Biodegradation of free phytol by bacterial communities isolated from marine sediments under aerobic and denitrifying conditions

Biodegradation of (E)-phytol [3,7,11, 15-tetramethylhexadec-2(E)-en-1-ol] by two bacterial communities isolated from recent marine sediments under aerobic and denitrifying conditions was studied at 20 degrees C. This isoprenoid alcohol is metabolized efficiently by these two bacterial communities via 6,10, 14-trimethylpentadecan-2-one and (E)-phytenic acid. The first step in both aerobic and anaerobic bacterial degradation of (E)-phytol involves the transient production of (E)-phytenal, which in turn can be abiotically converted to 6,10,14-trimethylpentadecan-2-one. Most of the isoprenoid metabolites identified in vitro could be detected in a fresh sediment core collected at the same site as the sediments used for the incubations. Since (E)-phytenal is less sensitive to abiotic degradation at the temperature of the sediments (15 degrees C), the major part of (E)-phytol appeared to be biodegraded in situ via (E)-phytenic acid. (Z)- and (E)-phytenic acids are present in particularly large quantities in the upper section of the core, and their concentrations quickly decrease with depth in the core. This degradation (which takes place without significant production of phytanic acid) is attributed to the involvement of alternating beta-decarboxymethylation and beta-oxidation reaction sequences induced by denitrifiers. Despite the low nitrate concentration of marine sediments, denitrifying bacteria seem to play a significant role in the mineralization of (E)-phytol.     

Biodegradation of Free Phytol by Bacterial Communities Isolated from Marine Sediments under Aerobic and Denitrifying Conditions

Biodegradation of (E)-phytol [3,7,11,15-tetramethylhexadec-2(E)-en-1-ol] by two bacterial communities isolated from recent marine sediments under aerobic and denitrifying conditions was studied at 20°C. This isoprenoid alcohol is metabolized efficiently by these two bacterial communities via 6,10,14-trimethylpentadecan-2-one and (E)-phytenic acid. The first step in both aerobic and anaerobic bacterial degradation of (E)-phytol involves the transient production of (E)-phytenal, which in turn can be abiotically converted to 6,10,14-trimethylpentadecan-2-one. Most of the isoprenoid metabolites identified in vitro could be detected in a fresh sediment core collected at the same site as the sediments used for the incubations. Since (E)-phytenal is less sensitive to abiotic degradation at the temperature of the sediments (15°C), the major part of (E)-phytol appeared to be biodegraded in situ via (E)-phytenic acid. (Z)- and (E)-phytenic acids are present in particularly large quantities in the upper section of the core, and their concentrations quickly decrease with depth in the core. This degradation (which takes place without significant production of phytanic acid) is attributed to the involvement of alternating β-decarboxymethylation and β-oxidation reaction sequences induced by denitrifiers. Despite the low nitrate concentration of marine sediments, denitrifying bacteria seem to play a significant role in the mineralization of (E)-phytol.     

Production of Wax Esters during Aerobic Growth of Marine Bacteria on Isoprenoid Compounds

This paper describes the production of isoprenoid wax esters during the aerobic degradation of 6,10,14-trimethylpentadecan-2-one and phytol by four bacteria (Acinetobacter sp. strain PHY9, Pseudomonas nautica [IP85/617], Marinobacter sp. strain CAB [DSMZ 11874], and Marinobacter hydrocarbonoclasticus [ATCC 49840]) isolated from the marine environment. Different pathways are proposed to explain the formation of these compounds. In the case of 6,10,14-trimethylpentadecan-2-one, these esters result from the condensation of some acidic and alcoholic metabolites produced during the biodegradation, while phytol constitutes the alcohol moiety of most of the esters produced during growth on this isoprenoid alcohol. The amount of these esters formed increased considerably in N-limited cultures, in which the ammonium concentration corresponds to conditions often found in marine sediments. This suggests that the bacterial formation of isoprenoid wax esters might be favored in such environments. Although conflicting evidence exists regarding the stability of these esters in sediments, it seems likely that, under some conditions, bacterial esterification can enhance the preservation potential of labile compounds such as phytol.     

