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Halogenases catalyze reactions that introduce halogen atoms into electron-rich organic molecules. Vanadium-dependent haloperoxidases are generally considered to be promiscuous halogenating enzymes that have thus far been derived exclusively from eukaryotes, where their cellular function is often disputed. We now report the first biochemical characterization of a bacterial vanadium-dependent chloroperoxidase, NapH1 from Streptomyces sp. CNQ-525, which catalyzes a highly stereoselective chlorination-cyclization reaction in napyradiomycin antibiotic biosynthesis. This finding biochemically links a vanadium chloroperoxidase to microbial natural product biosynthesis.

The marine red alga genus Laurencia is one of the richest producers of unique brominated compounds in the marine environment. The cDNAs for two Laurencia nipponica vanadium-dependent bromoperoxidases (LnVBPO1 and LnVBPO2) were cloned and expressed in Escherichia coli. Enzyme assays of recombinant LnVBPO1 and LnVBPO2 using monochlorodimedone revealed that they were thermolabile but their Km values for Br− were significantly lower than other red algal VBPOs. The bromination reaction was also assessed using laurediol, the predicted natural precursor of the brominated ether laurencin. Laurediol, protected by trimethylsilyl at the enyne, was converted to deacetyllaurencin by the LnVBPOs, which was confirmed by tandem mass spectrometry. Native LnVBPO partially purified from algal bodies was active, suggesting that LnVBPO is functional in vivo. These results contributed to our knowledge of the biosynthesis of Laurencia brominated metabolites.

Division of Marine Life Science, Faculty of Fisheries Sciences, Hokkaido University, 3-1-1, Minato-cho, Hakodate 0418611, Japan MC Food Specialties Inc., 4041, Ami, Ami-machi, Inashiki-gun, Ibaraki 300-0398, Japan Glico Dairy Products Co. Ltd., 2-14-1, Musashino, Akishima, Tokyo 196-0021, Japan Japan Food Research Laboratories, 7-4-41, Saitoasagi, Ibaraki, Osaka 567-0085, Japan Department of Fisheries Technology, Faculty of Fisheries, Bangabandhu Sheikh Mujibur Rahman Agricultural University, Gazipur-1706, Bangladesh Section of Integrated Environmental Science, Faculty of Environmental Earth Science, Hokkaido University, Kita 10, Nishi 5, Kita-ku, Sapporo 060-0810, Japan

Extensive chromatographic investigation of the ethanolic extract of Alnus japonica Steud stem bark led to the isolation of a new diarylheptanoid named alnuheptanoid A [(5S)-7-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-5-methoxyheptan-3-one] (8), together with seven known diarylheptanoid derivatives: platyphyllenone (5), (5S)-1,7-bis(4-hydroxyphenyl)-5-methoxyheptan-3-one (6), 1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-4-hepten-3-one (7), hirsutenone (9), (5R)-O-methylhirsutanonol (10), hirsutanonol (11) and oregonin (13), three triterpenes: α-amyrin (1), betulinaldehyde (3) and betulinic acid (4), and two sterols: β-sitosterol (2) and daucosterol (12). Compound 6 was isolated for the first time from natural source. The structures of the isolated compounds were determined on the basis of spectroscopic measurements (UV, IR, HR-ESI-MS, 1D and 2D NMR).

