Sesquiterpenoids from <i>Streptomyces anulatus</i> isolated from <i>Giraffa camelopardalis</i> feces

Ding, Nan; Han, Li; Jiang, Yi; Li, Gui-Ding; Liu, Jiang; Mu, Yu; Huang, Xueshi

doi:10.1002/mrc.4709

Cited by 11 publications

(17 citation statements)

References 22 publications

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“…Only recently was (4S,5S,7R,10S)-4β,10α-eudesmane-5β,11-diol (6) reported as a bacterial sesquiterpene from Streptomyces anulatus isolated from Giraf fa camelopardalis. 18 The 1 H NMR spectrum of 7 exhibits signals of an exomethylene (δ 4.96, δ 4.82, H-15), two oxygen-bonding methylenes (δ 3.92, H-1, δ 3.49, H-6), three methyl groups (δ 0.82, Me-12, δ 0.92, Me-13, δ 0.85 Me-14), and other aliphatic residues. The 13 C NMR spectrum shows 15 carbons signals, including those for two olefinic (δ 145.4, δ 114.2) and two oxygen-bonding carbons (δ 68.1, δ 67.1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Oxygenated Geosmins and Plant-like Eudesmanes from a Bacterial Mangrove Endophyte

Ding

Hertweck

2020

J. Nat. Prod.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Oxygenated Geosmins and Plant-like Eudesmanes from a Bacterial Mangrove Endophyte

Ding

Hertweck

2020

J. Nat. Prod.

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“…[26] Only recently, the same compound was detected as a metabolite of Streptomyces anulatus isolated from Giraffa camelopardalis feces. [30] 3 | CONCLUSIONS…”

Section: Resultsmentioning

confidence: 99%

Plant‐like cadinane sesquiterpenes from an actinobacterial mangrove endophyte

Ding

Görls

Hertweck

2020

Magnetic Reson in Chemistry

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Cadinanes are typical plant sesquiterpenes with a broad range of biological functions. We report the isolation of three cadinanes (1-3) from a bacterial endophyte (Streptomyces sp.) of the mangrove plant Bruguiera gymnorrhiza. The structures of two new cadinenes, (+)-11-hydroxy-epicubenol (1) and (+)-12-hydroxy-epicubenol (2) were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry. The bacterial product (+)-11-hydroxyepicubenol was elucidated to be an enantiomer of the plant product pubinernoid C. (+)-12-Hydroxy-epicubenol was established as a diastereomer of the basidiomycete product trichapargin A. In addition, a crystal structure analysis corroborated the structure and configuration of 5,11-epoxy-10-cadinanol (3), a cadinane cycloether initially described as a natural product from liverwort. The discovery of oxygenated cadinanes from a bacterial endophyte may set the basis for the production of cadinanes by bacterial fermentation.

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“…Three caryolane analogs of bacaryolanes A–C ( 12 – 14 ) were isolated from a mangrove endophyte Streptomyces sp [31] . Bacaryolanes B ( 13 ) and C ( 14 ), caryolan‐1,7 α ‐diol ( 10 ), and caryolan‐1,6 β ,9 β ‐triol ( 15 ) were also reported from Streptomyces anulatus (YIM 101882) isolated from Giraffa camelopardalis feces [32] . In spite of the origins, the tricyclic skeleton of caryolanes is relatively conserved and difference occurs in the position and/or degree of oxidation.…”

Section: Resultsmentioning

confidence: 99%

“…[31] Bacaryolanes B (13) and C (14), caryolan-1,7α-diol (10), and caryolan-1,6β,9β-triol (15) were also reported from Streptomyces anulatus (YIM 101882) isolated from Giraffa camelopardalis feces. [32] In spite of the origins, the tricyclic skeleton of caryolanes is relatively conserved and difference occurs in the position and/or degree of oxidation. Ding et al has proposed two diverging terpene pathways for plant and bacterial caryolanes, which produce the caryolan-1-ol intermediate with opposite absolute configurations.…”

Section: Relationship Between Structures and Origin Of Caryolanesmentioning

confidence: 99%

Micaryolanes A and B, Two New Caryolane‐Type Sesquiterpenoids from Marine Streptomyces sp. AH25

Zhu

Zhang

et al. 2020

Chemistry & Biodiversity

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Caryolanes, known as β-caryophyllene alcohols, are widely occurring sesquiterpenes in plants. From the cultures of marine Streptomyces sp. AH25, two new caryolane sesquiterpenes, micaryolanes A and B (1 and 2), together with caryolan-1,9β-diol (3) were isolated. Their structures were elucidated by extensive analyses of HR-MS and NMR spectroscopic data. The absolute configurations were assigned via the CD data of the in situ formed [Rh 2 (OCOCF 3) 4 ] complex and supported by comparison of experimental and calculated specific rotation values. Compounds 1-3 exhibited no activities against Hep3B or MG-63 cell lines or against Gram-positive and Gramnegative bacteria. The results not only enriched the caryolane family, but also proved bacteria as a productive source of terpene metabolites.

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Sesquiterpenoids from Streptomyces anulatus isolated from Giraffa camelopardalis feces

Cited by 11 publications

References 22 publications

Oxygenated Geosmins and Plant-like Eudesmanes from a Bacterial Mangrove Endophyte

Oxygenated Geosmins and Plant-like Eudesmanes from a Bacterial Mangrove Endophyte

Plant‐like cadinane sesquiterpenes from an actinobacterial mangrove endophyte

Micaryolanes A and B, Two New Caryolane‐Type Sesquiterpenoids from Marine Streptomyces sp. AH25

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