flavonoides recommendations

8/17/2019 Flavonoides Recommendations

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Nomenclature of Flavonoids

(IUPAC Provisional Recommendations)*

Amélia P. Rauter 1‡

, Bernardo J. Herold2, Derek Horton

3, Gerard Moss

4, Ida Schomburg

5, Karl-

Heinz Hellwich6, Marcus Ennis

7

1Universidade de Lisboa, Faculdade de Ciências, Departamento de Química e Bioquímica/Centro de

Química e Bioquímica, Ed. C8, Piso 5, Campo Grande, 1749-016 Lisboa, Portugal; 2Universidade de

Lisboa, Instituto Superior Técnico, Av. Rovisco Pais, 1041-001 Lisboa, Portugal;3 American University,

Department of Chemistry, Washington, D.C. 4400 Massachusetts Avenue NW, Washington, DC 20016, USA;4School of Biological and Chemical Sciences, Queen Mary, University of London, Mile End Road, London

E1 4NS, UK; 5Technische Universität Braunschweig, Institut für Biochemie, Biotechnologie und

Bioinformatik, Langer Kamp 19B, 38106 Braunschweig, Germany;6 Postfach 10 07 31, 63007 Offenbach,

Germany;7

European Bioinformatics Institute, Wellcome Trust Genome Campus, Hinxton, Cambridge CB101SD, UK

Abstract: Flavonoid structures, found in nature or obtained by synthesis, have become more and

more complex, and a guide for aglycone names is provided here to permit the construction of the

names for their polyglycosylated species with clarity and conciseness. A joint working party of

IUPAC/IUBMB members has prepared these recommendations, which establish rules for the

general nomenclature of flavonoids, providing examples of acceptable trivial names, and names

derived from trivial names, together with semi-systematic and fully systematic names that follow

the published IUPAC recommendations.

CONTENTS

Flv-0 Introduction 4

Flv-1 Flavonoids – Definitions and conventions 4

Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework 4

Flv-1.1.1 Flavonoids 5

Flv-1.1.1.1 Flavans 5

Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols) 5

Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides) 6

Flv-1.1.2 Isoflavonoids 6

Flv-1.1.2.1 Isoflavans 6

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Flv-1.1.2.2 Isoflavones 6

Flv-1.1.3 Neoflavonoids 7

Flv-1.1.3.1 Neoflavans 7

Flv-1.1.3.2 Neoflavones 7

Flv-1.1.4 Chalcones and dihydrochalcones 7

Flv-1.1.5 Aurones 8

Flv-1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans) 8

Flv-1.2 Rotenoids 8

Flv-1.3 Flavonolignans 9

Flv-1.4 Biflavonoids and other flavonoid oligomers 9

Flv-2 Guide to the construction of semi-systematic names 9

Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them 9

Flv-2.1.1 Flavans 10

Flv-2.1.1.1 Flavanaglycons 11

Flv-2.1.1.2 Flavan glycosides 11

Flv-2.1.1.3 Flavanones 11

Flv-2.1.2 Isoflavans 14

Flv-2.1.3 Neoflavans 15

Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them 16

Flv-2.2.1 Flavones 17

Flv-2.2.1.1 Flavone aglycons 17

Flv-2.2.1.2 Flavone glycosides 19

Flv-2.2.1.3 C -Glycosyl substituted flavones 22

Flv-2.2.1.4 Flavonols and flavonol glycosides 25

Flv-2.2.2 Isoflavones and isoflavone glycosides 26

Flv-2.2.2.1 Isoflavone aglycons 27

Flv-2.2.2.2 Isoflavone glycosides 28

Flv-2.2.3 Neoflavones and neoflavone glycosides 28

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Flv-2.2.3.1 Neoflavone aglycons 28

Flv-2.2.3.2 Neoflavone glycosides 29

Flv-2.3 Chalcones and dihydrochalcones 30

Flv-2.4 Aurones 32

Flv-2.4.1 Aurone aglycons 32

Flv-2.4.2 Aurone glycosides 34

Flv-2.5 Anthocyanidins and anthocyanidin 3-glycosides (anthocyanins) 34

Flv-2.5.1 Anthocyanidins 34

Flv-2.5.2 Anthocyanins 35

Flv-2.6 Flavonoids containing additional fused/spiro rings in their structures 38

Flv-2.6.1 Flavones 38

Flv-2.6.2 Chalcones 39

Flv-2.6.3 Aurones 39

Flv-2.6.4 Anthocyanidins/Anthocyanins 40

Flv-2.6.5 Pterocarpans 42

Flv-2.6.6 Rotenoids 43

Flv-2.7 Flavonolignans 46

Flv-2.8 Biflavonoids and other flavonoid oligomers 47

MEMBERSHIP OF SPONSORING BODIES 52

REFERENCES 52

*Sponsoring bodies: IUPAC Division(VIII) of Chemical Nomenclature and Structure

Representation (IUPAC project # 2009-018-2-800) and IUPAC-IUBMB Joint Commission on

Biochemical Nomenclature

‡Corresponding author: Amélia P. Rauter, Universidade de Lisboa, Faculdade de Ciências,

Departamento de Química e Bioquímica/Centro de Química e Bioquímica, Ed. C8, Piso 5, Campo Grande,

1749-016 Lisboa, Portugal. E-mail:[email protected]

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Flv-0 Introduction

Flavonoids, including the parent cyclic structures and their O‐ and C ‐glycosylated derivatives, are

natural or synthetic compounds that are structurally diverse, and many exhibit biological activity [1-

5]. They are quoted in the literature by researchers in diverse specialized areas, including natural

product chemistry, organic synthesis, medicinal and food chemistry, biology, and biochemistry.

Different workers have used a variety of alternative names and naming systems for such

compounds, and trivial names are commonly used to simplify complex names. Semi-systematic

names derived from parent structures are very useful for naming flavonoids, and have been widely

used, but they often lead to misunderstandings. There is an urgent need to avoid ambiguity in the

naming of flavonoids by clarifying acceptable usage and limiting the variety of options to a

reasonable extent.

These recommendations establish rules for the general nomenclature of flavonoids, providing

examples of acceptable trivial names, and names derived from trivial names, together with semi-

systematic and fully systematic names that follow the published IUPAC recommendations [6-8].

Class names for flavonoids, their parent structures, and the order of citation of primed or unprimedlocants are revisited and clarified. Names of O- and C -glycosylated derivatives follow established

carbohydrate nomenclature [9]. Semi-systematic names are based on the parent structures or their

functional parents. These are presented and illustrative examples are provided to avoid ambiguous

interpretations.