Antillatoxin (ATX) is a lipopeptide derived from the pantropical marine cyanobacterium Lyngbya majuscula . ATX is neurotoxic in primary cultures of rat cerebellar granule cells, and this neuronal death is prevented by either N- methyl- d -aspartate (NMDA) receptor antagonists or tetrodotoxin. To further explore the potential interaction of ATX with voltage-gated sodium channels, we assessed the influence of tetrodotoxin on ATX-induced Ca 2+ influx in cerebellar granule cells. The rapid increase in intracellular Ca 2+ produced by ATX (100 nM) was antagonized in a concentration-dependent manner by tetrodotoxin. Additional, more direct, evidence for an interaction with voltage-gated sodium channels was derived from the ATX-induced allosteric enhancement of [ 3 H]batrachotoxin binding to neurotoxin site 2 of the α subunit of the sodium channel. ATX, moreover, produced a strong synergistic stimulation of [ 3 H]batrachotoxin binding in combination with brevetoxin, which is a ligand for neurotoxin site 5 on the voltage-gated sodium channel. Positive allosteric interactions were not observed between ATX and either α-scorpion toxin or the pyrethroid deltamethrin. That ATX interaction with voltage-gated sodium channels produces a gain of function was demonstrated by the concentration-dependent and tetrodotoxin-sensitive stimulation of 22 Na + influx in cerebellar granule cells exposed to ATX. Together these results demonstrate that the lipopeptide ATX is an activator of voltage-gated sodium channels. The neurotoxic actions of ATX therefore resemble those of brevetoxins that produce neural insult through depolarization-evoked Na + load, glutamate release, relief of Mg 2+ block of NMDA receptors, and Ca 2 + influx.

Five new protease inhibitors, related to aeruginosins 298-A (5), 98-A (1) and 98-B (2), were isolated from the cyanobacterium Microcystis aeruginosa. Aeruginosins 98-C (3) and 101 (4) differed from 1 in the Hpla unit. Aeruginosin 298-B (6) lacked the argininol unit in 5. Aeruginosins 89-A (7) and 89-B (8) were observed as the tautomers in HPLC because of the presence of the argininal units. Structures 3, 4 and 6–8 were determined on the basis of spectral data and chromatographic analyses of degradation products. The absolute stereochemistry of 1–8 was deduced by a combination of spectral and chemical studies. Aeruginosins 98-A to 98-C, 101, 298-A, 298-B, 89-A and 89-B were isolated from the cyanobacterium Microcystis aeruginosa. These compounds except aeruginosin 298-B had trypsin, plasmin and thrombin inhibitory activities. Their structures were determined on the basis of spectral data and amino acid analysis. Their absolute stereochemistries were deduced by a combination of spectral and chemical studies.

Three new sesquiterpene carbonimide dichlorides have been isolated from a marine sponge of the genus Axinyssa, and a guaiane-type sesquiterpene peroxide from another Axinyssa sponge. A new isocyanosesquiterpene alcohol was obtained from the nudibranch PhyUidia pustulosa. Their structures were determined on the basis of 2D NMR data. These compounds showed potent antifouling activities against larvae of the barnacle Ba/anus amphitrite.

A biosynthetic study of polyether macrolide goniodomin A(1), isolated from the dinoflagellate Alexandrium hiranoi, was carried out by feeding sodium [1-13C]-, [2-13C]- and [1,2-13C2]-acetate, and [methyl-13C]-methionine. Considering the labelling patterns in a few compounds such as brevetoxins or dinophysistoxins (DTX), it is suggested that the TCA cycle participates, or single carbon deletion processes occur in the biosynthesis of goniodomin A.

NOBUHIRO FUSETANIFusetani Biofouling Project, ERATO, Research Development Corporation ofJapan, c/o Niigata Engineering Co. Ltd., Yokohama 235, JapanABSTRACT Methyl farnesoate (MF) and juvenile hormone III (JH-III) induced the metamor-phosis of unattached juveniles in cyprid larvae of the barnacle, Balanus amphitrite, in a dose-dependent manner. Because these effects were similar to PKC activation by phorbol esters, theeffects of assorted protein kinase inhibitors on the activity of MF and JH-III were examined.Staurosporine, a PKC inhibitor, and H7(1-(5-isoquinonylsulfonyl)-2-methylpiperazine), a proteinkinase inhibitor, significantly inhibited larval metamorphosis-inducing activity of MF and JH-III,suggesting that both MF and JH-III are involved in the PKC signal transduction system. More-over, the existence of MF in cyprids and adult barnacles was demonstrated by partial purificationfollowed by GCMS and HPLC analyses. These results may suggest that MF induces larval meta-morphosis via PKC signal transduction system in B. amphitrite cyprids. J. Exp. Zool. 278:349–355, 1997.

