Category:FL5F
From Metabolomics.JP
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| + | {{Huge|Flavonol}} | ||
{{Hierarchy|{{PAGENAME}}}} | {{Hierarchy|{{PAGENAME}}}} | ||
| − | == | + | =={{Bilingual|フラボノールの概要|Overview}}== |
| − | {{ | + | {{Twocolumn| |
| − | + | Flavonols are most widespread of the flavonoids and the main dietary flavonols are: | |
| − | + | [[FL5FAANS0001|kaempferol]], [[FL5FACNS0001|quercetin]], [[FL5FADNS0001|isorhamnetin]], and [[FL5FAGNS0001|myricetin]]. | |
| − | + | | | |
| − | + | フラボノールはフラボノイドの中でも最も幅広い植物に分布します。食品中の主なフラボノールは | |
| − | + | [[FL5FAANS0001|ケンフェロール]], [[FL5FACNS0001|クエルセチン]], [[FL5FADNS0001|イソラムネチン]]そして[[FL5FAGNS0001|ミリセチン]]です。 | |
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}} | }} | ||
| + | |||
| + | {{Twocolumn| | ||
| + | The majority of flavonol glycosides (including [[:Category:FL4|dihydroflavonols]]) are present as O-glycosides and not C-glycosides (see Glycosylation Patterns below). Most glycosides are 3-, 7-, 3'-, 4'-glycosides and their combinations. Only flavonols and flavones contain rare glycosidic sugars such as alloside (allose), mannoside (mannose), galacturonic acid (galacturonide), and apioside (this is found in isoflavone too).<br/> | ||
| + | |||
| + | Also, 2 flavonols ([[FL5FF8NS0002]] [[FL5FF8NSH001]]) are exceptionally found from a fungus ''Aspergillus candidus''. | ||
| + | | | ||
| + | ほとんどのフラボノール配糖体（[[:Category:FL4|ジヒドロフラボノール]]を含む)はＯ－配糖体でＣ－配糖体ではありません（以下の糖修飾パターンセクションを参照）。多くが3-, 7-, 3'-, 4'の配糖体とその組み合わせです。フラボノールとフラボンにのみ、アロース、マンノース、ガラクツロン酸、アピオースといった稀少糖の配糖体が見られます。（アピオース配糖体だけはイソフラボンにも存在。） | ||
| + | |||
| + | また二つのフラボノール([[FL5FF8NS0002]] [[FL5FF8NSH001]])が例外的に''Aspergillus candidus''（糸状菌）から見つかっています。 | ||
| + | }} | ||
| + | |||
| + | ==={{Bilingual|生合成|Biosynthesis}}=== | ||
| + | {{Bilingual|[[:Category:FL|フラボノイドトップページ]]からの抜粋|Excerpt from the [[:Category:FL|FL top page]]}} | ||
| + | <center> | ||
| + | {| style="text-align:center" | ||
| + | | | ||
| + | | style="background:pink"| [[FL2FAANS0001|naringenin]]<br/> [[Image:fl2.png|50px]]<br/>[[:Category:FL2|''FLAVANONE'']] | ||
| + | | | ||
| + | | style="background:yellowgreen"| [[FL5FAANS0001|kaempferol]]<br/>[[Image:FL5FAANS0001.png|80px]] | ||
| + | | style="background:yellowgreen" colspan="3" | [[Image:fl5.png|50px]]<br/>[[:Category:FL5|''FLAVONOLS'']] | ||
| + | | style="background:yellowgreen"| [[FL5FACNS0001|quercetin]]<br/>[[Image:FL5FACNS0001.png|80px]] | ||
| + | | | ||
| + | | style="background:yellowgreen"| [[FL5FAGNS0001|myricetin]]<br/>[[Image:FL5FAGNS0001.png|80px]] | ||
| + | |- | ||
| + | | | ||
| + | | F3H [[Image:Arrow00d35.png]] <small>(hydroxylase)</small> | ||
| + | | colspan="4" style="text-align:left"|[[Image:Arrow00ur35.png]] FLS:flavonol synthase <small>(oxygenase)</small> | ||
| + | | colspan="2" style="text-align:left"|[[Image:Arrow00ur35.png]] FLS | ||
| + | | | ||
| + | | colspan="2" style="text-align:left"|[[Image:Arrow00ur35.png]] FLS | ||
