Nature and nurture: confluence of pathway determinism with metabolic and chemical serendipity diversifies Monascus azaphilone pigments.

Abstract:

:Covering: up to June 2018 Understanding the biosynthetic mechanisms that generate the astounding structural complexity and variety of fungal secondary metabolites (FSMs) remains a challenge. As an example, the biogenesis of the Monascus azaphilone pigments (MonAzPs) has remained obscure until recently despite the significant medical potential of these metabolites and their long history of widespread use as food colorants. However, a considerable progress has been made in recent years towards the elucidation of MonAzPs biosynthesis in various fungi. In this highlight, we correlate a unified biosynthetic pathway with the diverse structures of the 111 MonAzPs congeners reported until June 2018. We also discuss the origins of structural diversity amongst MonAzPs analogues and summarize new research directions towards exploring novel MonAzPs. The case of MonAzPs illuminates the various ways that FSMs metabolic complexity emerges by the interplay of biosynthetic pathway determinism with metabolic and chemical serendipity.

journal_name

Nat Prod Rep

journal_title

Natural product reports

authors

Chen W,Feng Y,Molnár I,Chen F

doi

10.1039/c8np00060c

subject

Has Abstract

pub_date

2019-04-17 00:00:00

pages

561-572

issue

4

eissn

0265-0568

issn

1460-4752

journal_volume

36

pub_type

杂志文章,评审
  • Biosynthesis of polyketides by trans-AT polyketide synthases.

    abstract::This review discusses the biosynthesis of natural products that are generated by trans-AT polyketide synthases, a family of catalytically versatile enzymes that represents one of the major group of proteins involved in the production of bioactive polyketides. The article includes 609 references and covers the literatu...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c5np00125k

    authors: Helfrich EJ,Piel J

    更新日期:2016-02-01 00:00:00

  • Challenges and advances in genetic manipulation of filamentous actinomycetes - the remarkable producers of specialized metabolites.

    abstract::Covering: up to February 2019Actinomycetes are Gram positive bacteria of the phylum Actinobacteria. These organisms are one of the most important sources of structurally diverse, clinically used antibiotics and other valuable bioactive products, as well as biotechnologically relevant enzymes. Most strains were discove...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c9np00029a

    authors: Musiol-Kroll EM,Tocchetti A,Sosio M,Stegmann E

    更新日期:2019-09-01 00:00:00

  • The impact of structural biology on alkaloid biosynthesis research.

    abstract::In the recent past, macromolecular crystallography has gone through substantial methodological and technological development. The purpose of this review is to provide a general overview of structural biology and its impact on enzyme structure/function analysis and illustrate how it is modifying the focus of research r...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c2np20057k

    authors: Panjikar S,Stoeckigt J,O'Connor S,Warzecha H

    更新日期:2012-10-01 00:00:00

  • Synthetic endeavours towards oxasqualenoid natural products containing 2,5-disubstituted tetrahydrofurans--eurylene and teurilene.

    abstract::2,5-Disubstituted tetrahydrofurans constitute the core skeleton of several natural products and are pivotal synthetic analogues of medicinal importance that exhibit remarkable bioactivities. Oxasqualenoid natural products are implicated as potent biologically active molecules, particularly with regard to demonstrating...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c4np00029c

    authors: Sheikh NS

    更新日期:2014-09-01 00:00:00

  • On ovothiol biosynthesis and biological roles: from life in the ocean to therapeutic potential.

    abstract::Covering: up to 2018 Ovothiols are sulfur-containing natural products biosynthesized by marine invertebrates, microalgae, and bacteria. These compounds are characterized by unique chemical properties suggestive of numerous cellular functions. For example, ovothiols may be cytoprotectants against oxidative stress, serv...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c8np00045j

    authors: Castellano I,Seebeck FP

    更新日期:2018-12-12 00:00:00

  • The biosynthesis, molecular genetics and enzymology of the polyketide-derived metabolites.

    abstract::This review covers the biosynthesis of aliphatic and aromatic polyketides as well as mixed polyketide/NRPS metabolites, and discusses the molecular genetics and enzymology of the proteins responsible for their formation. ...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b301028g

    authors: Hill AM

    更新日期:2006-04-01 00:00:00

  • Total synthesis of complex terpenoids employing radical cascade processes.

    abstract::Covering: 2011-2017Radical cyclizations have a rich history in organic chemistry and have been particularly generous to the field of natural product synthesis. Owing to their ability to operate in highly congested molecular quarters, and with significant functional group compatibility, these transformations have enabl...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c7np00065k

    authors: Hung K,Hu X,Maimone TJ

    更新日期:2018-02-21 00:00:00

  • Conotoxins: natural product drug leads.

    abstract::Venomous marine cone snails harbour a variety of small disulfide-rich peptides called conotoxins, which target a broad range of ion channels, membrane receptors, and transporters. More than 700 species of Conus are thought to exist, each expressing a wide array of different peptides. Within this large repertoire of to...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b819311h

    authors: Halai R,Craik DJ

    更新日期:2009-04-01 00:00:00

  • Strategic innovation in the total synthesis of complex natural products using gold catalysis.