Two new microviridin-type peptides were isolated from the freshwater cyanobacterium Nostoc minutum (NIES-26), which we named microviridin G and H. Their structures were shown to be 1 and 2 respectively, on the basis of 2D NMR data and chemical degradation. These peptides inhibited elastase potently. © 1997 Elsevier Science Ltd. All rights reserved

Nostopeptins A and B were isolated from the cultured freshwater cyanobacterium Nostoc minutum (NIES-26). Their structures were elucidated on the basis of 2D NMR data and chemical degradation. These cyclic depsipeptides containing Ahp (3-amino-6-hydroxy-2-piperidone) inhibited elastase and chymotrypsin potently.

Aeruginosins 102-A and B were isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-102). Their structures were elucidated to be 1 and 2 on the basis of 2D NMR data and chemical degradation. These peptides inhibited thrombin potently.

Three new antifouling sesquiterpene isocyanides were isolated from nudibranchs of the family Phyllidiidae along with a new sesquiterpene peroxide and six known sesquiterpenes. Their structures were determined mainly on the basis of 2D NMR data. These compounds showed potent antifouling activity against larvae of the barnacle Balanus amphitrite .

Three new kalihinenes were isolated from the marine sponge Acanthella cavernosa together with kalihinol A and 10-formamidokalihinene. Their structures were elucidated to be 1–3 on the basis of 2D NMR data. These compounds showed potent antifouling activities against the barnacle larvae of Balanus amphitrite.

Microviridios B and C were isolated from the freshwater blue-green alga Microcystis aeruginosa (NIES-298). Their structures were elucidated to be 1 and 2 on the basis of 2D NMR data and chemical degradation. These peptides inhibited elastase potently.

Aeruginosins 98-A and B, trypsin inhibitors, were isolated from the cultured freshwater blue-green alga Microcystis aeruginosa. Their structures were elucidated to be 1 and 2 respectively on the basis of 2D NMR data and chemical degradation. These peptides inhibited trypsin potently with an IC50 of 0.6 μg/ml.

Chlorosulfolipids (CSLs) are unusual naturally occurring lipids with complex polychlorinated structures containing mono- or disulfate groups. The first reported CSLs were danicalipin A (2,2,11,13,15,16-hexachlorodocosane-1,14-disulfate) and related precursors from the freshwater microalga Chrysophyceae Ochromonas danica at the end of the 1960s. These planar structures were identified using elemental analysis and MS techniques, after chemical degradation. Although many CSL complexes are cytotoxic and exhibit various biological activities, CSLs from the alga have been ignored by synthetic chemists until recently because of their indeterminate stereochemistry and unclear activity. In the past decade, CSLs were isolated as cytotoxic agents from toxic Adriatic mussels in the course of Diarrheic Shellfish Poisoning research. The absolute configuration of these CSLs was elucidated using J-based configuration analysis (JBCA). The stereochemistry of CSLs in O. danica was determined using both synthetic chemical approaches and analytical chemical approaches. Further, the toxicity of natural isolated CSLs and synthetic CSLs was evaluated. This chapter is a comprehensive review of the isolation, structural determination (focusing on stereochemistry), bioactivity estimation, and roles in vivo of these naturally occurring CSLs, together with the synthetic chemical approaches for CSLs.

Aeruginosin 298-A was isolated from the freshwater blue-green alga Microcystis aeruginosa (NIES-298). Its structure was elucidated to be 1 on the basis of 2D NMR data. This linear peptide inhibited thrombin and trypsin potently.

Total syntheses of kalkitoxin, isolated from the Caribbean Lyngbya majuscula, and its analogues, 3-epi-, 7-epi-, 8-epi-, 10-epi-, 10-nor-, and 16-nor-kalkitoxin, were achieved via oxazolidinone-based diastereoselective 1,4-addition reaction of a methyl group and efficient TiCl(4)-mediated thiazoline ring formation as the key steps. The biological activities of synthetic kalkitoxin and its analogues were evaluated with brine shrimp.

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, and determination of its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, intermolecular Diels–Alder reaction and samarium diiodide induced Barbier-type cyclization were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined as (1S,6S,7R,10S) by comparison of the optical rotations between natural and synthetic samples. In addition, the authors successfully synthesized 10-epi- and di-1,6-epi-10-isocyano-4-cadinene through the same synthetic pathway. Antifouling activities against Balanus amphitrite with the cadinenes were also evaluated.

