Polyketide synthases of bacterial symbionts in sponges--evolution-based applications in natural products research.

Abstract:

:Marine sponges are an unusually rich source of bioactive natural products with clinical potential. They also often harbor rich communities of symbiotic bacteria that have often been suspected as the true producers of sponge-derived compounds. To date, these bacteria can in most cases not be cultivated, but culture-independent methods, such as isolating and analyzing biosynthetic gene clusters using metagenomic strategies, have recently provided first insights into their chemical potential. This review summarizes recent work of our laboratory on the study of polyketide synthases (PKSs). These studies revealed two evolutionarily distinct, unusual PKS types that are commonly found in sponge metagenomes and were shown to be of bacterial origin. One, the sup PKS, dominates sponge metagenomic DNA libraries, occurs widespread in bacteriosponges and is to date exclusively known from such animals. Data suggest that it is a type of synthase that generates methyl-branched fatty acids, which are commonly present in sponges. The other PKS type, termed trans-acyltransferase (AT) PKS, is responsible for the biosynthesis of complex, bioactive polyketides, such as the onnamides, and also occurs in free-living bacteria. The diversity of PKS genes present in a single sponge metagenome can be enormous. However, the phylogenetic approaches outlined in this review can provide valuable insights into the PKS function and structures of polyketides and can assist in the targeted isolation of gene clusters.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Hochmuth T,Piel J

doi

10.1016/j.phytochem.2009.04.010

subject

Has Abstract

pub_date

2009-10-01 00:00:00

pages

1841-9

issue

15-16

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(09)00161-7

journal_volume

70

pub_type

杂志文章,评审
  • Oleanane triterpenes with protein tyrosine phosphatase 1B inhibitory activity from aerial parts of Lantana camara collected in Indonesia and Japan.

    abstract::During the search for new protein tyrosine phosphatase (PTP) 1B inhibitors, EtOH extracts from the aerial parts of Lantana camara L. (lantana) collected at Manado (Indonesia) and two subtropical islands in Japan (Ishigaki and Iriomote Islands, Okinawa) exhibited potent inhibitory activities against PTP1B in an enzyme ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.08.020

    authors: Abdjul DB,Yamazaki H,Maarisit W,Rotinsulu H,Wewengkang DS,Sumilat DA,Kapojos MM,Losung F,Ukai K,Namikoshi M

    更新日期:2017-12-01 00:00:00

  • Acylated pregnane glycosides from Caralluma sinaica.

    abstract::Caralluma sinaica is sold on local markets of Saudi Arabia for various health benefits however no phytochemical study has specifically been performed on this species. NMR and UHPLC-ESI-TOF-MS profilings of the ethanolic extract of the whole plant reveal a very complex phytochemical composition dominated by pregnanes. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.04.003

    authors: Al-Massarani SM,Bertrand S,Nievergelt A,El-Shafae AM,Al-Howiriny TA,Al-Musayeib NM,Cuendet M,Wolfender JL

    更新日期:2012-07-01 00:00:00

  • Saponins from Astragalus hareftae (NAB.) SIRJ.

    abstract::Four cycloartane- (hareftosides A-D) and oleanane-type triterpenoids (hareftoside E) were isolated from Astragalus hareftae along with fifteen known compounds. Structures of the compounds were established as 3,6-di-O-β-D-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3,6,24-tri-O-β-D-xylopyranosyl-3β,6α,16β...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.07.015

    authors: Horo I,Bedir E,Masullo M,Piacente S,Ozgökçe F,Alankuş-Çalışkan O

    更新日期:2012-12-01 00:00:00

  • Antiviral benzofurans from Eupatorium chinense.

    abstract::Eleven benzofuran dimers, (+)-dieupachinins A-E, (-)-dieupachinins A-E and dieupachinin F, a benzofuran trimer trieupachinin A, as well as seven known compounds were isolated from the roots of Eupatorium chinense. The enantiomers of racemates dieupachinins A-E were separated by chiral HPLC. The structures with absolut...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.11.013

    authors: Wang WJ,Wang L,Liu Z,Jiang RW,Liu ZW,Li MM,Zhang QW,Dai Y,Li YL,Zhang XQ,Ye WC

