Displaying publications 1 - 20 of 51 in total

  1. Vairappan CS
    Biomol. Eng., 2003 Jul;20(4-6):255-9.
    PMID: 12919806
    Red algae genus Laurencia (Rhodomelaceae, Ceramiales) are known to produce a wide range of chemically interesting secondary halogenated metabolites. This investigation delves upon extraction, isolation, structural elucidation and antibacterial activity of inherently available secondary metabolites of Laurencia majuscula Harvey collected from two locations in waters of Sabah, Malaysia. Two major halogenated compounds, identified as elatol (1) and iso-obtusol (2) were isolated. Structures of these compounds were determined from their spectroscopic data such as IR, 1H-NMR, 13C-NMR and optical rotation. Antibacterial bioassay against human pathogenic bacteria was conducted using disc diffusion (Kirby-Bauer) method. Elatol (1) inhibited six species of bacteria, with significant antibacterial activities against Staphylococcus epidermis, Klebsiella pneumonia and Salmonella sp. while iso-obtusol (2) exhibited antibacterial activity against four bacterial species with significant activity against K. pneumonia and Salmonella sp. Elatol (1) showed equal and better antibacterial activity compared with tested commercial antibiotics while iso-obtusol (2) only equaled the potency of commercial antibiotics against K. pneumonia and Salmonella sp. Further tests conducted using dilution method showed both compounds as having bacteriostatic mode of action against the tested bacteria.
  2. Vairappan CS
    Indian J. Exp. Biol., 2003 Aug;41(8):837-45.
    PMID: 15248481
    Brown algae of genus Sargassum are known to produce relatively higher amount of alginic acid. Optimal extraction of this algalcolloid for local consumption requires in-depth studies on post-harvest treatment of the algal fronds. Present investigation endeavors to establish the dynamics and inter-relationship of moisture content and bacteria found on the surface of the alga and alginic acid content during post-harvest desiccation of Sargassum stolonifolium Phang et Yoshida. Harvested fronds were subjected to desiccation for 31 days and bacterial dynamics were monitored with relation to moisture content and water activity index (a(w)). There was 85% decrease in moisture content, however, a(w) showed a more gradual decrease. Total bacterial count increased during the first week and attained maximal value on day 7. Thereafter, a drastic decrease was seen until day 14, followed by a gradual decline. Six species of bacteria were isolated and identified, i.e. Azomonas punctata, Azomonas sp., Escherichia coli, Micrococcus sp., Proteus vulgaris and Vibrio alginolyticus. Calculated ratios for increase in alginic acid content and decrease in moisture content were almost the same throughout the desiccation process, implying that extracellular alginase-producing bacteria did not use the alginic acid produced by the algae as its carbon source. It became apparent that drastic decrease in bacterial count after day 7 could not be attributed to salinity, moisture content, a(w) or lack of carbon source for the bacteria. The possible exposure of these bacteria to algal cell sap which is formed due to the rupture of algal cells was seen as the most likely reason for the drop in bacterial population. Scanning electron microscope (SEM) micrograph taken on day 10 of desiccation showed the presence of cracks and localities where bacteria were exposed to algal cell sap. In vitro antibacterial tests were carried out to verify the effect of algal extracts. Separation and purification of crude algal extracts via bioassay guided separation methodology revealed the identity of active compounds (i.e. gylcolipids and free fatty acids) involved in this inherently available antibacterial defense mechanism during algal desiccation.
  3. Kamada T, Vairappan CS
    Nat Prod Commun, 2013 Mar;8(3):287-8.
    PMID: 23678792
    A Bomean red algal population of Laurencia similis Nam et Saito was analyzed for its secondary metabolite composition. Seven compounds were identified: ent-1(10)-aristolen-9beta-ol (1), (+)-aristolone (2), axinysone B (3), 9-aristolen-1alpha-ol (4), 2,3,5,6-tetrabromoindole (5), 1-methyl-2,3,5,6-tetrabromoindole (6), and 1-methyl-2,3,5-tribromoindole (7). Compound 1 was identified as a new optical isomer of 1(10)-aristolen-9beta-ol. Compounds 1, 4 and 5 exhibited good antibacterial activity against antibiotic resistant clinical bacteria and cytotoxic effects against selected cancer cell lines.
  4. Kamada T, Vairappan CS
    Molecules, 2012 Feb 21;17(2):2119-25.