    abstract::Novel organic reactions drive the advance of chemical synthesis in the same way that enabling technologies drive new scientific discoveries. One area of organic methodology that has undergone significant growth during the last decade is that of homogeneous gold-catalyzed transformations. This trend has been further en...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c3np70075e

    authors: Zhang Y,Luo T,Yang Z

    更新日期:2014-04-01 00:00:00

  • Triterpenoids.

    abstract::This review covers the isolation and structure determination of triterpenoids reported during 2012 including squalene derivatives, lanostanes, holostanes, cycloartanes, cucurbitanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, serratanes, i...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c4np00101j

    authors: Hill RA,Connolly JD

    更新日期:2015-02-01 00:00:00

  • Biosynthesis and incorporation of an alkylproline-derivative (APD) precursor into complex natural products.

    abstract::Covering: up to 2017This review covers the biosynthetic and evolutionary aspects of lincosamide antibiotics, antitumour pyrrolobenzodiazepines (PBDs) and the quorum-sensing molecule hormaomycin. These structurally and functionally diverse groups of complex natural products all incorporate rarely occurring 4-alkyl-l-pr...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c7np00047b

    authors: Janata J,Kamenik Z,Gazak R,Kadlcik S,Najmanova L

    更新日期:2018-03-01 00:00:00

  • Cytotoxic and antioxidant marine prenylated quinones and hydroquinones.

    abstract::Covering: 1972 to 2011. This review covers the literature of prenylated quinone, hydroquinone and naphthoquinone marine natural products with reported cytotoxic and/or antioxidant properties. The structures, biological activity and, where applicable, the syntheses of 159 cytotoxic/antioxidant compounds, isolated from ...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c2np00086e

    authors: Sunassee SN,Davies-Coleman MT

    更新日期:2012-05-01 00:00:00

  • Heparin and heparan sulfate: structure and function.

    abstract::This review covers the structure and function of heparin and heparan sulfate glycosaminoglycans. Their chemical structures are discussed, including recently developed methods for sequencing picomole to nanomole quantities of heparin- and heparan sulfate-derived oligosaccharides. The biosynthesis of heparin and heparan...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b100916h

    authors: Rabenstein DL

    更新日期:2002-06-01 00:00:00

  • Phenotypic taxonomy and metabolite profiling in microbial drug discovery.

    abstract::Microorganisms and in particular actinomycetes and microfungi are known to produce a vast number of bioactive secondary metabolites. For industrially important fungal genera such as Penicillium and Aspergillus the production of these compounds has been demonstrated to be very consistent at the species level. This mean...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b404943h

    authors: Larsen TO,Smedsgaard J,Nielsen KF,Hansen ME,Frisvad JC

    更新日期:2005-12-01 00:00:00

  • From Lobry de Bruyn to enzyme-catalyzed ammonia channelling: molecular studies of D-glucosamine-6P synthase.

    abstract::This review summarizes the state of knowledge on D-glucosamine-6P synthesis catalyzed by glucosamine-6P synthase. The mechanisms of L-glutamine hydrolysis, ammonia transfer and fructose-6P conversion into D-glucosamine-6P are analyzed with the E. coli enzyme in light of recent X-ray structures. With 92 references this...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b103713g

    authors: Teplyakov A,Leriche C,Obmolova G,Badet B,Badet-Denisot MA

    更新日期:2002-02-01 00:00:00

  • Recent advances in the total synthesis of pharmaceutically relevant diterpenes.

    abstract::A detailed overview is presented of recent total synthesis approaches to four different diterpenoids--the ginkgolides, tonantzitlolone, ingenol and eleutherobin. Due to their structural complexity, all pose major challenges for total synthesis, guaranteeing diverse strategic tours de force and a rich synthetic chemist...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b705652b

    authors: Busch T,Kirschning A

    更新日期:2008-04-01 00:00:00

  • Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.

    abstract::This review covers the literature on simple indole alkaloids and those with a nonrearranged monoterpenoid unit from the beginning of 2012 up to the end of 2013, which includes newly isolated alkaloids, structure determinations, total syntheses and biological activities. ...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c5np00032g

    authors: Ishikura M,Abe T,Choshi T,Hibino S

    更新日期:2015-09-23 00:00:00

  • Protein-protein interactions in polyketide synthase-nonribosomal peptide synthetase hybrid assembly lines.

    abstract::Covering: up to early 2018 Polyketides and nonribosomal peptides are two major families of natural product with a broad range of biological activities. Polyketide synthases (PKSs) assemble small acetic acid-type acyl building blocks into polyketides through C-C bonds, and nonribosomal peptide synthetases (NRPSs) assem...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c8np00022k

    authors: Miyanaga A,Kudo F,Eguchi T

    更新日期:2018-11-14 00:00:00

  • Glycosynthases as tools for the production of glycan analogs of natural products.

    abstract::Oligo-, polysaccharides, and glycoconjugates are a relevant part of the bioactive components of the natural products exploited in therapeutics, diagnostics, food additives, and biomaterials. Glycans are directly involved in important biological processes, such as immunostimulation, anti-inflammatory, antioxidant, and ...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c2np20032e

    authors: Cobucci-Ponzano B,Moracci M

    更新日期:2012-06-01 00:00:00

  • Largazole: from discovery to broad-spectrum therapy.