Flv-1 Flavonoids – Definition and conventions

The term “ flavonoid” is commonly used to include not only natural products, but also synthetic

compounds related to them. The structural feature of this family of compounds is based on

derivatives of a phenyl-substituted 1-phenylpropane possessing a C15 skeleton, except for the

rotenoids, which have a C16 skeleton but are also phenyl-substituted 1-phenylpropane derivatives,

and that of flavonolignans, whose structure is based on flavonoids condensed with C6-C3 lignan

precursors.

The following carbon frameworks characterize the various flavonoid classes:

Flv-1.1 Flavonoid classes with a C6-C3-C6 carbon framework

These are classes of compounds having a C6-C3-C6 carbon framework which contains a 1- benzopyran (chromene) ring system, in which the aromatic ring is defined as ring A and the pyran is

ring C, along with a benzenoid aromatic substituent on the pyran ring defined as ring B. Depending

on the position of the linkage of ring B to the 1-benzopyran (chromene) moiety, three different

classes can be assigned: flavonoids (Flv-1.1.1), isoflavonoids (Flv-1.1.2) and neoflavonoids (Flv-

1.1.3). The other flavonoid classes that have a structure with a C6-C3-C6 carbon framework are the

chalcones (Flv-1.1.4), the aurones (Flv-1.1.5) and the pterocarpans and their 3,4-didehydro

derivatives (coumestans) (Flv-1.1.6).

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Flv-1.1.1 Flavonoids

The flavonoids (2-aryl-1-benzopyrans) are compounds with a skeleton of type 1.

1

The oxidation state of ring C and its derivatization with hydroxy groups is used to classify

flavonoids into different categories, such as:

Flv-1.1.1.1 Flavans

Flavans include compounds derived from 1, as well as flavan-3-ols (compounds derived from 2)

and flavan-4-ones (compounds derived from 4), which are generically designated in the literature as

flavanols and flavanones, respectively. Compounds derived from 3 are flavan-3,4-diols, designated

leukoanthocyanidins because their structure can be considered as being derived from that of an

anthocyanidin (see Flv-1.1.1.3), specifically a 3,4-dihydroxy-1,2,3,4-tetrahydroanthocyanidin,

which renders such compounds colourless.

2 3 4

Flv-1.1.1.2 Flavones and 3-hydroxyflavones (flavonols)

Flavones and 3-hydroxyflavones (flavonols) are compounds derived from 5 and 6, respectively,

which possess a 2-phenyl-1-benzopyran-4-one (2-phenylchromen-4-one) skeleton. The term

“flavonol” is used as a class name for compounds derived from 6.

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5 6

Flv-1.1.1.3 Anthocyanidins/anthocyanins (anthocyanidin 3-glycosides)

Anthocyanidins are compounds derived from 7, which contains a flavylium ion (2-phenyl-1-

benzopyranylium or 2-phenylchromenylium) as a core structure. Anthocyanidins display colours

from red to purple and, together with their glycosides, the anthocyanins, represent a large group of

plant pigments.

7

Flv-1.1.2 Isoflavonoids

The isoflavonoids (3-aryl-1-benzopyrans) are compounds derived from 8.

8

Flv-1.1.2.1 Isoflavans

Isoflavans are compounds which have the skeleton 8. They may be substituted.

Flv-1.1.2.2 Isoflavones

Isoflavones are compounds with skeleton 9, the 2,3-didehydro structure 8 with a carbonyl group at

position 4. They may be substituted.

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9

Flv-1.1.3 Neoflavonoids

The neoflavonoids (4-aryl-1-benzopyrans) are compounds with parent structure 10.

10

Flv-1.1.3.1 Neoflavans

Neoflavans are compounds with skeleton 10. They may be substituted.

Flv-1.1.3.2 Neoflavones

Neoflavones are compounds with skeleton 11. They may be substituted.

11

Flv-1.1.4 Chalcones and dihydrochalcones

Chalcones are compounds derived from (2 E )-1,3-diphenylprop-2-en-1-one (chalcone, compound

12). They are early intermediates in the biosynthesis of flavonoids, in which the pyran ring C has

not yet been formed, and are therefore biogenetically and structurally related to them.

Dihydrochalcones are compounds derived from 1,3- diphenylpropan-1-one (compound 13).

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12 13

Flv-1.1.5 Aurones

Aurones are compounds derived from 14, which is based on (2 Z )-2-(arylmethylidene)-1-

benzofuran-3(2 H )-one.

14

Flv.1.1.6 Pterocarpans and their 3,4-didehydro derivatives (coumestans)

Pterocarpans are compounds derived from 15 and from their 3,4-didehydro derivatives 16

(coumestans). They may be substituted.

15 16

Flv-1.2 Rotenoids

Rotenoids comprise rotenanes which are compounds with skeleton 17 and rotenones with skeleton

18. They may be substituted.

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17 18

Flv-1.3 Flavonolignans

Flavonolignans have structures based on flavonoids condensed with C6-C3 lignan precursors (see

Flv-2.7).

Flv-1.4 Biflavonoids and other flavonoid oligomers

Biflavonoid and other flavonoid oligomers, which occur widely in nature, are exemplified and

named in Section Flv-2.8.

Flv-2 Guide to the construction of semi-systematic names

This section illustrates the construction of semi-systematic names and examples are given, with

trivial names, if known, and the systematic names are added.

Primed locants are placed immediately after the corresponding unprimed locants in a set arranged in

ascending order (R-0.2.4.2 in [6]).

Flv-2.1 Flavans, isoflavans, neoflavans and compounds derived from them

Names of flavans, isoflavans and neoflavans can be derived from the name of the respective parent

hydride (Figure 1). The presence of a characteristic group is denoted by a prefix or by a suffix

attached to the parent name. The suffix is used for the principal characteristic group(s) according to

the priority order given in R.4.1 [6].

1 8 10

Figure 1. Parent hydrides of flavans (1), isoflavans (8) and neoflavans (10).

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Flv-2.1.1 Flavans

Flv-2.1.1.1 Flavan aglycons

Example 1:

Semi-systematic name

flavan

Systematic names

2‐ phenyl-3,4-dihydro-2 H -1-benzopyran

2-phenyl-3,4-dihydro-2 H -chromene

Flv-2.1.1.2 Flavan glycosides

Example 2:

(c)

Note: Saccharide moiety shown in Mills depiction (a), in a conformational form (b) and in abbreviated form [9] (c).

