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黄酮类化合物

黄酮类化合物 定义与结构特征

黄酮类化合物是一大类天然存在的有机化合物,属于酚类衍生物。它们的分子结构通常包含两个苯环(A和B环)和一个三碳环(C环),形成一个基本骨架。该骨架由多个亚结构组成,包括黄烷醇、黄酮、黄酮醇等。

生物来源

黄酮类化合物广泛存在于植物界中,常见于许多蔬菜、水果及中药中。例如,在大豆、柑橘、茶叶和甘草中都可以找到它们的身影。

化学性质 亲水性与溶解度

由于其分子结构中含有多个酚羟基,因此具有一定的亲水性和良好的溶解性,这使得黄酮类化合物在药物设计中扮演重要角色。

稳定性与光敏性

大多数黄酮类化合物相对稳定,在适宜条件下不易发生降解。但某些类型的黄酮对光照比较敏感,容易被氧化,导致颜色变化。

生理活性与药用价值

黄酮类化合物因其丰富的生理活性而备受关注,主要包括:

  • 抗氧化作用:可有效清除体内自由基,保护细胞免受损伤。
  • 抗炎效应:有助于减轻炎症反应,缓解症状。
  • 心血管保护:可能通过多种机制改善心脑血管健康。
  • 抗癌潜力:研究表明某些黄酮类物质具有抑制肿瘤生长的能力。
应用领域 食品工业