| + | |- | ||
| + | | style="background:plum"| [[Image:fl4.png|50px]]<br/>[[:Category:FL4|''DIHYDRO<br/>FLAVONOLS'']] | ||
| + | | style="background:plum"| [[FL4DAANS0001|dihydro-kaempferol]]<br/>[[Image:FL4DAANS0001.png|80px]] | ||
| + | | colspan="3"| F3'H<br/>[[Image:Arrow00r100.png]]<br/>+OH in B-ring | ||
| + | | style="background:plum"| [[FL4DACNS0001|dihydro-quercetin]]<br/>[[Image:FL4DACNS0001.png|80px]] | ||
| + | | colspan="3"| F3'5'H<br/>[[Image:Arrow00r100.png]]<br/>+OH in B-ring | ||
| + | | style="background:plum"| [[FL4DAGNS0001|dihydro-myricetin]]<br/>[[Image:FL4DAGNS0001.png|80px]] | ||
| + | |} | ||
| + | </center> | ||
| + | |||
| + | {{FL_digit56|FL5F}} | ||
Latest revision as of 10:56, 19 August 2010
Flavonol
| Flavonoid Top | Molecule Index | Author Index | Journals | Structure Search | Food | New Input |
Upper classes : FL Flavonoid : FL5 Flavonol
Contents |
[edit] Overview
Flavonols are most widespread of the flavonoids and the main dietary flavonols are: kaempferol, quercetin, isorhamnetin, and myricetin.
The majority of flavonol glycosides (including dihydroflavonols) are present as O-glycosides and not C-glycosides (see Glycosylation Patterns below). Most glycosides are 3-, 7-, 3'-, 4'-glycosides and their combinations. Only flavonols and flavones contain rare glycosidic sugars such as alloside (allose), mannoside (mannose), galacturonic acid (galacturonide), and apioside (this is found in isoflavone too).
Also, 2 flavonols (FL5FF8NS0002 FL5FF8NSH001) are exceptionally found from a fungus Aspergillus candidus.
[edit] Biosynthesis
Excerpt from the FL top page
naringenin FLAVANONE |
kaempferol
|
 FLAVONOLS |
quercetin
|
myricetin
| ||||||
F3H  (hydroxylase)
|
 FLS:flavonol synthase (oxygenase)
|
FLS
|
FLS
| |||||||
 DIHYDRO FLAVONOLS |
dihydro-kaempferol
|
F3'H +OH in B-ring |
dihydro-quercetin
|
F3'5'H +OH in B-ring |
dihydro-myricetin
| |||||
[edit] Major Plant Families
|
|
The number in each family is counted as the number of genera (not species) listed in our registered references. Each reference record is accessible by clicking the link in compound pages. The taxonomy follows the APG-II classification. For details (or if the figure is broken), visit this page. 各科のカウントは種名でなく文献に記載された属名の数です。文献は代謝物ページのリンクからたどれ、分類はAPG-IIです。左の図が表示されない場合はここをクリックしてください。 |
[edit] Patterns of Hydroxylation
| Category Names in the 3rd Class | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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The 5th and 6th digits of our flavonoid ID indicates the hydroxylation patterns of A-ring and B-ring (See the upper-right figure. The leftmost ring is A, rightmost is B), respectively. The following chart is spanned by these 2 digits. R indicates H or CH3, and R' indicates H or R. Numbers are IUPAC positions. The value in each cell (such as GS: glycosilation only) corresponds to the 7th and 8th digits, which is explained at the bottom of this page.
