Table S 1
Synopsis of the main biological activities of acylphloroglucinols, considered with reference to the acyl
chain and other substituents present.
The compounds are listed in order of increasing length (number of C atoms) of the R chain. For isomeric R
chains, the compound with linear R is listed first. Compounds with more than one acyl chain are listed with
reference to the longest R chain.
Because of the length of the systematic (IUPAC) names of most of these compounds, common names are
reported when familiar; otherwise, the number ascribed to the given compound in the reviews utilized as
structure references is reported, preceded by comp- and followed by the reference number. The reference
numbering utilized in this table is independent of the one utilized in the article, and the references are listed
after the table.
The types of biological activities are denoted by acronyms, listed after the table. When measurements of the
biological activity are available, the values are reported together with the determination method and the
corresponding reference.
longest acyl chain
additional
acyl chains
additional structural
information a
reference-number of
compound
type b
biological activity
value (when available) and
determination method c
Compounds with one acylphloroglucinol moiety, in fully enol form
CHO
CHO
CHO
CHO
CHO
CHO
CHO
  CH2CH2CH(CH3)2,
 OCH2CH2CH(CH3)2
at C6
 complex R
 phloroglucinolterpene adducts
 terpenoid moiety
 chroman ring
 terpenoid moiety
 comp-19 [1]
AL [1]
CT [1]
IC50 : 10 g/mL ABA [1]
IC50 : 4.6 g/mL [1]
 comp-162 [3], comp-1
[2]
 eucalyptone [3]
 euglobals [3,4]
 comp-130 [3]
(euglobals G1)
 comp-130-133 [3]
(euglobals G1–G4)
 comp-142, 143 [3]
(robustadials A and B)
 comp-151 [3] (BF-2)
AB [2, 3]
MIC: 12.5 g/mL SD [2]
CT [3]
IC50 : 5 lg mL−1 [3, 5]
 macrocarpals [3]
AB [3]
ARI [3]
H-RT+P-I [3]
H-RT+P-I [3]
IC50 : 5.3 µM [3]
ARI [3]
IC50 : 2.02.8 µM [3]
H-RT+P-I [6]
H-RT+P-I [6]
H-RT+P-I [6]
H-RT+P-I [6]
H-RT+P-I [6]
10 M [6]
5.3 M [6]
8.4 M [6]
12 M [6]
8.1 M [6]
 comp-154 [3]
 comp-150, 151, 153
and 155 [3]
 comp-44 [6]
 comp-45 [6]
 comp-46 [6]
 comp-47 [6]
 comp-48 [6]
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
 R = R = CH3
  n-C3H7
  n-C4H9
  n-C5H11
  n-C6H13
  n-C7H15
  n-C8H17
  n-C9H19
  n-C10H21
  n-C12H25
 comp-16 [7]
 comp-38 [3]
 comp V-1 [8]
 comp V-2 [8]
 comp V-3 [8]
 comp V-4 [8]
 comp V-5 [8]
comp V-6 [8]
 comp V-7 [8]
 comp V-7 [8]
 comp V-9 [8]
EBVI [3, 4]
AT [3]
AL [3, 5]
IC50 : 3.6, 7.1, 3.9 and 12 lg
mL−1 respectively [3, 5]
AM [3]
CT [3]
AF [8]
AF [8]
AF [8]
AF [8]
AF [8]
AF [8]
AF [8]
AF [8]
AF [8]
COCH3
CHO
COCH3
COCH3
COCH3