Asymmetric total synthesis of danicalipin A was achieved. The synthesis was characterized by diastereoselective introduction of chlorine atoms. Biological activities with synthetic danicalipin A, its enantiomer, and racemate were also evaluated toward brine shrimp. Both enantiomers of danicalipin A showed almost the same activity.

Micropeptins A and B were isolated from the cultured freshwater blue-green alga Microcystis aeruginosa. Their structures were elucidated to be 1 and 2 on the basis of 2D NMR data and chemical degradation. These cyclic depsipeptides inhibited plasmin and trypsin potently.

Microginin, an angiotensin-converting enzyme inhibitory pentapeptide, was isolated from the freshwater blue-green alga Microcystis aeruginosa . Its structure was elucidated to be 1 on the basis of 2D NMR data and chemical degradation.

Aeruginosin 298-A was isolated from the freshwater blue-green alga Microcystis aeruginosa (NIES-298). Its structure was elucidated to be 1 on the basis of 2D NMR data. This linear peptide inhibited thrombin and trypsin potently.

Three new kalihinenes were isolated from the marine sponge Acanthella cavernosa together with kalihinol A and 10-formamidokalihinene. Their structures were elucidated to be 1–3 on the basis of 2D NMR data. These compounds showed potent antifouling activities against the barnacle larvae of Balanus amphitrite.

Microviridios B and C were isolated from the freshwater blue-green alga Microcystis aeruginosa (NIES-298). Their structures were elucidated to be 1 and 2 on the basis of 2D NMR data and chemical degradation. These peptides inhibited elastase potently.

Radiosumin, a novel potent trypsin inhibitory dipeptide, was isolated from the freshwater blue-green alga Plectonema radiosum (NIES-515). Its structure was elucidated to be 1 on the basis of 2D NMR data and chemical degradation. The IC50 of 1 against trypsin was 0.14 μg/mL.

Three new antifouling sesquiterpene isocyanides were isolated from nudibranchs of the family Phyllidiidae along with a new sesquiterpene peroxide and six known sesquiterpenes. Their structures were determined mainly on the basis of 2D NMR data. These compounds showed potent antifouling activity against larvae of the barnacle Balanus amphitrite .

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels−Alder reaction and a SmI2-induced Barbier-type reaction were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined to be (1S, 6S, 7R, 10S) on the basis of the total synthesis. Antifouling activities against Balanus amphitrite with both enantiomers of 10-isocyano-4-cadinene were also evaluated.

Three new sesquiterpene carbonimide dichlorides have been isolated from a marine sponge of the genus Axinyssa, and a guaiane-type sesquiterpene peroxide from another Axinyssa sponge. A new isocyanosesquiterpene alcohol was obtained from the nudibranch PhyUidia pustulosa. Their structures were determined on the basis of 2D NMR data. These compounds showed potent antifouling activities against larvae of the barnacle Ba/anus amphitrite.

Five new protease inhibitors, related to aeruginosins 298-A (5), 98-A (1) and 98-B (2), were isolated from the cyanobacterium Microcystis aeruginosa. Aeruginosins 98-C (3) and 101 (4) differed from 1 in the Hpla unit. Aeruginosin 298-B (6) lacked the argininol unit in 5. Aeruginosins 89-A (7) and 89-B (8) were observed as the tautomers in HPLC because of the presence of the argininal units. Structures 3, 4 and 6–8 were determined on the basis of spectral data and chromatographic analyses of degradation products. The absolute stereochemistry of 1–8 was deduced by a combination of spectral and chemical studies. Aeruginosins 98-A to 98-C, 101, 298-A, 298-B, 89-A and 89-B were isolated from the cyanobacterium Microcystis aeruginosa. These compounds except aeruginosin 298-B had trypsin, plasmin and thrombin inhibitory activities. Their structures were determined on the basis of spectral data and amino acid analysis. Their absolute stereochemistries were deduced by a combination of spectral and chemical studies.

