CN112209911B - Flavonoid component in fine She Yuanwei and antioxidant activity thereof - Google Patents

Flavonoid component in fine She Yuanwei and antioxidant activity thereof Download PDF

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CN112209911B
CN112209911B CN202011333186.4A CN202011333186A CN112209911B CN 112209911 B CN112209911 B CN 112209911B CN 202011333186 A CN202011333186 A CN 202011333186A CN 112209911 B CN112209911 B CN 112209911B
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蒋建勤
严惠靖
彭丹丹
吕昊宇
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China Pharmaceutical University
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    • C07—ORGANIC CHEMISTRY
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    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
    • C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/40—Separation, e.g. from natural material; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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Abstract

The invention belongs to the technical field of medicines. Relates to the extraction and separation of 6 compounds in iris tenuifolia and the antioxidant activity of the compounds, and the structural formula of the compounds is shown in the specification. Separating fine She Yuanwei% ethanol extract with macroporous resin, silica gel, MCI, reversed phase ODS column chromatography, and preparative high performance liquid chromatographyObtaining 6 compounds by a method; and the activity in terms of antioxidation is examined by DPPH experiment and ABTS experiment.

Description

Flavonoid component in fine She Yuanwei and antioxidant activity thereof
Technical Field
The invention relates to the technical field of medicines, in particular to 8 novel flavonoid components in fine She Yuanwei and extraction, separation and identification thereof; and application prospects of 6 new compounds of iris tenuifolia in antioxidation and related aspects.
Background
Thin She Yuanwei (Iris tenuifolia pall.) also known as old cow pulling, thin leaf Iris, silk She Malin, etc., is a perennial herb of Iridaceae (Iridaceae) Iris (Iris L), and is grown on fixed sand dunes or gritty. The traditional Mongolian medicine is an important component part of the traditional Mongolian medicine because the traditional Mongolian medicine is recorded to grow in the inner Mongolia and Mongolia areas of China. The fine She Yuanwei is mainly used as ornamental plant, and the root and seed of the ornamental plant can be used as medicines, and has the effects of preventing abortion, nourishing blood, clearing heat and detoxicating. Modern pharmacological research shows that iris has the activities of resisting oxidation, resisting inflammation, resisting tumor, resisting bacteria, protecting liver, reducing blood fat and the like, has a great development prospect, and accords with the major health subject advocated by China.
The chemical components of fine She Yuanwei are complex and various, mainly including flavone and its glycosides, terpenes, stilbenes and benzoquinones, wherein the chemical component research of iris is mainly focused on flavonoid compounds, and the separation research of new compounds in fine She Yuanwei is necessary for further understanding the active components of fine She Yuanwei.
Disclosure of Invention
(1) The invention provides a novel compound extracted and separated from iris tenuifolia and an extraction and separation method thereof, wherein the chemical structural formula of the novel compound is shown in formulas (I) - (VIII):
the chemical name is: (I) 5,7,2',3' -tetrahydroxy-8-methoxofenavone
(II)5，2′，3′-trihydroxy-7，8-dimethoxyisoflavone
(III)3，5，3′，4′-tetrahydroxy-7，2′-dimethoxyflavone
(IV)5，2′，3′-trihydroxy-7-methoxyflavone
(V)3，5，3′，4′-tetrahydroxy-7，2′-dimethoxyflavanone
(VI)2′，3′-dihydroxy-5-methoxy-6，7-methylenedioxyflavanone
(VII)5，7，2′，3′-tetrahydroxy-6-methoxyflavanone
(VIII)5，7，3′-trihydroxy-2′-methoxyflavanone
The invention provides a method for extracting and separating novel compounds from iris tenuifolia, which comprises the following steps:
1) Taking 2kg of dry aerial parts of iris tenuifolia, crushing, extracting with 95% ethanol under reflux for 3 times under heating for 3 hours each time, mixing the extractive solutions, and recovering under reduced pressure to obtain fine She Yuanwei ethanol total extract (about 370 g);
2) Suspending the total extract obtained in the step 1) in water, sequentially extracting with petroleum ether, ethyl acetate and water saturated n-butanol, extracting each solvent for 3 times respectively, mixing the extracts, and recovering solvent to obtain each part of extract;
3) Separating the ethyl acetate part Fraction B extract in the step 2) by polyamide column chromatography, performing gradient elution by using ethanol-water according to the volume ratio of 0:1-1:0 to respectively obtain 5 components of 10% ethanol part, 30% ethanol part, 50% ethanol part, 70% ethanol part and pure ethanol part, and respectively concentrating under reduced pressure to obtain extract for later use;
4) Separating 50% ethanol part in step 3) by silica gel column chromatography, MCI column chromatography, ODS column chromatography, high performance liquid chromatography, etc., to obtain new compounds (I) - (VIII) derived from fine She Yuanwei.
(2) The invention shows that the method has application prospect in antioxidation by measuring the activity of eliminating DPPH free radical of 6 new compounds of iris tenuifolia.
