Category:FL3F

FL3F: Flavone

Overview

The basic structure of flavone is 2-phenylbenzopyrone, the same as flavonol. The word 'flavone' first appeard in 1895^[1], indicating its yellow color. luteolin, quercetin, kaempferol were widespread natural dyes before synthetic dyes were invented in 1856 ^[2]. As a dye, flavone requires a mordant to chelate positions 4 and 5 with metallic salts. Ferric chloride gives green with 5-hydroxyflavones and brown with 3-hydroxyflavones (flavonol). Chrysin was the first flavone to be isolated in a pure form. Many members in Asteraceae contain unique flavones, especially the genus Cirsium and Onopordum in the tribe Cardueae (or equivalently, Cynareae), commonly known as thistles.

Polymethoxylated flavones

Most flavones are not widely distributed and often 7-O-glycosylated. Major dietary sources are celery, parsley, and some herbs. In citrus species, polymethoxylated flavones such as tangeretin and nobiletin are found.

apigenin

luteolin

tangeretin

nobiletin

Structure

Flavones are commonly present in vacuoles as O- and/or C-glycosides. Most glycosides are 7-, 3'-, and 4'-glycosides. 5-glycoside is rare because the 5-hydroxyl group forms a hydrogen bond with the adjacent 4-carbonyl group. Flavone glycosides have been frequently used as chemotaxonomic markers^[3].
Isovitexin (C-glycosylflavone) acts as co-pigments of anthocyanins in Iris ensata Thunb. (Japanese iris flower)^[4]

↑ S. von Kostanecki and J. Jambor, Ber. Deut. Chem. Ges. 28, 2302, 1895
↑ J. Piccard, Ber. Deut. Chem. Ges. 6, 884 (1873); 7, 888 (1874); 10, 176 (1877)
↑ Iwashina T & Hatta H: Flavonoid glycosides from leaves of Aucuba japonica and Helwingia japonica: Phytochemical relationship with the genus Cornus J. Jap. Bot. 72:337-346, 1997
Reference:Iwashina_T:Ootani_S:,Phytochemistry,1990,29,3639
Reference:Iwashina T:Kamenosono K:Ueno T:,Phytochemistry,1999,51,1109
↑ Iwashina T, Kamenosono K, and Yabuya T: Isolation and identification of flavonoid and related compounds as co-pigments from the flowers of Iris ensata. J. Jap. Bot. 71:281-287