    更新日期:2016-02-01 00:00:00

  • Sinapoyltransferases in the light of molecular evolution.

    abstract::Acylation is a prevalent chemical modification that to a significant extent accounts for the tremendous diversity of plant metabolites. To catalyze acyl transfer reactions, higher plants have evolved acyltransferases that accept beta-acetal esters, typically 1-O-glucose esters, as an alternative to the ubiquitously oc...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2009.07.023

    authors: Stehle F,Brandt W,Stubbs MT,Milkowski C,Strack D

    更新日期:2009-10-01 00:00:00

  • Bioactive polyketides and 8,14-seco-ergosterol from fruiting bodies of the ascomycete Daldinia childiae.

    abstract::Seven previously undescribed polyketides, namely childinins A-G, and one previously undescribed 8,14-seco-ergosterol, namely childinasterone A, were obtained from the fruiting bodies of Daldinia childiae. Their structures and absolute configurations were established via extensive spectroscopic analyses, single-crystal...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.06.020

    authors: Zhao ZZ,Chen HP,Huang Y,Zhang SB,Li ZH,Feng T,Liu JK

    更新日期:2017-10-01 00:00:00

  • Vacuolar transport of the glutathione conjugate of trans-cinnamic acid.

    abstract::Red beet (Beta vulgaris L.) tonoplast membrane vesicles and [14C]trans-cinnamic acid-glutatione were used to study the vacuolar transport of phynylpropanoid-glutathione conjugates which are formed in peroxidase-mediated reactions. It was determined that the uptake of [14C]trans-cinnamic acid-glutathione into the tonop...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00563-4

    authors: Walczak HA,Dean JV

    更新日期:2000-02-01 00:00:00

  • Antiplasmodial and antimycobacterial cyclopeptide alkaloids from the root of Ziziphus mauritiana.

    abstract::Investigation of the MeOH extract obtained from the root of the Ziziphus mauritiana grown in Thailand resulted in the isolation of two 14- and 13-membered cyclic alkaloids, mauritine L (1) and mauritine M (2), and three known cyclopeptide alkaloids, nummularines H (3), B (4) and hemsine A (5). Their structures were el...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.03.003

    authors: Panseeta P,Lomchoey K,Prabpai S,Kongsaeree P,Suksamrarn A,Ruchirawat S,Suksamrarn S

    更新日期:2011-06-01 00:00:00

  • Evolution of alkaloid biosynthesis in the genus Narcissus.

    abstract::In an attempt to reveal the relationships between alkaloid biosynthesis and phylogeny, we investigated by GC-MS the alkaloid patterns of 22 species and 3 hybrids (from 45 locations) from seven main sections of the genus Narcissus (Amaryllidaceae). The results indicate that the first alkaloids to evolve in the genus Na...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.11.002

    authors: Berkov S,Martínez-Francés V,Bastida J,Codina C,Ríos S

    更新日期:2014-03-01 00:00:00

  • Caffeoyl coenzyme A O-methyltransferase and lignin biosynthesis.

    abstract::Lignin, a complex phenylpropanoid compound, is polymerized from the monolignols p-coumaryl alcohol, coniferyl alcohol and sinapyl alcohol. These three monolignols differ only by the 3- and 5-methoxyl groups. Therefore, enzymatic reactions controlling the methylations of the 3- and 5-hydroxyls of monolignol precursors ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00051-6

    authors: Ye ZH,Zhong R,Morrison WH 3rd,Himmelsbach DS

    更新日期:2001-08-01 00:00:00

  • Acetylated glucuronide triterpene bidesmosidic saponins from Symplocos glomerata.

