
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 | – | – | – |