(3) The activity of the 6 new compounds of the iris tenuifolia for removing the ABTS free radical is measured, so that the iris tenuifolia has an application prospect in the aspect of antioxidation.
Drawings
FIG. 1 is a graph showing the effect of 6 novel compounds of Iris tenuifolia on DPPH radical scavenging activity.
FIG. 2 is a graph showing the effects of 6 novel compounds from Iris tenuifolia on the scavenging of ABTS free radical activity.
Detailed Description
The invention is further described in connection with the following examples, which are not intended to be limiting, but rather to be construed according to the invention.
Example 1
The chemical structural formula of the novel compound extracted and separated from iris tenuifolia is shown as the formulas (I) - (VIII):
the chemical name is: (I) 5,7,2',3' -tetrahydroxy-8-methoxofenavone
(II)5，2′，3′-trihydroxy-7，8-dimethoxyisoflavone
(m)3，5，3′，4′-tetrahydroxy-7，2′-dimethoxyflavone
(IV)5，2′，3′-trihydroxy-7-methoxyflavone
(V)3，5，3′，4′-tetrahydroxy-7，2′-dimethoxyflavanone
(VI)2′，3′-dihydroxy-5-methoxy-6，7-methylenedioxyflavanone
(VII)5，7，2′，3′-tetrahydroxy-6-methoxyflavanone
(VIII)5，7，3′-trihydroxy-2′-methoxyflavanone
The extraction, separation and preparation method of the novel compound comprises the following steps:
2kg of dry aerial parts of fine She Yuanwei, crushing, extracting with 95% EtOH under reflux for 3 times each for 3 hours, combining the extracts, and recovering under reduced pressure until no alcohol smell, to obtain fine She Yuanwei ethanol total extract (about 370 g). Suspending the total extract in water, sequentially extracting with petroleum ether, ethyl acetate and water saturated n-butanol, extracting each solvent for 3 times respectively, mixing the extractive solutions, and recovering solvent to obtain petroleum ether (Fraction A), ethyl acetate (Fraction B) and water saturated n-butanol (Fraction C). Separating the ethyl acetate part (Fraction B) extract by polyamide column chromatography, and performing gradient elution with ethanol-water at a volume ratio of 0:1-1:0 to obtain 5 components of 10% ethanol part (FrB-1), 30% ethanol part (FrB-2), 50% ethanol part (FrB-3), 70% ethanol part (FrB-4) and pure ethanol part (FrB-5), respectively. The FractionB-3 is subjected to gradient elution by a silica gel column and chloroform to methanol (100:0.fwdarw.0:100) to obtain 13 fractions (FrB-3 a-FrB-3 m).
Wherein FrB-3c was repeatedly separated by a silica gel column (chloroform-acetone system was used as a mobile phase), followed by prep-HPLC to obtain compound (IV) (2 mg). FrB-3g is subjected to gradient elution and separation by polyamide (mobile phase methanol-water system) to obtain 8 fractions FrB-3 g-1-FrB-3 g-8, the fraction FrB-3g-5 is subjected to separation by a polyamide column and a silica gel column (mobile phase chloroform-methanol system) to obtain 6 subfractions FrB-3 g-5-1-FrB-3 g-5-6, and the subfractions FrB-3g-5-2 are subjected to ODS column and gel column chromatography to obtain a compound (II) (2 mg); subjecting the subfraction FrB-3g-5-5 to silica gel column (mobile phase chloroform-acetone system), ODS column, and recrystallization to obtain compound (I) (21 mg), (III) (10 mg), (VI) (34 mg); the subfractions FrB-3g-5-6 were subjected to silica gel column (mobile phase chloroform-acetone system), polyamide column chromatography, recrystallization, prep-HPLC and the like to give compound (VII) (30 mg), (VIII) (26 mg). FrB-3m Compound (V) (133 mg) was obtained by MCI column, recrystallization and prep-HPLC.
And (3) structural identification: the spectrum technology mainly comprises nuclear magnetic resonance spectrum 1 H-NMR、 13 C-NMR, HSQC, HMBC, ROESY), mass spectrometry (HR-ESI-MS) to identify the structure of a compound.
The compound (I) is yellow crystal (methanol), can be dissolved in acetone and DMSO, has dark spots at 254nm of an ultraviolet lamp, can be fluorescent at 365nm, and has yellow iodine and 5% fragrance of TLCThe grass aldehyde-concentrated sulfuric acid reagent shows orange yellow, feCl 3 The reagent reaction appears dark green. HR-ESI-MS gives the experimental value m/z:317.0656[ M+H ]] + (calcd for C 16 H 13 O 7 317.0656) Z, the molecular formula is: c (C) 16 H 12 O 7 The molecular weight is 316.