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(2S )-2′,7-bis(β-D-glucopyranosyloxy)-8-(2-hydroxyethyl)-4′-methoxyflavan-5-ol

Systematic names

(2S )-2- [2,7′-(β-D-glucopyranosyloxy)-4-methoxyphenyl]-8-(2-hydroxyethyl)-3,4-dihydro-2 H -1-

benzopyran-5-ol

(2S )-2-[2,7′-(β-D-glucopyranosyloxy)-4-methoxyphenyl]-8-(2-hydroxyethyl)-3,4-dihydro-2 H -

chromen-5-ol

Example 3:

Semi-systematic names

(2S )-7-(β-D-glucopyranosyloxy)-4′-methoxy-8-(3-methylbut-2-en-1-yl)flavan-2′-ol

(2S )-2′--4′-methoxy-8-(3-methylbut-2-en-1-yl)flavan-7-yl β-D-glucopyranoside

Systematic names

(2S )-2-(2-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2 H -1-benzopyran-7-

ol

(2S )-2-(2-hydroxy-4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2 H -chromen-7-ol

Flv-2.1.1.3 Flavanones

Example 4:

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flavan-4-one

Systematic names

2-phenyl-2,3-dihydro-4 H -1-benzopyran-4-one

2-phenyl-2,3-dihydro-4 H -chromen-4-one

Example 5:


(2S )-4′,5,7-trihydroxyflavan-4-one

Trivial name

naringenin

Systematic names

(2S )-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4 H -1-benzopyran-4-one

(2S )-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4 H -chromen-4-one

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Example 6:


(2S )-4′,5,7-trihydroxy-6,8-bis(3-methylbut-2-en-1-yl)flavan-4-one

Trivial names

6,8-diprenylnaringenin, lonchocarpol A, senegalensein

Note: The trivial name “senegalesein” is used in the Dictionary of Flavonoids [4] and is kept as such in the present

recommendations. In the literature the incorrect spelling “senegalesien” is found in some instances.

Systematic names

(2S )-5,7-dihydroxy-2-(4-hydroxyphenyl) -6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-4 H -1-

benzopyran-4-one

(2S )-5,7-dihydroxy-2-(4-hydroxyphenyl) -6,8-bis(3-methylbut-2-en-1-yl)-2,3-dihydro-4 H -chromen-

4-one

Example 7:


(2 R,3 R)-3-hydroxyflavan-4-one

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Not: flavanon-3-ol (R-4.1, Table 10 [6]).

Systematic names

(2 R,3 R)-3-hydroxy-2-phenyl-2,3-dihydro-4 H -1-benzopyran-4-one

(2 R,3 R)-3-hydroxy-2-phenyl-2,3-dihydro-4 H -chromen-4-one

Example 8:


(2 R,3 R) -2′,3-dihydroxy-4′,7-dimethoxy-8-(3-methylbut-2-en-1-yl)flavan-4-one

Systematic names

(2 R,3 R)-3-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-2,3-

dihydro-4 H -1-benzopyran-4-one

(2 R,3 R)-3-hydroxy-2-(2-hydroxy-4-methoxyphenyl)-7-methoxy-8-(3-methylbut-2-en-1-yl)-2,3-

dihydro-4 H -chromen-4-one

Flv-2.1.2 Isoflavans

Example 9:

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(3S )-isoflavan-7-ol

Systematic names

(3S )-3-phenyl-7-hydroxy-2,3-dihydro-4 H -1-benzopyran-4-one

(3S )-3-phenyl-7-hydroxy-2,3-dihydro-4 H -chromen-4-one

Example 10:

(1:1)


rac-2′,4′,5,7-tetrahydroxyisoflavan-4-one

Trivial name

(±)-dalbergioidin

Systematic names

rac-3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4 H -1-benzopyran-4-one

rac-3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-4 H -chromen-4-one

Flv-2.1.3 Neoflavans

Example 11:

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(4 R)-neoflavan-7-ol

Systematic names

(4 R)-4-phenyl-3,4-dihydro-2 H -1-benzopyran-7-ol

(4 R)-4-phenyl-3,4-dihydro-2 H -chromen-7-ol

Flv-2.2 Flavones, isoflavones, neoflavones and compounds derived from them

Names of flavones, isoflavones and neoflavones can be derived from the names of the respective

functional parents (Figure 2) which already contain one carbonyl group as an implied suffix. When

substituents are among those characteristic groups with a lower priority than ketones, they have to

be cited as prefixes, according to Table 10, Section R-4.1 [6].

5 9 11

Figure 2. Functional parents of flavones (5), isoflavones (9) and neoflavones (11). Neoflavones are also

known in the literature as 4-arylcoumarins.

When the principal characteristic group has a higher priority than a ketone, according to Table 10,

Section R-4.1 [6], names of flavones, isoflavones and neoflavones are derived from the respective

flavan, isoflavan or neoflavan parent hydride. Such groups are radicals, ions, acids, acid derivatives

(anhydrides, esters, acyl halides, amides), nitriles, aldehydes and chalcogen analogues of aldehydes.

Flavones, isoflavones and neoflavones containing a substructure with more than one carbonyl group

are named systematically on the basis of the respective parent hydride modified by the appropriate

suffix, i.e. -dione, -trione, etc.

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Flv-2.2.1 Flavones

Flv-2.2.1.1 Flavone aglycons

Example 12:


flavone

Systematic names

2-phenyl-4 H -1-benzopyran-4-one

2-phenyl-4 H -chromen-4-one

Example 13:


4′,5,7-trihydroxyflavone

Trivial name

apigenin

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Systematic names

5,7-dihydroxy-2-(4-hydroxyphenyl)-4 H -1-benzopyran-4-one

5,7-dihydroxy-2-(4-hydroxyphenyl)-4 H -chromen-4-one

Example 14:


3′,5,7-trihydroxy-4′-methoxyflavone

Trivial name

diosmetin

Systematic names

5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4 H -1-benzopyran-4-one

5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4 H -chromen-4-one

Example 15:

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2-(piperidin-1-yl)ethyl 3-methyl-4-oxoflav-2-ene-8-carboxylate

Not: 2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2,3-didehydroflavan-8-carboxylate because of rule RF-

8.1 on introduction of unsaturation in parent names ending with ‘an’[10].

Trivial name

flavoxate

Note: flavoxate is an International Nonproprietary Name (INN) for the anticholinergic drug.

