Oridamycins A and B, Anti-<i>Saprolegnia parasitica</i> Indolosesquiterpenes Isolated from <i>Streptomyces</i> sp. KS84

Takada, Kentaro; Kajiwara, Hisatsugu; Imamura, Nobutaka

doi:10.1021/np1000522

Cited by 70 publications

(50 citation statements)

References 20 publications

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“…& Diels). ISTs are reminiscent of plant‐derived natural products, as described above, and a limited number of ISTs, such as oridamycins, xiamycins, and drimentines, have been isolated from Actinomyces species in the past ten years.…”

Section: Figurementioning

confidence: 99%

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

et al. 2018

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Indole sesquiterpene sespendole, which has been isolated from the filamentous fungus Pseudobotrytis terrestris FKA-25, is a specific inhibitor of lipid droplet synthesis in mouse macrophages. The biosynthetic pathway that involves genes encoding six enzymes (spdEMBQHJ) was elucidated through heterologous expression of spd genes in Aspergillus oryzae, biotransformation experiments, and in vitro enzymatic reactions with a recombinant protein, thereby revealing the mechanism underlying the characteristic modification on the indole ring, catalyzed by a set of prenyltransferase (SpdE)/cytochrome P450 (SpdJ) enzymes. Functional analysis of the homologous genes encoding these enzymes involved in the biosynthesis of lolitrem allowed a biosynthetic pathway for the bicyclic ring skeleton fused to the indole ring to be proposed.

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Section: Figurementioning

confidence: 99%

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

et al. 2018

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“…Sespendole (544) was isolated from Pseudobotrytis terrestris FKA-25 as an inhibitor of lipid droplet formation in macrophages [353][354][355]. strain KS84 [358]. Feeding experiments revealed that sespendole was formed from the condensation of a farnesyl residue and an anthranilate-derived indole-3-glycerol phosphate residue [356].…”

Section: Occurrence Classification and Biosynthesis Of Amino Acid-mmentioning

confidence: 99%

Drimane-Related Merosesquiterpenoids, a Promising Library of Metabolites for Drug Development

Shan

Ying

et al. 2015

Studies in Natural Products Chemistry

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“…These ‘plant-like’ terpenoids are actually produced by bacterial endophytes ( Streptomyces spp.). Endowed with a range of antiviral151617 and antimicrobial activities18192021222324 xiamycin and its congeners may aid in protecting the plant host from infections1620.…”

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confidence: 99%

Cryptic indole hydroxylation by a non-canonical terpenoid cyclase parallels bacterial xenobiotic detoxification

et al. 2017

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Terpenoid natural products comprise a wide range of molecular architectures that typically result from C–C bond formations catalysed by classical type I/II terpene cyclases. However, the molecular diversity of biologically active terpenoids is substantially increased by fully unrelated, non-canonical terpenoid cyclases. Their evolutionary origin has remained enigmatic. Here we report the in vitro reconstitution of an unusual flavin-dependent bacterial indoloterpenoid cyclase, XiaF, together with a designated flavoenzyme-reductase (XiaP) that mediates a key step in xiamycin biosynthesis. The crystal structure of XiaF with bound FADH2 (at 2.4 Å resolution) and phylogenetic analyses reveal that XiaF is, surprisingly, most closely related to xenobiotic-degrading enzymes. Biotransformation assays show that XiaF is a designated indole hydroxylase that can be used for the production of indigo and indirubin. We unveil a cryptic hydroxylation step that sets the basis for terpenoid cyclization and suggest that the cyclase has evolved from xenobiotics detoxification enzymes.

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Oridamycins A and B, Anti-Saprolegnia parasitica Indolosesquiterpenes Isolated from Streptomyces sp. KS84

Cited by 70 publications

References 20 publications

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

Drimane-Related Merosesquiterpenoids, a Promising Library of Metabolites for Drug Development

Cryptic indole hydroxylation by a non-canonical terpenoid cyclase parallels bacterial xenobiotic detoxification

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