcus aureus and some fungi including Aspergillus flavus, A. niger, Candida albicans, Fusarium oxysporum, F. udum and Penicillium citrinum. The antifungal activity of 3-PPA of the strain was evaluated in in vivo and in vitro conditions against Fusarium udum causing wilt disease in pigeon pea. The compound 3-PPA is an effective antifungal agent when compared to tricyclozole (fungicide) to control wilt caused by F. udum, but it exhibited less antifungal activity than carbendazim.

Extraction and bioactive profile of the compounds produced by Rhodococcus sp. VLD-10.

A potent actinobacterial strain isolated from the marine samples of Bheemunipatnam beach, Visakhapatnam, India, was identified as Rhodococcus sp. VLD-10 using the conventional and genomic (16S rRNA) approaches. Bioactive compounds responsible for the antimicrobial activity of the strain were elucidated by cultivating the strain VLD-10 in a modified yeast extract-malt extract-lactose broth followed by subsequent chromatographic and spectroscopic analyses. Extraction, purification, and structural confirmation of five compounds, viz., benzoic acid, 2-nitrobenzaldehyde, 4-chlorobenzaldehyde, nonadeconoic acid, and 3-isopropylhexahydro-1H-pyrido[1,2-a] pyrazine-1,4(6H)-dione, from Rhodococcus sp. VLD-10 were fruitfully described. The bioactivity of the compounds isolated from the strain VLD-10 against Gram-positive as well as Gram-negative bacteria, yeast, and molds was tested and their minimum inhibition concentration was reported. Antibacterial activity of 3-isopropylhexahydro-1H-pyrido[1,2-a] pyrazine-1,4(6H)-dione is more prominent against Bacillus subtilis, B. cereus, B. megaterium, Corynebacterium diphtheriae, and Escherichia coli, whereas its antifungal spectrum showed less potency against yeast and fungi. This is the first report on the natural occurrence and bioactivity of 3-isopropylhexahydro-1H-pyrido[1,2-a] pyrazine-1,4(6H)-dione from Rhodococcus sp. VLD-10.

Isolation, structural assignment and synthesis of (SE)-2-methyloctyl 3-(4-methoxyphenyl) propenoate from the marine soft coral Sarcophyton ehrenbergi.

A new metabolite 1 has been isolated from the marine soft coral Sarcophyton ehrenbergi along with two known diterpenoids 2 and 3 and cholesterol 4. The structure of 1 was determined by means of detailed spectroscopic analysis and unambiguously confirmed to have the S configuration by the synthesis of both enantiomers using 4-benzyl-2-oxazolidinone auxiliaries. (S)- and (R)-1, 3 and some of the synthetic intermediates were evaluated for cytotoxic activity against human lung cancer (A549), prostate cancer (DU145), cervical cancer (HeLa) and breast cancer (MCF-7) cell lines in an in vitro bioassay.

Purification and biological evaluation of the metabolites produced by Streptomyces sp. TK-VL_333.

An Actinobacterium strain isolated from laterite soils of the Guntur region was identified as Streptomyces sp. TK-VL_333 by 16S rRNA analysis. Cultural, morphological and physiological characteristics of the strain were recorded. The secondary metabolites produced by the strain cultured on galactose-tyrosine broth were extracted and concentrated followed by defatting of the crude extract with cyclohexane to afford polar and non-polar residues. Purification of the two residues by column chromatography led to isolation of five polar and one non-polar fraction. Bioactivity- guided fractions were rechromatographed on a silica gel column to obtain four compounds, namely 1H-indole-3-carboxylic acid, 2,3-dihydroxy-5-(hydroxymethyl) benzaldehyde, 4-(4-hydroxyphenoxy) butan-2-one and acetic acid-2-hydroxy-6-(3-oxo-butyl)-phenyl ester from three active polar fractions and 8-methyl decanoic acid from one non-polar fraction. The structure of the compounds was elucidated on the basis of FT-IR, mass and NMR spectroscopy. The antimicrobial activity of the bioactive compounds produced by the strain was tested against the bacteria and fungi and expressed in terms of minimum inhibitory concentration. Antifungal activity of indole-3-carboxylic acid was further evaluated under in vitro and in vivo conditions. This is the first report of 2,3-dihydroxy-5-(hydroxymethyl) benzaldehyde, 4-(4-hydroxyphenoxy) butan-2-one, acetic acid-2-hydroxy-6-(3-oxo-butyl)-phenyl ester and 8-methyl decanoic acid from the genus Streptomyces.

Isolation, characterization and biological evaluation of bioactive metabolites from Nocardia levis MK-VL_113.

An Actinomycete isolate found to be prominent in the laterite soils of Acharya Nagarjuna University (ANU) Campus, Guntur was identified as Nocardia levis MK-VL_113 by 16S rRNA analysis. Cultural, morphological and physiological characteristics of the strain were recorded. Screening of secondary metabolites obtained from 4-day old culture broth of the strain led to the isolation of two fractions active against a wide variety of Gram-positive, Gram-negative bacteria and fungi. The structure of the first active fraction was elucidated using FT-IR, EI-MS, (1)H NMR and (13)C NMR spectra and identified as 1-phenylbut-3-ene-2-ol which is first time reported as a natural product. The compound exhibited good antimicrobial potential against the opportunistic and pathogenic bacteria and fungi. The antifungal activity of the strain and its metabolite were further confirmed with in vitro and in vivo studies. Evidence for the antagonism of the strain against Fusarium oxysporum, causing wilt disease in sorghum was demonstrated by the formation of inhibition zone in in vitro plate assay and reduction in the incidence of wilt of sorghum plants by using a green house trial. Analysis of the rhizosphere soil extracts by high performance liquid chromatography also demonstrated the production of the compound by the strain under in vivo conditions. As compared to the commercial fungicide mancozeb, the bioactive compound, 1-phenylbut-3-ene-2-ol was highly effective in controlling wilt of sorghum. Besides, the partially purified second fraction (PPF) subjected to gas chromatography-mass spectrometry revealed the presence of phenylethyl alcohol, dibutyl phthalate and 1,2-benzenedicarboxylic acid, 3-nitro.