Of compounds 1 H-NMR(500MHz，DMSO-d 6 ) In the map, combine with 1 H- 1 H COSY and HSQC spectra, the putative compounds contained: methoxy proton signal, delta 3.83 (3H, s, 8-OCH) 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Delta 6.88 (1 h, dd, j=7.7, 1.9hz, h-6 '), delta 6.73 (1 h, t, j=7.7 hz, h-5'), delta 6.69 (1 h, dd, j=7.6, 1.8hz, h-4 '), and delta 115.5 (C-6'), delta 118.7 (C-5 '), delta 121.9 (C-4'), have a direct correlation to form an ABX coupling system for three hydrogen signals on the B ring on a flavone compound structure, exhibiting a 2',3' -disubstituted on the B ring. Delta 6.38 (1H, s, H-6) is a hydrogen signal on the A ring of the flavone compound, which is directly related to delta 99.2 (C-6), and the substitution on the A ring is presumed to be 5,7, 8-trisubstituted. Delta 8.34 (1H, s, H-2), which is a hydrogen signal on the C ring of the flavone structure, is directly related to delta 155.3 (C-2). In addition, in the case of the optical fiber, 13 C-NMR(125MHz，DMSO-d 6 ) In the graph, a ketocarbonyl carbon signal delta 180.3 (C-4) is given in the low field region, and according to delta 155.3 (C-2) and delta 120.6 (C-3), the compound is presumed to be an isoflavone compound.
According to HMBC spectra, delta 8.34 (1H, s, H-2) is related to delta 144.0 (C-2 '), delta 145.4 (C-3 '), delta 118.5 (C-1 ') in addition to delta 120.6 (C-3), delta 0180.3 (C-4), delta 1150.0 (C-9), indicating a dioxy substituent at the 2',3' position of the B ring. Delta 12.67 (1H, s, 5-OH) is related to the carbon of delta 99.2 (C-6) in addition to delta 104.3 (C-10), delta 156.6 (C-5), in addition to the methoxy proton signal delta 3.83 (3H, s, 8-OCH) 3 ) Has a signal related to carbon signal delta 127.5 (C-8), which indicates that the A ring is 5,7, 8-trisubstituted and has 8-OCH 3 Is a structural fragment of (a).
In summary, compound (I) was identified as 5,7,2',3' -tetrahydroxy-8-methoxyisoflavone.
The compound (II) of the present invention isYellow crystal (methanol) soluble in acetone and DMSO, dark spot at 254nm, visible fluorescence at 365nm, yellow color of iodine, orange color of TLC 5% vanillin-concentrated sulfuric acid reagent, feCl 3 The reagent reaction appears dark green. HR-ESI-MS gives the experimental value m/z:331.0798[ M+H ]] + (calcd for C 17 H 15 O 7 331.0798) to give a molecular formula of: c (C) 17 H 14 O 7 The molecular weight was 330.
Of compounds 1 H-NMR(400MHz，DMSO-d 6 ) In combination with HSQC spectra, the putative compounds contained: two sets of methoxy proton signals, delta 3.77 (3H, s, 8-OCH) 3 )，δ3.93(3H，s，7-OCH 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Three sets of phenolic hydroxyl proton signals, δ12.75 (1 h, s, 5-OH), δ8.81 (1 h, s,2 '-OH), δ 08.73 (1 h, s,3' -OH). δ16.71 (1 h, dd, j=7.2, 1.9hz, h-6 '), δ26.65 (1 h, d, j=2.9 hz, h-5'), δ6.63 (1 h, s, h-4 '), directly related to δ116.1 (C-6'), δ118.0 (C-5 '), δ116.3 (C-4'), form an ABX coupling system for three hydrogen signals on the B-ring on the structure of the flavonoid, exhibiting 2',3' -disubstituted on the B-ring. Delta 6.63 (1H, s, H-6) is a hydrogen signal on the A ring of the flavone compound, which is directly related to delta 96.1 (C-6), and the substitution on the A ring is presumed to be 5,7, 8-trisubstituted. Delta 8.34 (1H, s, H-2), which is a hydrogen signal on the C ring of the flavone structure, is directly related to delta 156.1 (C-2). In addition, in the case of the optical fiber, 13 C-NMR(150MHz，DMSO-d 6 ) In the graph, the low field region gives a ketocarbonyl carbon signal delta 180.5 (C-4), and according to delta 156.1 (C-2) and delta 120.3 (C-3), the compound is presumed to be an isoflavone compound.
Delta 8.34 (1H, s, H-2) in HMBC spectra is related to delta 120.3 (C-3), delta 180.5 (C-4), delta 149.2 (C-9) and delta 147.9 (C-2 '), delta 149.5 (C-3 '), delta 118.0 (C-1 '), indicating that the 2',3' position of the B ring has a dioxy substituent. And delta 3.77 (3H, s, -OCH) 3 ) In addition to delta 128.3 (C-8), delta 56.6 (7-OCH) 3 ) In addition, delta 3.93 (3H, s, -OCH) 3 ) Has a signal related to the carbon signal delta 158.3 (C-7), indicating that the ring A has 7,8-OCH 3 Is a structural fragment of (a).
In summary, compound (II) was identified as 5,2',3' -trihydroxy-7, 8-dimethoxy isoflavone.