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Position of -OH (-OCH3) groups |
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| A (593 pages) | B (66 pages) | C (679 pages) | D (148 pages) | E (38 pages) | F (21 pages) | G (142 pages) | H (16 pages) | I (18 pages) | J (16 pages) | K (12 pages) | L (73 pages) | 8 (23 pages) | 9 (90 pages) | ||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
A (992 pages) | CS (2 pages) DS (1 pages) GA (47 pages) GI (16 pages) GL (113 pages) GM (2 pages) GP (1 pages) GS (141 pages) NC (2 pages) NI (11 pages) NM (2 pages) NN (2 pages) NP (3 pages) NR (1 pages) NS (6 pages) | GA (1 pages) GI (29 pages) GL (3 pages) GP (1 pages) GS (12 pages) NI (3 pages) NS (2 pages) | CS (2 pages) GA (44 pages) GI (1 pages) GL (80 pages) GM (1 pages) GS (127 pages) NC (1 pages) ND (1 pages) NF (2 pages) NI (7 pages) NM (1 pages) NP (7 pages) NS (16 pages) | GA (26 pages) GL (41 pages) GS (36 pages) NI (2 pages) NS (6 pages) | GA (3 pages) GI (1 pages) GL (5 pages) GS (5 pages) NF (1 pages) NS (2 pages) | GL (3 pages) GS (2 pages) NS (1 pages) | GA (8 pages) GL (11 pages) GM (1 pages) GN (2 pages) GS (36 pages) NM (1 pages) NS (1 pages) | GA (1 pages) GL (6 pages) GS (5 pages) NS (1 pages) | CS (1 pages) GA (4 pages) GL (5 pages) GS (5 pages) NS (1 pages) | GA (2 pages) GS (3 pages) NM (2 pages) NS (1 pages) | GS (2 pages) NS (1 pages) | GL (1 pages) GS (3 pages) NI (2 pages) NS (20 pages) | GL (2 pages) GS (1 pages) NS (7 pages) | GL (3 pages) GM (1 pages) GS (6 pages) NI (3 pages) NM (6 pages) NN (1 pages) NP (3 pages) NS (8 pages) |
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B (20 pages) | GA (2 pages) NI (1 pages) NS (1 pages) | NS (1 pages) | GA (1 pages) GL (2 pages) GS (2 pages) NS (1 pages) | NS (1 pages) | NS (1 pages) | GS (1 pages) NS (1 pages) | GA (1 pages) GL (1 pages) GS (2 pages) NS (1 pages) | |||||||
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C (114 pages) | CS (1 pages) GA (4 pages) GI (1 pages) GL (11 pages) GS (14 pages) NI (1 pages) NM (1 pages) NS (2 pages) | GL (2 pages) GS (1 pages) NC (1 pages) NS (2 pages) | CS (1 pages) DS (1 pages) GA (9 pages) GL (4 pages) GS (13 pages) NS (5 pages) | GA (4 pages) GL (4 pages) GS (4 pages) NS (2 pages) | GA (1 pages) GI (1 pages) GL (4 pages) GS (1 pages) NI (2 pages) NS (3 pages) | GS (3 pages) NS (1 pages) | CS (1 pages) GA (1 pages) GS (3 pages) NS (1 pages) | GA (1 pages) NS (1 pages) | NS (2 pages) | |||||
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D (129 pages) | GS (8 pages) NF (4 pages) NI (3 pages) NM (4 pages) NS (4 pages) | GS (1 pages) NC (1 pages) NF (1 pages) NM (2 pages) NS (3 pages) | GS (16 pages) NF (2 pages) NI (4 pages) NM (5 pages) NP (2 pages) NS (5 pages) | GS (4 pages) NF (3 pages) NI (6 pages) NM (5 pages) NS (4 pages) | CS (1 pages) GS (3 pages) NI (1 pages) NS (3 pages) | GL (1 pages) GS (1 pages) NF (1 pages) NM (1 pages) NS (5 pages) | GS (4 pages) NM (2 pages) NS (1 pages) | NS (3 pages) | NS (2 pages) | GS (2 pages) NM (2 pages) NS (2 pages) | NS (7 pages) | |||
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E (284 pages) | GA (5 pages) GL (10 pages) GS (26 pages) NI (7 pages) NM (1 pages) NS (26 pages) | GA (4 pages) GL (15 pages) GS (70 pages) NF (1 pages) NI (2 pages) NM (4 pages) NS (55 pages) | GL (1 pages) GS (1 pages) NS (18 pages) | GS (5 pages) NS (18 pages) | NS (2 pages) | GS (1 pages) NF (1 pages) NM (1 pages) NS (10 pages) | ||||||||