A high dimensional QSAR study on the aldose reductase inhibitory activity of some flavones: topological descriptors in modeling the activity.

The quantitative structure-activity relationships (QSAR) of the Aldose Reductase (AR) inhibitory activity of 48 flavones were studied using Free-Wilson, Combinatorial Protocol in Multiple Linear Regression (CP-MLR), and Partial Least Squares (PLS) procedures. For the latter two procedures 152 Molconn-Z parameters and six indicators corresponding to the hydroxyls of flavones were used as molecular descriptors. Independently, all procedures suggested the significance of hydroxyls in modulating the activity of these compounds. The CP-MLR procedure identified 26 descriptors to model the activity. They suggested that structures rich in aromatic CH fragments, with a limited number of aliphatic fragments such as -CH2-, -CH<, and free hydroxyls at 7-, 3'-, and 4'-positions of the 2-arylbenzpyran-4-one core would be preferred for the activity. The PLS analysis agreed with the information content and the relative significance of the descriptors identified in the CP-MLR for modeling the activity. The study offers the scope to modulate the inhibitory activity of these compounds.

New acylated iridoid glucosides from Vitex altissima.

Six new iridoid glucosides, 6'-O-trans-feruloylnegundoside (1), 6'-O-trans-caffeoylnegundoside (2), 2'-O-p-hydroxybenzoyl-6'-O-trans-caffeoylgardoside (3), 2'-O-p-hydroxybenzoyl-6'-O-trans-caffeoyl-8-epiloganic acid (4), 2'-O-p-hydroxybenzoyl gardoside (5), and 2'-O-p-hydroxybenzoyl-8-epiloganic acid (6), along with two known iridoids, agnuside and negundoside, have been isolated from the ethyl acetate extractive of the leaves of Vitex altissima. The structures of these compounds were elucidated on the basis of spectral data interpretation. These isolates did not exhibit significant 5-lipoxygenase enzyme inhibitory activity, but compounds 2-4 showed potent antioxidant activity by both the superoxide (NBT riboflavin photoreduction) free-radical-scavenging and DPPH-radical-scavenging methods. Compounds 1, 2, and negundoside were evaluated in a rat paw edema assay.

Anti-HIV active petrosins from the marine sponge Petrosia similis.

A marine sponge Petrosia similis afforded two compounds which belongs to bis-quinolizidine alkaloids namely, petrosin (1) and petrosin-A (2), respectively. Petrosin (1) and petrosin-A (2) showed anti-HIV inhibition with IC(50) values of 41.3 and 52.9 microm respectively. MAGI cell assays indicated that the compounds inhibited early steps of HIV replication. In extracellular HIV-1 Reverse Transcriptase inhibition assay petrosin and petrosin-A inhibited HIV-1 RT at 10.6 and 14.8 microm. This is the first report of petroisns with anti-HIV activity.

Three new ingol diterpenes from Euphorbia nivulia: evaluation of cytotoxic activity.

The latex of Euphorbia nivulia afforded three new ingol diterpenes, 3-acetyl-8-methoxyl-7-angolyl-12-hydroxylingol (7), 3,12-diacetyl-7-hydroxy-8-methoxylingol (8), and 3,12-diacetyl-7-angolyl-8-hydroxylingol (9) along with five known ingol diterpenes 2-6 and a known triterpene cyclonivulinol (1). Their structures were established by means of spectroscopic analysis. Diterpenes 2-9 were evaluated for their cytotoxic activity.

Two new macrocyclic diaryl ether heptanoids from Boswellia ovalifoliolata.

The stems of Boswellia ovalifoliolata BAL. & HENRY (Burseraceae) afforded two new macrocyclic diaryl ether heptanoids, ovalifoliolatin A (1) and B (2) together with three known compounds; acerogenin C (3), 3 alpha-hydroxyurs-12-ene (4), and sitost-4-en-3-one (5). The structures were established by means of spectroscopic analysis and compounds 1, 3-5 were evaluated for their antibacterial activity.

Two new bromotyrosine-derived metabolites from the sponge Psammaplysilla purpurea.

Two new bromotyrosine-derived metabolites (1, 2) have been isolated along with the known compounds 3,5-dibromo-4-methoxyphenylacetonitrile, 3-bromo-4-methoxyphenylacetonitrile, 3-bromo-4-hydroxyphenylacetonitrile, 1-hydroxyuracil, 1-methoxyhemibastadin 2, purpuramine H and a steroid 5alpha,8alpha-epidioxycholest-6-en-3beta-ol from the sponge Psammaplysilla purpurea. Compounds 1 and 2 were characterized by interpretation of their spectral data. The antibacterial activity of these compounds is summarized.