The compound (III) of the invention is yellow crystal (methanol) which can be dissolved in acetone and DMSO, has dark spots at 254nm of an ultraviolet lamp, can be fluorescent at 365nm, and has yellow iodine, and has orange yellow TLC 5% vanillin-concentrated sulfuric acid reagent, feCl 3 The reagent reaction appears dark green. HR-ESI-MS gives the experimental value m/z:347.0762[ M+H ]] + (calcd for C 17 H 15 O 8 347.0762) to give a molecular formula of: c (C) 17 H 14 O 8 The molecular weight was 346.
Of compounds 1 H-NMR(500MHz，DMSO-d 6 ) Is combined with 1 H- 1 H COSY and HSQC spectra, the putative compounds contained: two sets of methoxy proton signals, delta 3.84 (3H, s, 7-OCH) 3 )，δ3.76(3H，s，2′-OCH 3 ). Delta 6.83 (1 h, d, j=8.4 hz, h-6 '), delta 6.66 (1 h, d, j=8.4 hz, h-5 '), directly related to delta 120.7 (C-6 '), delta 110.6 (C-5 '), form an AB coupling system for two hydrogen signals on the B-ring on the structure of flavonoids, exhibiting 2',3',4' -trisubstituted on the B-ring. Delta 6.59 (1 h, d, j=2.3 hz, h-8), delta 6.37 (1 h, d, j=2.3 hz, h-6) is the hydrogen signal on the a ring of the flavone compound, which is directly related to delta 91.9 (C-8), delta 97.4 (C-6), assuming a substitution on the a ring as a 5, 7-disubstituted. In addition, in the case of the optical fiber, 13 C-NMR(125MHz，DMSO-d 6 ) In the graph, the low field region gives a ketocarbonyl carbon signal delta 176.4 (C-4), and according to delta 149.0 (C-2) and delta 137.0 (C-3), the compound is presumed to be a flavonol compound.
Delta 6.83 (1 h, d, j=8.4 hz, h-6 ') is remotely correlated with delta 110.6 (C-5 '), delta 0138.5 (C-3 '), delta 147.0 (C-2 '), delta 149.1 (C-4 ') in HMBC spectra; delta 6.66 (1 h, d, j=8.4 hz, h-5 ') is remotely related to delta 115.4 (C-1'), delta 120.7 (C-6 '), delta 138.5 (C-3'), delta 149.1 (C-4 '), and delta 3.76 (3 h, s,2' -OCH) 3 ) Related to delta 147.0 (C-2 '), indicating that the 2',3',4' position of the B ring has a trioxygen substituent and has 2' -OCH 3 Is a structural fragment of (a). Furthermore, methoxy proton signalδ3.84(3H，s，7-OCH 3 ) Has a signal associated with carbon signal delta 164.9 (C-7), indicating 5, 7-disubstituted on ring A and 7-OCH 3 Is a structural fragment of (a).
In summary, compound (III) was identified as 3,5,3',4' -tetrahydroxy-7, 2' -dimethoxyflavone.
The compound (IV) is yellow crystal (methanol), can be dissolved in acetone and DMSO, has dark spots at 254nm of an ultraviolet lamp, can be fluorescent at 365nm, and has yellow iodine, and has orange yellow TLC 5% vanillin-concentrated sulfuric acid reagent, and FeCl 3 The reagent reaction appears dark green. HR-ESI-MS gives the experimental value m/z:301.0761[ M+H ]] + (calcd for C 16 H 13 O 6 301.0761) to give a molecular formula of: c (C) 16 H 12 O 6 The molecular weight was 300.
Of compounds 1 H-NMR(300MHz，DMSO-d 6 ) Is combined with 1 H- 1 H COSY and HSQC spectra, the putative compounds contained: methoxy proton signal, delta 3.87 (3H, s, 7-OCH) 3 ). Delta 7.37 (1 h, dd, j=8.1, 1.6hz, h-6 '), delta 6.99 (1 h, dd, j=7.8, 1.6hz, h-4'), delta 6.81 (1 h, t, j=7.9 hz, h-5 '), and delta 118.4 (C-6'), delta 117.8 (C-4 '), delta 119.1 (C-5'), have a direct correlation, forming an ABX coupling system for three hydrogen signals on the B ring on the flavonoid structure, exhibiting a 2',3' -disubstituted on the B ring. Delta 6.76 (1 h, d, j=2.2 hz, h-8), delta 6.39 (1 h, d, j=2.2 hz, h-6) is the hydrogen signal on the a ring of the flavone compound, which is directly related to delta 92.6 (C-8), delta 97.9 (C-6), assuming a substitution on the a ring as a 5, 7-disubstituted. In addition, in the case of the optical fiber, 13 C-NMR(125MHz，DMSO-d 6 ) In the graph, a ketocarbonyl carbon signal delta 182.1 (C-4) is given in the low field region, and according to delta 162.1 (C-2) and delta 109.2 (C-3), the compound is presumed to be a flavonoid compound.