COCH3
CHO
CHO
COCH3
COCH3
COCH3
COCH3
CHO
COCH3
two CHO
groups
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
 comp-33 [1]
 comp-16 [7]
  CH3
  OCH2CH2CH(CH3)2
  CH3 at C5
 OCH3 at C6
  CH3 at C5
 OCH3 at C4
  CH3 at C3
 OCH3 at C6
  CH3 at C5
 OCH3 at C6
 comp-30 [1]
 comp-15 [1]
 comp-32 [3]
 comp-34 [3]
 comp-38 [3]
 comp-39 [3]
 comp-45 [3]
 comp-33 [7]
 comp-4 [1]
 comp-18 [9]
AB1 [1]
AB3 [9]
AL [9]
CT [9]
CT [9]
AL [1]
AB [3]
 comp-186 [3]
 comp-301 [3]
 comp-302 [3]
AF, AB [3]
 comp-303 [3]
AF, AB [3]
 comp-29 [3]
IT medaka [3]
1.5 g/mL [3]
AF(V) [1]
CT [1]
CT [1]
GI [7]
AF(I) [1]
AF(V) [1]
GI [7]
GI [7]
GI [7]
GI [7]
AB2 [10]
IC50 : 15 g/mL [1]
IC50 : 18 g/mL+ [1]
IC50 : 11 g/mL++ [1]
GI50 : 16 x 10-5 M CSB [7]
IC50 : 5 g/mL [1]
IC50 : 20 g/mL [1]
GI50 : 14 x 10-5 M CSB [7]
GI50 : 7.2 x 10-5 M CSB [7]
GI50 : 6.9 x 10-5 M CSB [7]
GI50 : 13 x 10-5 M CSB [7]
MIC : 125 g/mL TD [10]
MBC : 125 g/mL TD [10]
MIC : 32 g/mL TD [10]
MBC : 32 g/mL TD [10]
COCH2CH3
CHO
  CH3,
 comp-29 [1]
 comp-25 [7]
COCH2CH3
COCH2CH3
COCH2CH3
COCH2CH2CH3
CHO
CHO
COCH3
  CH2CH3
  CH2CH2CH3
H
 comp-26 [7]
 comp-27 [7]
 comp-28 [7]
 comp-C5 [10]
 comp III-1 [8]
 comp IV-1 [8]
 comp IV-7 [8]
 comp-32 [1]
 comp-17 [7]
AB4 [10]
  isopentenyl
  n-pentyl
  isopentyl
CHO
COCH2CH
91.1 mm PD [9]
29.2 mm PD [9]
IC50 : 27 g/mL ABA [1]
IC50 : 12 g/mL+ [1]
IC50 : 11 g/mL++ [1]
IC50 : 40 g/mL [1]
AF(I) [3]
AF(II) ($) [3]
AF(III) ($) [3]
ATB [3]
AF, AB [3]
 comp-41 [3]
CHO
COCH2CH2CH3
COCH2CH2CH3
COCH2CH2CH3
COCH2CH2CH3
COCH2CH2CH3
GI50 : 28 x 10-5 M CSB [7]
 comp-17 [1]
 comp-39 [3]
COCH2CH3
COCH2CH3
COCH2CH3
COCH2CH3
COCH2CH3
AB [3]
CT [3]
AB [3]
CT [3]
AB [3]
AF [3]
GI [7]
IC50 : 17.5 g/mL+ [1]
IC50 : 10 g/mL++ [1]
GI50 : 15 x 10-5 M CSB [7]
IC50 : 15 g/mL [1]
IC50 : 7.8 g/mL ABA [1]
IC50 : 10 g/mL [3]
  OCH2CH2CH(CH3)2
  CH3
 OCH3 at C4
 OCH3 at C4
 O-glycoside at C4
  CH2Y, where Y is a
multisubstituted
pyrane ring with the
 substituent
different for the three
compounds
 CH2CHC(CH3)(CH2)2
CHC(CH3)2 at C5
  CH3
 OCH3 at C6
  isopentenyl
  n-pentyl
  isopentyl
 R = R = H
COCH3
COCH3
CT [1]
CT [1]
GI [7]
AF(I) [1]
AL [1]
AB [3]
AB [3]
ED50 : 45 M [3]
ED50 : 410 M [3]
 comp III-2 [8]
 comp IV-2 [8]
 comp IV-8 [8]
 comp-18 [7]
 comp-29 [7]
GI [7]
GI [7]
GI50 : 16 x 10-5 M CSB [7]
GI50 : 22 x 10-5 M CSB [7]
 comp-30 [7]
GI [7]
GI50 : 78 x 10-5 M CSB [7]
3
COCH2CH2CH3
COCH2
CH2CH3
  CH2CH=CH2
COCH2CH2CH3
 comp-C8 [10]
AB2 [10]
AB4 [10]
AF(I) [10]
AF(IV) [10]
COCH2CH2CH3
 COCH3 at C4
 R = R = CH3
 COCH3 at C4
COCH(CH3)2
COCH(CH3)2
  CH3
COCH2CH2CH3
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
CO (CH2) 3CH3
