Homoisoflavones as the antioxidants responsible from bulbs of<i>Scilla scilloides</i>

Nishida, Youichirou; Wada, Kensuke; Toyohisa, Daiki; Tanaka, Toshiharu; Ono, M.; Yasuda, Shin

doi:10.1080/14786419.2013.830218

Cited by 9 publications

(4 citation statements)

References 9 publications

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“…Among them, homoisoflavones were first focused on the evaluation in various biological tests for medicinal use of this plant and found to be the antioxidants responsible for 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay (Nishida et al, 2013). In view of the antiinflammatory activity, seven homoisoflavones isolated from the roots and heartwood of Caesalpinia sappan possesses anti-allergic activities upon b-hexosaminidase inhibition system (Yodsaoue et al, 2009).…”

Section: Lipoxygenase and Hyaluronidase Inhibition By Homoisoflavonesmentioning

confidence: 99%

Inhibitory effects of the ethyl acetate extract from bulbs ofScilla scilloideson lipoxygenase and hyaluronidase activities

Nishida

Sugahara

Wada

et al. 2014

Pharmaceutical Biology

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Context: Scilla scilloides Druce (Liliaceae) is a folk medicine to treat dermal inflammation; however, the medicinal properties of this plant have not been completely established. Objective: The current study investigates the potent anti-inflammatory effects of S. scilloides bulbs for its traditional usage using lipoxygenase and hyaluronidase as the inflammation model. To gain insight into the active constituents, nine homoisoflavones (1-9) were subsequently tested. Materials and methods: Lipoxygenase and hyaluronidase inhibition of ethyl acetate extract from the bulbs of this plant within 2000 mg/mL or homoisoflavones within 1000 mM were determined by colorimetric methods. RAW264.7 cells were incubated with 10 or 50 mM homoisoflavones plus lipopolysaccharide (LPS) for 24 h. The culture media were collected and analyzed for determination of the nitric oxide (NO) level by the colorimetric Griess method to measure the extent of inflammation. Results: The extract exhibited inhibitory effects on lipoxygenase and hyaluronidase activities with IC 50 values 31.5 and 169 mg/mL, respectively. Among the nine homoisoflavones tested, four (1 and 3-5) resulted in 79.3-97.9% higher lipoxygenase inhibition than 6.7-32.7% of the others at 500 mM. Calculated IC 50 values indicated 5 as the compound responsible for strong lipoxygenase inhibition with 15.8 mM as the IC 50 value. In the hyaluronidase assay, all homoisoflavones tested at 1000 mM demonstrated 16.2-58.0% inhibition. Incubating the cells in the presence of all nine homoisoflavones tested at 50 mM significantly suppressed the NO production, downward to 1.5-66.0%, in the LPS-activated macrophage cells as a model. Discussion and conclusion: These results may indicate a potential role of S. scilloides for anti-inflammatory purposes.

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Section: Lipoxygenase and Hyaluronidase Inhibition By Homoisoflavonesmentioning

confidence: 99%

Inhibitory effects of the ethyl acetate extract from bulbs ofScilla scilloideson lipoxygenase and hyaluronidase activities

Nishida

Sugahara

Wada

et al. 2014

Pharmaceutical Biology

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“…Nishida et al (2013) [ 116 ] investigated antioxidant activities in DPPH (Trolox, curcumin, and α-tocopherol as positive controls), hydrogen peroxide (H 2 O 2 ; Trolox as a positive control), and nitric oxide (NO; Trolox and curcumin as positive controls) scavenging assays of scillascillin-type homoisoflavonoids 49 , 51 , 52 , and 59 isolated from bulbs of Scilla scilloides . Isomuscomosin ( 52 ) tested at 500 μM showed more than 90% DPPH radical scavenging activity (EC 50 = 22.9 μM; the other compounds tested were below 40%).…”

Section: Biological Activities Of 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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“…Homoisoflavonoids were reported to be responsible for the biomedical activities of these plants, such as antibacterial, antifungal, antiallergic, antioxidant, cytotoxic and anti-angiogenic activities. They also inhibit in-vitro the growth and sporogenesis of several microorganisms (Heller, Tamm, 1981;Kouno, Komori, Kawasaki, 1973;Nishida et al, 2013;Shim et al, 2004). Stilbenes of scilla bulbs has been used in the treatment of asthma, coughs, bronchitis, heart disease (adjusted HR), rheumatism, diuretic, expectorant (Gupta, Raina, 2001), internal tumors, dilate blood vessels, anti-allergic and anti-mutagenic (Dias, Graça, Gonçalves, 2000;Yasuda et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Isolation and characterization of homoisoflavonoids from Scilla persica HAUSSKN

Ghoran

Ebrahimi

Mighani

et al. 2015

Braz. J. Pharm. Sci.

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Medicinal plants have many traditional claims including the treatment of ailments of infectious origin. In the evaluation of traditional claims, scientific research is extremely important. In this study, five homoisoflavonoids named 3-(4'-hydroxybenzylidene)-5,7-dihydroxy-6-methoxychroman-4-one(Autumnalin),3-(4'-hydroxybenzyl)-5,7-dihydroxy-6-methoxychroman-4-one (3,9-dihydro-autumnalin), 3-(3',4'-dihydroxybenzyl)-5,8-dihydroxy-7-methoxychroman-4-one,3-(3',4'-dihydroxybenzylidene)-5,8-dihydroxy-7-methoxychroman-4-one and 3-(3',4'-dihydroxybenzylidene)-5,7-dihydroxy-6-methoxychroman-4-one, were isolated from the bulbs of the plant Scilla persica HAUSSKN. Their structures were established on the basis of extensive spectroscopic analyses such as NMR, MS, IR and UV.

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Homoisoflavones as the antioxidants responsible from bulbs ofScilla scilloides

Cited by 9 publications

References 9 publications

Inhibitory effects of the ethyl acetate extract from bulbs ofScilla scilloideson lipoxygenase and hyaluronidase activities

Inhibitory effects of the ethyl acetate extract from bulbs ofScilla scilloideson lipoxygenase and hyaluronidase activities

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

Isolation and characterization of homoisoflavonoids from Scilla persica HAUSSKN

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