Delta 13.03 (1H, s, 5-OH) in HMBC spectra is related to delta 97.9 (C-6), delta 165.3 (C-7) carbons in addition to delta 104.7 (C-10), delta 161.1 (C-5), in addition to methoxy proton signals delta 3.87 (1H, s, 7-OCH) 3 ) Is related to delta 165.3 (C-7), indicating 5, 7-disubstituted on ring A and having 7-OCH 3 Is a structural fragment of (a).
In summary, compound (IV) was identified as 5,2',3' -trihydroxy-7-methoxyflavone.
The compound (V) is yellow crystal (methanol), can be dissolved in acetone and DMSO, has dark spots at 254nm of an ultraviolet lamp, can be fluorescent at 365nm, and has yellow iodine, and has red color by TLC 5% vanillin-concentrated sulfuric acid reagent and dark green color by FeCl3 reagent reaction. HR-ESI-MS gives the experimental value m/z:349.0918[ M+H ]] + (calcd for C 17 H 17 O 8 349.0918) to give a molecular formula of: c (C) 17 H 17 O 8 The molecular weight is 348.
Of compounds 1 H-NMR(400MHz，DMSO-d 6 ) Is combined with 1 H- 1 H COSY and HSQC spectra, the putative compounds contained: two sets of methoxy proton signals, delta 3.78 (3H, s, 7-OCH) 3 )，δ3.72(3H，s，2′-OCH 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Three sets of phenolic hydroxyl proton signals, δ11.90 (1H, s, 5-OH), δ9.38 (1H, s,4 '-OH), δ08.58 (1H, s,3' -OH). δ16.82 (1 h, d, j=8.6 hz, h-6 '), δ 26.61 (1 h, d, j=8.5 hz, h-5 '), directly related to δ 3118.3 (C-6 '), δ110.9 (C-5 '), form an AB coupling system for the two hydrogen signals on the B ring on the structure of the flavonoid, exhibiting 2',3',4' -trisubstituted on the B ring. Delta 6.11 (1 h, d, j=2.3 hz, h-6), delta 6.06 (1 h, d, j=2.3 hz, h-8) is the hydrogen signal on the a ring of the flavone compound, which is directly related to delta 94.9 (C-6), delta 93.7 (C-8), assuming a substitution on the a ring as a 5, 7-disubstituted. Delta 5.85 (1 h, d, j=6.1 hz, 3-OH), delta 5.32 (1 h, d, j=11.7 hz, h-2), delta 4.75 (1 h, dd, j=11.7, 5.8hz, h-3) is a hydrogen signal on the C ring on the structure of the flavone compound. In addition, in the case of the optical fiber, 13 C-NMR(125MHz，DMSO-d 6 ) In the graph, the low field region gives a ketocarbonyl carbon signal delta 198.8 (C-4), and according to delta 78.2 (C-2) and delta 70.6 (C-3), the compound is presumed to be a flavonol compound.
Delta 6.82 (1 h, d, j=8.6 hz, h-6 ') in HMBC spectra are remotely correlated with delta 110.9 (C-5 '), delta 138.1 (C-3 '), delta 147.8 (C-2 '), delta 147.3 (C-4 '); delta 6.61 (1H, d, J=8.5 Hz, H-5 ') and delta 120.7 (C-1') Delta 118.3 (C-6 '), delta 138.1 (C-3 '), delta 147.3 (C-4 '), which are remotely related, indicate that the 2',3',4' positions of the B ring have a trioxysubstituent, and in addition, delta 9.38 (1H, s,4' -OH) is related to delta 6.61 (1H, d, J=8.5 Hz, H-5 ') and delta 9.38 (1H, s,4' -OH) is also related to delta 8.58 (1H, s,3' -OH), which are ortho to each other, i.e., 2' -OCH on the B ring, according to the ROESY spectrum 3 3',4' -OH structural fragments. Delta 11.90 (1H, s, 5-OH) is related to the carbon of delta 94.9 (C-6) in addition to delta 101.4 (C-10), delta 163.1 (C-5), and in addition, methoxy proton signal delta 3.78 (3H, s, -OCH) 3 ) Has a signal associated with carbon signal delta 167.6 (C-7), indicating 5, 7-disubstituted on ring A and 7-OCH 3 Is a structural fragment of (a).
In summary, compound (V) was identified as 3,5,3',4' -tetrahydroxy-7, 2' -dimethoxy-flavanone.
The compound (VI) is yellow crystal (methanol), can be dissolved in acetone and DMSO, has dark spots at 254nm of an ultraviolet lamp, can be fluorescent at 365nm, and has yellow iodine, and has orange yellow TLC 5% vanillin-concentrated sulfuric acid reagent, and FeCl 3 The reagent reaction appears dark green. HR-ESI-MS gives the experimental value m/z:331.0818[ M+H ]] + (calcd for C 17 H 15 O 7 331.0818) to give a molecular formula of: c (C) 17 H 14 O 7 The molecular weight was 330.
