Chemistry of Myrtaceous Phloroglucinols

Biogenetic Precursors for Myrtaceous Phloroglucinols

 

Fig. 1. Phloroglucinol-type biogenetic precursors for myrtaceous phloroglucinols.

 

No.

Name

R1

R2

R3

R4

A1

Acetophloroglucine

H

–

–

–

A2

Methylacetylphloroglucinol

CH3

–

–

–

A3

Aspidinol   B

H

CH3

H

–

A4

1-(2,6-Dihydroxy-4-methoxy-3,5-dimethylphenyl)-1-butanone

CH3

CH3

H

–

A5

–

CH3

CH3

CH3

–

A6

–

CH3

CHO

H

–

A7

–

CHO

CHO

H

–

A8

Isobutyrylphloroglucinol

H

H

H

H

A9

2-Methyl-1-(2,4,6-trihydroxy-3-methylphenyl)propan-1-one

CH3

H

H

H

A10

–

CH3

H

CHO

H

A11

2,4,6-trihydroxy-5-(2-methyl-1-oxopropyl)-1,3-Benzenedicarboxaldehyde

CHO

H

CHO

H

A12

Robustaol   B

H

H

H

CH3

A13

2',6'-Dihydroxy-4'-methoxyisobutyrophenone

H

CH3

H

H

A14

Pulverulentone   A

CH3

CH3

H

H

A15

1-(2,4-Dihydroxy-6-methoxy-3,5-dimethylphenyl)-2-methyl-1-propanone

CH3

H

CH3

CH3

A16

–

CH3

–

–

–

A17

–

CHO

–

–

–

A18

(2-Methylbutyryl)phloroglucinol

H

H

H

H

A19

2-Methyl-1-(2,4,6-trihydroxy-3-methylphenyl)butan-1-one

H

H

CH3

H

A20

2-Methyl-1-(2,4,6-trihydroxy-3,5-dimethylphenyl)-1-butanone

CH3

H

CH3

H

A21

–

H

H

H

CH3

A22

Callisalignone   A

H

CH3

H

H

A23

Aspidinol   D

CH3

CH3

H

H

A24

Isovaleroylphloroglucinol

H

H

H

H

A25

2-Methyl-4-isovalerylphloroglucin

H

H

CH3

H

A26

1-(2,4-Dihydroxy-6-methoxyphenyl)-3-methyl-1-butanone

H

H

H

CH3

A27

2,6-dihydroxy-4-methoxyisovalerophenone

H

CH3

H

H

A28

3-methyl-1-(2,4,6-trihydroxy-3,5-dimethylphenyl)-1-Butanone

CH3

H

CH3

H

A29

2,4,6-Trihydroxy-3-(3-methylbutanoyl)benzaldehyde

H

H

CHO

H

A30

Grandinol

CH3

H

CHO

H

A31

Jensenone

CHO

H

CHO

H

A32

Phlorocaprophenone

H

H

–

–

A33

–

CH3

CHO

–

–

A34

–

CHO

CHO

–

–

A35

2,4,6-trihydroxy-3,5-dimethyl-Benzophenone

CH3

H

CH3

–

A36

3-benzoyl-2,4,6-trihydroxy-5-methyl-Benzaldehyde

CHO

H

CH3

–

A37

–

CHO

H

CHO

–

A38

2,6-Dihydroxy-4-methoxy-3-methyl-benzophenone

H

CH3

CH3

–

A39

2',4',6'-Trihydroxydihydrochalcone

H

H

H

–

A40

3-Phenyl-1-(2,4,6-trihydroxy-3-methylphenyl)-1-propanone

H

H

CH3

–

A41

Myrigalone   G

CH3

CH3

H

–

A42

2',4'-Dihydroxy-3',5'-dimethyl-6'-methoxychalcone

H

CH3

CH3

H

A43

Aurentiacin   A

CH3

H

H

H

A44

3-Hydroxy-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenyl-2-propen-1-one

CH3

H

CH3

OH

A45

(−)-Cryptostrobin

β-H

H

H

CH3

A46

(±)-Cryptostrobin

H

H

H

CH3

A47

6-C-Methylpinocembrin

β-H

CH3

H

H

A48

–

α-H

CH3

CH3

OH

A49

–

β-H

CH3

CH3

OH

A50

Luteolin

H

–

–

–

A51

Tricetin

CH3

–

–

–

A52

1-(4,5-dihydro-6,8-dihydroxy-4,4-dimethyl-2-phenyl-2,5-methano-1,3-benzodioxepin-9-yl)-2-methyl-1-Propanone

–

–

–

–

   

Fig. 2. β-Triketone-type biogenetic precursors for myrtaceous phloroglucinols.

 

No.