Systematic names

2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4 H -1-benzopyran-8-carboxylate

2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4 H -chromene-8-carboxylate

Flv-2.2.1.2 Flavone glycosides

Example 16:


7-(β-D-glucopyranosyloxy)-4′,5-dihydroxy-3′-methoxyflavone

Trivial name

7-O-β-D-glucopyranosylchrysoeriol

Systematic names

7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4 H -1-benzopyran-4-one

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7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4 H -chromen-4-one

Example 17:

O

O

HO

HO O O

HO

OH

OH

CH3

O O

OOH

OCH3

OH

7

54

2

3'4'

O

O

OH

HO

HOH2C

O

OH

OH

OHHOH2C

(b)

Note: Saccharide moiety in Mills depiction (a) and in a conformational form (b).


7-{β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-

glucopyranosyloxy}-3′,5-dihydroxy-4′-methoxyflavone

Trivial name

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7-O-{β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-

glucopyranosyl}diosmetin

Not: diosmetin 7-β-D-glucopyranosyl- (1→2) -β-D-glucopyranosyl- (1→2) - [α-L-

rhamnopyranosyl- (1→6)]-β-D-glucopyranoside (because it specifies the oxygen atom at position 7

twice)

Systematic names


glucopyranosyloxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4 H -1-benzopyran-4-one


glucopyranosyloxy}-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4 H -chromen-4-one

Example 18:


methyl (4′,5-dihydroxy-4-oxoflav-2-en-7-yl 2-O-acetyl-β-D-glucopyranosid)uronate

Not: methyl (4′,5-dihydroxy-4-oxo-2,3-didehydroflavan-7-yl 2-O-acetyl-β-D-

glucopyranosid)uronate because of rule RF-8.1 on introduction of unsaturation in parent names

ending with ‘an’ [10].

Not: methyl (4′,5-dihydroxyflavon-7-yl 2-O-acetyl-β-D-glucopyranosid)uronate because doubled

suffixes such as “on-7-yl” (which is “one” + “yl”) are not permitted in IUPAC chemical

nomenclature.

Trivial name

7-O-(methyl 2-O-acetyl-β-D-glucopyranosyluronate)apigenin

Not: methyl [apigenin 7-(2-O-acetyl-β-D-glucopyranosiduronate)] (because it specifies the oxygen

atom at position 7 twice)

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Note: The general rule that a name cannot contain two suffixes can be sometimes infringed in carbohydrate

nomenclature, such as with “yluronate” in the trivial name (see 2-Carb-22 in [9]).

Systematic names

methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4 H -1-benzopyran-7-yl 2-O-acetyl-β-D-

glucopyranosid]uronate

methyl [5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4 H -chromen-7-yl 2-O-acetyl-β-D-

glucopyranosid]uronate

Flv-2.2.1.3 C -Glycosyl substituted flavones

Compounds arising formally from the elimination of water from the anomeric hydroxy group and a

hydrogen atom bound to a carbon atom (thus creating a C‐C bond) are named using the appropriate

glycosyl group [8]. In the past they have been named as flavonoid C‐glycosides, but this

terminology should not be used (2-Carb‐33.7 [9]).

Example 19:


6-(β-D-glucopyranosyl)-4′,5,7-trihydroxyflavone

Trivial names

isovitexin

6-(β-D-glucopyranosyl)apigenin

Not: 6-C -β-D-glucopyranosylapigenin

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Systematic names

6-(β-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4 H -1-benzopyran-4-one

6-(β-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4 H -chromen-4-one

Example 20:


6-(β-D-glucopyranosyl)-4′,5-dihydroxy-7-methoxyflavone

Trivial name

6-(β-D-glucopyranosyl)-7-O-methylapigenin

Systematic names

6-(β-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-4 H -1-benzopyran-4-one

6-(β-D-glucopyranosyl)-5-hydroxy-2-(4-hydroxyphenyl)-4 H -chromen-4-one

Example 21:

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6,8-di-(α-L-arabinopyranosyl)-4′,5,7-trihydroxyflavone

Trivial name

6,8-di-(α-L-arabinopyranosyl)apigenin

Not: apigenin 6,8-di-C -α-L-arabinopyranoside

Systematic names

6,8-di-(α-L-arabinopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4 H -1-benzopyran-4-one

6,8-di-(α-L-arabinopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4 H -chromen-4-one

Example 22:


6-(α-L-arabinopyranosyl)-8-(β-D-glucopyranosyl)-3′,4′,5,7-tetrahydroxyflavone

Trivial names

isocarniloside

6-(α-L-arabinopyranosyl)-8-(β-D-glucopyranosyl)luteolin

Not: luteolin 6-C -α-L-arabinopyranosyl-8-β-D-glucopyranoside

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Systematic names

6-(α-L-arabinopyranosyl)-2-(3,4-dihydroxyphenyl)-8-(β-D-glucopyranosyl)-5,7-dihydroxy-4 H -1-

benzopyran-4-one

6-(α-L-arabinopyranosyl)-2-(3,4-dihydroxyphenyl)-8-(β-D-glucopyranosyl)-5,7-dihydroxy-4 H -

chromen-4-one

Example 23:


4′,5,7-trihydroxy-6-[α-D-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl]flavone

Trivial names

dulcinoside

6-[α-D-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl]apigenin

Not: 6-C - [6′′-O-(α-D-rhamnopyranosyl)-β-D-glucopyranosyl]apigenin

Systematic names

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[α-D-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl]-4 H -1-

benzopyran-4-one

5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[α-D-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl]-4 H -chromen-4-one

Flv-2.2.1.4 Flavonols and flavonol glycosides

Example 24:

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3-hydroxyflavone

Systematic name

3-hydroxy-2-phenyl-4 H -chromen-4-one

Example 25:

O

O

OH

2

4

4'

7

O

OHHO

HO

CH3

O

O

O OH

O

O

O

HOOH

OH

CH3

O

O

OHHO

HO

CH3

O

3

OH

OCH3


4′-hydroxy-3-{4-O-[(2 E )-3-(4-hydroxy-3-methoxyphenyl)acryloyl]-[α-L-rhamnopyranosyl-(1→2)]-

[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranosyloxy}-7-(α-L-rhamnopyranosyloxy)flavones

Systematic names

3-{4-O-[(2 E )-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-[α-L-rhamnopyranosyl-(1→2)]-[α-L-

rhamnopyranosyl-(1→6)]-β-D-galactopyranosyloxy}-2-(4-hydroxyphenyl)-7-(α-L-

rhamnopyranosyloxy)-4 H -1-benzopyran-4-one

3-{4-O-[(2 E )-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]-[α-L-rhamnopyranosyl-(1→2)]-[α-L-

rhamnopyranosyl-(1→6)]-β-D-galactopyranosyloxy}-2-(4-hydroxyphenyl)-7-(α-L-

rhamnopyranosyloxy)-4 H -chromen-4-one

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Flv-2.2.2 Isoflavones and isoflavone glycosides