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。

Patterns of Hydroxylation

Category Names in the 3rd Class

ID	Description
FL3F18 (3 pages)	7,2',(3'),(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3F19 (12 pages)	7,(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3F1A (15 pages)	7,4'-Dihydroxyflavone and O-methyl derivatives
FL3F1C (12 pages)	7,3',4'-Trihydroxyflavone and O-methyl derivatives
FL3F1G (3 pages)	7,3',4',5'-Tetrahydroxyflavone and O-methy derivatives
FL3F1L (5 pages)	7,2',(3'),4',(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3F29 (6 pages)	6,7,(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3F2C (6 pages)	6,7,3',4'-Tetrahydroxyflavone and O-methyl flavonoids
FL3F2G (4 pages)	6,7,3',4',5'-Pentahydroxyflavone and O-methyl derivatives
FL3F39 (2 pages)	7,8,(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3F3C (1 pages)	7,8,3',4'-Tetrahydroxyflavone and O-methyl derivatives
FL3F3G (3 pages)	7,8,3',4',5'-Pentahydroxyflavone and O-methyl derivatives
FL3F4A (1 pages)	6,7,8,4'-Tetrahydroxyflavone and O-methyl derivatives
FL3F98 (16 pages)	(5),(6),(8),2',(3'),(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3F99 (10 pages)	(5),(6),(8),(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3F9A (2 pages)	(5),(6),(8),4'-Hydroxyflavone O-methyl derivatives
FL3F9C (2 pages)	(5),(6),(8),3',4'-Hydroxyflavone O-methyl derivatives
FL3F9G (4 pages)	(5),(6),(8),3',4',5'-Hydroxyflavone O-methyl derivatives
FL3F9L (2 pages)	(5),(6),(8),2',(3'),4',(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FA8 (22 pages)	5,7,2',(3'),(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FA9 (54 pages)	5,7,(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3FAA (246 pages)	Apigenin
FL3FAB (37 pages)	Acacetin
FL3FAC (195 pages)	Luteolin
FL3FAD (63 pages)	Chrysoeriol
FL3FAE (28 pages)	Diosmetin
FL3FAF (4 pages)	Luteolin 3',4'-dimethyl ether
FL3FAG (18 pages)	Tricetin
FL3FAH (3 pages)	Tricetin 3'-methyl ether
FL3FAI (22 pages)	Tricin
FL3FAJ (2 pages)	Tricetin 4'-methyl ether
FL3FAK (8 pages)	Tricetin O-methyl derivatives (5,7-Hydroxy, without FL3FAH-FL3FAJ)
FL3FAL (74 pages)	5,7,2',(3'),4',(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FBA (2 pages)	Thevetiaflavone
FL3FBB (3 pages)	Apigenin 5,4'-dimethyl ether
FL3FBC (6 pages)	Luteolin 5-methyl ether
FL3FBD (2 pages)	Luteolin 5,3'-dimethyl ether
FL3FBE (1 pages)	Luteolin 5,4'-dimethyl ether
FL3FBF (1 pages)	Luteolin 5,3',4'-trimethyl ether
FL3FCA (49 pages)	Genkwanin
FL3FCB (12 pages)	Apigenin 7,4'-dimethyl ether
FL3FCC (16 pages)	Luteolin 7-methyl ether
FL3FCD (7 pages)	Velutin
FL3FCE (4 pages)	Pilloin
FL3FCF (5 pages)	Luteolin 7,3',4'-trimethyl ether
FL3FCG (1 pages)	Tricetin 7-methyl ehter
FL3FCI (1 pages)	Tricetin 7,3',5'-trimethyl ether
FL3FCK (6 pages)	Tricetin O-methyl derivatives (5-Hydroxy-7-methoxy, without FL3FCG-FL3FCJ)
FL3FDB (1 pages)	Apigenin 5,7,4'-trimethyl ether
FL3FDC (2 pages)	Luteolin 5,7-dimethyl ether
FL3FDF (1 pages)	Luteolin 5,7,3',4'-tetramethyl ether
FL3FDH (1 pages)	Tricetin 5,7,3'-trimethyl ether
FL3FDK (3 pages)	Tricetin O-methyl derivatives (5,7-Methoxy, without FL3FDH)
FL3FE8 (4 pages)	5,6,7,2',(3'),(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FE9 (21 pages)	5,6,7,(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3FEA (72 pages)	Scutellarein and O-methyl derivatives
FL3FEC (86 pages)	6-Hydroxyluteolin and O-methyl derivatives
FL3FEG (21 pages)	6-Hydroxytricetin and O-methyl derivatives
FL3FEL (9 pages)	5,6,7,2',(3'),4',(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FF8 (29 pages)	5,7,8,2',(3'),(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FF9 (18 pages)	5,7,8,(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3FFA (35 pages)	Isoscutellarein and O-methyl derivatives
FL3FFC (37 pages)	Hypolaetin and O-methyl derivatives
FL3FFG (11 pages)	8-Hydroxytricetin and O-methyl derivatives
FL3FFL (5 pages)	5,7,8,2',(3'),4',(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FG8 (9 pages)	5,6,7,8,2',(3'),(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FG9 (5 pages)	5,6,7,8,(3'),(5')-Hydroxyflavone O-methyl derivatives
FL3FGA (21 pages)	5,6,7,8,4'-Pentahydroxyflavone and O-methyl derivatives
FL3FGC (32 pages)	5,6,7,8,3',4'-Hexahydroxyflavone and O-methyl derivatives
FL3FGG (12 pages)	5,6,7,8,3',4',5'-Heptahydroxyflavone and O-methyl derivatives
FL3FGL (9 pages)	5,6,7,8,2',(3'),4',(5'),(6')-Hydroxyflavone O-methyl derivatives
FL3FQU (6 pages)	Flavone quinone
FL3FRN (28 pages)	Flavone include extra rings

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.