The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels-Alder reaction and a SmI(2)-induced Barbier-type reaction were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined to be (1S, 6S, 7R, 10S) on the basis of the total synthesis. Antifouling activities against Balanus amphitrite with both enantiomers of 10-isocyano-4-cadinene were also evaluated.

We isolated eight chlorosulfolipids (1-8) from the chrysophyta Ochromonas danica (IAM CS-2), including five new chlorosulfolipids (2-5, 8). The planar structures of all the compounds were elucidated by 1D and 2D NMR and ESI-MS/MS analyses. We determined the relative configuration of seven chlorosulfolipids (1-7), including the most commonly known chlorosulfolipid, 2,2,11,13,15,16-hexachlorodocosane-1,14-disulfate (1), by J-based configuration analysis (JBCA). The absolute configuration of each compound was determined using a modified Mosher's method after chemical degradation. 2,2,11,13,15,16-Hexachloro-14-docosanol-1-sulfate (2) was the most toxic to brine shrimp (Artemia salina) larvae (LC(50) 0.27 microg/mL). Compounds 1 and 4-8 were less toxic (LC(50) 2.2-6.9 microg/mL). Compound 3 was not toxic at 30 microg/mL.

Two antifouling compounds, aureobasidin (1), a new ester with an unusual 4,6-dihydroxydecanoic acid residue, and (3R,5S)-3,5-dihydroxydecanoic acid (2), were isolated from the marine-derived fungus Aureobasidium sp., in addition to (5R,3Z)-5-hydroxydec-3-enoic acid (3) and (R)-3-hydroxydecanoic acid (4). The structures were unambiguously established by IR, 1D and 2D NMR spectroscopic and mass spectral data. Compounds 1-3 were found to be active against Bacillus subtilis, Escherichia coli and Staphyllococcus aureus. Compound 3 showed fungistatic activity against Candida albicans.

Micropeptins C (1), D (2), E (3), and F (4) have been isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-100). The structures were elucidated by analyses of MS, NMR spectra, and chemical degradation. Micropeptins C, D, E, and F inhibited chymotrypsin with IC(50)'s of 1.1, 1.2, 1.0, and 1.5 microg/mL, respectively.

A marine fungal isolate, Penicillium sp. fungus isolated from seaweed, Ulva sp., led to the isolation of a new chromone derivatives, 2-(hydroxymethyl)-8-methoxy-3-methyl-4H-chromen-4-one (chromanone A). The structure was determined by interpretation of their spectroscopic data (1D and 2D NMR, MS, UV and IR). At the nitiation stage of carcinogenesis, carcinogens is activated by cytochrome P-450 1A (CYP1A) and detoxified by glutathione S-transferases (GST), quinine reductase (QR), and epoxide hydrolase (mEH). We tested the modulatory effect of chromanone A on these carcinogen metabolizing enzymes. The results indicated that chromanone A (4μg/ml) is a promising inhibitor of CYP1A activity up to 60% of the stimulated-CYP1A in murine hepatoma cells (Hepa1c1c7), and it significantly induced GST but not total thiols at low concentrations. Chromanone A had no influence on QR activity, while it resulted in a significant dose-dependant enhancement mEH activity in Hepa1c1c7 cells (P

The new phytosphingosine-type ceramide asteriaceramide A (1) and glucocerebroside asteriacerebroside G (2), together with two known cerebrosides, asteriacerebrosides A and B, were isolated from lipophilic fractions of the whole bodies of the Northern Pacific starfish Asterias amurensis Lutken. The water-soluble fraction afforded two known asterosaponins, glycoside B(2) and asterosaponin-1. The structures of 1 and 2 were determined on the basis of chemical and spectroscopic evidence as (2S,3S,4R,13Z)-2-[(2'R)-2-hydroxyhexadecanoylamino]-13-docosene-1,3,4-triol (1) and 1-O-(beta-d-glucopyranosyl)-(2S,3R,4E,13Z)-2-[(2'R)-2-hydroxytetradecanoylamino]-4,13-docosadiene-1,3-diol (2). Compounds 1, 2, and asteriacerebrosides A and B promoted plant growth in sprouts of Brassica campestris.