Flv-2.2.2.1 Isoflavone aglycons

Example 26:


isoflavone

Systematic name


Example 27:


4′,5,7-trihydroxyisoflavone

Trivial name

genistein

Systematic names

5,7-dihydroxy-3-(4-hydroxyphenyl)-4 H -1-benzopyran-4-one

5,7-dihydroxy-3-(4-hydroxyphenyl)-4 H -chromen-4-one

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Flv-2.2.2.2 Isoflavone glycosides

Example 28:


7-(β-D-glucopyranosyloxy)-4′,5-dihydroxyisoflavone

Trivial names

genistin

7-O-(β-D-glucopyranosyl)genistein

Systematic names

7-(β-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4 H -1-benzopyran-4-one

7-(β-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4 H -chromen-4-one

Flv-2.2.3 Neoflavones and neoflavone glycosides

Flv-2.2.3.1 Neoflavone aglycons

Example 29:


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neoflavone

Trivial name

4-phenylcoumarin

Systematic names

4-phenyl-2 H -1-benzopyran-2-one


Example 30:


4′,6-dihydroxy-7-methoxyneoflavone

Trivial name

melannin

Systematic names

6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2 H -1-benzopyran-2-one

6-hydroxy-4-(4-hydroxyphenyl)-7-methoxy-2 H -chromen-2-one

Flv-2.2.3.2 Neoflavone glycosides

Example 31:

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7-(β-D-glucopyranosyloxy)-8-methylneoflavone

Trivial name

7-(β-D-glucopyranosyloxy)-8-methyl-4-phenylcoumarin

Systematic names

7-(β-D-glucopyranosyloxy)-8-methyl-4-phenyl-2 H -1-benzopyran-2-one

7-(β-D-glucopyranosyloxy)-8-methyl-4-phenyl-2 H -chromen-2-one

Flv-2.3 Chalcones and dihydrochalcones

There is ambiguity in the literature concerning the numbering of the carbon atoms in chalcone.Most authors, following IUPAC rule C-313.2 [8] as applied with acylaryl ketones such as

acetophenone, have assigned primed numbers to atoms in the phenyl ring attached to the carbonyl

group, and unprimed numbers to atoms in the other phenyl group. Atoms of the ethene-1,2-diyl

linker have been designated α and β. Some authors have used a reverse system, assigning unprimed

numbers to the phenyl ring attached to the carbonyl group and primed numbers to the other phenyl

ring. [The latter usage correlates with the numbering scheme in the flavan parent structure (Flv-

1.1.1.1) that arises biosynthetically from a chalcone.]

Because of this ambiguity, the term chalcone has been restricted since 1993 to its use as a retained

name of “Type 3, no substitution” (R-9.1, table 27a, ref. 6), and individual substituted chalcones are

named systematically, based usually on (2 E )-prop-2-en-1-one.

The Dictionary of Flavonoids [5] and other standard sources [ref. 1, for example] adhere

consistently to the numbering of chalcones according to IUPAC rule C-313.2, and the alternative

usage has been largely abandoned. Since the use of Greek letters as locants is now discouraged, it is

now proposed that the term chalcone as a functional parent be retained as a “Type 2, Limited

substitution” name. This allows substitution in the phenyl rings, except where a substituent has

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priority over the carbonyl group, in which situation a fully systematic name is required (Examples

33, 34, and 35).

Example 32:


chalcone

Systematic name

(2 E )-1,3-diphenylprop-2-en-1-one

Example 33:


2′,5′-dihydroxy-4-( N , N -dimethylamino)chalcone

Systematic name

(2 E )-1-(2,5-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

Example 34:

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Systematic name

4-[(1 E )-3-oxo-3-phenylprop-1-en-1-yl]benzonitrile

Example 35:

Systematic name

2-[(2 E )-1-oxo-3-phenylprop-2-en-1-yl]benzoic acid

Example 36:

Systematic name

1-(4-hydroxy-2-methoxyphenyl)-3-phenylpropan-1-one

Flv-2.4 Aurones

Flv-2.4.1 Aurone aglycons

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Example 37:


aurone

Systematic name

(2 Z )-2-benzylidene-1-benzofuran-3(2 H )-one

Example 38:


3′,4,4’,6-tetrahydroxyaurone

Trivial name

aureusidin

Systematic name

(2 Z )-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3(2 H )-one

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Flv-2.4.2 Aurone glycosides

Example 39:


6-(β-D-glucopyranosyloxy)-4,4′-dihydroxyaurone

Systematic name

(2 Z )-6-(β-D-glucopyranosyloxy)-4-hydroxy-2-[(4-hydroxyphenyl)methylidene]-1-benzofuran-

3(2 H )-one

Flv-2.5 Anthocyanidins and anthocyanidin 3-glycosides (anthocyanins)

Flv-2.5.1 Anthocyanidins

Anthocyanidins contain a flavylium ion (2-phenylchromenylium, 2-phenyl-1λ 4-benzopyran-1-

ylium) as a parent structure.

Example 40:


3,3′,4′,5,7-pentahydroxyflavylium

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Trivial name

cyanidin

Systematic names

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-1λ 4

-benzopyran-1-ylium

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromenylium

Flv-2.5.2 Anthocyanins

Example 41:


3-(β-D-glucopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavylium

Trivial name

3-O-β-D-glucopyranosylcyanidin

Systematic names

2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-1λ 4-benzopyran-1-ylium

2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxychromenylium

Example 42:

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O

23

5

7

3'4'

HO

OH

OH

O

O OH

OH

OH

OH

O

O

OH


3-{6-O-[( E )-3-(4-hydroxyphenyl)acryloyl]-β-D-glucopyranosyloxy}-3′,4′,5,7-

tetrahydroxyflavylium

Trivial name

3-O-{6-O-[(2 E )-3-(4-hydroxyphenyl)acryloyl]-β-D-glucopyranosyl}cyanidin

Systematic names

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{6-O-[(2 E )-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-

glucopyranosyloxy}-1λ 4-benzopyran-1-ylium

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{6-O-[(2 E )-3-(4-hydroxyphenyl)prop-2-enoyl]-β-D-

glucopyranosyloxy}chromenylium

Example 43:

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O

2

3

5

7

3'4'

HO

OH

OH

O

OH

O

OH

OH

OH

OOH

OHHO

H3

C

O


3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-3′,4′,5,7-tetrahydroxyflavylium

Trivial name

3-O-β-rutinosylcyanidin

Systematic names

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-

1λ 4-benzopyran-1-ylium

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-

glucopyranosyloxy]chromenylium

Example 44:

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3,7-bis(β-D-glucopyranosyloxy)-3′,4′,5-trihydroxyflavylium

Trivial name

3,7-di-O-(β-D-glucopyranosyl)cyanidin

Note: The multiplicative prefix “di” is used with non-substituted substituents, but with substituted substituents “bis”

must be used (R-0.1.4 in [1]).