    abstract::Nine new bidesmosidic 3-O-glucuronide oleanane triterpenoid saponins were isolated from the stem bark of Symplocos glomerata King along with two known saponins, salsoloside C and copteroside E, and two major lignans, (-)-pinoresinol and (-)-pinoresinol-4'-O-beta-D-glucopyranoside. The structures of the new saponins we...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.01.012

    authors: Waffo-Téguo P,Voutquenne L,Thoison O,Dumontet V,Nguyen VH,Lavaud C

    更新日期:2004-03-01 00:00:00

  • Guaianolide sesquiterpenes from Pulicaria crispa (Forssk.) Oliv.

    abstract::A phytochemical study of the asteraceous herb Pulicaria crispa (Forssk.) Oliv. resulted in the characterisation of three guaianolide sesquiterpenes, 2alpha,4alpha-dihydroxy-7alphaH,8alphaH,10alphaH-guaia-1(5),11(13)-dien-8beta,12-olide (1), 1alpha,2alpha-epoxy-4beta-hydroxy-5alphaH,7alphaH,8alphaH,10alphaH-guaia-11(13...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.03.012

    authors: Stavri M,Mathew KT,Gordon A,Shnyder SD,Falconer RA,Gibbons S

    更新日期:2008-06-01 00:00:00

  • Curtisians E-H: four p-terphenyl derivatives from the inedible mushroom Paxillus curtisii.

    abstract::Four p-terphenyl derivatives named curtisians E-H (1-4) were isolated from the methanolic extract of fruit bodies of the Basidiomycete Paxillus curtisii by a combination of Sephadex LH-20, silica gel column chromatography and preparative reversed phase HPLC. The relative stereochemistries of the curtisians were elucid...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00263-2

    authors: Quang DN,Hashimoto T,Nukada M,Yamamoto I,Tanaka M,Asakawa Y

    更新日期:2003-09-01 00:00:00

  • Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity.

    abstract::Natural compounds offer interesting pharmacological perspectives for antiviral drug development with regard to broad-spectrum antiviral properties and novel modes of action. In this study, we have analyzed polysaccharide fractions isolated from Grateloupia indica. The crude water extract (GiWE) as well as one fraction...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.02.008

    authors: Chattopadhyay K,Mateu CG,Mandal P,Pujol CA,Damonte EB,Ray B

    更新日期:2007-05-01 00:00:00

  • Volatile constituents of Capillipedium parviflorum.

    abstract::The essential oil of aerial parts of Capillipedium parviflorum (family Poaceae) was obtained by hydrodistillation in 0.4% yield on dry weight basis. The oil was analysed by capillary GC and GC-MS techniques. Two new compounds from plant source 4-nonanol 51.7% and 4-undecanone 23.5% predominated in the essential oil an...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.04.003

    authors: Mahmood U,Kaul VK,Acharya R

    更新日期:2004-07-01 00:00:00

  • Lycophlegmariols A-D: cytotoxic serratene triterpenoids from the club moss Lycopodium phlegmaria L.

    abstract::Lycopodium serratene triterpenoids, along with an abietane-type diterpene were isolated from the methanol extract of club moss Lycopodium phlegmaria L. The structures of these hitherto unknown lycopodium terpenoids were elucidated on the basis of spectroscopic analysis. Pentacyclic triterpenoids, 21β-hydroxy-serrat-14...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.01.006

    authors: Wittayalai S,Sathalalai S,Thorroad S,Worawittayanon P,Ruchirawat S,Thasana N

    更新日期:2012-04-01 00:00:00

  • The C-terminal zinc finger domain of Arabidopsis cold shock domain proteins is important for RNA chaperone activity during cold adaptation.