Synthesis of racemic 6,10,14-trimethylpentadecan-2-ol, a pheromone of rice moth and 5,9,13-trimethyltetradecanoic acid, a component of marine sponge from a common intermediate

A facile synthesis of dl-6,10,14-trimethylpentadecan-2-ol (1) a pheromone component of rice moth, Corcyra cephalonica Stainton and 5,9,13-trimethyltetradecanoic acid (2) a component of marine sponge, Cinachyrella alloclada Uliczka, using a common intermediate, hexahydrofarnesol is accomplished. The salient features for 1 are: Grignard coupling of 5 with allylmagnesium bromide and oxymercuration-demercuration whereas for 2 they are: Knoevenagel condensation and subsequent hydrogenation.     

Anaerobic Degradation of Hexadecan-2-one by a Microbial Enrichment Culture under Sulfate-Reducing Conditions

A microbial enrichment culture from marine sediment was able to grow on hexadecan-2-one as the sole source of carbon and energy under sulfate-reducing conditions. Oxidation of the ketone involved carboxylation reactions and was coupled to sulfide production. This enrichment culture also grew on 6,10,14-trimethylpentadecan-2-one.     

化感植物向日葵叶化学成分的研究

从向日葵(Helianthus annuus L.)叶子的甲醇提取物中分离得到了8个已知化合物,其结构经波谱解析分别确定为:(-)-kaur-16-en-19-oic acid(1)、(6R,10R)-6,10,14-三甲基-十五烷-2-酮(2)、维生素E(3)、dehydrocos-tus lactone(4)、(-)-α-tocospirone(5)、angeloygrandifloric acid(6)、trans-phytol(7)及3(20)-phytene-1、2-diol(8)。其中化合物2,5和8为首次从该植物中分离得到。     

Kaurane and kaurene diterpenes from the stem bark of Xylopia acutiflora

Four diterpenes were isolated from the stem bark of Xylopia acutiflora and characterized as (?)-kauran-16α-ol, 7,8-acetoxy-(?)-kaur-16-en-19-oic acid, 15-oxo-(?)-kaur-16-en-19-oic acid, and 16α- hydroxy-(?)-kauran-19-oic acid.     

Triterpenoids from Viburnum suspensum

Three triterpenoids, 3-oxo-11,13(18)-oleanadien-28-oic acid, 24-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid, 6β-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid have been isolated together with the previously known virgatic acid, vibsanin B and 3-hydroxyvibsanin E from the leaves of Viburnum suspensum. Their structures were determined by spectroscopic methods and by comparison of their NMR spectral data with those of the previously known 11,13(18)-oleanadien-3β-ol.     

Ent-kauren-19-oic acid derivatives from the stem bark of Croton pseudopulchellus Pax

Two new ent-kauren-19-oic acid derivatives, ent-14S*-hydroxykaur-16-en-19-oic acid and ent-14S*,17-dihydroxykaur-15-en-19-oic acid together with eleven known compounds ent-kaur-16-en-19-oic acid, ent-kaur-16-en-19-al, ent-12β-hydroxykaur-16-en-19-oic acid, ent-12β-acetoxykaur-16-en-19-oic acid, 8R,13R-epoxylabd-14-ene, eudesm-4(15)-ene-1β,6α-diol, (?)-7-epivaleran-4-one, germacra-4(15), 5E,10(14)-trien-9β-ol, acetyl aleuritolic acid, β-amyrin, and stigmasterol were isolated from the stem bark of Croton pseudopulchellus (Euphorbiaceae). Structures were determined using spectroscopic techniques. Ent-14S*-hydroxykaur-16-en-19-oic acid, ent-kaur-16-en-19-oic acid, ent-12β-hydroxykaur-16-en-19-oic acid, ent-12β-acetoxykaur-16-en-19-oic acid and 8R,13R-epoxylabd-14-ene were tested for their effects on Semliki Forest virus replication and for cytotoxicity against human liver tumour cells (Huh-7 strain) but were found to be inactive. Ent-kaur-16-en-19-oic acid, the major constituent, showed weak activity against the Plasmodium falciparum (CQS) D10 strain.     

