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Search for "meroterpenoid" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.

Production of non-natural 5-methylorsellinate-derived meroterpenoids in Aspergillus oryzae

  • Jia Tang,
  • Yixiang Zhang and
  • Yudai Matsuda

Beilstein J. Org. Chem. 2024, 20, 638–644, doi:10.3762/bjoc.20.56

Graphical Abstract
  • and three additional biosynthetic enzymes for the formation of (6R,10′R)-epoxyfarnesyl-5-MOA methyl ester, which served as a non-native substrate for four terpene cyclases from DMOA-derived meroterpenoid pathways. As a result, we successfully generated six unnatural 5-MOA-derived meroterpenoid species
  • -dimethylorsellinic acid (DMOA) serves as a precursor for a wide array of structurally diverse meroterpenoid species [7][8]. The fully substituted nature of DMOA leads to dearomatizing prenylation during the biosynthesis of DMOA-derived meroterpenoids (Figure 1A), facilitating the rearrangement reactions of the
  • into distinct cyclized products (Figure 1C) [17][18][19]. In addition, a recent study has demonstrated that some of these transmembrane terpene cyclases can accept synthetic substrate analogues to yield several unnatural meroterpenoid molecules [20]. By mimicking nature’s strategy to synthesize diverse
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Published 20 Mar 2024

Recent developments in the engineered biosynthesis of fungal meroterpenoids

  • Zhiyang Quan and
  • Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

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  • members exhibit beneficial biological activities. This mini-review highlights recent advances in the engineered biosynthesis of meroterpenoid compounds with C15 and C20 terpenoid moieties, with the reconstruction of fungal meroterpenoid biosynthetic pathways in heterologous expression hosts and the
  • will be discussed as examples of engineering biosynthetic pathways and key enzymes involved in fungal meroterpenoid biosynthesis. Furthermore, a construction of the artificial biosynthetic pathway composed of the fungal meroterpenoids pathway and the pathway from other species, in fungal host
  • Aspergillus oryzae, will be also introduced. Review Standard reactions of fungal meroterpenoid biosynthesis The skeletal diversity within this group of compounds arises from polyketide synthesis, prenyl transfer, terpenoid cyclizations, and post-cyclization modifications [5]. In these reactions, terpenoid
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Review
Published 13 Mar 2024

Combining the best of both worlds: radical-based divergent total synthesis

  • Kyriaki Gennaiou,
  • Antonios Kelesidis,
  • Maria Kourgiantaki and
  • Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

Graphical Abstract
  • -fused tetracycle instead, were reported to possess NF-kB-inhibitory activity and anticancer activity against NCI H-929 cancer cell lines (Scheme 6) [39]. In 2021 Lu’s group reported the total synthesis of members of both meroterpenoid families based on a highly chemoselective α-alkylation in the
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Review
Published 02 Jan 2023

Natural products in the predatory defence of the filamentous fungal pathogen Aspergillus fumigatus

  • Jana M. Boysen,
  • Nauman Saeed and
  • Falk Hillmann

Beilstein J. Org. Chem. 2021, 17, 1814–1827, doi:10.3762/bjoc.17.124

Graphical Abstract
  • its role in conidial protection in the environment [105]. Fumagillin Fumagillin (9) belongs to the meroterpenoid class of secondary metabolites. It was discovered in 1949 from A. fumigatus [127]. Strikingly, unlike other secondary metabolite synthesizing clusters, the fumagillin biosynthetic cluster
  • meroterpenoid class of secondary metabolites. It was originally isolated from A. fumigatus, but later several other pyripyropene A producing members of Aspergillus and Penicillium ssp. were identified [98][99][170][171]. In A. fumigatus 9 genes form a pyripyropene A (pyr) biosynthetic cluster that spans a 23 kb
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Published 28 Jul 2021

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

  • Heather J. Lacey,
  • Cameron L. M. Gilchrist,
  • Andrew Crombie,
  • John A. Kalaitzis,
  • Daniel Vuong,
  • Peter J. Rutledge,
  • Peter Turner,
  • John I. Pitt,
  • Ernest Lacey,
  • Yit-Heng Chooi and
  • Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

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  • side chains present in the (iso)nanangenines could be derived either from a fatty acid synthase (FAS) or polyketide synthase (PKS). For example, in aflatoxin biosynthesis, the hexanoyl started unit is supplied by a FAS [31], while in the meroterpenoid fumagillin biosynthesis, the unsaturated acyl chain
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Published 05 Nov 2019

Synthesis of acremines A, B and F and studies on the bisacremines

  • Nils Winter and
  • Dirk Trauner

Beilstein J. Org. Chem. 2019, 15, 2271–2276, doi:10.3762/bjoc.15.219

Graphical Abstract
  • acremines A and B. The dimerization of acremine F to bisacremine E was investigated but could not be achieved, shedding light on the formation of the acremine dimers in nature. Keywords: meroterpenoid; natural product; selective oxidation; total synthesis; Introduction Endophytic fungi grow in a symbiotic
  • relationship with their plant hosts [1], which is mediated by secondary metabolites [2]. In 2005, Torta and co-workers reported the isolation of six meroterpenoid natural products, acremines A–F from A20, a strain of Acreonium byssoides, isolated from grapevine leaves that were artificially inoculated with
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Published 23 Sep 2019
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