Structure elucidation and NMR assignments of daldinone E and rickenyl F from the fungus <i>Hypoxylon</i> sp. DWS T‐P‐6

Shi, Hong; Feng, Bao Min; Chen, Gang; Bai, Jiao; Hua, Hui; Zhao, Dan; Wang, Hai Feng; Pei, Yue Hu

doi:10.1002/mrc.4429

Cited by 4 publications

(4 citation statements)

References 5 publications

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“…29 Daldinone E (27) was isolated in 2014 from Daldinia sp., 23 daldinones F (28) and G (29) were isolated in 2015 from D. eschscholzii, 25,30 and 28 is additionally produced from Annulohypoxylon annularum. 27 Daldinones H (30) and J (32) were found in Annulohypoxylon sp. in 2017.…”

Section: ■ Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

“…d 31 is an artifact formed during chromatography of 30. 31a e 33 was originally named daldinone E 32 and is here renamed to avoid misunderstanding. dichroism (ECD) spectra were compared with the respective calculated values.…”

Section: ■ Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

“… d 31 is an artifact formed during chromatography of 30 e 33 was originally named daldinone E and is here renamed to avoid misunderstanding. …”

Section: Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

“…The concomitantly published daldinone I ( 31 ) is not a natural product but was found to be an artifact formed from 30 during its chromatographic purification. A further toxin, 33 , was isolated in 2016 from Hypoxylon sp . and was erroneously assigned with the already allocated name daldinone E. We herein recommend to abolish this duplicate name and instead name this compound daldinone K. Truncatone ( 34 ) was isolated in 2005 from Hypoxylon truncatum and later from H. annulatum and other Hypoxylon sp., from Annulohypoxylon stygium , and from further Annulohypoxylon sp. , 34 was later renamed truncatone A to distinguish it from truncatones B–D ( 35 – 37 ), which were isolated in 2016 from Annulohypoxylon sp .…”

Section: Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

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Benzo[j]fluoranthene-Derived Natural Products

Podlech,

Gutsche

2023

J. Nat. Prod.

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In this overview the literature on benzo[j]fluoranthene-derived toxins produced by fungi is discussed with a view on isolation, structure, biological activities, biosynthesis, and total syntheses of the natural products. This class of compounds consists until now of 33 naturally occurring compounds, where 25 are chiral and eight contain no stereogenic centers. The relative configuration of xylarenol was clarified by comparison of experimental and calculated ECD spectra, and absolute configurations of four toxins were corrected. The compounds show various biological activities including antibiotic and cytotoxic properties.

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Section: ■ Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

Section: ■ Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

“… d 31 is an artifact formed during chromatography of 30 e 33 was originally named daldinone E and is here renamed to avoid misunderstanding. …”

Section: Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

Section: Chiral Benzo[j]fluoranthene-derived Natural Productsmentioning

confidence: 99%

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Benzo[j]fluoranthene-Derived Natural Products

Podlech,

Gutsche

2023

J. Nat. Prod.

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Total Synthesis of Bulgarein

Swieca

Spiteller

2022

Eur J Org Chem

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Here we report an efficient and short total synthesis of bulgarein (1), a natural compound from Bulgaria inquinans with cytotoxic activity. Key steps in the total synthesis are a Suzuki-Miyaura coupling reaction of two substituted naphthalene derivates followed by a polyphosphoric acid (PPA) mediated condensation reaction to form the benzo[j]fluoranthene skeleton. Bulgarein (1) was achieved over 4 steps with an overall yield of 25 %.

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