Pravat Manjari Mishra

Isolation of a deoxy lupane triterpene carboxylic acid from Finlaysonia obovata (a mangrove plant)

A deoxy lupane triterpene carboxylic acid, lup-20(29)-en-24-oic acid (1), was isolated from the active chloroform extract of Finlaysonia obovata, a latex exuding mangrove plant. Its structure was evaluated on the basis of different spectroscopic methods, including extensive 1D and 2D NMR spectroscopy. Lup-20(29)-en-24-oic acid (1) has shown moderate antimicrobial activity, against some fish pathogens.

Antibacterial study and fatty acid analysis of lipids of the sponge Myrmekioderma granulata

The composition of the lipophilic extract of the sponge Myrmekioderma granulata (Esper) collected from 13 m depth of the Bay of Bengal of the Orissa coast was investigated. Fatty acids as well as volatiles and sterols were identified. 4,8,12-Trimethyltridecanoic acid was identified for the first time along with the important PUFAs such as linoleic acid (n-6, C18:2), dihomo-γ-linolenic acid (n-6, C20:3), 5,8,11,14-eicosatetraenoic acid (n-3, C20:4), and 5,8,11,14,17-eicosapentaenoic acid (EPA) (n-3, C20:5) from this species. The branched polyunsaturated fatty acids like br-C26:2, 25-methyl-5,9-heptacosadienoic acid and 24-methyl-5,9heptacosadienoic acid were also identified by GC-MS. The lipid extract exhibited limited activity against different pathogens.

Chemical investigation and antibacterial study of hexane extract of leaves of Finlaysonia obovata

Finlaysonia obovata, a latex – exuding mangrove plant (Fam. Periplocaceae), is found in the tidal flats in India, Burma, and Malay, the leaves of which are reported to be eaten as salad in the Moluccas. Mangrove latex-bearing plants were found to show antibacterial and antiviral activity [1]. Earlier we have studied the antibacterial activity, performed the GCMS analysis of extracts, studied the lipids of the leaf, and isolated a rare antibacterial triterpene from F. obovata [2, 3]. The present paper deals with the antibacterial screening of column fractions of an active hexane extract, and isolation and spectral characterization of stigmast-4-en-3β-ol from leaves of F. obovata. The antibacterial assay of the hexane extract of leaves of F. obovata was carried out against seven freshwater fish pathogenic bacteria (see Experimental) [3]. The hexane extract was found active against all except S. aureus and E. tarda. This extract was further taken up for fractionations and isolations of secondary metabolites. The results of anti-pathogenic screening of the active column fraction of the hexane extract [compound 2 is isolated] are presented in Table1. The column fraction (EtOAc:hexane-1:9) showed activity against S. aureus, which clearly proves the enrichment of the active components during

Fatty acid profile and sterol composition of the marine sponge Azorica pfeifferae

0009-3130/12/4801-0122 2012 Springer Science+Business Media, Inc. Natural Product Department, Institute of Minerals & Materials Technology, Bhubaneswar, 751013, Orissa, India, fax: 91 674 2581637, e-mail: pravatmanjari@yahoo.co.in; pravatmanjari@immt.res.in. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 110–112, January–February, 2012. Original article submitted December 13, 2010. Chemistry of Natural Compounds, Vol. 48, No. 1, March, 2012 [Russian original No. 1, January–February, 2012]

Biosorption of Praseodymium (III) using Terminalia arjuna bark powder in batch systems: isotherm and kinetic studies

The high demand for rare earth elements (REEs) used in various advanced materials implies demand for increased production of REEs or the recycling of solutions to recover the REEs they contain. In this study, the biosorption of Pr(III) from aqueous solution by bark powder of Terminalia arjuna was examined in a batch system as a function of metal concentration, biosorbent dosage, pH and contact time. Results showed that T. arjuna bark powder has a high affinity for adsorbing Pr(III): more than 90% at pH 6.63. The adsorption of Pr(III) by T. arjuna bark powder was investigated by the Langmuir, Freundlich, Temkin and Dubinin-Radushkevich isotherm models. The kinetics of the biosorption process was tested with pseudo-first-order and pseudo-second-order models, and the results showed that the biosorption process was better fitted to the pseudo-second-order model. From Fourier transform infrared spectroscopy (FT-IR) analysis, it is confirmed that the biomolecules of T. arjuna bark powder are involved in the biosorption process of Pr(III) metal ions.