Details of the 3rd Class: Hydroxylation pattern of A and B rings (5th and 6th digits)
Position of -OH (-OCH₃) groups 6th digit → 5th digit ↓		A (443 pages)	B (53 pages)	C (395 pages)	D (72 pages)	E (33 pages)	F (11 pages)	G (77 pages)	H (4 pages)	I (23 pages)	J (2 pages)	K (17 pages)	L (104 pages)	8 (83 pages)	9 (128 pages)
Position of -OH (-OCH₃) groups 6th digit → 5th digit ↓
	A (776 pages)	CC (2 pages) CS (95 pages) DS (46 pages) GM (2 pages) GN (3 pages) GS (74 pages) NF (1 pages) NI (9 pages) NM (2 pages) NP (8 pages) NS (4 pages)	CS (11 pages) DS (2 pages) GS (23 pages) NS (1 pages)	CS (64 pages) DS (26 pages) GM (1 pages) GS (88 pages) ND (1 pages) NI (4 pages) NM (1 pages) NN (1 pages) NP (2 pages) NR (1 pages) NS (6 pages)	CS (25 pages) DS (4 pages) GS (27 pages) NI (2 pages) NP (3 pages) NS (2 pages)	CS (8 pages) DS (1 pages) GS (13 pages) NF (1 pages) NI (1 pages) NS (4 pages)	GS (2 pages) NM (1 pages) NS (1 pages)	CS (6 pages) GI (1 pages) GS (7 pages) NI (1 pages) NS (3 pages)	GS (3 pages)	CS (5 pages) DS (1 pages) GS (13 pages) NI (1 pages) NP (1 pages) NS (1 pages)	GS (1 pages) NS (1 pages)	CS (1 pages) GS (1 pages) NM (1 pages) NS (5 pages)	CS (1 pages) GS (7 pages) NF (1 pages) NI (22 pages) NP (19 pages) NR (9 pages) NS (15 pages)	CS (1 pages) GS (7 pages) NM (1 pages) NS (13 pages)	CS (6 pages) GM (2 pages) GS (8 pages) NC (6 pages) ND (2 pages) NF (4 pages) NI (4 pages) NM (8 pages) NP (8 pages) NR (2 pages) NS (4 pages)
	B (15 pages)	NI (1 pages) NS (1 pages)	CS (1 pages) GS (1 pages) NP (1 pages)	CS (1 pages) GS (3 pages) NP (1 pages) NS (1 pages)	GS (1 pages) NS (1 pages)	NS (1 pages)	GS (1 pages)
	C (101 pages)	CS (33 pages) DS (7 pages) GS (5 pages) NI (1 pages) NM (2 pages) NS (1 pages)	CS (9 pages) NM (2 pages) NS (1 pages)	CS (4 pages) DS (3 pages) GS (2 pages) NI (1 pages) NM (2 pages) NP (2 pages) NS (2 pages)	CS (2 pages) GS (4 pages) NS (1 pages)	CS (1 pages) GS (2 pages) NS (1 pages)	CS (3 pages) GS (1 pages) NS (1 pages)	GS (1 pages)		NS (1 pages)		GS (4 pages) NS (2 pages)
	D (8 pages)		NS (1 pages)	CS (1 pages) NS (1 pages)			NS (1 pages)		NS (1 pages)			GS (2 pages) NS (1 pages)
	E (213 pages)	CS (2 pages) GN (1 pages) GS (53 pages) NC (1 pages) NS (15 pages)		GS (53 pages) NS (33 pages)				GS (6 pages) NI (1 pages) NS (14 pages)					NS (9 pages)	GS (3 pages) NS (1 pages)	GS (14 pages) NS (7 pages)
	F (135 pages)	CS (3 pages) GS (23 pages) NS (9 pages)		GS (27 pages) NP (1 pages) NS (9 pages)				CS (1 pages) DS (1 pages) GS (1 pages) NP (2 pages) NS (6 pages)					GS (1 pages) NS (4 pages)	GS (12 pages) NS (17 pages)	GS (10 pages) NS (8 pages)
	G (88 pages)	GS (6 pages) NS (15 pages)		GS (13 pages) NS (19 pages)				NS (12 pages)					NS (9 pages)	GS (1 pages) NS (8 pages)	NS (5 pages)
	1 (50 pages)	CS (2 pages) GS (3 pages) NF (2 pages) NI (5 pages) NP (1 pages) NS (2 pages)		GS (4 pages) NP (1 pages) NS (7 pages)				GS (2 pages) NS (1 pages)					NI (2 pages) NS (3 pages)	GS (1 pages) NF (2 pages)	GF (1 pages) NF (8 pages) NI (1 pages) NP (1 pages) NS (1 pages)
	2 (16 pages)			GS (1 pages) NI (1 pages) NP (1 pages) NS (3 pages)				NS (4 pages)							GF (1 pages) ND (1 pages) NF (2 pages) NS (2 pages)
	3 (6 pages)			NS (1 pages)				NS (3 pages)							NF (1 pages) NS (1 pages)
	4 (1 pages)	GS (1 pages)
	9 (36 pages)	NM (1 pages) NS (1 pages)		GS (1 pages) NS (1 pages)				NS (4 pages)					NS (2 pages)	NS (16 pages)	NI (1 pages) NS (9 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;