Systematic names

2-(3,4-dihydroxyphenyl)-3,7-bis(β-D-glucopyranosyloxy)-5-hydroxy-1λ 4-benzopyran-1-ylium

2-(3,4-dihydroxyphenyl)-3,7-bis(β-D-glucopyranosyloxy)-5-hydroxychromenylium

Flv-2.6 Flavonoids containing additional fused/spiro rings in their structures

Locants for additional rings must be double primed to prevent confusion with those for the phenyl

ring, which are already single primed.

Flv-2.6.1 Flavones

Example 45:


5-hydroxy-6,7-[methylenebis(oxy)]flavones

Systematic names

9-hydroxy-6-phenyl-8 H -[1,3]dioxolo[4,5- g ]chromen-8-one

9-hydroxy-6-phenylpyrano[2,3- f ][1,3]benzodioxol-8-one

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Flv-2.6.2 Chalcones

Example 46:


3,4-[methylenebis(oxy)]chalcone

Systematic names

(2 E )-3-(1,3-benzodioxol-5-yl)-1-phenylprop-2-en-1-one

Flv-2.6.3 Aurones

Example 47:


2-methoxy-2,21-dihydrofuro[2′′,3′′:6,7]aurone

Trivial name

castillene A

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Systematic name

2-benzyl-2-methoxybenzo[1,2-b:3,4-b′ ]difuran-3(2 H )-one

Example 48:


3′′,4,4′,5′,6-pentahydroxy-3′′,6′′-dihydropyrano[2′′,3′′,4′′,5′′:2,21,1′,2′]aurone

Trivial name

crombenin

Systematic name

4,4′,6,6′,7′-pentahydroxy-1′,4′-dihydro-3 H -spiro[1-benzofuran-2,3′-[2]benzopyran]-3-one

Flv-2.6.4 Anthocyanidins/Anthocyanins

Example 49:

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6′′-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-4′,7-dihydroxy-3′,5′-

dimethoxypyrano[4′′,3′′,2′′:4,4a,5]flavylium

Trivial name

vitisin A

Systematic names

5-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-8-hydroxy-2-(4-hydroxy-3,5-

dimethoxyphenyl)pyrano[4,3,2-de]-1λ 4-benzopyran-1-ylium

5-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-8-hydroxy-2-(4-hydroxy-3,5-

dimethoxyphenyl)pyrano[4,3,2-de]chromenylium

Example 50:


3′,4′,7,8′′,9′′-pentahydroxy-6′′-oxo-6′′ H -[1,5]dioxaphenaleno[4′′3a′′,3′′,2′′:3,4,4a,5]flavylium

Trivial name

rosacyanin B

Systematic name

11-(3,4-dihydroxyphenyl)-4,5,8-trihydroxy-2 H -1,6-dioxa-10-oxoniabenzo[cd ]pyren-2-one

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Flv-2.6.5 Pterocarpans

Although simple pterocarpans are ring-closure products of isoflavonoids, systematic numbering is

used [8,11].

Note: Systematic numbering and names of the pterocarpan skeleton are given below:

Systematic names

(6a R,11a R)-6a,11a-dihydro-6 H -[1]benzofuro[3,2-c][1]benzopyran

(6a R,11a R)-6a,11a-dihydro-6 H -[1]benzofuro[3,2-c]chromene

Example 51:


9-methoxypterocarpan-3-ol

Trivial name

(-)-medicarpin

Systematic names

(6a R,11a R)-9-methoxy-6a,11a-dihydro-6 H -[1]benzofuro[3,2-c][1]benzopyran-3-ol

(6a R,11a R)-9-methoxy-6a,11a-dihydro-6 H -[1]benzofuro[3,2-c]chromen-3-ol

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Example 52:

Semi-systematic names

3,9-dihydroxypterocarp-6a-en-6-one

3,9-dihydroxycoumestan-6-one

Not:3,9-dihydroxy-6a,11a-didehydropterocarpan-6-one, because of rule RF-8.1 on introduction of

unsaturation in parent names ending with ‘an’ [10].

Trivial name

Coumestrol

Systematic names

3,9-dihydroxy-6 H -[1]benzofuro[3,2-c][1]benzopyran-6-one

3,9-dihydroxy-6 H -[1]benzofuro[3,2-c]chromen-6-one

Flv-2.6.6 Rotenoids

Example 53:


rotenane

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Systematic names

(6aS ,12aS )-6,6a,12,12a-tetrahydro[1]benzopyrano[3,4-b][1]benzopyran

(6aS ,12aS )-6,6a,12,12a-tetrahydrochromeno[3,4-b]chromene

Example 54:


5-hydroxy-4′,5′,7-trimethoxyrotenan-4-one

Trivial name

sermundone

Systematic names

(6aS ,12aS )-11-hydroxy-2,3,9-trimethoxy-6a,12a-dihydro[1]benzopyrano[3,4-b][1]benzopyran-

12(6 H )-one

(6aS ,12aS )-11-hydroxy-2,3,9-trimethoxy-6a,12a-dihydrochromeno[3,4-b]chromen-12(6 H )-one

Example 55:

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(5′′ R)-4′,5′-dimethoxy-5′′-(prop-1-en-2-yl) -4′′,5′′-dihydrofuro[2′′,3′′:7,8]rotenan-4-one

Trivial name

(5′′ R)-4′,5′-dimethoxy-5′′-(prop-1-en-2-yl)- 4′′,5′′-dihydrofuro[2′′,3′′:7,8]rotenone

Systematic names

(2 R,6aS ,12aS )-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydro[1]benzopyrano[3,4-

b]furo[2,3-h][[1]benzopyran]-6(6a H )-one

(2 R,6aS ,12aS )-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-

h]chromen-6(6a H )-one

Example 56:


(5′′ R)-4′,5′-dimethoxy-5′′-(prop-1-en-2-yl)-4′′,5′′-dihydrofuro[2′′,3′′:7,8]roten-2-ene-21,4-dione

Not: (5′′ R)-4′,5′-dimethoxy-5′′-(prop-1-en-2-yl)-2,3-didehydro-4′′,5′′-

dihydrofuro[2′′,3′′:7,8]rotenane-2

1

,4-dione, because of rule RF-8.1 on introduction of unsaturationin parent names ending with ‘an’ [10].