Fatty Acids of Marine Sponges

Among all organisms, thus also marine sponges, accumulate fatty acids (FAs) with a very rich chemistry and are the source of an unprecedented diverse range of chemical structures. This chapter accounts the most recent developments concerning the occurrence of different FA structures in marine sponges and their potential applications. While the first section of the chapter deals with the importance of FAs in various applications, the second section of the chapter focuses on the diversity of FAs with different structural features in marine sponges. FAs in marine sponges differ in the number of olefinic bonds, the extent of branching, the length of the hydrocarbon chain, and the number of functional groups. The last section of the chapter deals with the biomedical potential of the FAs of marine sponges including antibacterial, antifungal, antimalarial, and cytotoxic activities, etc.

Fatty Acid Profile and Sterol Composition of the Marine Sponge Petrosia testudinaria

The interest of chemists, biochemists, and biotechnologists in lipids and fatty acids from marine sponges has been stimulated because among aquatic animals, sponges possess the greatest diversity of fatty acids, sterols, etc. Various applications of lipids, phospholipids, and saturated and unsaturated fatty acids in pharmaceutical formulations have been reported [1, 2]. Some unusual FAs of sponges exhibit biological activity. Petrosia testudinaria (Lamarck) is a barrel marine sponge widely distributed in the Bay of Bengal of the Odisha coast [3]. Sponges of the genus Petrosia have yielded various types of secondary metabolites, viz. isoquinoline antibiotic alkaloids, bisquinolizidine alkaloids, polyacetylenes, and steroids [3–8]. A novel steroid, 23-ethyl-24-methyl-27-norcholesta-5,25-diene-3 -23-diol, is isolated from the sponge P. testudinaria [9]. The methanol and dichloromethane extract of this species have shown broad-spectrum larvicidal and insecticidal activity [10]. The present paper deals with the study of the FA profile and sterol of the lipid composition of P. testudinaria, collected from the Bay of Bengal region of the Odisha coast. The study of the FA and sterols of the lipophilic extract of P. testudinaria was carried out mainly to search for new FA structures, to evaluate a new source of major polyunsaturated fatty acids (PUFAs) of biological interest, and to get valuable information on its chemotaxonomy. Analysis of Fatty Acids. Twenty-three fatty acids were identified in the mixture of total lipids of P. testudinaria by GC-MS analysis (Table 1). Peak identification was carried out by comparison of the mass spectra with those available in the NIST and WILEY libraries and also confirmed by comparison of their chromatographic retention times as well as mass fragmentations with those of authentic standards C4–C24 (Supelco standard FAME mixtures). Among the identified FAs, linear saturated FAs constituted 45.26% of the total FA content. Generally among linear saturated FAs, 16:0 and 18:0 dominated in most of the marine sponges. In the present analysis, 19:0 (17.13%) was the major one among the linear FAs. Fatty acids 18:0 (9.76%) and 16:0 (7.44%) were also present in good amount. Branched saturated FAs constituted 15.26% of the total FA content, and 13-methyl-14:0 (7.42%) was the major one. The position of the methyl branch was confirmed by analysis of their pyrrolidide derivatives and further confirmed by comparing their key mass fragments with those already reported for similar fatty acids. In the mass spectrum of 13-methyl-14:0 (iso), there was a gap of 28 amu between two peaks at m/z 252 and 280 due to the loss of carbon 13 with its methyl group. Similarly in the mass spectrum of 12-methyl-14:0 (anteiso), two peaks m/z 238 and 266 occurred at a gap of 28 amu due to the loss of carbon 12 and its methyl group. In the mass spectrum of 10-methyl-15:0, there was a gap of 28 amu between two peaks at m/z 210 and 238 due to loss of carbon 10 with its methyl group. A gap of 28 amu between two peaks at m/z 196 and 224 in the mass spectrum of 9-methyl-16:0 is due to the loss of carbon 9 with its methyl group, and the structure is confirmed. In the mass spectrum of 6-methyl-18:0 there was a gap of 28 amu between two key mass fragments m/z 154 and 182 due to the loss of carbon 6 with its methyl group, whereas in 18-methyl-20:0, two peaks m/z 322 and 350 occurred at a gap of 28 amu due to the loss of carbon 18 and its methyl group. It is considered that saturated iso and anteiso C15–C20 acids have a bacterial origin [11]. Thus, in the sponge P. testudinaria, the content of iso and anteiso may be due to symbiotic bacteria.