Of compounds 1 H-NMR(300MHz，DMSO-d 6 ) Is combined with 1 H- 1 H COSY and HSQC spectra, the putative compounds contained: methoxy proton signal, delta 3.90 (3H, s, 5-OCH) 3 ) Two sets of phenolic hydroxyl proton signals, δ9.51 (1 h, s,2 '-OH), δ8.70 (1 h, s,3' -OH). Delta 6.88 (1 h, dd, j=7.7, 1.7hz, h-6 '), delta 6.78 (1 h, dd, j=7.9, 1.7hz, h-4'), delta 6.68 (1 h, t, j=7.8 hz, h-5 '), and delta 116.9 (C-6'), delta 115.1 (C-4 '), delta 119.0 (C-5') are directly related to form an ABX coupling system for three hydrogen signals on the B ring on the flavonoid structure, exhibiting 2',3' -disubstituted on the B ring. Delta 6.45 (1H, s, H-8) is the hydrogen signal on the A ring of the flavone compound, which is directly related to Delta 93.4 (C-8), and is presumed to be taken from the A ringSubstituted by 5,6, 7-trisubstituted. Delta 6.05 (2h, d, j=4.6 Hz, -O-CH 2 -O-) presumably contains a methylenedioxy group in the compound. Delta 5.63 (1 h, dd, j=13.1, 2.9hz, h-2), delta 2.95 (1 h, dd, j=16.6, 13.1hz, h-3α), delta 2.60 (1 h, dd, j=16.6, 3.0hz, h-3β) is a hydrogen signal on the C-ring of the flavone structure. In addition, in the case of the optical fiber, 13 C-NMR(125MHz，DMSO-d 6 ) In the graph, a ketocarbonyl carbon signal delta 188.9 (C4) is given in the low field region, and according to delta 74.2 (C-2) and delta 43.6 (C-3), the compound is presumed to be a dihydroflavonoid compound.
Delta 6.05 (2 h, d, j=4.6 Hz, -O-CH in HMBC spectra 2 O-) is related to δ132.3 (C-6), δ154.0 (C-7), and furthermore, the methoxy proton signal δ3.90 (3H, s, -OCH) 3 ) Has a signal related to carbon signal delta 142.2 (C-5), which indicates that the A ring is 5,6, 7-trisubstituted and has 6, 7-methylenedioxy and 5-OCH 3 Is a structural fragment of (a).
In summary, compound (VI) was identified as 2',3' -dihydroxy-5-methoxy-6, 7-methylenedioxy-flavanone.
The compound (VII) of the invention is orange yellow crystal (methanol), can be dissolved in acetone and DMSO, has dark spots at 254nm of an ultraviolet lamp, can be fluorescent at 365nm, and has yellow iodine, and TLC 5% vanillin-concentrated sulfuric acid reagent has orange yellow color and FeCl 3 The reagent reaction appears dark green. HR-ESI-MS gives the experimental value m/z:319.0815[ M+H ]] + (calcd for C 16 H 15 O 7 319.0815) to give a molecular formula of: c (C) 16 H 14 O 7 The molecular weight was 318.
Of compounds 1 H-NMR(500MHz，DMSO-d 6 ) Is combined with 1 H- 1 H COSY and HSQC spectra, the putative compounds contained: methoxy proton signal, delta 3.68 (3H, s, 6-OCH) 3 ). Delta 6.89 (1 h, dd, j=7.8, 1.5hz, h-6 '), delta 6.80 (1 h, dd, j=7.9, 1.6hz, h-4'), delta 6.70 (1 h, t, j=7.8 hz, h-5 '), directly related to delta 117.1 (C-6'), delta 115.2 (C-4 '), delta 119.1 (C-5'), form an ABX coupling system for three hydrogen signals on the B ring on the structure of the flavonoid, showing 2',3' -bix on the B ringAnd (3) substitution. Delta 6.00 (1 h, d, j=1.7hz, h-8) is a hydrogen signal on the a ring of the flavone compound, which is directly related to delta 95.1 (C-8), and the substitution on the a ring is presumed to be 5,6, 7-trisubstituted. Delta 5.68 (1 h, dd, j=13.0, 3.0hz, h-2), delta 3.17 (1 h, dd, j=17.1, 12.9hz, h-3α), delta 2.70 (1 h, dd, j=17.2, 2.6hz, h-3β) is a hydrogen signal on the C-ring of the flavone structure. In addition, in the case of the optical fiber, 13 C-NMR(125MHz，DMSO-d 6 ) In the graph, a ketocarbonyl carbon signal delta 197.1 (C-4) is given in the low field region, and according to delta 74.1 (C-2) and delta 41.2 (C-3), the compound is presumed to be a dihydroflavonoid compound.
Delta 6.00 (1 h, d, j=1.7hz, h-8) in HMBC spectra correlates with delta 197.1 (C-4), delta 101.8 (C-10), delta 158.3 (C-9), delta 159.6 (C-7), delta 129.0 (C-6), and in addition, methoxy proton signal delta 3.68 (3 h, s, -OCH) 3 ) Has a signal related to the carbon signal delta 129.0 (C-6), which indicates that the A ring is 5,6, 7-trisubstituted and has 6-OCH 3 Is a structural fragment of (a).
In summary, compound (VII) was identified as 5,7,2',3' -tetrahydroxy-6-methoxyflavanone.