CO (CH2) 3CH3
CO (CH2) 3CH3
COCH2CH2CH2CH3
COCH2CH(CH3)2
COCH2CH(CH3)2
COCH2CH(CH3)2
COCH2CH(CH3)2
COCH2CH(CH3)2
  isopentenyl
  n-pentyl
  isopentyl
 R = R = CH3
 OCH3 at C4 and C6
  prenyl-ester chain
 comp-III-3 [8]
 comp-IV-3 [8]
 comp-IV-9 [8]
 BF-1 [15]
  (CH2)2C(CH3)OH
(CH2)2CHC(CH3)2
 O-glycoside at C6
 O-glycoside at C4
  CH3,
 OCH3 at C6
 comp-262 [1]
(hyperjovinol A)
 comp-1 [13]
 comp-4 [13]
 1,5- dihydroxy-2-(2 0
-methylpropionyl)-3methoxy-6methylbenzene [18]
 comp III-4 [8]
 comp IV-4 [8]
 comp IV-10 [8]
 comp-19 [7]
 comp III-5 [8]
 comp IV-5 [8]
 comp IV-11 [8]
 comp-181 [3]
 comp-3 [13]
 comp-2 [1]
 comp-1 [3]
 comp-1 [7]
 comp-1 [17]
  isopentenyl
  n-pentyl
  isopentyl
CHO
  isopentenyl
  n-pentyl
  isopentyl
 O-glycoside at C6
CHO
 comp-25 [3]
 comp-9 [11]
 comp-26 [3]
 desaspidinol [12]
 comp-5 [13]
 isobutyrophenone [14]
  CH3
 caespitate [16]
IT medaka [3]
FASI [11]
AT [12]
AI [13]
AIa [14]
AIb [14]
MIC : 125 g/mL TD [10]
MBC : 125 g/mL TD [10]
MIC : 32 g/mL TD [10]
MBC : 32 g/mL TD [10]
MIC : 50 g/mL [10]
MIC : 50 g/mL [10]
1.5 g/mL [3]
IC50 : 49.1 ±2.7 M [11]
IC50 : 3.8 M [13]
IC50 : 5 μM [14]
IC50 10 μM [14]
CT [15]
AB [16]
AF [16]
CT
AO
MIC : 0.5 g/ml
AD [16]
MIC : 0.55 g/ml AD [16]
AI [13]
AI [13]
AB3 [18]
IC50 : 23.7M [13]
IC50 : 58.7 M [13]
MIC : 16 –32 g/ml MA [18]
GI [7]
GI50 : 140 x 10-5 M CSB [7]
AI [13]
GI50 : 9.8 x 10-5 M CSB [7]
COCH2CH(CH3)2
CHO
  CH3CH2
 comp-22 [7]
GI [7]
EBVI [3]
AB1 [3]
AB2 [3]
MRSA [1]
AL [1]
CT [1]
AF(I) [1]
AF(V) [1]
GI [7]
COCH2CH(CH3)2
CHO
  CH3CH2CH2
 comp-23 [7]
GI [7]
GI50 : 15 x 10-5 M CSB [7]
COCH2CH(CH3)2
CHO
  CH3 (CH2)3
 comp-24 [7]
GI [7]
GI50 : 29 x 10-5 M CSB [7]
COCH2CH(CH3)2
CHO
 OCH2CH=CH2 at C4
 comp-12 [1]
IC50 : 5.3 μg/mL ABA [1]
IC50 : 17.0 μg/mL+ [1]
COCH2CH(CH3)2
two CHO
 comp-22 [9]
AL [1]
CT [1]
AFE [1]
AF(I) [1]
AB2 [1]
AL [1]
AB1 [9]
 comp-8 [7]
GI [7]
GI50 : 8.1 x 10-5 M CSB [7]
COCH2CH(CH3)2
COCH2C
H(CH3)2
COCH2CH(CH3)2
CHO
 comp-3 [1,3]
(jensenone)
  CH3,
 OCH3 at C6
IC50 : 5 μg/mL [3]
IC50 : 25 μg/mL [3]
IC50 : 8 μg/mL [1]
IC50 : 21 μg/mL ABA [1]
IC50 : 8 μg/mL+ [1]
IC50 : 10 μg/mL [1]
IC50 : 10 μg/mL [1]
GI50 : 9.2 x 10-5 M CSB [7]
IC50 : 5.5 μg/mL [1]
20 µg/mL [1]
IC50 : 19 µg/mL [1]
74.1mm PD [9]
COCH2CH(CH3)2
COCH2C
H(CH3)2
 OCH2CH=CH2 at C4
 comp-14 [1]
AL [1]
IC50 : 14 μg/mL
ABA [1]
COCH2CH(CH3)2
COCH2C
H(CH3)2
 OCH2CH2CH(CH3)2
at C4
 comp-18 [1]
AL [1]
IC50 : 24 μg/mL
ABA [1]
  CH2CH=CH2
 comp-C9 [10]
AB1 [10]
MIC : 64 g/mL TD [10]
MBC : 250 g/mL TD [10]
MIC : 4 g/mL TD [10]
MBC : 8 g/mL TD [10]
COCH2CH(CH3)2
AB4 [10]
COCH2CH(CH3)2
COCH2CH(CH3)2
CHO
COCH2CH(CH3)2
CHO
COCH2CH
(CH3)CH2CH3
COCH(CH3)CH2CH3