CHEMICAL INVESTIGATION OF LIPIDS OF A MARINE SPONGE Spirastrella vagabunda

Sponges are among the simplest of multicellular animals and are often described as the most primitive of all. Study of sponge lipids is as important as other secondary metabolites and has been well documented in a series of extensive reviews by Berge and Barnathan, Rod kina, etc. [1, 2]. Regular research into lipids of sponges began in the 1970s [3] and continues till today because they have the greatest diversity of fatty acids, sterols etc. Studies on fatty acids and sterols as lipid components of sponges and other organisms have been elaborately taken up by a number of investigators [4, 5]. There are only a few investigations on this species, Spirastrella vagabunda. The aqueous extract of this species has shown high phospholipase A2 catalytic activity [6]. The bacteria isolated from this sponge produced acetylcholinesterase, an essential enzyme [7], but no investigation on the chemistry of this species has been done so far. This paper presents a study of the fatty acid profile and sterol composition of the total lipid of S. vagabunda for the first time (Table 1). A significant number of fatty acids were identified by GC-MS. The fatty acids were characterized by linear saturated fatty acids, monobranched saturated fatty acids, polybranched saturated fatty acid, monounsaturated fatty acids, and polyunsaturated fatty acids. The percentage of straight-chain fatty acids was 28.22% of the total fatty acids. Generally, among the saturated fatty acids, C16:0 and C18:0 dominated in most of the sponges. In the present investigation, the main saturated fatty acids are also C16:0 (6.37%) and C18:0 (5.77%). It is interesting that long-chain saturated fatty acids like C23:0, C24:0, C25:0, and C28:0 are present in good quantity in S. vagabunda. S. vagabunda contains the highest percentage of monomethyl branched fatty acids, i.e., 45.5% of the total fatty acid content, as in the marine sponge species Geodia gibberosa, which also contains 40–50% of branched fatty acids [8]. Among these branched fatty acids the amount of 11-methyloctadecanoic acid was significantly high, i.e., 13.31% of the total FA. A long-chain branched fatty acid, i.e., br-24-methylhexacosanoic acid, is also present in good quantity (8.97%). The identification of 11-methyl-18:0 and 24-methyl-26:0 (ante-iso) acids was finally confirmed by comparing their key mass fragments (11-methyl-18:0: m/z 312 M+, 269, 213, 185, 143; 24-methyl-26:0: m/z 424 M+, 381, 339, 199, 266, 143) obtained by GC-MS analysis with their literature data. The presence of saturated isoand ante-iso acids (branched fatty acids) is known to have a bacterial origin [9, 10]. So, the presence of symbiotic bacteria cannot be excluded. 3,7,11-Trimethyldodecanoic acid, a very rarely found polymethyl branched fatty acid, which was earlier identified from the marine sponge Xestospongia muta [11], was reported to be present in S. vagabunda, which is an important finding. The identification of 3,7,11-trimethyldodecanoic acid was confirmed by the key mass fragments at m/z 101 and at m/z 171, which indicate the methyl branching at 3 and 7 position [11]. Generally in various sponge species, the percentage of monoenes varies from 2% to 50% of the total FA content. But in the present investigation, only one monoenic acid C18:1 (2.42%) is identified. C18:1 (9) and C18:1 (11) are the principal isomers of C18 monoenes in sponges [2]. The GC-MS spectrum of the C18:1 showed important mass fragments at m/z 296 (M+), 264, 221, 180, 123, 109, and 96, and by comparing with the literature data, the monoenic acid is identified as C18:1 (9). The polyunsaturated FA of this species is represented by one diene and one trienoic acids with total content of 17.91%.