Other Unusual Patterns

These types are not classified in the above chart.

Quinone	QU (6 pages)	alpha-Hydroxy	HX (0 pages)	beta-Hydroxy	HY (0 pages)	Peltogynoid	PT (0 pages)
Retrocalchone	RT (0 pages)	Dehydro-backbone	WX (0 pages)	Additional rings	RN (28 pages)	Others	UN (0 pages)
Pyranoanthocyanin (FL7 only)			RX (0 pages)

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.

Details of the 4th Class: Glycosylation patterns (7th and 8th digits)
7th digit → 8th digit ↓		No glycosylation N (551 pages)	O-glycoside G (549 pages)	C-glycoside C (288 pages)	O- & C-glycoside D (91 pages)
no modification	S (1255 pages)	19 (1 pages) 1A (2 pages) 1C (7 pages) 1G (1 pages) 1L (3 pages) 29 (2 pages) 2C (3 pages) 2G (4 pages) 39 (1 pages) 3C (1 pages) 3G (3 pages) 98 (16 pages) 99 (9 pages) 9A (1 pages) 9C (1 pages) 9G (4 pages) 9L (2 pages) A8 (13 pages) A9 (4 pages) AA (4 pages) AB (1 pages) AC (6 pages) AD (2 pages) AE (4 pages) AF (1 pages) AG (3 pages) AI (1 pages) AJ (1 pages) AK (5 pages) AL (15 pages) BA (1 pages) BC (1 pages) BD (1 pages) BE (1 pages) CA (1 pages) CB (1 pages) CC (2 pages) CD (1 pages) CE (1 pages) CF (1 pages) CI (1 pages) CK (2 pages) DB (1 pages) DC (1 pages) DF (1 pages) DH (1 pages) DK (1 pages) E8 (1 pages) E9 (7 pages) EA (15 pages) EC (33 pages) EG (14 pages) EL (9 pages) F8 (17 pages) F9 (8 pages) FA (9 pages) FC (9 pages) FG (6 pages) FL (4 pages) G8 (8 pages) G9 (5 pages) GA (15 pages) GC (19 pages) GG (12 pages) GL (9 pages) QU (1 pages)	18 (1 pages) 1A (3 pages) 1C (4 pages) 1G (2 pages) 2C (1 pages) 4A (1 pages) 9C (1 pages) A8 (7 pages) A9 (8 pages) AA (74 pages) AB (23 pages) AC (88 pages) AD (27 pages) AE (13 pages) AF (2 pages) AG (7 pages) AH (3 pages) AI (13 pages) AJ (1 pages) AK (1 pages) AL (7 pages) BB (1 pages) BC (3 pages) BD (1 pages) BF (1 pages) CA (5 pages) CC (2 pages) CD (4 pages) CE (2 pages) CF (1 pages) CG (1 pages) CK (4 pages) DK (2 pages) E8 (3 pages) E9 (14 pages) EA (53 pages) EC (53 pages) EG (6 pages) F8 (12 pages) F9 (10 pages) FA (23 pages) FC (27 pages) FG (1 pages) FL (1 pages) G8 (1 pages) GA (6 pages) GC (13 pages)	1A (2 pages) A8 (1 pages) A9 (6 pages) AA (95 pages) AB (11 pages) AC (64 pages) AD (25 pages) AE (8 pages) AG (6 pages) AI (5 pages) AK (1 pages) AL (1 pages) BB (1 pages) BC (1 pages) CA (33 pages) CB (9 pages) CC (4 pages) CD (2 pages) CE (1 pages) CF (3 pages) DC (1 pages) EA (2 pages) FA (3 pages) FG (1 pages)	AA (46 pages) AB (2 pages) AC (26 pages) AD (4 pages) AE (1 pages) AI (1 pages) CA (7 pages) CC (3 pages) FG (1 pages)
