Cyclic Sesquiterpene–Flavanone [4+2] Hybrids, Syzygioblanes A–C, Found in an Indonesian Traditional Medicine, “Jampu Salo” (Syzygium oblanceolatum) DOI

N. Koga,

Yohei Saito, Katsunori Miyake

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4302 - 4307

Published: May 10, 2024

A plant used in an Indonesian traditional herbal medicine as a diabetes treatment and known locally "Jampu Salo" was collected on Sulawesi Island, Indonesia. It identified Syzygium oblanceolatum (C. B. Rob.) Merr. (Myrtaceae) found for the first time Sulawesi; it previously reported only eastern Philippines Borneo. phytochemical study of S. led to isolation three unprecedented meroterpenoids, syzygioblanes A–C (1–3, respectively). These compounds might be biosynthesized through [4+2] cycloaddition various germacrane-based cyclic sesquiterpenoids with flavone desmethoxymatteucinol form spiro skeleton. The unique complex structures were elucidated by microcrystal electron diffraction analysis addition general analytical techniques such high-resolution mass spectrometry, nuclear magnetic resonance methods, infrared spectroscopy. Synchrotron X-ray calculations electronic circular dichroism spectra helped determine absolute configurations. newly isolated exhibited collateral sensitivity more strongly inhibit growth multidrug resistant tumor cell line compared chemosensitive line.

Language: Английский

Genomic characterization of three marine fungi, including Emericellopsis atlantica sp. nov. with signatures of a generalist lifestyle and marine biomass degradation DOI Creative Commons
Ole Christian Hagestad, Lingwei Hou, Jeanette H. Andersen

et al.

IMA Fungus, Journal Year: 2021, Volume and Issue: 12(1)

Published: Aug. 9, 2021

ABSTRACT Marine fungi remain poorly covered in global genome sequencing campaigns; the 1000 fungal genomes (1KFG) project attempts to shed light on diversity, ecology and potential industrial use of overlooked resolved taxa. This study characterizes three marine fungi: Emericellopsis sp. TS7, wood-associated Amylocarpus encephaloides algae-associated Calycina marina. These species were sequenced their genomic features, biosynthetic phylogenetic placement using multilocus data. C. marina placed Helotiaceae Pezizellaceae (Helotiales) , respectively, based a 15-gene analysis. two had fewer gene clusters (BGCs) carbohydrate active enzymes (CAZymes) than TS7 isolate. ( Hypocreales Ascomycota ) was isolated from sponge Stelletta normani . A six-gene analysis isolate clade morphological examination confirmed that represents new species, which is described here as E. atlantica Analysis its CAZyme repertoire culturing experiment one terrestrial substrates indicated psychrotrophic generalist fungus able degrade several types biomass. FungiSMASH revealed presence 35 BGCs including, eight non-ribosomal peptide synthases (NRPSs), six NRPS-like, polyketide synthases, nine terpenes hybrid, mixed or other clusters. Of these BGCs, only five homologous with characterized BGCs. The unknown sets large set stage for further investigations monotypic genus represent first published filamentous are restricted occurrence habitat form thus valuable resource community can be used studying ecological adaptions comparative genomics.

Language: Английский

Citations

29

Engineering fungal terpene biosynthesis DOI

Zhiyong Yin,

Jeroen S. Dickschat

Natural Product Reports, Journal Year: 2022, Volume and Issue: 40(1), P. 28 - 45

Published: May 23, 2022

This review summarises recent research on metobolic engineering approaches towards terpenes, including work to investigate unknown pathways and improve accessibility of known compounds.

Language: Английский

Citations

22

Spiroluchuene A Synthase: A Cyclase from Aspergillus luchuensis Forming a Spirotetracyclic Diterpene DOI Creative Commons
Zhengyu Huang, Kizerbo A. Taizoumbe, Cheng-Qin Liang

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(52)

Published: Nov. 14, 2023

The diterpene synthase AlTS was identified from Aspergillus luchuensis. catalyses the formation of hydrocarbon spiroluchuene A, which exhibits a novel skeleton characterised by spirocyclic ring system. cyclisation mechanism towards this compound elucidated through isotopic labelling experiments in conjunction with DFT calculations and metadynamic simulations. biosynthetic intermediate luchudiene, besides derivative B, captured an enzyme variant obtained site-directed mutagenesis. With its 10-membered luchudiene is structurally related to germacrenes can undergo Cope rearrangement luchuelemene.

Language: Английский

Citations

12

Biosynthesis of Cosmosporasides Reveals the Assembly Line for Fungal Hybrid Terpenoid Saccharides DOI Open Access

Guanyin Yuan,

Jin‐Mei Zhang,

Qing‐Dong Xu

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(41)

Published: Aug. 30, 2023

Fungal hybrid terpenoid saccharides constitute a new and growing family of natural products with significant biomedical agricultural activities. One representative is the cosmosporasides, which feature oxidized units saccharide moieties; however, assembly line these building blocks has been elusive. Herein, cos cluster from Fusarium orthoceras was discovered for synthesis cosmosporaside C (1) by genome mining. A UbiA intramembrane prenyltransferase (UbiA-type PT), multifunctional cytochrome P450, an α,β-hydrolase, acetyltransferase, dimethylallyl transferase (DMAT-type PT) glycosyltransferase function cooperatively in scaffold 1 using primary central metabolites. The absolute configuration at C4, C6 C7 also established. Our work clarifies unexpected functions UbiA-type DMAT-type PTs provides example understanding synthetic logic fungi.

Language: Английский

Citations

11

Cyclic Sesquiterpene–Flavanone [4+2] Hybrids, Syzygioblanes A–C, Found in an Indonesian Traditional Medicine, “Jampu Salo” (Syzygium oblanceolatum) DOI

N. Koga,

Yohei Saito, Katsunori Miyake

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4302 - 4307

Published: May 10, 2024

A plant used in an Indonesian traditional herbal medicine as a diabetes treatment and known locally "Jampu Salo" was collected on Sulawesi Island, Indonesia. It identified Syzygium oblanceolatum (C. B. Rob.) Merr. (Myrtaceae) found for the first time Sulawesi; it previously reported only eastern Philippines Borneo. phytochemical study of S. led to isolation three unprecedented meroterpenoids, syzygioblanes A–C (1–3, respectively). These compounds might be biosynthesized through [4+2] cycloaddition various germacrane-based cyclic sesquiterpenoids with flavone desmethoxymatteucinol form spiro skeleton. The unique complex structures were elucidated by microcrystal electron diffraction analysis addition general analytical techniques such high-resolution mass spectrometry, nuclear magnetic resonance methods, infrared spectroscopy. Synchrotron X-ray calculations electronic circular dichroism spectra helped determine absolute configurations. newly isolated exhibited collateral sensitivity more strongly inhibit growth multidrug resistant tumor cell line compared chemosensitive line.

Language: Английский

Citations

4