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F (224 pages) | GA (1 pages) GL (11 pages) GS (28 pages) NI (4 pages) NM (2 pages) NS (25 pages) | GA (6 pages) GL (14 pages) GS (28 pages) NI (9 pages) NS (38 pages) | GS (3 pages) NS (10 pages) | GS (1 pages) NS (7 pages) | NN (1 pages) NS (9 pages) | NI (6 pages) NM (6 pages) NS (15 pages) | ||||||||
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G (95 pages) | GL (1 pages) GS (3 pages) NI (3 pages) NS (10 pages) | GA (2 pages) GL (3 pages) GS (2 pages) NI (1 pages) NS (29 pages) | GS (1 pages) NS (17 pages) | NS (13 pages) | NS (1 pages) | NI (1 pages) NS (8 pages) | ||||||||
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1 (42 pages) | CS (1 pages) GL (1 pages) GS (2 pages) NF (1 pages) NS (2 pages) | CS (1 pages) GL (2 pages) GS (5 pages) NF (1 pages) NP (3 pages) NS (7 pages) | GS (3 pages) NF (1 pages) NS (6 pages) | GL (1 pages) | NF (2 pages) NP (1 pages) NS (2 pages) | |||||||||
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2 (14 pages) | GS (1 pages) NP (1 pages) NS (2 pages) | NI (1 pages) NP (1 pages) NS (4 pages) | NS (1 pages) | NS (1 pages) | GF (1 pages) NP (1 pages) | |||||||||
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3 (14 pages) | NS (4 pages) | NS (6 pages) | NS (1 pages) | GS (2 pages) NS (1 pages) | ||||||||||
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4 (2 pages) | NS (1 pages) | GS (1 pages) | ||||||||||||
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9 (5 pages) | GL (1 pages) NI (1 pages) | NM (1 pages) NS (1 pages) | NS (1 pages) | |||||||||||
Abbreviations used in the above chart
- First Characters
N not glycosylated; G O-glycoside; C C-glycoside; D both glycosides;
- Second Characters
S not modified; M alkylated; I prenylated; R cyclic-prenylated; F furanoFL; P pyranoFL; D furano and pyranoFL; N phenylpropanoid; C others;
- Special Second Character only for Anthycyanin (FL7)
A Galactosylated; L Glucosylated; O modified with other sugars;
[edit] Other Unusual Patterns
These types are not classified in the above chart.
| Quinone | QU (0 pages) | alpha-Hydroxy | HX (0 pages) | beta-Hydroxy | HY (0 pages) | Peltogynoid | PT (8 pages) |
| Retrocalchone | RT (0 pages) | Dehydro-backbone | WX (0 pages) | Additional rings | RN (0 pages) | Others | UN (0 pages) |
| Pyranoanthocyanin (FL7 only) | RX (0 pages) | ||||||
[edit] Patterns of Glycosylation
The 7th and 8th digits of the flavonoid ID indicates the glycosylation, and other modification patterns, respectively. The following chart is spanned by these 2 digits. The value in each cell (such as AA for the standard form) corresponds to the 5th and 6th digits.
| 7th digit → 8th digit ↓ |
No glycosylation N (681 pages) | O-glycoside G (1249 pages) | C-glycoside C (11 pages) | O- & C-glycoside D (2 pages) | |
|---|---|---|---|---|---|
| no modification | S (1160 pages) | 19 (2 pages) 1A (2 pages) 1C (7 pages) 1G (6 pages) 2A (2 pages) 2C (4 pages) 2G (1 pages) 2L (1 pages) 39 (1 pages) 3A (4 pages) 3C (6 pages) 3L (1 pages) 4A (1 pages) 9C (1 pages) 9G (1 pages) A8 (7 pages) A9 (8 pages) AA (6 pages) AB (2 pages) AC (16 pages) AD (6 pages) AE (2 pages) AF (1 pages) AG (1 pages) AH (1 pages) AI (1 pages) AJ (1 pages) AK (1 pages) AL (20 pages) BA (1 pages) BB (1 pages) BC (1 pages) BD (1 pages) BE (1 pages) BF (1 pages) BG (1 pages) CA (2 pages) CB (2 pages) CC (5 pages) CD (2 pages) CE (3 pages) CF (1 pages) CG (1 pages) CJ (1 pages) CK (2 pages) DA (4 pages) DB (3 pages) DC (5 pages) DD (4 pages) DE (3 