alkylated	M (27 pages)	9A (1 pages) A8 (1 pages) A9 (8 pages) AA (2 pages) AC (1 pages) AF (1 pages) AK (1 pages) CA (2 pages) CB (2 pages) CC (2 pages) QU (1 pages)	A9 (2 pages) AA (2 pages) AC (1 pages)
prenylated	I (0 pages)	19 (1 pages) 1A (5 pages) 1L (2 pages) 2C (1 pages) 99 (1 pages) A9 (4 pages) AA (9 pages) AC (4 pages) AD (2 pages) AE (1 pages) AG (1 pages) AI (1 pages) AL (22 pages) BA (1 pages) CA (1 pages) CC (1 pages) EG (1 pages) RN (1 pages)	AG (1 pages)
cyclic prenylated	R (0 pages)	A9 (2 pages) AC (1 pages) AL (9 pages) QU (1 pages) RN (7 pages)
furano FL	F (30 pages)	18 (2 pages) 19 (8 pages) 1A (2 pages) 29 (2 pages) 39 (1 pages) A9 (4 pages) AA (1 pages) AE (1 pages) AL (1 pages) RN (6 pages)	19 (1 pages) 29 (1 pages)
pyrano FL	P (64 pages)	19 (1 pages) 1A (1 pages) 1C (1 pages) 2C (1 pages) A9 (8 pages) AA (8 pages) AC (2 pages) AD (3 pages) AI (1 pages) AL (19 pages) BB (1 pages) BC (1 pages) CC (2 pages) FC (1 pages) FG (2 pages) QU (3 pages) RN (9 pages)
furano & pyrano FL	D (9 pages)	29 (1 pages) A9 (2 pages) AC (1 pages) RN (5 pages)
prenylpropanoid	N (5 pages)	AC (1 pages)	AA (3 pages) EA (1 pages)
others	C (9 pages)	A9 (6 pages) EA (1 pages)		AA (2 pages)
3-Gal related	A	N.A.		N.A.	N.A.
3-Glc related	L	N.A.		N.A.	N.A.
other sugar at 3	O	N.A.		N.A.	N.A.

This category currently contains no pages or media.

[0] S. von Kostanecki and J. Jambor, Ber. Deut. Chem. Ges. 28, 2302, 1895

[1] J. Piccard, Ber. Deut. Chem. Ges. 6, 884 (1873); 7, 888 (1874); 10, 176 (1877)

[2] Iwashina T & Hatta H: Flavonoid glycosides from leaves of Aucuba japonica and Helwingia japonica: Phytochemical relationship with the genus Cornus J. Jap. Bot. 72:337-346, 1997
Reference:Iwashina_T:Ootani_S:,Phytochemistry,1990,29,3639
Reference:Iwashina T:Kamenosono K:Ueno T:,Phytochemistry,1999,51,1109

[3] Iwashina T, Kamenosono K, and Yabuya T: Isolation and identification of flavonoid and related compounds as co-pigments from the flowers of Iris ensata. J. Jap. Bot. 71:281-287

[1]

[2]

[3]

[4]

Category:FL3F

Contents

Overview

Structure

Major Plant Families

Patterns of Hydroxylation

Other Unusual Patterns

Patterns of Glycosylation

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