    PMID: 22354189 DOI: 10.3390/molecules17022119
    Six populations of Laurencia nangii were found to produce three bromoallenes; dihydroitomanallene B (1), itomanallene B (2) and pannosallene (3). Prior to this report, L. nangii were only known to produce C(15)-acetogenins with acetylene functionality. This could be regarded as a new chemical race of L. nangii. The compound structures were elucidated on the basis of spectroscopic analysis and comparison with those previously reported in literature. Compound 1, dihydroitomanallene B, was isolated as a new compound representing a minor variation of itomanallene B (2).
  5. Kamada T, Vairappan CS
    Nat Prod Res, 2017 Feb;31(3):333-340.
    PMID: 27707003
    Two new non-halogenated sesquiterpenes, snakeol (1) and snakediol (2) were isolated together with 9 known sesquiterpenes such as (R,Z)-33-dimethyl-5-methylene-4-(3-methylpenta-24-dien-1-yl)cyclohex-1-ene (3), palisol (4), pacifigorgiol (5), palisadin D (6), palisadin A (7), palisadin B (8), 5-acetoxypalisadin B (9), debromolaurinterol (10) and α-bromocuparane (11) from the red algae Laurencia snackeyi. The structures of two new metabolites were determined from their spectroscopic data (IR, 1D and 2D NMR and MS). Compounds 1, 2, 10 and 11 showed strong antibacterial activity against selected human clinical bacterial pathogens.
  6. Phan CS, Vairappan CS
    Nat Prod Res, 2017 Apr;31(7):742-748.
    PMID: 27750446 DOI: 10.1080/14786419.2016.1241997
    Four new bicyclogermacrenes, capgermacrenes D (1) E (2) F (3) and G (4) were isolated from a population of Bornean soft coral Capnella imbricata. The structures of these metabolites were elucidated based on their nuclear magnetic resonance and high-resolution electrospray ionisation mass spectrometry spectral data. These compounds showed bacteriastatic and bacteriacidal activities against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus.
  7. Vairappan CS, Nagappan T, Palaniveloo K
    Nat Prod Commun, 2012 Feb;7(2):239-42.
    PMID: 22474969
    Essential oils obtained by hydrodistillation from the rhizomes of Etlingera pyramidosphaera (K. Schum.) R. M. Sm, E. megalocheilos (Griff.) A.D. Poulsen, comb. nov., E. coccinea (Blume) S. Sakai & Nagam, E. elatior (Jack) R. M. Sm, and E. brevilabrum (Valeton) R. M. Sm were analyzed by GCMS. The highest oil yield was obtained from E. pyramidosphaera (0.45%), followed by E. elatior (0.38%), E. coccinea (0.30%), E. brevilabrum (0.28%) and E. megalocheilos (0.25%). The major constituents of the essential oils were oxygenated monoterpenes, followed by sesquiterpenes, oxygenated sesquiterpenes, oxygenated diterpenes and diterpenes. The essential oils from E. pyramidosphaera and E. brevilabrum exhibited the best cytotoxicity against MCF 7 (LC50: 7.5 +/- 0.5 mg mL(-1)) and HL 60 (LC50: 5.0 mg mL(-1)), respectively. Strong inhibition was also observed for the essential oils of E. coccinea and E. megalocheilos against Staphylococcus aureus (MIC: 8.0 +/- 0.5 mg mL(-1), and 5.0 +/- 0.5 mg mL(-1)) and Streptococcus pyrogenes (MIC: 6.0 +/- 0.5 mg mL(-1) and 8.0 +/- 0.5 mg mL(-1)).
  8. Ishii T, Zhaoqi Z, Vairappan CS
    Molecules, 2010 May 26;15(6):3857-62.
    PMID: 20657412 DOI: 10.3390/molecules15063857
    A new cembrane diterpene, 6-acetoxy-7,8-epoxynephthenol acetate (1) was isolated along with a known compound, epoxynephthenol acetate (2), from the organic extract of a Bornean soft coral Nephthea sp. Their structures were elucidated on the basis of spectroscopic analyses and comparison with those previous literature data.
  9. Nagappan T, Ramasamy P, Vairappan CS
    Nat Prod Commun, 2012 Oct;7(10):1375-8.