Isolation of a lupane triterpene fatty acid ester with antibacterial activity from the leaves of Finlaysonia obovata

0009-3130/12/4801-0161 2012 Springer Science+Business Media, Inc. Natural Product Department, Institute of Minerals & Materials Technology, Bhubaneswar-751013, Orissa, India, fax: 91 674 2581637, e-mail: pravatmanjari@yahoo.co.in; pravatmanjari@immt.res.in. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 144–146, January–February, 2012. Original article submitted September 06, 2010. Chemistry of Natural Compounds, Vol. 48, No. 1, March, 2012 [Russian original No. 1, January–February, 2012]

Fatty Acid Profile, Sterol Composition of Lipids, and Antibacterial Study of the Marine Sponge Psammaplysilla purpurea Collected from the Bay of Bengal (Odisha Coast)

Marine sponges are the most primitive multicellular sedentary animals that produce bioactive metabolites. Among the aquatic animals, sponges are characterized by the greatest diversity of fatty acids (FA), sterols, etc. Fatty acids and sterols as lipid components of sponges have been elaborately studied by a number of investigators [1–6]. Some lipids of sponges are characterized as biologically active [7–9]. The sponge Psammaplysilla purpurea (order Verongida, family Aplysinellidae) is a well-known source of several bromotyrosine alkaloids of unique structural features and exhibiting promising biological activities such as cytotoxicity, antimicrobial properties, etc. [10–13]. The methanol and dichloromethane extracts of this species have shown broad-spectrum larvicidal and insecticidal activity [14]. However there has been no report on the FA profile of the lipid composition of P. purpurea. This is the first report on the analysis of the FA and sterol composition of the sponge P. purpurea collected from the Bay of Bengal region of the Odisha coast. The search for FAs and sterols of the lipophilic extract of P. purpurea can give valuable information on its chemotaxonomy. Thus, these minor components appear as biomarkers for such organisms. Forty-nine fatty acids were identified in the mixture of total lipids of P. purpurea by GC-MS analysis (Table 1). Peak identification was carried out by comparison of the mass spectra with those available in the NIST and WILEY libraries and also confirmed by comparison of their chromatographic retention times as well as mass fragmentations with those of authentic standards C-4–C-24 (Supelco standard FAME mixtures). Among the identified fatty acids, saturated linear FAs account for more than 50% of the total FA content, which is an important observation. All of the acids from 12:0 to 27:0 were found except 13:0. Generally, among saturated fatty acids, 16:0 and C18:0 dominated in most of the sponges. But in the present investigation, the acids 19:0 and 16:0 were dominant. Long-chain saturated fatty acids like 22:0 to 27:0 are present, among which 26:0 is present in good amount (6.04%). In sponges, branched saturated iso/anteiso acids with a total number of carbon atoms from C-14 to C-29 were found, among which C-15–C-20 acids were the most widespread [15]. In the present investigation, 24 saturated monobranched FAs were identified (29.92%), br-16:0 and br-14:0 being the major ones. It is considered that saturated iso and anteiso C-15–C-20 acids have a bacterial origin [16]. The ratio of iso and anteiso FAs is much higher in sponges, a significant part of whose biomass is compounded by bacterial symbionts. Thus, in the sponge P. purpurea the content of iso and anteiso may be due to symbiotic bacteria. Only one polybranched FA was identified, i.e., 3,7,11,15-tetramethylhexadecanoic acid (br-16:0, 4.38%), which is very often found in marine sponges [17]. The identification of 3,7,11,15-tetramethyl-16:0 was finally confirmed by comparing its key mass fragments (3,7,11,15-tetramethyl-16:0: m/z 326 M+, 311, 139, 112, 101, 97, 74, 57) obtained by GC-MS analysis with literature data. The mass spectrum of methyl esters of all saturated FAs exhibited the presence of the corresponding ions [M]+, [M – 31]+, and [M – 43]+ and intense peaks with m/z 74, 87, and 143 characteristic of the saturated FA methyl ester [18]. Monoenes vary from 2 to 50% of the FA total content in various sponge species [15]. In the present investigation, the total content of monoenoic FAs was only 6.75%. The content of 18:1( 9) and 19:1 was the major among them [17]. The identification of 18:1 and 19:1 is confirmed by comparing their key mass fragments (18:1 m/z 296 M+, 264, 222, 180, 151, 137, 123, 98, 84, 69; 19:1: m/z 310 M+, 278, 236, 208, 194, 163, 152, 138, 123, 97, 69, 55) obtained by GC-MS analysis with literature data. The mass spectra of methyl esters of the monoenoic FA exhibited the corresponding [M]+, [M – 32]+, and [M – 72]+ ions.