Demospongic Acids of the Marine Sponge &lt;i&gt;Halichondria panicea&lt;/i&gt; from the Coast of Hokkaido, Japan

Ando, Yasuhiro; Kawabata, Yasunosuke; Narukawa, Keiichi; Ota, Toru

doi:10.2331/fishsci.64.136

Cited by 16 publications

(12 citation statements)

References 25 publications

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“…In whole-cell extracts, we detected a previously unreported very-long-chain FA (VLCFA; Ͼ18 carbons) that appears to be a heptacosatrienoic (3 C 27:3 ) acid, a type of omega-3 PUFA (63)(64)(65). To the best of our knowledge, a PUFA of this same structure and chain length has been found in marine sponges only (66). A different VLCFA, n-C 31:9 , has been reported for G. obscuriglobus (57).…”

Section: Discussionmentioning

confidence: 87%

Global and Targeted Lipid Analysis of Gemmata obscuriglobus Reveals the Presence of Lipopolysaccharide, a Signature of the Classical Gram-Negative Outer Membrane

et al. 2016

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Planctomycete bacteria possess many unusual cellular properties, contributing to a cell plan long considered to be unique among the bacteria. However, data from recent studies are more consistent with a modified Gram-negative cell plan. A key feature of the Gram-negative plan is the presence of an outer membrane (OM), for which lipopolysaccharide (LPS) is a signature molecule. Despite genomic evidence for an OM in planctomycetes, no biochemical verification has been reported. We attempted to detect and characterize LPS in the planctomycete Gemmata obscuriglobus. We obtained direct evidence for LPS and lipid A using electrophoresis and differential staining. Gas chromatography-mass spectrometry (GC-MS) compositional analysis of LPS extracts identified eight different 3-hydroxy fatty acids (3-HOFAs), 2-keto 3-deoxy-D-manno-octulosonic acid (Kdo), glucosamine, and hexose and heptose sugars, a chemical profile unique to Gram-negative LPS. Combined with molecular/structural information collected from matrix-assisted laser desorption ionization-time of flight (MALDI-TOF) MS analysis of putative intact lipid A, these data led us to propose a heterogeneous hexa-acylated lipid A structure (multiple-lipid A species). We also confirmed previous reports of G. obscuriglobus whole-cell fatty acid (FA) and sterol compositions and detected a novel polyunsaturated FA (PUFA). Our confirmation of LPS, and by implication an OM, in G. obscuriglobus raises the possibility that other planctomycetes possess an OM. The pursuit of this question, together with studies of the structural connections between planctomycete LPS and peptidoglycans, will shed more light on what appears to be a planctomycete variation on the Gram-negative cell plan. IMPORTANCEBacterial species are classified as Gram positive or negative based on their cell envelope structure. For 25 years, the envelope of planctomycete bacteria has been considered a unique exception, as it lacks peptidoglycan and an outer membrane (OM). However, the very recent detection of peptidoglycan in planctomycete species has provided evidence for a more conventional cell wall and raised questions about other elements of the cell envelope. Here, we report direct evidence of lipopolysaccharide in the planctomycete G. obscuriglobus, suggesting the presence of an OM and supporting the proposal that the planctomycete cell envelope is an extension of the canonical Gram-negative plan. This interpretation features a convoluted cytoplasmic membrane and expanded periplasmic space, the functions of which provide an intriguing avenue for future investigation.T he planctomycete bacterium Gemmata obscuriglobus (1) is of considerable interest to the fields of cell and evolutionary biology due to its uncommon cellular features and evolutionary placement within the Bacteria (2-5). G. obscuriglobus possesses an extensive endomembrane system (6) with superficial eukaryotelike properties, including the presence of membrane coat-like (MC-like) proteins (7), large quantities of sterols (8, 9), a propos...

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Section: Discussionmentioning

confidence: 87%

Global and Targeted Lipid Analysis of Gemmata obscuriglobus Reveals the Presence of Lipopolysaccharide, a Signature of the Classical Gram-Negative Outer Membrane

et al. 2016

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“…In addition, fatty acid profiles for the extracts of the 2 Mycale sponges differed and the Hong Kong sponge had a more diverse fatty acid composition (Table 7). The dominant fatty acid for both sponges was 5, 9-hexacosadienoic acid, which is a major fatty acid in Demospongia (Ando et al 1998). Surprisingly, there has been no report on bioactivity of this fatty acid.…”

Section: Discussionmentioning

confidence: 98%

“…The main components of sponge membranes, phospholipids, consist of unusual, long-chained fatty acids (Ando et al 1998). Many unusual fatty acids isolated from sponges have potent cytotoxic (Tachibana et al 1981), antimicrobial (Carballeira et al 2002), and antifungal (Fusetani et al 1993) activities.…”

Section: Introductionmentioning

confidence: 99%

Surface bacterial community, fatty acid profile, and antifouling activity of two congeneric sponges from Hong Kong and the Bahamas

Lee¹,

Yang²,

Li³

et al. 2007

Mar. Ecol. Prog. Ser.