Systematic names

(2 R)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2-dihydro[1]benzopyrano[3,4-b]furo[2,3-

h][[1]benzopyran]-6,12-dione

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(2 R)-8,9-dimethoxy-2-(prop-1-en-2-yl)-1,2-dihydrochromeno[3,4-b]furo[2,3-h]chromene-6,12-

dione

Example 57:


6′′′,6′′′-dimethyl-5′′′,6′′′-dihydro-4′′′ H -1,3-dioxolo[4,5:4′,5′]pyrano[2′′′,3′′:7,8]rotenan-4-one

Trivial name

millettone

Systematic names

(5aS ,12bS )-2,2-dimethyl-5a,12b-dihydro-2 H -[1,3]dioxolo[4,5- g ]pyrano[2,3-c:6,5-

f ′ ]bis[1]benzopyran-13(6 H )-one

(5aS ,12bS )-2,2-dimethyl-5a,12b-dihydro-2 H -[1,3]dioxolo[4,5- g ]pyrano[2,3-c:6,5- f ′ ]dichromen-

13(6 H )-one

Flv-2.7 Flavonolignans

Example 58:

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(2 R,3 R,5′′ R,6′′ R)-3-hydroxy-6′′-(4-hydroxy-3-methoxyphenyl)-5′′-(hydroxymethyl)-5′′,6′′-

dihydro[1,4]dioxino[2′′,3′′:3′,4′]flavan-4-one

Trivial names

silibinin, also called silybin

Systematic names

(2 R,3 R)-3-hydroxy-2-[(2 R,3 R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-

benzodioxin-6-yl]-2,3-dihydro-4 H -1-benzopyran-4-one

(2 R,3 R)-3-hydroxy-2-[(2 R,3 R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-

benzodioxin-6-yl]-2,3-dihydro-4 H -chromen-4-one

Flv-2.8 Biflavonoids and other flavonoid oligomers

Biflavonoids and other flavonoid oligomers have been widely reported in the flavonoid literature

[12-16] and are also included in the present recommendations. The recommended semi-systematic

names consider the terminal flavonoid as the preferred one that is substituted by the other

components. If the flavonoids are identical, the lower locant is linked to the higher one.

Example 59:


[(3 R)-4′-methoxyisoflavan-2′,7-diol]-(3′→4)-[(3S ,4 R)-4′-methoxyisoflavan-2′,7-diol]

Systematic names

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(3S ,4 R)-4-{4-hydroxy-5-[(3 R)-7-hydroxy-3,4-dihydro-2 H -1-benzopyran-3-yl]-2-methoxyphenyl}-

3-(2-hydroxy-4-methoxyphenyl)-3,3-dihydro-2 H -1-benzopyran-7-ol

(3S ,4 R)-4-{4-hydroxy-5-[(3 R)-7-hydroxy-3,4-dihydro-2 H -chromen-3-yl]-2-methoxyphenyl}-3-(2-

hydroxy-4-methoxyphenyl)-3,3-dihydro-2 H -chromen-7-ol

Example 60:

O

OOH

H3CO

OCH3

HO OH

O

O

OH

OH

2

4

3'4'

56

7

2'

4'

7

5 4


[(2S )-5-hydroxy-4′,7-dimethoxyflavan-4-one]-(2′→6)-[(2S )-3′,4′,5,7-tetrahydroxyflavan-4-one]

Trivial name

[(2S )-4′,7-di-O-methylnaringenin]-(2′→6)-[(2S )-3′-hydroxynaringenin]

Systematic names

(2S )-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-{2-[(2S )-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro-

2 H -1-benzopyran-2-yl]-5-methoxyphenyl}-2,3-dihydro-4 H -1-benzopyran-4-one

(2S )-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-{2-[(2S )-5-hydroxy-7-methoxy-4-oxo-3,4-dihydro-

2 H -chromen-2-yl]-5-methoxyphenyl}-2,3-dihydro-4 H -chromen-4-one

Example 61:

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O

OOH

HO

OH

OH2'

HO OH

O

O

OH

HO

OH

OH

O

OH

OH

O

5

6

7

5

7 2

4

3'

4'

4

2

2'

3'4'

5

7

6

4

3'

4'


(3′,4′,5,7-tetrahydroxyflavone)-(2′→6)-(3′,4′,5,7-tetrahydroxyflavone)-(2′→6)-(3′,4′,5,7-

tetrahydroxyflavone)

Systematic names

2-{2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4 H -1-benzopyran-6-yl]-3,4-

dihydroxyphenyl}-6-{2-(5,7-dihydroxy-4-oxo-4 H -1-benzopyran-2-yl)-3,4-dihydroxyphenyl}-5,7-

dihydroxy-4 H -1-benzopyran-4-one

2-{2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4 H -chromen-6-yl]-3,4-dihydroxyphenyl}-6-

{2-(5,7-dihydroxy-4-oxo-4 H -chromen-2-yl)-3,4-dihydroxyphenyl}-5,7-dihydroxy-4 H -chromen-4-

one

Note: In order to facilitate interpretation of the systematic name, systematic numbering is given below:

O

OOH

HO

OH

OH

HO OH

O

O

OH

HO

OH

OH

O

OH

OH

O

56

7

5

7 2

4

3

4

4

2

34

5

7

64

4

3

2

2

2

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Example 62:


(5,7-dihydroxyflavone)-(4′-epoxy-6)-(4′,5,7-trihydroxyflavone)

Trivial name

hinokiflavone

Systematic names

6-[4-(5,7-dihydroxy-4-oxo-4 H -1-benzopyran-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-

4 H -1-benzopyran-4-one

6-[4-(5,7-dihydroxy-4-oxo-4 H -chromen-2-yl)phenoxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4 H -

chromen-4-one

Example 63:


[(3 R)-2′-methoxyisoflavan-3′,7-diol]-(4′-epoxy-4′)-[(3 R)-2′-methoxyflavan-3′,7-diol]

