Bioactive sesquiterpenoids from the flower buds of Tussilago farfara

Song, Xiu‐Qing; Yu, Jin‐Hai; Sun, Jun; Liu, Kailu; Zhang, Jun‐Sheng; Zhang, Hua

doi:10.1016/j.bioorg.2021.104632

Cited by 15 publications

(7 citation statements)

References 19 publications

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“…The dicyclic 141 obtained from the rhizomes of Curcuma longa displayed more potent anti-inflammatory activity against the LPS-activated production of NO (IC 50 , 25.5 μM), when compared with the positive control dexamethasone (IC 50 , 33.6 μM) ( Cheng et al, 2019 ). The aromatic bisabolanes 182 and 183 potently inhibited α-glucosidase with the IC 50 values of 14.9 and 19.4 μM, respectively, approximately 30 times stronger than the positive control acarbose (IC 50 , 496 μM) ( Song et al, 2021 ). The attractive bioactivities make many of these compounds suitable lead compounds or even candidates for the development of new medicines and agrochemicals and may trigger further pharmacological and synthesis studies.…”

Section: Discussionmentioning

confidence: 99%

Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

Liu

Yang

et al. 2022

Front. Chem.

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Natural products, characterized by intriguing scaffold diversity and structural complexity, as well as significant agricultural and medicinal activities, have been a valuable source of agrochemicals/drugs development and have historically made a huge contribution to pharmacotherapy. Structurally, bisabolanes are a family of naturally occurring sesquiterpenoids that featured a hexatomic ring core incorporating with eight continuous carbons, which cause high structural variability along the alkyl side chain to form abundant functionalities. Moreover, apart from their interesting structures, bisabolanes have shown multitudinous bioactivities. Bisabolanes are distributed in a variety of marine invertebrates, terrestrial plant, and microbial sources. Interestingly, bisabolanes characterized from marine environment possess unique characteristics both structurally and biologically. A total of 296 newly-discovered bisabolanes were searched. Among them, 94 members were isolated from marine organisms. This review particularly focuses on the new bisabolanes characterized from marine organisms (covering from 2000 to 2021), including marine-derived fungi, algae, soft corals, and sponges, with emphasis on the diversity of their chemical structures as well as the novelty and differences between terrestrial and marine sources. Moreover, a wide range of bioactivities of marine-derived bisabolanes, including antimicrobial, anti-inflammatory, enzyme inhibitory, and cytotoxic properties, are presented herein, which is considered to be a promising resource for the discovery of new drug leads and agrochemicals.

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Section: Discussionmentioning

confidence: 99%

Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

Liu

Yang

et al. 2022

Front. Chem.

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“…Plant materials: The collection and authentication information of the plant materials was reported previously. [19] Extraction and isolation: The dried flower buds of T. farfara were processed as previously described, [19] and the n-BuOH soluble part was obtained through partitioning with the water suspension of the crude extract. This polar component (531 g) was then subjected to CC over D101-macroporous absorption resin (EtOH-H 2 O, 30 %, 50 % and 95 %) to afford three fractions (A, B and C).…”

Section: Methodsmentioning

confidence: 99%

“…To date, several classes of small molecule inhibitors of GalNAc-Ts have been reported to inhibit GalNAc-T3, -T2 or other isoenzymes in the in vitro enzyme activity assays (for a recent review, please see Hu et al, ChemBioChem 2018, 19,[2503][2504][2505][2506][2507][2508][2509][2510][2511][2512][2513][2514][2515][2516][2517][2518][2519][2520][2521]). [3,5b, 11] However, the on-target effects of most of these inhibitors were not directly validated in cells, and they also suffered from promiscuity, causing them to inhibit other protein targets and induce cytotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Novel Quinic Acid Glycerates from Tussilago farfara Inhibit Polypeptide GalNAc‐Transferase

Feng

et al. 2021

ChemBioChem

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The discovery of a bioactive inhibitor tool for human polypeptide N‐acetylgalactosaminyl transferases (GalNAc‐Ts), the initiating enzyme for mucin‐type O‐glycosylation, remains challenging. In the present study, we identified an array of quinic acid derivatives, including four new glycerates (1–4) from Tussilago farfara, a traditional Chinese medicinal plant, as active inhibitors of GalNAc‐T2 using a combined screening approach with a cell‐based T2‐specific sensor and purified enzyme assay. These inhibitors dose‐dependently inhibited human GalNAc‐T2 but did not affect O‐linked N‐acetylglucosamine transferase (OGT), the other type of glycosyltransferase. Importantly, they are not cytotoxic and retain inhibitory activity in cells lacking elongated O‐glycans, which are eliminated by the CRISPR/Cas9 gene editing tool. A structure‐activity relationship study unveiled a novel quinic acid‐caffeic acid conjugate pharmacophore that directs inhibition. Overall, these new natural product inhibitors could serve as a basis for developing an inhibitor tool for GalNAc‐T2.

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“…Another SQ compound, tussilagone isolated from the flower bud of Tussilago farfara (Compositae) [162] was tested in an ovalbumin-induced allergic asthma model in guinea pigs, in which 25 and 50 mg/kg of tussilagone was intraperitoneally administrated, and serum and nasal tissue samples were evaluated for features of inflammation [163]. A decrease in inflammatory cell infiltrates, lower histamine, ovalbumin-specific IgE, as well as IL-6 levels were observed after tussilagone administration.…”

Section: Fukinonementioning

confidence: 99%

The Complexity of Sesquiterpene Chemistry Dictates Its Pleiotropic Biologic Effects on Inflammation

et al. 2022

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Sesquiterpenes (SQs) are volatile compounds made by plants, insects, and marine organisms. SQ have a large range of biological properties and are potent inhibitors and modulators of inflammation, targeting specific components of the nuclear factor-kappaB (NF-κB) signaling pathway and nitric oxide (NO) generation. Because SQs can be isolated from over 1600 genera and 2500 species grown worldwide, they are an attractive source of phytochemical therapeutics. The chemical structure and biosynthesis of SQs is complex, and the SQ scaffold represents extraordinary structural variety consisting of both acyclic and cyclic (mono, bi, tri, and tetracyclic) compounds. These structures can be decorated with a diverse range of functional groups and substituents, generating many stereospecific configurations. In this review, the effect of SQs on inflammation will be discussed in the context of their complex chemistry. Because inflammation is a multifactorial process, we focus on specific aspects of inflammation: the inhibition of NF-kB signaling, disruption of NO production and modulation of dendritic cells, mast cells, and monocytes. Although the molecular targets of SQs are varied, we discuss how these pathways may mediate the effects of SQs on inflammation.

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Bioactive sesquiterpenoids from the flower buds of Tussilago farfara

Cited by 15 publications

References 19 publications

Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

Chemistry and Bioactivity of Marine-Derived Bisabolane Sesquiterpenoids: A Review

Novel Quinic Acid Glycerates from Tussilago farfara Inhibit Polypeptide GalNAc‐Transferase

The Complexity of Sesquiterpene Chemistry Dictates Its Pleiotropic Biologic Effects on Inflammation

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