Fragranol A: A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans

Omar, Ashraf M.; Sun, Sijia; Kim, Min Jo; Tawila, Ahmed M.; Dibwe, Dya Fita; Phrutivorapongkul, Ampai; Toyooka, Naoki; Awale, Suresh

doi:10.1016/j.tetlet.2020.152099

Cited by 8 publications

(14 citation statements)

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“…The ECD calculations were performed as previously reported. 27 For comparison between experimental and calculated spectra, SpecDis was used employing the following UV shifts and σ for the calculated curves: (2) 15 nm at 0.35 eV; (3) −15 nm at 0.35 eV; (5) −15 nm at 0.4 eV; (6) −15 nm at 0.45 eV; (7) 7 nm at 0.55 eV. 28 Preferential Cytotoxicity Assay against PANC-1 Cells, Morphological Analysis, Time-Lapse Imaging, and Colony Formation Assay.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Benzophenones from Betula alnoides with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line

et al. 2021

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The antiausterity strategy is a promising approach for the discovery of lead compounds with unprecedented anticancer activities by targeting the tolerance of cancer cells to nutrition starvation. These agents are selectively cytotoxic under the tumor microenvironment-mimicking condition of nutrition starvation, without apparent toxicity in the normal nutrient-rich condition. In this study, an ethanol extract of Betula alnoides showed antiausterity activity against PANC-1 human pancreatic cancer cells under nutrient-deprived conditions, with a PC50 value of 13.2 μg/mL. Phytochemical investigation of this active extract led to the isolation of eight benzophenones (1–8), including six new compounds, named betuphenones A–F (2–7), and three known xanthones (9–11). The structure elucidation of the new compounds was achieved by HRFABMS, NMR, and ECD spectroscopic analyses. A plausible biogenetic pathway of the new compounds was proposed. Compounds 1–7 displayed antiausterity activity with PC50 values of 4.9–8.4 μM. Moreover, compounds 2 and 7 induced alterations in PANC-1 cell morphology under nutrient-deprived conditions and also inhibited PANC-1 colony formation under nutrient-rich conditions.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Benzophenones from Betula alnoides with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line

et al. 2021

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“… whole plant 23 [ 34 ] Cupressaceae Glyptostrobus pensilis (D.Don) K.Koch trunk bark 1–4, 10, 11 [ 35 ] Fabaceae Caesalpinia sappan L. heartwood 65 [ 36 ] Pentaphylacaceae Anneslea fragrans Wall. twigs 2, 8, 9, 30 [ 37 , 38 ] Pinaceae Abies chensiensis Tiegh. aerial parts 1–3 [ 39 ] Abies delavayi Franch.…”

Section: Occurrence In Naturementioning

confidence: 99%

“…Fragranol A, a spiro-triflavonoid containing two spiro-centers and six chiral carbon atoms, was isolated from twigs of Anneslea fragrans ( Table 3 ) [ 37 ]. The RelC of the comp.…”

Section: Stereochemistry Of the Isolated Spiro-flavonoidsmentioning

confidence: 99%

Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity

et al. 2023

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Based on the literature data from 1973 to 2022, this work summarizes reports on spiro-flavonoids with a spiro-carbon at the center of their structure and how this affects their isolation methods, stereochemistry, and biological activity. The review collects 65 unique structures, including spiro-biflavonoids, spiro-triflavonoids, spiro-tetraflavonoids, spiro-flavostilbenoids, and scillascillin-type homoisoflavonoids. Scillascillin-type homoisoflavonoids comprise spiro[bicyclo[4.2.0]octane-7,3′-chromane]-1(6),2,4-trien-4′-one, while the other spiro-flavonoids contain either 2H,2′H-3,3′-spirobi[benzofuran]-2-one or 2′H,3H-2,3′-spirobi[benzofuran]-3-one in the core of their structures. Spiro-flavonoids have been described in more than 40 species of eight families, including Asparagaceae, Cistaceae, Cupressaceae, Fabaceae, Pentaphylacaceae, Pinaceae, Thymelaeaceae, and Vitaceae. The possible biosynthetic pathways for each group of spiro-flavonoids are summarized in detail. Anti-inflammatory and anticancer activities are the most important biological activities of spiro-flavonoids, both in vitro and in vivo. Our work identifies the most promising natural sources, the existing challenges in assigning the stereochemistry of these compounds, and future research perspectives.

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“…, 2012; Omar et al. , 2019, 2020a,2020b). Its extract or isolates have antioxidant, cytotoxic and antimalarial activities.…”

Section: Introductionmentioning

confidence: 96%

“…In addition, its bark is also used as folk medicine in the treatment of dysentery and diarrhoea, while the leaves have been used for the treatment of fever, indigestion and liver inflammation in China and Cambodia (Nguyen-Pouplin et al, 2007;Ma et al, 2018). Previous phytochemical investigation on A. fragrans led to the isolation of chalcones, dihydrochalcones, flavonols and triterpenoids (Huang et al, 2012;Omar et al, 2019Omar et al, , 2020aOmar et al, ,2020b. Its extract or isolates have antioxidant, cytotoxic and antimalarial activities.…”

Section: Introductionmentioning

confidence: 99%

Phenolic composition, antioxidant and cytoprotective effects of aqueous‐methanol extract from Anneslea fragrans leaves as affected by drying methods

Cui

Wang

Zhou

et al. 2021

Int J of Food Sci Tech

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Summary The present study is aimed to evaluate the effect of three different drying methods, including shade drying (SD), freeze drying (FD) and hot air dying (HAD), on the chemical components, antioxidant and cytoprotective activities of aqueous‐methanol extracts from A. fragrans leaves. The total phenolic and flavonoid content were determined by spectroscopic methods, whereas the chemical profile of different extracts was determined by ultra‐high‐performance liquid chromatography coupled with a tandem mass spectrometry (UHPLC‐MS/MS). A total of thirteen compounds were characterised and 9 phenolic compounds have been quantified. Two dihydrochalcone glycosides named confusoside and vacciniifolin were found to be the most abundant phenolic compounds in the SD extract of A. fragrans leaves, which also showed the strongest antioxidant and cytoprotective activities. The results showed that shade drying is an efficient method for preserving the chemical constituents and maintaining the antioxidant and cytoprotective activities of A. fragrans leaves.

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Fragranol A: A new class of spiro-triflavanoid hybrid with an unprecedented carbon skeleton from Anneslea fragrans

Cited by 8 publications

References 11 publications

Benzophenones from Betula alnoides with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line

Benzophenones from Betula alnoides with Antiausterity Activities against the PANC-1 Human Pancreatic Cancer Cell Line

Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity

Phenolic composition, antioxidant and cytoprotective effects of aqueous‐methanol extract from Anneslea fragrans leaves as affected by drying methods

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