Name

R

B1

Methylacetylphloroglucinol

–

B2

–

–

B3

Agglomerone

H

B4

3-Hydroxy-5-methoxy-4,6,6-trimethyl-2-(2-methyl-1-oxopropyl)-2,4-cyclohexadien-1-one

CH3

B5

3-hydroxy-2-isobutyryl-5-methoxy-4,4,6-trimethyl-2,5-Cyclohexadien-1-one

–

B6

–

–

B7

Syncarpic   acid

H

B8

5-Hydroxy-2,2,4,6,6-pentamethyl-4-cyclohexene-1,3-dione

CH3

B9

4-Isobutyryl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione

CH3

B10

–

OH

B11

Norleptospermone

H

B12

Leptospermone

CH3

B13

Isoleptospermone

–

B14

6-benzoyl-2,2,4,4-tetramethyl-1,3,5-Cyclohexanetrione

–

B15

Grandiflorone

–

B16

–

–

B17

Champanone   B

–

B18

(+)-Xanchryone   E

α-OH

B19

(−)-Xanchryone   E

β-OH

 


Fig. 3. Terpenoid-type biogenetic precursors for myrtaceous phloroglucinols.

 

No.

Name

R1

R2

C1

α-Phellandrene

H

–

C2

(R)-α-Phellandrene

α-H

–

C3

(S)-α-Phellandrene

β-H

–

C4

1-Isopropyl-4-methylcyclohexa-2,4-dienol

α-OH

–

C5

α-Terpinene

–

–

C6

γ-Terpinene

H

–

C7

2-Methyl-5-(1-methylethyl)-2,5-cyclohexadien-1-ol

OH

–

C8

δ-Terpinene

–

–

C9

β-Phellandrene

H

–

C10

(−)-β-Phellandrene

α-H

–

C11

(+)-β-Phellandrene

β-H

–

C12

p-Cymene

–

–

C13

p -Cymenene

–

–

C14

(−)-α-Thujene

–

–

C15

(+)-α-Thujene

–

–

C16

(−)-Sabinene

–

–

C17

(+)-Sabinene

–

–

C18

(+)-β-Pinene

–

–

C19

(S)-β-Pinene

–

–

C20

(+)-α-Pinene

–

–

C21

geranylpyrophospha

–

–

C22

Myrcene

–

–

C23

Germacrene   C

–

–

C24

(+)-Germacrene   A

β-H

–

C25

(−)-Germacrene   A

α-H

–

C26

(+)-Hedycaryol

α-H

–

C27

(±)-Hedycaryol

H

–

C28

Germacrene   E

–

–

C29

Allohedycaryol

β-H

α-H

C30

α,α,4,8-Tetramethyl-2,7-cyclodecadiene-1-methanol

H

H

C31

(−)-Allohedycaryol

α-H

β-H

C32

[1R-(1R*,2E,4R*,7E)]-4-hydroxy-α,α,4,8-tetramethyl-2,7-Cyclodecadiene-1-methanol

α-OH

α-H

C33

Litseagermacrane

–

–

C34

–

–

–

C35

Hydroxygermacrene   D

–

–

C36

–

–

–

C37

(+)-Bicyclogermacrene

–

–

C38

–

–

–

C39

(−)-Bicyclogermacrene

–

–

C40

[1S-(1R*,2R*,6E,10S*)]-7,11,11-trimethyl-3-methylene Bicyclo[8.1.0]undec-6-en-2-ol

–

–

C41

–

–

–

C42

–

–

–

C43

α-Humulene

–

–

C44

β-Calacorene

–

–

C45

(−)-Cadina-1(6),4-diene

–

–

C46

(−)-Cadina-3,5-diene

–

–

C47

(+)-Cadina-3,5-diene

–

–

C48

(1S,4S,4aS)-1,2,3,4,4a,5,6,7-Octahydro-4-methyl-7-methylene-1-(1-methylethyl)naphthalene

α-H

β-CH3

C49

Bicyclosesquiphellandrene

β-H

α-CH3

C50

–

–

–

C51

(1R-cis)-1,2,3,5,6,8a-hexahydro-α,α,4,7-tetramethyl-1-Naphthalenemethanol

–

–

C52

–

–

–

C53

6-epi-β-Cubebene

–

–

C54

(3aS,3bR,4R,7R,7aR)-octahydro-7-methyl-3-methylene-4-(1-methylethyl)-1H-Cyclopenta[1,3]cyclopropa[1,2]benzene

H

–

C55

–

OH

–

C56

Calarene

–

–

C57

[5R-(5α,8β,8aα)]-   1,5,6,7,8,8a-hexahydro-α,α,3,8-tetramethyl-5-azulenemethanol

–

 

C58

(5R)-1,2,4,5,6,7-hexahydro-α,α,3,8-tetramethyl-5-azulenemethanol

–

–

C59

(5R,8R,8aR)-1,2,4,5,6,7,8,8a-Octahydro-α,α,3,8-tetramethyl-5-azulenemethanol

–

 

C60

(−)-α-Gurjunene

–

–

C61

(+)-Aromadendrene

–

–

C62

α-Cubebene

–

–

C63

β-Cubebene

–

–

C64

β-caryophyllene

–

–

C65

α-Caryophyllenol

β-OH

–

C66

Caryophyllenol   II

α-OH

–

C67

Dihydrocaryophyllene-4β,5α-diol

–

–

C68

Caryophylladienol   II

β-OH

–

C69

Caryophylladienol   I

α-OH

–

C70

1S,2S,5R-1,4,4-Trimethyltricyclo[6.3.1.0(2,5)]dodec-8-en

–

–

C71

–

–

–