The compound (VIII) is orange red crystal (methanol), can be dissolved in acetone and DMSO, has dark spots at 254nm of an ultraviolet lamp, can be fluorescent at 365nm, and has yellow iodine, and has red TLC 5% vanillin-concentrated sulfuric acid reagent, feCl 3 The reagent reaction appears dark green. HR-ESI-MS gives the experimental value m/z:303.0865[ M+H ]] + (calcd for C 16 H 14 O 6 303.0865) to give a molecular formula of: c (C) 16 H 14 O 6 The molecular weight was 302.
Of compounds 1 H-NMR(300MHz，DMSO-d 6 ) Is combined with 1 H- 1 H COSY and HSQC spectra, the putative compounds contained: methoxy proton signal, delta 3.77 (3H, s,2' -OCH) 3 ). Delta 6.99 (1 h, d, j=3.5 hz, h-6 '), delta 6.97 (1 h, s, h-5 '), delta 6.91 (1 h, dd, j=6.3, 3.4hz, h-4 '), directly related to delta 117.3 (C-6 '), delta 124.1 (C-5 '), delta 117.2 (C-4 '), form ABX coupling system for three hydrogen signals on the B ring on flavonoid structure, exhibiting 2',3 on the B ring' -disubstituted. Delta 5.90 (2H, s, H-6, 8) is the hydrogen signal on the A ring of the flavone compound, which is directly related to delta 96.0 (C-6), delta 95.0 (C-8), and the substitution on the A ring is presumed to be 5, 7-disubstituted. Delta 5.72 (1 h, dd, j=13.1, 3.0hz, h-2), delta 3.25 (1 h, dd, j=17.1, 13.1hz, h-3α), delta 2.66 (1 h, dd, j=17.1, 3.0hz, h-3β) is a hydrogen signal on the C-ring of the flavone structure. In addition, in the case of the optical fiber, 13 C-NMR(125MHz，DMSO-d 6 ) In the graph, a ketocarbonyl carbon signal delta 192.2 (C-4) is given in the low field region, and according to delta 73.9 (C-2) and delta 41.4 (C-3), the compound is presumed to be a dihydroflavonoid compound.
Delta 5.72 (1 h, dd, j=13.1, 3.0hz, h-2) in HMBC spectra is correlated with delta 41.4 (C-3), delta 196.2 (C-4), delta 131.9 (C-1 '), delta 117.3 (C-6 '), delta 145.2 (C-2 '), and furthermore, methoxy proton signal delta 3.77 (3 h, s, -OCH) 3 ) Has a signal related to the carbon signal delta 145.2 (C-2 '), indicating that the B ring has 2' -OCH 3 Is a structural fragment of (a).
In summary, compound (VIII) was identified as 5,7,3 '-trihydroxy-2' -methoxyflavanone.
Example 2
The DPPH radical scavenging activity of the fine She Yuanwei of the present invention is further illustrated by the following detailed description, which is merely to aid in understanding the present invention and should not be construed as limiting the invention in any way.
Main experimental materials: a microplate reader (VarioskanFlash, 4.00.53,ThermoFisher Scientific); absolute ethanol (analytically pure), 2-biphenyl-1-picrylhydrazyl (DPPH), ascorbic acid (Vc).
Preparing a test solution: the novel compound of fine She Yuanwei, example 1, had a mother liquor concentration of 1mg/mL; when in use, the sample solution is diluted into sample solutions with the concentration of 150, 100, 50, 25, 10,5 mug/mL in sequence by absolute ethyl alcohol for standby.
Preparing DPPH solution: 6mg of DPPH powder is precisely weighed and dissolved in 50mL of absolute ethyl alcohol to prepare 0.12mg/mL of DPPH solution (for preparation at present), and the solution is refrigerated and stored in a dark place.
Preparing a reference substance solution: precisely weighing Vc 1.0mg, and dissolving with ethanol to obtain mother solution with concentration of 1mg/mL for later use.
Sample measurement: sample group, control group and blank group are added with test sample solution and DPPH solution with various concentrations, the reaction is carried out at room temperature (26 ℃) and in the dark for 30min, absorbance value is measured at 517nm, the parallel operation is carried out for 3 times (3 compound holes are formed), the average value is obtained, the clearance effect of the compound on DPPH is expressed by clearance rate (SR%), and the activity strength is expressed by IC (integrated circuit) 50 And (3) representing.
Sample group (A) i ): 100. Mu.L of test solution+100. Mu.L of DPPH solution;
control group (A) j ): 100 mu L of test solution and 100 mu L of absolute ethanol solution;
blank group (A) 0 ): 100. Mu.L of absolute ethanol solution+100. Mu.L of DPPH solution;
the clearance rate calculation formula: SR% = (a 0 -(A i -A j ))/A 0 ×100％。
And (3) determination of a reference substance: and (5) measuring the same as the sample.
Sample measurement results: DPPH free radical-eliminating IC with 6 new compounds of iris tenuifolia 50 The values are shown in Table 1 below.