Aerobic and anaerobic metabolism of squalene by a denitrifying bacterium isolated from marine sediment

The aerobic and anaerobic metabolism of the isoprenoid alkene squalene was investigated in a new type of marine denitrifying bacterium, strain 2sq31, isolated from marine sediment. Strain 2sq31 was identified as a species of Marinobacter. Under denitrifying conditions, the strain efficiently degraded squalene; of 0.7 mmol added per liter of medium, 77% was degraded within 120 days under anoxic conditions with nitrate as electron acceptor. Tertiary diols and methyl ketones were identified as metabolites, and an anaerobic pathway was suggested to explain the formation of such compounds. The first step in anaerobic degradation of squalene by strain 2sq31 involves hydration of double bonds to tertiary alcohols. Under oxic conditions, the degradation of squalene by strain 2sq31 was rapid and involved oxidative splitting of the C-10/C-11 or C-14/C-15 double bonds, in addition to the pathways observed under denitrifying conditions.     

Triterpenoids from Viburnum suspensum

Three triterpenoids, 3-oxo-11,13(18)-oleanadien-28-oic acid, 24-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid, 6β-hydroxy-3-oxo-11,13(18)-oleanadien-28-oic acid have been isolated together with the previously known virgatic acid, vibsanin B and 3-hydroxyvibsanin E from the leaves of Viburnum suspensum. Their structures were determined by spectroscopic methods and by comparison of their NMR spectral data with those of the previously known 11,13(18)-oleanadien-3β-ol.     

ent-Kaurenoic acids from Mikania hirsutissima (Compositae)

Four ent-kaurenoic acid derivatives, 2beta,16alpha,17-trihydroxy-ent-kauran-19-oic acid (1), 3beta,16alpha,17-trihydroxy-ent-kauran-19-oic acid (2), 11alpha,15beta-dihydroxy-7-O-beta-d-glucopyranosyl-ent-kaur-16-en-19-oic acid (3) and 1alpha,15beta-dihydroxy-7-O-beta-d-glucopyranosyl-ent-kaur-16-en-19-oic acid (4), were isolated together with five known compounds, 1,5-dicaffeoyl-quinic acid (5), 2-O-glucosyloxy-4-methoxy-cinnamic acid (6), phenethyl alcohol glucoside (7), phenethyl-1-O-beta-d-apiofuranosyl (1-->2) beta-d-glucopyranoside (sayaendoside) (8) and 3,6-dihydroxy-beta-ion-9-ol (9) from the 50% aqueous acetone extract of the aerial parts of Mikania hirsutissima DC. (Compositae). Compounds 1-9 were tested for their proliferative activity toward peripheral blood mononuclear cells (hPBMC); compounds 1 and 2 showed significant activity (43.8% and 36.7%, at 100 microM, respectively) on the lymphocyte.     

Secondary metabolites from Senecio burtonii (Compositae)

A cacalolide derivative named 4alpha-[2'-hydroxymethylacryloxy]-1beta-hydroxy-14-(5-->6) abeo eremophilan-12,8-olide and a shikimic acid derivative named (3'E)-(1alpha)-3-hydroxymethyl-4beta,5alpha-dimethoxycyclohex-2-enyloctadec-3'-enoate along with three known compounds, octacosan-1-ol, 3beta-hydroxyolean-12-en-28-oic acid and 3beta-acetoxyolean-12-en-28-oic acid were isolated from Senecio burtonii. Their structures and relative configurations were established on the basis of spectroscopic analysis.     