    PMID: 23157015
    The composition of the essential oils of Murraya koenigii (L.) Spreng, cultivated at six locations in Peninsula Malaysia and Borneo are presented. The oils were obtained from fresh leaves by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS); 61 compounds were identified, of which eleven were present in all the specimens analyzed. The two major volatile metabolites were identified as beta-caryophyllene (16.6-26.6%) and alpha-humulene (15.2-26.7%) along with nine minor compounds identified as beta-elemene (0.3-1.3%), aromadendrene (0.5-1.5%), beta-selinene (3.8-6.5%), spathulenol (0.6-2.7%), caryophyllene oxide (0.7-3.6%), viridiflorol (1.5-5.5%), 2-naphthalenemethanol (0.7-4.8%), trivertal (0.1-1.0%) and juniper camphor (2.6-8.3%). The results suggest that beta-caryophyllene and alpha-humulene could be used as chemotaxonomical markers for Malaysian M. koenigii, hence these specimens could be of the same stock and different from the ones in India, Thailand and China.
  10. Ishii T, Kamada T, Vairappan CS
    J Asian Nat Prod Res, 2016 May;18(5):415-22.
    PMID: 26983053 DOI: 10.1080/10286020.2016.1145670
    Three new cembranoid diterpenes, 10-hydroxy-nephthenol acetate (1), 7,8-epoxy-10-hydroxy-nephthenol acetate (2), and 6-acetoxy-7,8-epoxy-10-hydroxy-nephthenol acetate (3), along with a known compound, 6-acetoxy-7,8-epoxy-nephthenol acetate (4), were isolated from the Bornean soft coral Nephthea sp. Antibacterial and anticancer activities were exhibited by compounds 1 and 2 against Staphylococcus aureus (ATCC 6538)/Escherichia coli (ATCC 13311) and Hela/MCF-7, respectively.
  11. Suzuki M, Daitoh M, Vairappan CS, Abe T, Masuda M
    J Nat Prod, 2001 May;64(5):597-602.
    PMID: 11374951
    In connection with our chemotaxonomic studies of Malaysian species of the red algal genus Laurencia, the chemical composition of Laurencia pannosa Zanardini was examined. Two halogenated sesquiterpenoids, named pannosanol (1) and pannosane (2), have been isolated along with a halogenated C15-acetogenin, (3Z)-chlorofucin (3). The structures of these compounds were determined from their spectroscopic data (IR, 1H NMR, 13C NMR, 2D NMR, and MS). Pannosanol and pannosane are novel halometabolites with an unusual rearranged chamigrane framework. Antibacterial activities of these metabolites against marine bacteria are also described.
  12. Kamada T, Phan CS, Vairappan CS
    Nat Prod Res, 2019 Feb;33(4):464-471.
    PMID: 29092618 DOI: 10.1080/14786419.2017.1396593
    Three new halogenated tricyclic sesquiterpenes, omphalaurediol (1), rhodolaurenones B (2) and C (3) were isolated together with nine known haloganated sesquiterpenes such as rhodolaurenone A (4), rhodolaureol (5), isorhodolaureol (6), (-)-laurencenone D (7), elatol (8), (+)-deschloroelatol (9), cartilagineol (10), (+)-laurencenone B (11) and 2-chloro-3-hydroxy-α-chamigren-9-one (12) from a population of Bornean red algae Laurencia majuscula. The structures of three new metabolites were determined based on their spectroscopic data (IR, 1D and 2D NMR, and MS). These compounds showed antibacterial activity against three human pathogenic bacteria (Escherichia coli, Salmonella typhi and Vibrio cholera).
  13. Kamada T, Phan CS, Vairappan CS
    J Asian Nat Prod Res, 2019 Mar;21(3):241-247.
    PMID: 29281900 DOI: 10.1080/10286020.2017.1417265
    Two new halogenated nonterpenoids C15-acetogenins, nangallenes A-B (1-2), together with two known halogenated compounds itomanallene A (3) and 2,10-dibromo-3-chloro-α-chamigrene (4), were isolated and identified from the organic extract of the marine red alga Laurencia nangii Masuda collected from the coastal waters in Semporna, Borneo. Their structures were established by means of spectroscopic analysis including IR, high-resolution electrospray ionization mass spectrometry (HRESI-MS), and 1D and 2D NMR techniques. All these metabolites were submitted for the antifungal assay against four species of selected marine fungi. Compounds 1-4 showed potent activity against Haliphthoros sabahensis and Lagenidium thermophilum.
  14. Phan CS, Kamada T, Vairappan CS
    Nat Prod Res, 2020 Apr;34(7):1008-1013.