pages) DF (5 pages) DG (1 pages) DH (3 pages) DI (2 pages) DJ (2 pages) DK (7 pages) E8 (2 pages) E9 (10 pages) EA (26 pages) EC (55 pages) EG (18 pages) EL (18 pages) F8 (9 pages) F9 (15 pages) FA (25 pages) FC (38 pages) FG (10 pages) FL (7 pages) G8 (1 pages) G9 (8 pages) GA (10 pages) GC (29 pages) GG (17 pages) GL (13 pages) PT (8 pages) | 1A (2 pages) 1C (5 pages) 1G (3 pages) 2A (1 pages) 39 (2 pages) 4G (1 pages) A8 (1 pages) A9 (6 pages) AA (141 pages) AB (12 pages) AC (127 pages) AD (36 pages) AE (5 pages) AF (2 pages) AG (36 pages) AH (5 pages) AI (5 pages) AJ (3 pages) AK (2 pages) AL (3 pages) BC (2 pages) BF (1 pages) BG (2 pages) CA (14 pages) CB (1 pages) CC (13 pages) CD (4 pages) CE (1 pages) CF (3 pages) CG (3 pages) DA (8 pages) DB (1 pages) DC (16 pages) DD (4 pages) DE (3 pages) DF (1 pages) DG (4 pages) DJ (2 pages) E9 (1 pages) EA (26 pages) EC (70 pages) EG (1 pages) EL (5 pages) FA (28 pages) FC (28 pages) FG (3 pages) FL (1 pages) GA (3 pages) GC (2 pages) GG (1 pages) | 1A (1 pages) 1C (1 pages) AA (2 pages) AC (2 pages) AI (1 pages) CA (1 pages) CC (1 pages) CG (1 pages) DE (1 pages) | AA (1 pages) CC (1 pages) |
| alkylated | M (54 pages) | 9C (1 pages) A9 (6 pages) AA (2 pages) AC (1 pages) AG (1 pages) AJ (2 pages) CA (1 pages) DA (4 pages) DB (2 pages) DC (5 pages) DD (5 pages) DF (1 pages) DG (2 pages) DJ (2 pages) E9 (1 pages) EA (1 pages) EC (4 pages) F9 (6 pages) FA (2 pages) | A9 (1 pages) AA (2 pages) AC (1 pages) AG (1 pages) | ||
| prenylated | I (0 pages) | 2C (1 pages) 9A (1 pages) A9 (3 pages) AA (11 pages) AB (3 pages) AC (7 pages) AD (2 pages) AL (2 pages) BA (1 pages) CA (1 pages) CE (2 pages) DA (3 pages) DC (4 pages) DD (6 pages) DE (1 pages) EA (7 pages) EC (2 pages) F9 (6 pages) FA (4 pages) FC (9 pages) G9 (1 pages) GA (3 pages) GC (1 pages) | AA (16 pages) AB (29 pages) AC (1 pages) AE (1 pages) CA (1 pages) CE (1 pages) | ||
| cyclic prenylated | R (0 pages) | AA (1 pages) | |||
| furano FL | F (22 pages) | 19 (2 pages) 1A (1 pages) 1C (1 pages) 1G (1 pages) AC (2 pages) AE (1 pages) DA (4 pages) DB (1 pages) DC (2 pages) DD (3 pages) DF (1 pages) E9 (1 pages) EC (1 pages) | 29 (1 pages) | ||
| pyrano FL | P (24 pages) | 19 (1 pages) 1C (3 pages) 29 (1 pages) 2A (1 pages) 2C (1 pages) A9 (3 pages) AA (3 pages) AC (7 pages) DC (2 pages) | AA (1 pages) AB (1 pages) | ||
| furano & pyrano FL | D (1 pages) | AC (1 pages) | |||
| prenylpropanoid | N (6 pages) | A9 (1 pages) AA (2 pages) F8 (1 pages) | AG (2 pages) | ||
| others | C (5 pages) | AA (2 pages) AC (1 pages) CB (1 pages) DB (1 pages) | |||
| 3-Gal related | A | N.A. | AA (47 pages) AB (1 pages) AC (44 pages) AD (26 pages) AE (3 pages) AG (8 pages) AH (1 pages) AI (4 pages) AJ (2 pages) BA (2 pages) BC (1 pages) BG (1 pages) CA (4 pages) CC (9 pages) CD (4 pages) CE (1 pages) CG (1 pages) CJ (1 pages) EA (5 pages) EC (4 pages) FA (1 pages) FC (6 pages) GC (2 pages) | N.A. | N.A. |
| 3-Glc related | L | N.A. | 1A (1 pages) 1C (2 pages) 1L (1 pages) 9A (1 pages) A8 (2 pages) A9 (3 pages) AA (113 pages) AB (3 pages) AC (80 pages) AD (41 pages) AE (5 pages) AF (3 pages) AG (11 pages) AH (6 pages) AI (5 pages) AL (1 pages) BC (2 pages) BG (1 pages) CA (11 pages) CB (2 pages) CC (4 pages) CD (4 pages) CE (4 pages) DF (1 pages) EA (10 pages) EC (15 pages) EG (1 pages) FA (11 pages) FC (14 pages) GA (1 pages) GC (3 pages) | N.A. | N.A. |
| other sugar at 3 | O | N.A. | N.A. | N.A. | |
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