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Bacterial communities on the surfaces of 2 congeneric sponges, Mycale adhaerens from Hong Kong and M. laxissima from the Bahamas, were compared using conventional cultivation techniques and terminal restriction fragment length polymorphism (TRFLP) analysis -a cultureindependent DNA fingerprinting technique. The bacterial community on the Hong Kong sponge was more diverse, in terms of the number and type of species isolated, and different from that on the Bahamas sponge, as evident from distinct clusters formed in TRFLP analysis. Distinctive bacterial types (i.e. TRFs) were commonly found on both sponge surfaces, but none of their bacterial isolates were common. At tissue level concentration, extract of the Hong Kong sponge inhibited the growth of a wide range of bacteria isolated from the Hong Kong reference surface, but did not affect any of those isolated from the Bahamas reference surface, indicating highly specific antibacterial activity. Extracts of both sponges, when incorporated into hydrogels and exposed to the natural environment for bacterial film development, dramatically altered the bacterial community in the films, either by shifting the bacterial composition or decreasing bacterial density. Settlement assays of the resulting films using larvae of the polychaete Hydroides elegans showed that the filmed hydrogels with Hong Kong sponge extracts either inhibited larval settlement or were toxic to the larvae; however, those with the Bahamas sponge extracts had no observable effect. HPLC (high performance liquid chromatography) and GC-MS (gas chromatography-mass spectrometry) analyses revealed different chemical profiles in the extracts; the Hong Kong sponge had a more diverse fatty acid profile. Our results suggest that the 2 congeneric sponges from geographically separated regions have 'speciesspecific', surface-associated bacterial communities and antifouling activities, which might be due to the differences in the chemical and fatty acid compositions of the 2 sponges. Alternately, different sponge-associated bacterial communities may reflect habitat differences in sympatric bacterial and fouling communities.

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“…Among a variety of NMIFA, (5Z,9Z)-fatty acids bearing an exceptionally long chain have received a great deal of attention due to their structures and interesting biological activities, and the class of such fatty acids are often called "demospongic acids" which were found especially from numerous sponge species [1][2][3]. Carballeira found several unique fatty acids with a 5,9-dienoic structure (7)(8)(9)(10)(11)(12)(13)(14) from the sea anemones Stoichactis helianthus, Condylactis gigantea, and from a zoanthid Palythoa caribaeorum in 1994-1995 [7,8]. Carballeira found several unique fatty acids with a 5,9-dienoic structure (7)(8)(9)(10)(11)(12)(13)(14) from the sea anemones Stoichactis helianthus, Condylactis gigantea, and from a zoanthid Palythoa caribaeorum in 1994-1995 [7,8].…”

Section: Introductionmentioning

confidence: 99%

“…For example, Litchfield isolated 26:2∆5,9 (1) and 26:3∆5,9,19 (2) from marine sponges Microciona prolifera and Xestospongia halichondroides [4,5], and Warkup also reported several 5,9-dienoic acids 3-6 from a sponge Aplysina fistularis in 1981 [6]. Since then, it is widely recognized that trace amounts of various NMIFA with a 5,9-dienoic acid structure are frequently found in marine sponges and mollusks [9][10][11][12][13][14][15][16][17][18][19][20][21] (Scheme 1). Since then, it is widely recognized that trace amounts of various NMIFA with a 5,9-dienoic acid structure are frequently found in marine sponges and mollusks [9][10][11][12][13][14][15][16][17][18][19][20][21] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis and Structural Elucidation of Two Unusual Non‐Methylene‐Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma

Shimada

Sugawara

Korenaga

et al. 2017

Lipids

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In our previous study, unusual odd-numbered dienoic acids with a terminal olefin were found as minor components in ovaries of the Japanese limpet Cellana toreuma, and the synthetic interests have been focused onto their structural confirmation and the inspection into their potential biological activity. Here, we describe an efficient and stereoselective total synthesis of two new unusual dienoic acids, 19:2∆7,18 and 21:2∆7,20, through a common pathway involving the strategic combination of alkyne-zipper reaction and Lindlar hydrogenation for the construction of their unique carbon chains. In our synthetic study, 2-propyn-1-ol was at first subjected to alkylation and alkyne-zipper reaction to form the two fragments, and the subsequent carbon chain elongation was achieved by the usual coupling reaction to obtain the C-19 and C-21 products bearing an internal acetylenic group. Then, the internal acetylenic group of these products was subjected to Lindlar hydrogenation to form a Z-alkenyl moiety, and the subsequent deprotection of the products was carried out under an acidic condition without isomerization of the internal Z-alkenyl group. Total synthesis of target fatty acids, 19:2∆7,18 and 21:2∆7,20, was finally accomplished by two-step oxidation of the resulting alcohols into carboxylic acids in a highly chemoselective manner, and the structures of these unusual natural fatty acids were finally elucidated by identifying the GC-MS spectra of the methyl esters of authentic and synthetic fatty acids.

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Demospongic Acids of the Marine Sponge <i>Halichondria panicea</i> from the Coast of Hokkaido, Japan

Cited by 16 publications

References 25 publications

Global and Targeted Lipid Analysis of Gemmata obscuriglobus Reveals the Presence of Lipopolysaccharide, a Signature of the Classical Gram-Negative Outer Membrane

Global and Targeted Lipid Analysis of Gemmata obscuriglobus Reveals the Presence of Lipopolysaccharide, a Signature of the Classical Gram-Negative Outer Membrane

Surface bacterial community, fatty acid profile, and antifouling activity of two congeneric sponges from Hong Kong and the Bahamas

Total Synthesis and Structural Elucidation of Two Unusual Non‐Methylene‐Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma

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