Halomonas mongoliensis sp. nov. and Halomonas kenyensis sp. nov., new haloalkaliphilic denitrifiers capable of reducing N2O, isolated from soda lakes

In the course of the search for N2O-utilizing microorganisms, two novel strains of haloalkaliphilic denitrifying bacteria, Z-7009 and AIR-2, were isolated from soda lakes of Mongolia and Kenya. These microorganisms are true alkaliphiles and grow in the pH ranges of 8.0-10.5 and 7.5-10.6, respectively. They are facultative anaerobes with an oxidative type of metabolism, able to utilize a wide range of organic substrates and reduce nitrate, nitrous oxide, and, to a lesser extent, nitrite to gaseous nitrogen. They can oxidize sulfide in the presence of acetate as the carbon source and nitrous oxide (strain Z-7009) or nitrate (strain AIR-2) as the electron acceptor. The strains require Na+ ions. They grow at medium mineralization levels of 0.16-2.2 M Na+ (Z-7009) and 0.04-2.2 M Na+ (AIR-2). The G+C contents of the DNA of strains Z-7009 and AIR-2 are 67.9 and 65.5 mol %, respectively. According to the results of 16S rRNA gene sequencing and DNA-DNA hybridization, as well as on the basis of physiological properties, the strains were classified as new species of the genus Halomonas: Halomonas mongoliensis, with the type strain Z-7009T (=DSM 17332, =VKM B2353), and Halomonas kenyensis, with the type strain AIR-2T (=DSM 17331, =VKM B2354).     

The male sex pheromone of the butterfly Bicyclus anynana: towards an evolutionary analysis

Background

Female sex pheromones attracting mating partners over long distances are a major determinant of reproductive isolation and speciation in Lepidoptera. Males can also produce sex pheromones but their study, particularly in butterflies, has received little attention. A detailed comparison of sex pheromones in male butterflies with those of female moths would reveal patterns of conservation versus novelty in the associated behaviours, biosynthetic pathways, compounds, scent-releasing structures and receiving systems. Here we assess whether the African butterfly Bicyclus anynana, for which genetic, genomic, phylogenetic, ecological and ethological tools are available, represents a relevant model to contribute to such comparative studies.

Methodology/Principal Findings

Using a multidisciplinary approach, we determined the chemical composition of the male sex pheromone (MSP) in the African butterfly B. anynana, and demonstrated its behavioural activity. First, we identified three compounds forming the presumptive MSP, namely (Z)-9-tetradecenol (Z9-14:OH), hexadecanal (16:Ald ) and 6,10,14-trimethylpentadecan-2-ol (6,10,14-trime-15-2-ol), and produced by the male secondary sexual structures, the androconia. Second, we described the male courtship sequence and found that males with artificially reduced amounts of MSP have a reduced mating success in semi-field conditions. Finally, we could restore the mating success of these males by perfuming them with the synthetic MSP.

Conclusions/Significance

This study provides one of the first integrative analyses of a MSP in butterflies. The toolkit it has developed will enable the investigation of the type of information about male quality that is conveyed by the MSP in intraspecific communication. Interestingly, the chemical structure of B. anynana MSP is similar to some sex pheromones of female moths making a direct comparison of pheromone biosynthesis between male butterflies and female moths relevant to future research. Such a comparison will in turn contribute to understanding the evolution of sex pheromone production and reception in butterflies.     

Oxidized kaurene derivatives from leaves of Solidago missouriensis and S. Rigida

Oxidized kaurene derivatives were isolated from the leaves of Solidago missouriensis and S. rigida and identified as kauran-16β-ol, kaur-16-en-19-oic acid and 7β-hydroxykaur-16-en-19-oic acid. The structure of the latter compound was determined by X-ray crystallographic analysis of its methyl ester.     

Ceriopsins F and G,diterpenoids from Ceriops decandra

Chemical examination of the ethyl acetate solubles of the CH(3)OH:CH(2)Cl(2) (1:1) extract of the roots of Ceriops decandra collected from Kauvery estuary resulted in the isolation of two more diterpenoids, ceriopsins F and G (1-2) and five known compounds, ent-13-hydroxy-16-kauren-19-oic acid (steviol, 3), methyl ent-16beta,17-dihydroxy-9(11)-kauren-19-oate (4), ent-16beta,17-dihydroxy-9(11)-kauren-19-oic acid (5), ent-16-oxobeyeran-19-oic acid (isosteviol, 6), 8,15R-epoxypimaran-16-ol (7). The structures of the new diterpenoids were elucidated by a study of their physical and spectral data as methyl ent-13,17-epoxy-16-hydroxykauran-19-oate (1) and ent-16-oxobeyeran-19-al (2).     

