Spiroflavonoid compounds: Structure and distribution in nature review

Fedorova, T. E.; Ivanova, S. Z.; Babkin, V. A.

doi:10.1134/s1068162010070022

Cited by 10 publications

(6 citation statements)

References 15 publications

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“…In the proceeding of the study we performed the identification of constituents with HPLC-MS n analysis based mainly on fragmentation patterns by comparison of reference compounds, or with literature data [ 15 ]. Identified compounds are reported in Table 4 .…”

Section: Resultsmentioning

confidence: 99%

Larix decidua Bark as a Source of Phytoconstituents: An LC-MS Study

Baldan

Sut

Faggian³

et al. 2017

Molecules

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Larix decidua bark is a waste of the timber industry and is widely diffused in Northern Italy. This material can be considered a good source of antioxidants and phytoconstituents with possible use in cosmetic or nutraceutical products. In this study, simple extraction of larch bark was performed using mixtures of ethanol/water. Furthermore, the phytochemical composition of larch bark extract was studied using LC-MSn methods and the main constituents were identified as flavonoids, spiro-polyphenols, and procyanidins. To confirm the identification by LC-MS semi-preparative HPLC was performed in order to isolate the main constituents and verify the structures by 1H-NMR. Antioxidant properties were studied using an in vitro approach combining DPPH assay and LC-MS in order to establish different roles of the various classes of phytochemicasl of the extract. DPPH activity of some of the isolated compounds was also assessed. The overall results indicate this waste material as a good source of antioxidant compounds, mainly procyanidins, whichresulted the most active constituents in the DPPH assay.

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Section: Resultsmentioning

confidence: 99%

Larix decidua Bark as a Source of Phytoconstituents: An LC-MS Study

Baldan

Sut

Faggian³

et al. 2017

Molecules

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“…White crystals, C NMR data as well as the chemical structure of the compound were identical with those of p-hydroxyphenyl [13], the chemical structure of which is given in Figure 1(b (1 H, m, H-7 (C-6), 125.4 (C-4'), 127.7 (C-2', 6'), 128.6 (C-3', 5'), 130.2 (C-5), 131.0 (C-l'), 133.6 (C-7), 138.5 (C-3), 144.9 (C-9), 155.4 (C-2), 173.5 (C-4). Based on the spectroscopic data, the compound was identified [15,16] as 3-hydroxyflavone.…”

Section: Pure Compoundmentioning

confidence: 65%

Fractionation and structural identification of antibiotic activity substances from <i>Streptomyces herbaricolor</i> HNS2-2

Chen¹,

Li²,

Zhu³

et al. 2012

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Four groups of antibiotic activity compounds were separated and purified from the ethyl acetate fraction of a broth culture of Streptomyces herbaricolor HNS2-2. Trace analyses were performed and anti-microbial activities were determined. The antibiotic activity compounds were identified as quercetin dehydrate ①, p-hydroxyphenyl ②, 4'-hydroxyflavanone ③, and 3-hydroxyflavone ④ based on spectroscopic data. Compounds 1 -4 showed significant antimicrobial activities against Staphylococcus aureus and the tobacco mosaic virus in vitro, suggesting their potential agricultural and medical applications.

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“…Common numbering of carbon atoms of spiro compounds was used according to Nakashima et al (2016) and Pecio et al (2023) [7,11]. The only review paper on spiro-flavonoids was published by Fedorova et al [8] and covered eight spiro-biflavonoids and one spiro-triflavonoid that had been isolated prior to 2010, without any discussion of their stereochemistry. Thanks to modern and increasingly available spectroscopic techniques, more than 50 additional spiro-flavonoids have been characterized to date, resulting in a total of 65 unique structures, and are reported here.…”

Section: Introductionmentioning

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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Spiroflavonoid compounds: Structure and distribution in nature review

Cited by 10 publications

References 15 publications

Larix decidua Bark as a Source of Phytoconstituents: An LC-MS Study

Larix decidua Bark as a Source of Phytoconstituents: An LC-MS Study

Fractionation and structural identification of antibiotic activity substances from <i>Streptomyces herbaricolor</i> HNS2-2

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

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Spiroflavonoid compounds: Structure and distribution in nature review

Cited by 10 publications

References 15 publications

Larix decidua Bark as a Source of Phytoconstituents: An LC-MS Study

Larix decidua Bark as a Source of Phytoconstituents: An LC-MS Study

Fractionation and structural identification of antibiotic activity substances from &lt;i&gt;Streptomyces herbaricolor&lt;/i&gt; HNS2-2

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

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Fractionation and structural identification of antibiotic activity substances from <i>Streptomyces herbaricolor</i> HNS2-2