    abstract::Among the four cold shock domain proteins (CSDPs) identified in Arabidopsis thaliana, it has recently been shown that CSDP1 harboring seven CCHC-type zinc fingers, but not CSDP2 harboring two CCHC-type zinc fingers, function as a RNA chaperone during cold adaptation. However, the structural features relevant to this d...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.12.006

    authors: Park SJ,Kwak KJ,Jung HJ,Lee HJ,Kang H

    更新日期:2010-04-01 00:00:00

  • Deposition of stearate-oleate rich seed fat in Mangifera indica is mediated by a FatA type acyl-ACP thioesterase.

    abstract::Although the mechanism of accumulation of C8-C16 saturated fatty acids in seed oils has been well-studied, the control of stearic (C18:0) acid deposition in high stearate seed fat is still unclear. We investigated the mechanism that regulates high level of stearate and oleate (C18:1) accumulation in mango (Mangifera i...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.11.004

    authors: Bhattacharjee A,Ghosh SK,Neogi K,Aich A,Willard B,Kinter M,Sen SK,Ghosh D,Ghosh S

    更新日期:2011-02-01 00:00:00

  • Profile and quantification of glucosinolates in Pentadiplandra brazzeana Baillon.

    abstract::Glucosinolates (GLs) present in root, seed, and leaf extracts of Pentadiplandra brazzeana Baillon were characterized and quantified according to the ISO 9167-1 method based on the HPLC analysis of desulfo-GLs. The analyses were complemented by GC-MS analyses of the isothiocyanates (ITCs) generated from GL degradation ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.09.006

    authors: De Nicola GR,Nyegue M,Montaut S,Iori R,Menut C,Tatibouët A,Rollin P,Ndoyé C,Zollo PH

    更新日期:2012-01-01 00:00:00

  • Cardenolide glycosides from root of Streptocaulon juventas.

    abstract::Six cardenolides were isolated from the anti-tumor active fraction of the 75% ethanol extract of Streptocaulon juventas (Asclepiadaceae), mainly found in southwest of China. These were named 1α, 14β-dihydroxy-5β-card-20 (22)-enolide 3-O-[O-β-D-glucopyranosyl-(1→2)-β-D-digitalopyranoside] (1), acovenosigenin A 3-O-[O-β...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.12.004

    authors: Xue R,Han N,Ye C,Wang HB,Yin J

    更新日期:2013-04-01 00:00:00

  • Cytotoxic heterodimers of meroterpene phenol from the fruits of Psoralea corylifolia.

    abstract::Seventeen undescribed heterodimers of meroterpene phenol, psocorylins A-Q, were isolated from the fruits of Psoralea corylifolia. Their another monomeric unit derived from flavonone, chalcone, coumarin and isoflavone, respectively. Psocorylins A-E were rare natural spiroketals with the skeleton of 1,4,8-trioxaspiro[4....

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112394

    authors: Xu QX,Zhang YB,Liu XY,Xu W,Yang XW

    更新日期:2020-08-01 00:00:00

  • Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae).

    abstract::The incorporation of [1-13C]-labeled glucose into the irregular monoterpene artemisia ketone, the regular monoterpenes camphor and beta-thujone, the sesquiterpene germacrene D, the diterpene trans-phytol and beta-sitosterol and isofucosterol has been studied in axenic cultures of Tanacetum vulgare L. (Asteraceae). Qua...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.08.019

    authors: Umlauf D,Zapp J,Becker H,Adam KP

    更新日期:2004-09-01 00:00:00

  • Dermatolactone, a cytotoxic fungal sesquiterpene with a novel skeleton.

    abstract::The nematicidal 5-pentyl-2-furaldehyde and the cytotoxic sesquiterpene dermatolactone were isolated from the extracts of an Ascomycete belonging to the Dermateaceae. The furan has previously been reported from the Basidiomycete Irpex lacteus, while dermatolactone is a new compound the structure of which was determined...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(96)00326-3

    authors: Mayer A,Köpke B,Anke H,Sterner O

    更新日期:1996-09-01 00:00:00

  • Nitrogen depletion and small R3-MYB transcription factors affecting anthocyanin accumulation in Arabidopsis leaves.