    PMID: 30600714 DOI: 10.1080/14786419.2018.1543681
    Two new C15-acetogenins, 4-epi-isolaurallene (1) and 4-epi-itomanallene A (2) were isolated from a population of marine red alga Laurencia nangii Masuda from Carrington Reef. The structures of these compounds were determined intensively by NMR and HRESIMS data. Their configurations were elucidated by detailed comparison of chemical shifts, germinal protons splitting and NOE correlations with known and synthesized analogues. In addition, antibacterial activities of these compounds were evaluated. These compounds would serve as diastereomeric models for future reference. Since the isolaurallene, neolaurallene, 9-acetoxy-1,10,12-tribromo-4,7:6,13-bisepoxypentadeca-1,2-diene, itomanallene A and laurendecumallene A were isolated, compounds 1 and 2 were the sixth example of C15-acetogenin with dioxabicyclo[7.3.0]dodecene skeleton.
  15. Vairappan CS, Daitoh M, Suzuki M, Abe T, Masuda M
    Phytochemistry, 2001 Sep;58(2):291-7.
    PMID: 11551553
    Two halogenated C15 acetogenins, named lembyne-A and lembyne-B, have been isolated from an unrecorded Laurencia species collected off the Malaysian waters. Their structures were deduced on the basis of spectroscopic evidence. Previously known elatol and iso-obtusol showed potent antibacterial activity against some marine bacteria.
  16. Vairappan CS, Ishii T, Lee TK, Suzuki M, Zhaoqi Z
    Mar Drugs, 2010;8(6):1743-9.
    PMID: 20631866 DOI: 10.3390/md8061743
    In our continuous interest to study the diversity of halogenated metabolites of Malaysian species of the red algal genus Laurencia, we examined the chemical composition of five populations of unrecorded Laurencia sp. A new brominated diterpene, 10-acetoxyangasiol (1), and four other known metabolites, aplysidiol (2), cupalaurenol (3), 1-methyl-2,3,5-tribromoindole (4), and chamigrane epoxide (5), were isolated and identified. Isolated metabolites exhibited potent antibacterial activities against clinical bacteria, Staphylococcus aureus, Staphylococcus sp., Streptococcus pyogenes, Salmonella sp. and Vibrio cholerae.
  17. Ishii T, Matsuura H, Zhaoqi Z, Vairappan CS
    Molecules, 2009;14(11):4591-6.
    PMID: 19924087 DOI: 10.3390/molecules14114591
    A new germacrane-type norsesquiterpenoid, 1-acetoxy-germacra-5E,10(14)-diene-4-one (1), as well as three known compounds, were isolated from the organic extracts of a Bornean soft coral Nephthea sp. Their structures were elucidated on the basis of spectroscopic data analysis.
  18. Ishii T, Matsuura H, Zhaoqi Z, Vairappan CS
    Molecules, 2009;14(9):3360-6.
    PMID: 19783930 DOI: 10.3390/molecules14093360
    A new 4alpha-methyl sterol, 4alpha-methyl-ergosta-6,8(14),22E-triene-3beta-ol (1), was isolated along with cholesterol from a Nephthea sp. Bornean soft coral The structure of compound 1 was elucidated on the basis of spectroscopic analysis and comparison of the data with those of the related compounds.
  19. Ng SY, Kamada T, Suleiman M, Vairappan CS
    J Asian Nat Prod Res, 2016 Jul;18(7):690-6.
    PMID: 26828126 DOI: 10.1080/10286020.2015.1134503
    A new compound, chandonanol (1), along with four known compounds, chandonanthone (2), iso-chandonanthone (3), anastreptene (4), and (6R,7S)-sesquiphellandrene (5), was isolated from the MeOH extract of Bornean liverwort Chandonanthus hirtellus. The structure of the new metabolite was established by analyses of the spectroscopic data (1D NMR, 2D NMR, HRESIMS, and IR). These compounds were tested for their activity against antibiotic-resistant clinical strains. Chandonanol (1) exhibited potent bactericidal activity against Staphylococcus aureus and Escherichia coli.
  20. Tani K, Kamada T, Phan CS, Vairappan CS
    Nat Prod Res, 2019 Dec;33(23):3343-3349.
    PMID: 29772929 DOI: 10.1080/14786419.2018.1475387
    Three new cembrane diterpenes, nephthecrassocolides A-B (1-2) and 6-acetoxy nephthenol acetate (3) along with three known compounds, 6-acetoxy-7,8-epoxy nephthenol acetate (4), epoxy nephthenol acetate (5) and nephthenol (6) were isolated from one population of Nephthea sp. Their structures were elucidated based on spectroscopic data analysis and the antifungal activities of compounds 1-6 were evaluated.
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