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Trivial name

biscyclolobin

Systematic names

3,3′-oxybis(3-hydroxy-2-methoxy-4,1-phenylene)bis[(3 R)-3,4-dihydro-2 H -1-benzopyran-7-ol]

3,3′-oxybis(3-hydroxy-2-methoxy-4,1-phenylene)bis[(3 R)-3,4-dihydro-2 H -chromen-7-ol]

Example 64:


(3′,4′,5,7-tetrahydroxyflavone)-2-(2′→8,8→2′)-(3′,4′,5,7-tetrahydroxyflavone)

Trivial name

Anhydrobartramiaflavone

Systematic names

15,1

6,2

5,2

7,3

5,3

6,4

5,4

7-octahydroxy-1,3(1,2)-dibenzena-2,4(2,8)-bis(4 H -1-

benzopyrana)cyclotetraphane-24,4

4-dione

15,1

6,2

5,2

7,3

5,3

6,4

5,4

7-octahydroxy-1,3(1,2)-dibenzena-2,4(2,8)-di(4 H -chromena)cyclotetraphane-

24,4

4-dione

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MEMBERSHIP OF SPONSORING BODIES

Membership of the IUPAC-IUBMB Joint Commission on Biochemical Nomenclature for (a) the

period of 2010–2012; (b) present membership: (a)Chair Dietmar Schomburg; Secretary Richard

Cammack; Titular members Gerard Moss; Keith Tipton; Johannes Vliegenthart; Associate members

Kristian Axelsen; Ron Caspi; Athel Cornish-Bowden; Derek Horton. (b) Titular members NC-

IUBMB and JCBN Chair Gerard Moss; Secretary Richard Cammack; NC-IUBMB Ron Caspi;

Andrew McDonalds; Dietmar Schomburg; NC-IUBMB and JCBN: Kristian Axelsen; Keith Tipton;

JCBN: Markus Ennis; Associate members NC-IUBMB Ida Schomburg; Johannes Vliegenthart;

JCBN Athel Cornish-Bowden; Derek Horton; Karl-Heinz Hellwich; Ture Damhus; Amelia P.

Rauter.

Membership of the IUPAC Division (VIII) of Chemical Nomenclature and Structure Representation

for (a) the period 2010-2011; (b) 2012. (a) President Richard Hartshorn; Past-President Gerard

Moss; Secretary Ture Damhus; Titular Members Jonathan Brecher, Kirill Degtyarenko, Philip

Hodge, Alan Hutton, Jeff Leigh, Jeffery Wilson, Andrey Yerin; Associate Members Karl-Heinz

Hellwich, Jaroslav Kahovec, Ebbe Nordlander, József Nyitrai, Warren Powell, Jan Reedijk;

National Representatives: Sundarababu Baskaran, Abdul Jalil Miah, Patrick Moyna, Hiroshi Ogino,

Amélia Rauter, Ricardo Bicca de Alencastro.(b) President Richard Hartshorn; Vice-President Karl-

Heinz Hellwich; Secretary Ture Damhus; Titular members Michael Beckett; Ebbe Nordlander;

Warren Powell; Amélia P. Rauter; Hinnerk Rey; Antony Williams; Andrey Yerin; Associate

Members Kirill Degtyarenko; Philip Hodge; Alan Hutton; Jan Reedijk; Nigel Wheatley; Jeffrey

Wilson; National Representatives Vefa Ahsen; Itrat Anis; Sundarababu Baskaran; Gernot Eller;

Md. Hashem; Wei Huang; Jaroslav Kahovec; Lupituko Mkayula; József Nagy; Supawan

Tantayanon.

REFERENCES

1. Flavonoids – Chemistry, Biochemistry and Applications (ø.M.Andersen, K. R. Markham,eds.), CRC Press, Taylor and Francis Group, Boca Raton (2006).

2. The Science of Flavonoids (E. Grotewold, ed.), Springer, New York (2006).

3. Flavonoids and Related Compounds: Bioavailability and Function (J. P. E. Spencer, A.

Crozier, eds.), Oxidative Stress and Disease Series, Taylor and Francis, Boca Raton (2012).

4. J. Buckingham. Dictionary of Flavonoids, Taylor and Francis, Boca Raton (2012).

5. J. B. Harborne, H. Baxter. The Handbook of Natural Flavonoids (J. B. Harborne, H. Baxter,

eds.), Vols. 1 and 2, John Wiley, New York (1999).

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6. IUPAC. A Guide to IUPAC Nomenclature of Organic Compounds. R. Panico, W. H. Powell,

J.-C. Richer (Eds.), Blackwell Scientific Publications, Oxford (1993).

7. H. A. Favre, K.-H. Hellwich, G. P. Moss, W. H. Powell, J. G. Traynham, Corrections to 'A

Guide to IUPAC Nomenclature of Organic Compounds'. Pure Appl. Chem. 77, 1327 (1999).

8. IUPAC Recommendations 1979. Nomenclature of Organic Chemistry (the 'Blue Book').

Sections A, B, C, D, E, F, H. Prepared for publication by J. Rigaudy and S. P. Klesney. S. P.

Klesney (Ed.), Pergamon Press, Oxford (1979).

9. A. D. McNaught. Nomenclature of carbohydrates (IUPAC Recommendations 1996), Pure

Appl. Chem. 68, 1919 (1996).

10. P. M. Giles, Jr. Section F:Natural Products and Related Compounds, Pure Appl. Chem. 71,

587 (1999); Corrections and modifications: H. A. Favre, P. M. Giles Jr., K.-H. Hellwich, A.

D. McNaught, G. P. Moss, W. H. Powell. Pure Appl. Chem. 76, 1283 (2004).

11. G. P. Moss. Nomenclature of fused and bridged ring systems (IUPAC recommendations

1998), Pure Appl. Chem.70, 143 (1998).

12. H. Geiger, Biflavonoids and Triflavonoids, in The Flavonoids: Advances in Research since

1986 (J. B. Harborne, ed.), pp 95-115. Chapman & Hall, London (1994).

13. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids: Advances in Research since 1980 (J.

B. Harborne, T. J. Mabry, eds.), pp. 99-124. Chapman & Hall, London (1988).

14. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids (J. B. Harborne, T. J. Mabry, eds.), pp.

505-534. Chapman & Hall, London (1982).

15. H. Geiger, C. Quinn, Biflavonoids, in The Flavonoids (J. B. Harborne, T. J. Mabry, H.

Mabry, eds.), pp. 692-742. Chapman & Hall, London (1975).

16. H. D. Lockley, Fortschr. Chem. Org. Naturst . 30, 207 (1973).

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