Triquinane Sesquiterpene Glycosides from the Basidiomycete <i>Antrodiella zonata</i>

Gao, Meijia; Wu, Feng; Teng, Si-Qiong; Chen, He‐Ping; Li, Zheng-Hui; He, Juan; Feng, Tao; Liu, Ji-Kai

doi:10.1021/acs.jnatprod.3c00200

Cited by 5 publications

(1 citation statement)

References 16 publications

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“…N-glycosides are compounds in which an aglycone is connected to a sugar component through a nitrogen atom. [1] Unlike the numerous O-glycosides [2][3][4][5][6][7][8] that have been isolated from natural sources, N-glycosides are not so common in the nature. To the best of our knowledge, only 30 natural N-glycosides have been isolated and characterized between 1980 and 2023.…”

Section: Introductionmentioning

confidence: 99%

Research progress in natural N-glycosides and synthetic methodologies for the formation of N-glycosidic bonds

Xia,

Xu,

Herron

et al. 2024

Sci Tradit Chin Med

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N-glycosides comprise a broad range of compounds, some of which have demonstrated a variety of bioactivities, such as antiviral, antitumor, and antibacterial activities. Serving as essential building blocks for DNA and RNA, nucleosides are a particularly important subclass of N-glycosides. Accordingly, natural N-glycosides and their analogs have garnered great interests of both organic and pharmaceutical chemists, who have developed numerous synthetic methods for the preparation of N-glycosides. By reviewing the natural N-glycosides published between 1980 and 2023, this article summarizes current strategies for synthesizing N-glycosides, aiming to provide support for the development and research of N-glycosides.

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Section: Introductionmentioning

confidence: 99%

Research progress in natural N-glycosides and synthetic methodologies for the formation of N-glycosidic bonds

Xia,

Xu,

Herron

et al. 2024

Sci Tradit Chin Med

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Metathesis Mastery: Crafting Linear Triquinane Frameworks for Natural Product Synthesis

Cheekatla,

Seema,

Marri

et al. 2024

ChemistrySelect

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Organic and medicinal chemists have shown great interest in developing simple approaches for creating linear triquinane structures, as they are crucial for synthesizing both natural and synthetic products. Linear triquinane shows various biological characteristics like being commonly used for antitumor, antibacterial, and antimalarial purposes, making it a popular subject of study among synthetic chemists. These come from different sources like marine organisms, plants, and fungi and make up a significant group of sesquiterpenoids. These can be classified as cis‐syn‐cis or cis‐anti‐cis based on the stereochemistry at the ring junction, with cis‐anti‐cis being the most common type and exhibiting significant biological activity. In this review, we summarized different methods using a combination of photothermal and olefin metathesis strategy to construct a triquinane framework by utilizing both traditional heat and microwave radiation. Some commonly used synthetic methods, including metathesis protocol and key reactions like Grignard reaction and Diels–Alder reaction, were utilized together with ring‐closing, ring‐opining, and ring‐rearrangement metathesis to create the linear triquinane core for use in total synthesis of natural products. Additionally, the use of photothermal olefin metathesis along with Hosomi‐Sakurai reaction conditions allows for the creation of intricate polyquinanes, which can be used to produce complex natural compounds and for designing unique molecules theoretically.

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Anemhupehins D F, sterols and chromone derivative from Anemone hupehensis and their anti-inflammatory activity

Ning,

Qin,

et al. 2024

Phytochemistry Letters

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Triquinane Sesquiterpene Glycosides from the Basidiomycete Antrodiella zonata

Cited by 5 publications

References 16 publications

Research progress in natural N-glycosides and synthetic methodologies for the formation of N-glycosidic bonds

Research progress in natural N-glycosides and synthetic methodologies for the formation of N-glycosidic bonds

Metathesis Mastery: Crafting Linear Triquinane Frameworks for Natural Product Synthesis

Anemhupehins D F, sterols and chromone derivative from Anemone hupehensis and their anti-inflammatory activity

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