作为一种天然色素和抗氧化剂,被广泛应用于食品加工中以提高其保质期及营养价值。

化妆品行业

利用其良好的生物相容性和抗衰老特性,在化妆品配方中应用广泛。

药物开发

由于黄酮类化合物展现出广泛的药理活性,已成为新药研发的重要候选目标之一。

中文名称 英文名称 CAS号 化学式 结构式图片
—— (2R,3R,8R)-8-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,10a-dihydroxy-5,7a-dimethoxy-2-(3,4,5-trimethoxy-phenyl)-3,4,7a,10a-tetrahydro-2H,8H-furo[3',4':4,5]furo[2,3-h]chromen-10-one 126715-97-7 C29H34O13
(2R,3R,8R)-8-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,10a-dihydroxy-5,7a-dimethoxy-2-(3,4,5-trimethoxy-phenyl)-3,4,7a,10a-tetrahydro-2H,8H-furo[3',4':4,5]furo[2,3-h]chromen-10-one
—— Carbonic acid (2R,3R)-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chroman-3-yl ester methyl ester 68742-19-8 C21H24O8
Carbonic acid (2R,3R)-2-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-chroman-3-yl ester methyl ester
—— (2R,3aR,4S,9bS)-2-ethyl-4-(4-hydroxy-phenyl)-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromen-8-ol 787622-72-4 C20H22O3
(2R,3aR,4S,9bS)-2-ethyl-4-(4-hydroxy-phenyl)-1,2,3,3a,4,9b-hexahydro-cyclopenta[c]chromen-8-ol
—— methyl rac-2-(4-chloro-3-(trifluoromethyl)phenyl)-2H-chromene-3-carboxylate 1204754-58-4 C18H12ClF3O3
methyl rac-2-(4-chloro-3-(trifluoromethyl)phenyl)-2H-chromene-3-carboxylate
—— 3-(4-fluorophenyl)-3-(4-(N-piperidinyl)phenyl) 5,7-difluoro-10,12-dibromo-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran 1311274-89-1 C39H30Br2F3NO
3-(4-fluorophenyl)-3-(4-(N-piperidinyl)phenyl) 5,7-difluoro-10,12-dibromo-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran
—— 1311276-95-5 C30H27BrN4O4
—— 2-(3-nitro-phenyl)-2,3-dihydro-benzo[<i>h</i>]chromen-4-one 109941-50-6 C19H13NO4
2-(3-nitro-phenyl)-2,3-dihydro-benzo[<i>h</i>]chromen-4-one
—— 4-chloro-7-iodo-1-methyl-8-phenyl-1H-chromeno[7,8-d]imidazol-6-one 1279089-02-9 C17H10ClIN2O2
4-chloro-7-iodo-1-methyl-8-phenyl-1H-chromeno[7,8-d]imidazol-6-one
—— 6-azidoflavonol 1332713-52-6 C15H9N3O3
6-azidoflavonol
—— Acetic acid 2,9,11-triacetoxy-6-(4-acetoxy-3-methoxy-phenyl)-5-methyl-8-oxo-8H-7,13-dioxa-benzo[3,4]cyclohepta[1,2-b]naphthalen-4-yl ester 61276-43-5 C35H28O14
Acetic acid 2,9,11-triacetoxy-6-(4-acetoxy-3-methoxy-phenyl)-5-methyl-8-oxo-8H-7,13-dioxa-benzo[3,4]cyclohepta[1,2-b]naphthalen-4-yl ester
—— (2S,3R)-6-sec-Butyl-3-iodo-2-phenyl-chroman 76336-87-3 C19H21IO
(2S,3R)-6-sec-Butyl-3-iodo-2-phenyl-chroman
—— [4,8’]-2,3-trans-3.4-trans:2’,3’-cis-decabenzyloxy-(+)-gallocatechin-(-)-epigallocatechin 1499167-15-5 C100H86O14
[4,8’]-2,3-trans-3.4-trans:2’,3’-cis-decabenzyloxy-(+)-gallocatechin-(-)-epigallocatechin
—— 5-(4-bromophenyl)-2-(4-methoxyphenyl)-6-[(E)-3-(4-methoxyphenyl)acryloyl]-7-methylchroman-4-one 1365935-32-5 C33H27BrO5
5-(4-bromophenyl)-2-(4-methoxyphenyl)-6-[(E)-3-(4-methoxyphenyl)acryloyl]-7-methylchroman-4-one
—— N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-4,5-dibromo-2-thiophenesulfonamide 260064-00-4 C20H11Br2NO7S2
N-[2-(Benzo[1,3]dioxol-5-yl)-3-hydroxy-4-oxo-4H-chromen-6-yl]-4,5-dibromo-2-thiophenesulfonamide
—— 8-(Bromomethyl)-2-(4-methylphenyl)chromen-4-one 87165-55-7 C17H13BrO2
8-(Bromomethyl)-2-(4-methylphenyl)chromen-4-one
—— 5-Hydroxy-7-methyl-4'-methoxy-6-azaflavanon 70542-09-5 C16H15NO4
5-Hydroxy-7-methyl-4'-methoxy-6-azaflavanon
—— 2,2,9,9-tetraphenyl-1,2,9,10-tetrahydronaphtho[2,1-b:7,8-b']difuran 1443012-03-0 C38H28O2
2,2,9,9-tetraphenyl-1,2,9,10-tetrahydronaphtho[2,1-b:7,8-b']difuran
—— 5-β-D-glucopyranosyloxy-3,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-chromenylium; chloride 35775-62-3 C23H25O12*Cl
5-β-D-glucopyranosyloxy-3,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxy-phenyl)-chromenylium; chloride
—— methyl 7-fluoro-2-(3-nitrophenyl)-4-oxo-4H-chromene-3-carboxylate 1439357-13-7 C17H10FNO6
methyl 7-fluoro-2-(3-nitrophenyl)-4-oxo-4H-chromene-3-carboxylate
—— 3',4'-diacetoxy-5-hydroxy-3,6,7-trimethoxyflavone 97389-87-2 C21H18O9
3',4'-diacetoxy-5-hydroxy-3,6,7-trimethoxyflavone
—— 5-(4-chlorophenyl)-7-methyl-2-(naphthalen-1-yl)-6-[(E)-3-(naphthalen-1-yl)acryloyl]chroman-4-one 1365935-64-3 C39H27ClO3
5-(4-chlorophenyl)-7-methyl-2-(naphthalen-1-yl)-6-[(E)-3-(naphthalen-1-yl)acryloyl]chroman-4-one
—— (-)-epigallocatechin 119439-94-0 C15H12O8
(-)-epigallocatechin
—— ethyl 3,7-dihydro-7-oxo-2,3-diphenyl-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate 1388154-60-6 C26H21NO4