Composition of the volatiles from intact and tea aphid-damaged tea shoots and their allurement to several natural enemies of the tea aphid

Abstract: The comparison between the composition of the volatiles from intact tea shoots (ITS) and that from tea aphid-damaged tea shoots (TADTS) was accomplished, and the difference of both volatiles in attraction to natural enemies of the tea aphid, Toxoptera aurantii , i.e the ladybug, Leis axyridis (Pallas), the aphid parasite, Aphidius sp., and the lacewing, Chrysopa septempunctata Wesmeal, was investigated in the current paper. Volatile components from ITS, obtained by air entrainment, were identified by their mass spectra and retention times and comfirmed by comparison with authentic samples. They are E-2-hexenal, ocimene, Z-3-hexenyl acetate, Z-3-hexen-1-ol, butanoic acid-3-hexenyl ester, linalool, 1-octanol, geraniol and indole. Volatiles from TADTS have been identified as E-2-hexenal, ocimene, Z-3-hexenyl acetate, Z-3-hexen-1-ol, linalool, geraniol, indole, benzaldehyde and E-2-hexenoic acid. Z-3-hexen-1-ol is the main component in the two kinds of volatiles, whilst benzaldehyde is the another main component in TADTS volatiles. The air entrainment extracts of TADTS and benzaldehyde elicit the stronger electroantennogram (EAG) responses, and the stronger upwind flight and arresting behaviour from each natural enemy in wind tunnel. EAG responses from Leis axyridis and Chrysopa septempunctata were bigger than those from Aphidius sp., whereas Leis axyridis responds to these odours slightly less than Aphidius sp. and Chrysopa septempunctata in wind tunnel bioassay. So TADTS emits volatile synomones, in which the amount of benzaldehyde is ample and its allurement is the strongest.     

<Emphasis Type="Italic">Halomonas mongoliensis</Emphasis> sp. nov. and <Emphasis Type="Italic">Halomonas kenyensis</Emphasis> sp. nov., new haloalkaliphilic denitrifiers capable of N<Subscript>2</Subscript>O reduction,isolated from soda lakes

In the course of the search for N₂O-utilizing microorganisms, two novel strains of haloalkaliphilic denitrifying bacteria, Z-7009 and AIR-2, were isolated from soda lakes of Mongolia and Kenya. These microorganisms are true alkaliphiles and grow in the pH ranges of 8.0–10.5 and 7.5–10.6, respectively. They are facultative anaerobes with an oxidative type of metabolism, able to utilize a wide range of organic substrates and reduce nitrate, nitrous oxide, and, to a lesser extent, nitrite to gaseous nitrogen. They can oxidize sulfide in the presence of acetate as the carbon source and nitrous oxide (strain Z-7009) or nitrate (strain AIR-2) as the electron acceptor. The strains require Na⁺ ions. They grow at 0.16–2.2 M Na⁺ (Z-7009) and 0.04–2.2 M Na⁺ (AIR-2) in the medium. The G+C contents of the DNA of strains Z-7009 and AIR-2 are 67.9 and 65.5 mol %, respectively. According to the results of 16S rRNA gene sequencing and DNA-DNA hybridization, as well as on the basis of physiological properties, the strains were classified as new species of the genus Halomonas: Halomonas mongoliensis, with the type strain Z-7009^T (=DSM 17332, =VKM B2353), and Halomonas kenyensis, with the type strain AIR-2^T (=DSM 17331, =VKM B2354).     

Terpenoids and a flavan-3-ol from viguiera quinqueradiata

The isolation is reported of the new natural products from Viguiera quinqueradiata, acetylleptocarpin and (2R,3S-4′-hydroxy-3′,5,7-tri-O-methyl-flavan-3-ol. The diterpenes 15α-angeloyloxy-ent-kaur-16-en-19-oic acid, 15α-tigloyloxy-ent-kaur-16-en-19-oic acid and the sesquiterpene lactones leptocarpin and budlein A were also found.