TABLE 1 DPPH radical scavenging Activity of 6 novel Compounds from Iris tenuifolia
Example 3
The ABTS radical scavenging activity of the novel compounds of fine She Yuanwei of the present invention will be further illustrated by the following detailed description, which is merely to aid in the understanding of the present invention and should not be construed as limiting the invention in any way.
Main experimental materials: a microplate reader (VarioskanFlash, 4.00.53,ThermoFisher Scientific); absolute ethanol (analytically pure), 2-diaza-di (3-ethyl-benzothiazole-6-sulfonic acid) diammonium salt (ABTS), potassium persulfate, ascorbic acid (Vc).
Sample solution preparation: the novel compound of fine She Yuanwei, example 1, had a mother liquor concentration of 1mg/mL; the sample solutions with the concentrations of 150, 100, 50, 25, 10,5 mug/mL are diluted in turn by absolute ethyl alcohol for standby.
Preparation of ABTS stock solution: 300mg of ABTS is precisely weighed, 73.5mL of pure water is precisely added for dissolution, and 7.4mmol/L of ABTS stock solution is prepared.
Preparation of potassium persulfate stock solution: 50mg of potassium persulfate was precisely weighed, and 71.5mL of pure water was precisely added for dissolution to prepare a potassium persulfate stock solution having a concentration of 2.6 mmol/L.
ABTS· + Preparing a working solution: mixing the prepared ABTS stock solution and potassium persulfate stock solution according to the ratio of 1:1, reacting for 12-16h at 4 ℃ in dark place, diluting with absolute ethanol for 10-20 times when the solution is used, and enabling the absorbance value to be within the range of 0.70+/-0.02, wherein the solution is ABTS · + And (5) working fluid.
Preparing a reference substance solution: precisely weighing 1.0mg of Vc, and dissolving Vc in purified water to obtain mother solution with the concentration of 1mg/mL for later use.
Sample measurement: sample group, control group and blank group are added with test solution and ABTS of each concentration according to the following formula + Working solution, room temperature (26 ℃) and light-shielding reaction for 8min, measuring absorbance value at position of 284 nm, operating for 3 times in parallel (3 compound holes are formed), taking an average value, wherein the clearance effect of a compound on ABTS is expressed by clearance rate (SR%), and the activity strength is expressed by IC (integrated circuit) 50 And (3) representing.
Sample group (A) i ): 100. Mu.L of test solution+100. Mu.L of ABTS · + A working fluid;
control group (A) j ): 100 mu L of test solution and 100 mu L of absolute ethanol solution;
blank group (A) 0 ): 100 mu L absolute ethanol solution+100 mu L ABTS · + A working fluid;
the clearance rate calculation formula: SR% = (a 0 -(A i -A j ))/A 0 ×100％。
And (3) determination of a reference substance: and (5) measuring the same as the sample.
Sample measurement results: ABTS. Clear by 6 novel compounds of Iris tenuifolia + Free radical IC 50 The values are given in Table 2 below.
TABTS. Clear of 6 New Compounds from Iris tenuifolia + Free radicalsActivity(s)

Claims (4)

1. The chemical structural formulas of 6 compounds extracted and separated from iris tenuifolia are shown as follows:
the chemical name is: (I) 5,7,2',3' -tetrahydroxy-8-methoxofenavone
(III)3，5，3′，4′-tetrahydroxy-7，2′-dimethoxyflavone
(V)3，5，3′，4′-tetrahydroxy-7，2′-dimethoxyflavanone
(VI)2′，3′-dihydroxy-5-methoxy-6，7-methylenedioxyflavanone
(VII)5，7，2′，3′-tetrahydroxy-6-methoxyflavanone
(VIII)5，7，3′-trihydroxy-2′-methoxyflavanone。
2. The process for preparing 6 compounds extracted and isolated from iris tenuifolia as claimed in claim 1, comprising the steps of: reflux-extracting 2kg of dry aerial part of fine She Yuanwei with 95% ethanol, concentrating the extractive solution under reduced pressure to obtain total extract, suspending the total extract in water, sequentially extracting with petroleum ether, ethyl acetate and water saturated n-butanol, and recovering solvent to obtain petroleum ether Fraction A, ethyl acetate Fraction B and water saturated n-butanol Fraction C; separating the ethyl acetate Fraction B extract by polyamide column chromatography, gradient eluting with ethanol-water at volume ratio of 0:1-1:0, collecting 50% ethanol Fraction, detecting by silica gel column chromatography, MCI column chromatography, ODS column chromatography, and high performance liquid chromatography, collecting fractions containing each compound, concentrating, and recrystallizing to obtain 6 compounds (I), (III), (V), (VI), (VII) and (VIII) of rhizoma Iridis Tectori.
3. The use of a compound according to claim 1 or a compound prepared by the preparation method according to claim 2 for preparing an antioxidant drug, wherein the compound has DPPH radical scavenging activity.
4. The use of a compound according to claim 1 or a compound prepared by the preparation method according to claim 2 for preparing an antioxidant drug, wherein the compound has an ABTS radical scavenging activity.
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