Xylarins A–D, Two Pairs of Diastereoisomeric Isoindoline Alkaloids from the Endolichenic Fungus <i>Xylaria</i> sp.

Xu, Ke; Li, Ruijuan; Zhu, Rongxiu; Li, Xiaobin; Xu, Yuliang; He, Qiaobian; Xie, Fei; Qiao, Yanan; Luan, Xiaoyi; Lou, Hongxiang

doi:10.1021/acs.orglett.1c02730

Cited by 11 publications

(12 citation statements)

References 29 publications

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“…In 2021, Xu et al reported the isolation of two pairs of diastereoisomeric isoindoline alkaloids, xylarins A-D (348-351), from the endolichenic fungus Xylaria sp., which was obtained from the lichen of Parmelia sp. [81]. Among them, compounds 348 and 349 possess an unprecedented skeleton comprising a complex 5/6/5-5/6 polycyclic ring system and exist as a pair of diastereoisomers, while another pair of diastereoisomers, diastereoisomers 350 and 351, contain an additional N,N-dimethylaniline moiety at the C-3 ′ position.…”

Section: Alkaloids and Their Biological Activitiesmentioning

confidence: 99%

Endolichenic Fungi: A Promising Medicinal Microbial Resource to Discover Bioactive Natural Molecules—An Update

Zhang,

Ran,

et al. 2024

JoF

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Lichens are some of the most unique fungi and are naturally encountered as symbiotic biological organisms that usually consist of fungal partners (mycobionts) and photosynthetic organisms (green algae and cyanobacteria). Due to their distinctive growth environments, including hot deserts, rocky coasts, Arctic tundra, toxic slag piles, etc., they produce a variety of biologically meaningful and structurally novel secondary metabolites to resist external environmental stresses. The endofungi that live in and coevolve with lichens can also generate abundant secondary metabolites with novel structures, diverse skeletons, and intriguing bioactivities due to their mutualistic symbiosis with hosts, and they have been considered as strategically significant medicinal microresources for the discovery of pharmaceutical lead compounds in the medicinal industry. They are also of great importance in the fundamental research field of natural product chemistry. In this work, we conducted a comprehensive review and systematic evaluation of the secondary metabolites of endolichenic fungi regarding their origin, distribution, structural characteristics, and biological activity, as well as recent advances in their medicinal applications, by summarizing research achievements since 2015. Moreover, the current research status and future research trends regarding their chemical components are discussed and predicted. A systematic review covering the fundamental chemical research advances and pharmaceutical potential of the secondary metabolites from endolichenic fungi is urgently required to facilitate our better understanding, and this review could also serve as a critical reference to provide valuable insights for the future research and promotion of natural products from endolichenic fungi.

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Section: Alkaloids and Their Biological Activitiesmentioning

confidence: 99%

Endolichenic Fungi: A Promising Medicinal Microbial Resource to Discover Bioactive Natural Molecules—An Update

Zhang,

Ran,

et al. 2024

JoF

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“…Xylariaceae is one of the largest, most commonly encountered, and highly diverse fungal families of the Ascomycota [4]. The genus Xylaria, belonging to the family Xylariaceae, is medicinal fungi commonly found in decaying plant tissues and is widely distributed in temperate, tropical, and subtropical regions [5,6]. So far, more than 200 bioactive compounds (>100 new ones) were isolated from Xylaria, including cytochalasins, α-pyrones, cyclopeptides, terpenoids, lactones, and succinic acid derivatives [7].…”

Section: Introductionmentioning

confidence: 99%

New Pyranone Derivatives and Sesquiterpenoid Isolated from the Endophytic Fungus Xylaria sp. Z184

Zhang,

Jin,

Yan

et al. 2024

Molecules

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The fungus Xylaria sp. Z184, harvested from the leaves of Fallopia convolvulus (L.) Á. Löve, has been isolated for the first time. Chemical investigation on the methanol extract of the culture broth of the titles strain led to the discovery of three new pyranone derivatives, called fallopiaxylaresters A–C (1–3), and a new bisabolane-type sesquiterpenoid, named fallopiaxylarol A (4), along with the first complete set of spectroscopic data for the previously reported pestalotiopyrone M (5). Known pyranone derivatives (6–11), sesquiterpenoids (12–14), isocoumarin derivatives (15–17), and an aromatic allenic ether (18) were also co-isolated in this study. All new structures were elucidated by the interpretation of HRESIMS, 1D, 2D NMR spectroscopy, and quantum chemical computation approach. The in vitro antimicrobial, anti-inflammatory, and α-glucosidase-inhibitory activities of the selected compounds and the crude extract were evaluated. The extract was shown to inhibit nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells, with an inhibition rate of 77.28 ± 0.82% at a concentration of 50 μg/mL. The compounds 5, 7, and 8 displayed weak antibacterial activity against Staphylococcus areus subsp. aureus at a concentration of 100 μM.

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“…The isoindole skeleton is ubiquitous in a large variety of biologically active molecules and natural products, showing prominent biological and pharmaceutical activities . Over the past years, many efforts have been made to develop efficient methods for synthesizing isoindoles and isoindolines, including metal-catalyzed enantioselective C–H activation .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Isoindole N-Oxides by Palladium-Catalyzed C–H Functionalization of Aldonitrones

Brześkiewicz

Loska

2023

J. Org. Chem.

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A palladium-catalyzed strategy for isoindole N-oxide ring construction by C−H functionalization of aldonitrones is described. Our protocol is of general character, providing isoindole N-oxides with a variety of functional groups, including very sterically congested products. Further transformations into spirocyclic isoindolines, isoindoles, or a polycyclic isoquinolinium salt have been demonstrated as well. A mechanistic study suggests that the catalytic process proceeds via a Heck-type addition to the double C�N bond.

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Xylarins A–D, Two Pairs of Diastereoisomeric Isoindoline Alkaloids from the Endolichenic Fungus Xylaria sp.

Cited by 11 publications

References 29 publications

Endolichenic Fungi: A Promising Medicinal Microbial Resource to Discover Bioactive Natural Molecules—An Update

Endolichenic Fungi: A Promising Medicinal Microbial Resource to Discover Bioactive Natural Molecules—An Update

New Pyranone Derivatives and Sesquiterpenoid Isolated from the Endophytic Fungus Xylaria sp. Z184

Synthesis of Isoindole N-Oxides by Palladium-Catalyzed C–H Functionalization of Aldonitrones

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