Rearranged ergostane-type natural products: chemistry, biology, and medicinal aspects

Duecker, Fenja L.; Reuß, Franziska; Heretsch, Philipp

doi:10.1039/c8ob02325e

Cited by 47 publications

(47 citation statements)

References 32 publications

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“…Various enzymatic or semisynthetic methods have also been exploited in the synthesis of steroids [2][3][4]. A more challenging synthesis of secosteroids with unique broken tetracyclic carbon skeletons and abeo-steroids with migrated bonds has received attention only recently [5,6]. As the bond cleavage may occur at the 5,6-, 9,11-, 9,10-, 8,9-, 8,14-or 13,17-positions (Figure 1A), the selection of synthetic methods for secosteroids is wide.…”

Section: Introductionmentioning

confidence: 99%

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

Kõllo¹,

Kasari²,

Kasari³

et al. 2021

Beilstein J. Org. Chem.

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A method for the synthesis of 9,11-secosteroids starting from the natural corticosteroid cortisol is described. There are two key steps in this approach, combining chemistry and synthetic biology. Stereo- and regioselective hydroxylation at C9 (steroid numbering) is carried out using whole-cell biocatalysis, followed by the chemical cleavage of the C–C bond of the vicinal diol. The two-step method features mild reaction conditions and completely excludes the use of toxic oxidants.

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Section: Introductionmentioning

confidence: 99%

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

Kõllo¹,

Kasari²,

Kasari³

et al. 2021

Beilstein J. Org. Chem.

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“…Sterols have long been regarded as important compounds in drug discovery because of their varied biological activities, such as cytotoxicity, neurite outgrowth-promoting activity, anti-NO production and acetylcholinesterase inhibition [ 103 ]. Steroids are predominant secondary metabolites with various structural features, both their isolation and synthesis have gained attention in recent years [ 104 , 105 ].…”

Section: Secondary Metabolites From Stereum Andmentioning

confidence: 99%

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

Tian

Zhao

et al. 2020

Microorganisms

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Natural metabolites from microorganisms play significant roles in the discovery of drugs, both for disease treatments in humans, and applications in agriculture. The Basidiomycetes Stereum genus has been a source of such bioactive compounds. Here we report on the structures and activities of secondary metabolites from Stereum. Their structural types include sesquiterpenoids, polyketides, vibralactones, triterpenoids, sterols, carboxylic acids and saccharides. Most of them showed biological activities including cytotoxic, antibacterial, antifungal, antiviral, radical scavenging activity, autophagy inducing activity, inhibiting pancreatic lipase against malarial parasite, nematocidal and so on. The syntheses of some metabolites have been studied. In this review, 238 secondary metabolites from 10 known species and various unidentified species of Stereum were summarized over the last seven decades.

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“…A third mode of complexity generation is the cleavage of a C−C bond leading to a truncated or ring‐opened carbon skeleton [9–16] . This process gives rise to nor ‐ and seco ‐terpenoids, and leads to increased chemical diversity in a cluster of related secondary metabolites by modification of the parent carbocyclic core.…”

Section: Introductionmentioning

confidence: 99%

seco‐Labdanes: A Study of Terpenoid Structural Diversity Resulting from Biosynthetic C−C Bond Cleavage

Grant

Brimble

2021

Chemistry A European J

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The cleavage of a C−C bond is a complexity generating process, which complements oxidation and cyclisation events in the biosynthesis of terpenoids. This process leads to increased structural diversity in a cluster of related secondary metabolites by modification of the parent carbocyclic core. In this review, we highlight the diversifying effect of C−C bond cleavage by examining the literature related to seco‐labdanes—a class of diterpenoids arising from such C−C bond cleavage events.

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Rearranged ergostane-type natural products: chemistry, biology, and medicinal aspects

Abstract: Rearranged ergostane-type natural products are structurally intriguing and exhibit biologically relevant properties.

Cited by 47 publications

References 32 publications

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

In Depth Natural Product Discovery from the Basidiomycetes Stereum Species

seco‐Labdanes: A Study of Terpenoid Structural Diversity Resulting from Biosynthetic C−C Bond Cleavage

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