    abstract::The cyclic depsipeptide largazole from a cyanobacterium of the genus Symploca is a marine natural product with a novel chemical scaffold and potently inhibits class I histone deacetylases (HDACs). Largazole possesses highly differential growth-inhibitory activity, preferentially targeting transformed over non-transfor...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c2np00066k

    authors: Hong J,Luesch H

    更新日期:2012-04-01 00:00:00

  • Marine-derived fungi: a chemically and biologically diverse group of microorganisms.

    abstract::A diverse array of secondary metabolites have been isolated and characterized from marine-derived fungi. The structures and biological activities of these metabolites are presented. Additionally, some basic principles of mycology are covered. Overall, 273 structures are presented and the review contains 162 references...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b301926h

    authors: Bugni TS,Ireland CM

    更新日期:2004-02-01 00:00:00

  • Ptaquiloside, the major toxin of bracken, and related terpene glycosides: chemistry, biology and ecology.

    abstract::Bracken (Pteridium spp.) is a ubiquitous fern which has been described as one of the five most common plants on the earth. The toxic effects of bracken on livestock have been recorded since the end of the 19th century, and extensive and intensive investigations for the bracken toxin(s) led to the isolation of ptaquilo...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b614160a

    authors: Yamada K,Ojika M,Kigoshi H

    更新日期:2007-08-01 00:00:00

  • Steroids: reactions and partial synthesis.

    abstract::The article reviews the progress in the chemistry of the steroids that was published between January and December, 2001. The reactions and partial syntheses of estrogens, androgens, pregnanes, cholic acid derivatives, cholestanes and vitamin D analogues are covered. There are 184 references. ...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b212061p

    authors: Hanson JR

    更新日期:2003-06-01 00:00:00

  • The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs.

    abstract::Covering: 2000 up to 2020 Few classes of natural products have inspired as many chemists and biologists as have the iboga alkaloids. This family of monoterpenoid indole alkaloids includes the anti-addictive compound ibogaine as well as catharanthine, a precursor to the chemotherapeutic vinblastine. Despite being known...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/d0np00033g

    authors: Iyer RN,Favela D,Zhang G,Olson DE

    更新日期:2020-08-14 00:00:00

  • Fungal polyketide biosynthesis - a personal perspective.

    abstract::This Viewpoint article provides a personal viewpoint of research in the area of fungal polyketide biosynthesis. It spans the period from the first applications and subsequent development of modern stable-isotope labelling methods, the isolation, sequencing and expression of PKS genes, biochemical and structural charac...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c4np00065j

    authors: Simpson TJ

    更新日期:2014-10-01 00:00:00

  • The biosynthesis of adenosylcobalamin (vitamin B12).

    abstract::Vitamin B12, or cobalamin, is one of the most structurally complex small molecules made in Nature. Major progress has been made over the past decade in understanding how this synthesis is accomplished. This review covers some of the most important findings that have been made and provides the reader with a complete de...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b108967f

    authors: Warren MJ,Raux E,Schubert HL,Escalante-Semerena JC

    更新日期:2002-08-01 00:00:00

  • Naturally-occurring nitro compounds.

    abstract::Naturally-occurring nitro compounds display great structural diversity, and a wide range of biological activities. This review summarizes current information on the structures of naturally-occurring nitro compounds and on the biosynthesis of the nitro group. ...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c0np00024h

    authors: Parry R,Nishino S,Spain J

    更新日期:2011-01-01 00:00:00

  • Cytochromes P450 for natural product biosynthesis in Streptomyces: sequence, structure, and function.

    abstract::Covering: up to January 2017Cytochrome P450 enzymes (P450s) are some of the most exquisite and versatile biocatalysts found in nature. In addition to their well-known roles in steroid biosynthesis and drug metabolism in humans, P450s are key players in natural product biosynthetic pathways. Natural products, the most ...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c7np00034k

    authors: Rudolf JD,Chang CY,Ma M,Shen B

    更新日期:2017-08-30 00:00:00

  • Molecular recognition in copper trafficking.

    abstract::From the basic export of unwanted metal ions in simple organisms to the complex orchestration of metal handling and usage in higher eukaryotes, cellular systems are based on a variety of molecular mechanisms that constrain the right metal to bind to the right protein partner at the right time when needed. A failure to...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/b906678k

    authors: Banci L,Bertini I,McGreevy KS,Rosato A

    更新日期:2010-05-01 00:00:00

  • Natural products and Pharma 2011: strategic changes spur new opportunities.

    abstract::Although natural products have been marginalized by major pharmaceutical companies over the last 20-30 years, the changing landscape of drug discovery now favors a greatly enhanced role for Nature's privileged structures. Screening for drug leads in phenotypic screens provides the best opportunity to realize the value...

    journal_title:Natural product reports

    pub_type: 杂志文章,评审

    doi:10.1039/c1np00033k

    authors: Carter GT

    更新日期:2011-10-01 00:00:00