Two new diterpene formamides were isolated from the marine sponge Acanthella cavernosa collected off Yakushima Island, along with seven known diterpenes. Their structures proved to be kalihipyran derivatives on the basis of spectral data. All nine compounds showed potent antifouling activity against larvae of the barnacle Balanus amphitrite.

Radiosumin, a novel potent trypsin inhibitory dipeptide, was isolated from the freshwater blue-green alga Plectonema radiosum (NIES-515). Its structure was elucidated to be 1 on the basis of 2D NMR data and chemical degradation. The IC50 of 1 against trypsin was 0.14 μg/mL.

Kalkitoxin, a potent neurotoxin isolated from the marine cyanobacteria Lyngbya majuscula , and its congeners ( 1 – 7 ) were efficiently synthesized utilizing Hruby's diastereoselective 1,4-addition and the Wipf's oxazoline-thiazoline conversion as key steps. These synthetic efforts in combination with spectral studies of natural kalkitoxin clearly determined the absolute stereostructure of kalkitoxin to be 7 .

Aeruginosin 298-A was isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-298) and is an equipotent thrombin and trypsin inhibitor. A variety of analogs were synthesized to gain insight into the structure–activity relations. We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogs, in which all stereocenters were controlled by catalytic asymmetric phase-transfer reaction promoted by two-center asymmetric catalysts and catalytic asymmetric epoxidation promoted by a lanthanide–BINOL complex. Furthermore, serine protease inhibitory activities of aeruginosin 298-A and its analogs were examined.

Bioassay-guided fractionation of organic extracts from two Lyngbya majuscula collections led to the isolation of a new secondary metabolite, antillatoxin B, an unusual N-methyl homophenylalanine analogue of the potent neurotoxin antillatoxin. Its structure was deduced from 2D NMR and data comparisons with antillatoxin. Antillatoxin B exhibited significant sodium channel-activating (EC(50) = 1.77 microM) and ichthyotoxic (LC(50) = 1 microM) properties.

The effects of thyrotropin-releasing hormone (TRH) and its metabolites, cyclo(His-Pro) and TRH-OH, on growth hormone (GH) and prolactin (PRL) synthesis were investigated using primary cultured pituitary cells of the common carp, Cyprinus carpio. The effects of these pep tides on GH and PRL were compared to those of human GH-releasing hormone (hGHRH) and somatostatin (somatotropin-releasing inhibiting factor; SRIF). GH and PRL synthesis were determined by measuring the incorporation of [3H]leucine into GH and PRL. TRH stimulated the release of newly synthesized GH and PRL, but not thyroid-stimulating hormone. In addition, TRH stimulated a dose-related increase in the release of newly synthesized GH and PRL at 10(-9) to 10(-7) M. Cyclo(His-Pro) stimulated the release of newly synthesized GH dose- dependently. TRH, cyclo(His-Pro), and hGHRH stimulated GH synthesis, while SRIF inhibited this at 10(-7) M. The release of newly synthesized PRL into culture medium was also stimulated by TRH and hGHRH, but inhibited by SRIF. PRL synthesis was not affected by TRH-OH and cyclo(His-Pro). Intracellular contents of GH and PRL in the pituitary did not change significantly. The present study demonstrates that TRH plays an important role in both GH and PRL synthesis and release. This is the first report in which the effects of cyclo(His-Pro) on GH synthesis in teleosts are demonstrated.

Two antifouling compounds, aureobasidin (1), a new ester with an unusual 4,6-dihydroxydecanoic acid residue, and (3 R,5 S)-3,5-dihydroxydecanoic acid (2), were isolated from the marine-derived fungus Aureobasidium sp., in addition to (5 R,3 Z)-5-hydroxydec-3-enoic acid (3) and ( R)-3-hydroxydecanoic acid (4). The structures were unambiguously established by IR, 1D and 2D NMR spectroscopic and mass spectral data. Compounds 1-3 were found to be active against Bacillus subtilis, Escherichia coli and Staphyllococcus aureus. Compound 3 showed fungistatic activity against Candida albicans.