    abstract::Ternary complexes consisting of a R2R3-MYB, a bHLH and a WD40 protein (MBW complexes) regulate trichome formation and anthocyanin synthesis in plants. Small R3-MYBs interact with the MBW complexes to exert a negative feedback, and thereby participate in regulation of epidermal cell fate, for example trichome numbers a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.12.006

    authors: Nemie-Feyissa D,Olafsdottir SM,Heidari B,Lillo C

    更新日期:2014-02-01 00:00:00

  • Accumulation of trans-piceid in sorghum seedlings infected with Colletotrichum sublineolum.

    abstract::Sorghum SbSTS1, a pathogen inducible gene, was previously demonstrated to encode an enzyme with stilbene synthase activity. In this study, we attempt to identify the stilbene derivatives that accumulate in infected sorghum seedlings after inoculation with the anthracnose pathogen Colletotrichum sublineolum. Scanning f...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.09.012

    authors: Yu CK,Shih CH,Chu IK,Lo C

    更新日期:2008-02-01 00:00:00

  • Heterologous expression of the plant proteins strictosidine synthase and berberine bridge enzyme in insect cell culture.

    abstract::The heterologous expression of cDNAs encoding the alkaloid biosynthetic enzymes, strictosidine synthase [EC 4.3.3.2] from Rauvolfia serpentina and the berberine bridge enzyme [(S)-reticuline: oxygen oxidoreductase (methylene-bridge-forming), EC 1.5.3.9] from Eschscholtzia californica, has been achieved in a cell cultu...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)94763-0

    authors: Kutchan TM,Bock A,Dittrich H

    更新日期:1994-01-01 00:00:00

  • Composition of the epicuticular waxes coating the adaxial side of Phyllostachys aurea leaves: Identification of very-long-chain primary amides.

    abstract::The present study presents comprehensive chemical analyses of cuticular wax mixtures of the bamboo Phyllostachys aurea. The epicuticular and intracuticular waxes were sampled selectively from the adaxial side of leaves on young and old plants and investigated by gas chromatography-mass spectrometry and flame ionizatio...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.06.005

    authors: Racovita RC,Jetter R

    更新日期:2016-10-01 00:00:00

  • Thelephantins D-H: five p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta.

    abstract::Five p-terphenyl derivatives named thelephantins D-H (1-5) together with nine known compounds, thelephantins A-C (6-8), ganbajunin E (9), p-hydroxylbenzoic acid (10), ganbajunin C (11), thelephorin A (12), 2-O-methylatromentin (13) and atromentin (14), were isolated from the methanolic extract of fruit bodies of the T...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00220-6

    authors: Ngoc Quang D,Hashimoto T,Hitaka Y,Tanaka M,Nukada M,Yamamoto I,Asakawa Y

    更新日期:2003-08-01 00:00:00

  • Prenylated phenyl polyketides and acylphloroglucinols from Hypericum peplidifolium.

    abstract::In search for new or chemo-taxonomically relevant bioactive compounds from chemically unexplored Hypericum species, four previously undescribed natural products, named peplidiforones A-D were isolated and characterized from Hypericum peplidifolium A. Rich., together with six known compounds. The structures of all comp...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.02.003

    authors: Fobofou SA,Harmon CR,Lonfouo AH,Franke K,Wright SM,Wessjohann LA

    更新日期:2016-04-01 00:00:00

  • Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids.

    abstract::Brugmansia arborea is a woody plant species that produces tropane alkaloids (TAs). The gene encoding tropine-forming reductase or tropinone reductase I (BaTRI) in this plant species was functionally characterised. The full-length cDNA of BaTRI encoded a 272-amino-acid polypeptide that was highly similar to tropinone r...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2016.03.008

    authors: Qiang W,Xia K,Zhang Q,Zeng J,Huang Y,Yang C,Chen M,Liu X,Lan X,Liao Z

    更新日期:2016-07-01 00:00:00