ethyl 3,7-dihydro-7-oxo-2,3-diphenyl-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate
—— 88038-18-0 C60H43Br5O24
—— 3,4-cis-4-acetoxy-3-O-acetyl-4-4-dehydro-5,7,3',4'-tetra-O-benzyl-(-)-epicatechin 1030624-94-2 C47H42O9
3,4-cis-4-acetoxy-3-O-acetyl-4-4-dehydro-5,7,3',4'-tetra-O-benzyl-(-)-epicatechin
—— 1215089-92-1 C16H8ClNO2
—— (8S)-8-(2-formylphenyl)-N,N,2,3-tetramethyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-carboxamide 1172118-91-0 C22H23N3O3
(8S)-8-(2-formylphenyl)-N,N,2,3-tetramethyl-7,8-dihydro-6H-pyrano[2,3-e]benzimidazole-5-carboxamide
—— (+-)-3c,4t-Bis-benzoyloxy-2r-(4-methoxy-phenyl)-6-methyl-chroman 103271-46-1 C31H26O6
(+-)-3c,4t-Bis-benzoyloxy-2r-(4-methoxy-phenyl)-6-methyl-chroman
—— [4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin 664351-42-2 C88H76O13
[4,8]-2,3-cis-3,4-trans:2,3-trans-octa-O-benzyl-(-)-3-O-acetyl-(-)-epicatechin-(+)-catechin
—— 3-chlorooctacetyldiosmin 827346-25-8 C44H47ClO23
3-chlorooctacetyldiosmin
—— Rhamnocitrin-3-O-β-isorhamninosid-deca-O-acetat 73519-12-7 C54H62O29
Rhamnocitrin-3-O-β-isorhamninosid-deca-O-acetat
—— N-((2R,3R)-6-Chloro-2-phenyl-chroman-3-yl)-hydroxylamine 112513-96-9 C15H14ClNO2
N-((2R,3R)-6-Chloro-2-phenyl-chroman-3-yl)-hydroxylamine
—— Norartocarpanon-trimethylether 121927-86-4 C18H18O6
Norartocarpanon-trimethylether
—— 4,4',6'-Trihydroxy-2'-O-β-D-galactopyranosyl-dihydrochalkon 40816-73-7 C21H24O10
4,4',6'-Trihydroxy-2'-O-β-D-galactopyranosyl-dihydrochalkon
—— 6-<(5-chloropentyl)oxy>flavone 140439-45-8 C20H19ClO3
6-<(5-chloropentyl)oxy>flavone
—— cichonain II 4'-benzylthioether 101401-65-4 C31H26O9S
cichonain II 4'-benzylthioether
—— 7-methoxy-2-(2,4,6-trimethoxy-phenyl)-chromen-4-one 744210-77-3 C19H18O6
7-methoxy-2-(2,4,6-trimethoxy-phenyl)-chromen-4-one
—— 3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran 761409-23-8 C43H42N2O4
3-(4-methoxyphenyl)-3-(4-morpholinophenyl)-11-morpholino-13,13-dimethyl-3H,13H-indeno[2',3':3,4]naphtho[1,2-b]pyran
—— 9-methyl-2-phenyl-3,11-dihydro-2H-pyrano[2,3-a]carbazol-4-one 875535-10-7 C22H17NO2
9-methyl-2-phenyl-3,11-dihydro-2H-pyrano[2,3-a]carbazol-4-one
—— ethyl 4-[(4-oxo-4H-1-benzopyran-2-phenyl-6-yl)oxy]butyrate 301206-21-3 C21H20O5
ethyl 4-[(4-oxo-4H-1-benzopyran-2-phenyl-6-yl)oxy]butyrate
—— 4'-(benzyloxy)3,7-dimethylflavone 132020-91-8 C24H20O3
4'-(benzyloxy)3,7-dimethylflavone
—— (E)-N-(4-fluorophenethyl)-3-(7-methoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-3-yl)acrylamide 1412410-92-4 C28H24FNO5
(E)-N-(4-fluorophenethyl)-3-(7-methoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-3-yl)acrylamide
—— 7-(2-morpholinoethoxy)-5-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one hydrochloride 1389320-59-5 C21H21NO7*ClH
7-(2-morpholinoethoxy)-5-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one hydrochloride
—— 2-(3,4-Bis-benzyloxy-phenyl)-5-hydroxy-6,7-dimethoxy-3-methyl-chromen-4-one 134082-32-9 C32H28O7
2-(3,4-Bis-benzyloxy-phenyl)-5-hydroxy-6,7-dimethoxy-3-methyl-chromen-4-one
—— 8-Methoxy-2-phenyl-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one 98910-19-1 C19H16O4
8-Methoxy-2-phenyl-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one
—— 2-Phenyl-6-(6-piperidinylhexoxy)-4H-1-benzopyran-4-one hydrochloride 139652-81-6 C26H31NO3*ClH
2-Phenyl-6-(6-piperidinylhexoxy)-4H-1-benzopyran-4-one hydrochloride
—— 1198053-66-5 C21H15ClO4
—— 4-[21-Methoxy-14,14-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,20,23-trioxahexacyclo[15.8.0.02,10.03,8.011,16.019,24]pentacosa-1(25),2(10),3,5,7,11(16),12,17,19(24)-nonaene-9,3'-cyclohexane]-22-yl]morpholine 1268817-15-7 C50H53NO7
4-[21-Methoxy-14,14-bis(4-methoxyphenyl)-1',1',5',5'-tetramethylspiro[15,20,23-trioxahexacyclo[15.8.0.02,10.03,8.011,16.019,24]pentacosa-1(25),2(10),3,5,7,11(16),12,17,19(24)-nonaene-9,3'-cyclohexane]-22-yl]morpholine
—— (2R,3R,8R)-8-((S)-1,2-Dihydroxy-ethyl)-3-hydroxy-5,7a,10a-trimethoxy-2-(3,4,5-trimethoxy-phenyl)-3,4,7a,10a-tetrahydro-2H,8H-furo[3',4':4,5]furo[2,3-h]chromen-10-one 126715-96-6 C27H32O13
(2R,3R,8R)-8-((S)-1,2-Dihydroxy-ethyl)-3-hydroxy-5,7a,10a-trimethoxy-2-(3,4,5-trimethoxy-phenyl)-3,4,7a,10a-tetrahydro-2H,8H-furo[3',4':4,5]furo[2,3-h]chromen-10-one
—— Isoanhydroicaritin-triacetat 28610-32-4 C27H26O9
Isoanhydroicaritin-triacetat