CHO
  CH3
 OCH2CH(CH3)2 at C4
 OCH2CH2CH(CH3)2
at C4
CH3 at C3
 O-glycoside at C6
  isopentenyl
  n-pentyl
  isopentyl
  prenyl
CO(CH2 )4CH3
CO(CH2 )4CH3
CO(CH2 )4CH3
COCH2CH2CH(CH3)2
 comp-280 [3]
 comp-16 [1]
AM [3]
AF [3]
AL [1]
 comp-130 [3]
 comp-131 [3]
 comp-132 [3]
 comp-133 [3]
 comp-2 [3]
AT, AL [3]
AL [3]
AL [3]
AL [3]
EBVI [3]
 comp-178 [3]
 comp-2 [13]
 comp III-6 [8]
 comp IV-6 [8]
 comp IV-12 [8]
 comp-C1 [10]
(caespitin)
AI [3,13]
AB1 [10]
AB4 [10]
AF(I) [10]
AF(IV) [10]
 comp-16 [9]
COC6H5
COC6H5
CO-CH=CH(C6H5)OH
 comp-17 [9]
COCH3
  prenyl
 OCH3 at C6
 xanthohumol [19]
 comp-13 [20]
CO(CH2)8CH3
AB1 [9]
AB3 [9]
AB1 [9]
AB3 [9]
CT [19]
Anti-HIV [18]
MRSA [20]
VRE [20]
DTM [20]
CT P388 [20]
AB1 [20]
 comp-15 [20]
CO(CH2)10CH3
MRSA [20]
VRE [20]
DTM [20]
CT P388 [20]
IC50 : 4.2 μg/mL ABA [1]
IC50 :
IC50 :
IC50 :
IC50 :
3.6 μg/mL
7.1 μg/mL
3.9 μg/mL
12 μg/mL
 prenyl at C3 and C5
 OCH3 at C5
 helihumulone [20]
AB1 [21]
AB2 [21]
AB3 [21]
AB7 [21]
AB8 [21]
AB9 [21]
[3]
[3]
[3]
[3]
MIC : 16 g/mL TD [10]
MBC : 16 g/mL TD [10]
MIC : 8 g/mL TD [10]
MBC : 8 g/mL TD [10]
MIC : 25 g/mL [10]
MIC : 6 g/mL [10]
28.4 mm PD [9]
50.3 mm PD [9]
74.8 mm PD [9]
18.1 mm PD [9]
CC50 : 8.82  0.43g/ml [19]
MIC: 815 g/ml DDA [20]
MIC: 1.6–3.1g/ml DDA
[20]
1 mm at 60 g/disc [20]
IC50 : 16.9 g/mL [20]
1 mm at 60 g/disc [20]
MIC : 4-8 g/ml DDA [20]
MIC : 1.6–3.1 g/ml DDA
[20]
3 mm at 60 g/disc [20]
IC50 > 25 g/mL [20]
Compounds with one acylphloroglucinol moiety, and the OH at C6 replaced by a keto O
COCH2CH2-C6H5
ABA
ABA
ABA
ABA
MIC : 0.063 mg/ml
(TLC)BA [21]
MIC : 0.125 mg/ml
(TLC)BA [21]
MIC : 0.063 mg/ml
(TLC)BA [21]
MIC : 0.031mg/ml
(TLC)BA [21]
MIC : 0.063 mg/ml
(TLC)BA [21]
MIC : 0.016 mg/ml
(TLC)BA [21]
AB10 [21]
AB11 [21]
AF(V) [21]
AF(I) [21]
AM [21]
MIC : 0.063 mg/ml
(TLC)BA [21]
MIC : 0.016 mg/ml
(TLC)BA [21]
MIC : 0.031 mg/ml
(TLC)BA [21]
MIC : 0.063 mg/ml
(TLC)BA [21]
IC50 : 14.89 1 .88g/ml
INT [21]
Compounds with two acylphloroglucinol moieties, both in fully enol form d
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
 OCH3 at C4
 CH3 at C5
 prenyl at C5
 comp-A [25]
(mallotojapon)
RTI [25]
 OCH3 at C4
 CH3 at C5
 CH2CHOHC(CH3)CH2
at C5
 OCH3 at C4
 CH3 at C5
 pyranoid ring
fused at C5C6
(chromene unit)
 comp-B [25]
(mallotolerin)
RTI [25]
 comp-C [25]
(mallotochromene)
RTI [25]
 comp-409 [3]
AM [3]
AB [3]
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH(CH3)2
COCH(CH3)2
CT [3]
H-RT+P-I [3]
 OCH3 at C4
 CH3 at C4
 prenyl at C5
 comp-524 [3]
CT [3]
 prenyl at C5,
 OCH3 at C6
 prenyl at C5
 comp-525 [3]
CT [3]
 comp-D [25]
(mallotophenone)
RTI [25]
 comp-526 [3]
CT [3]
AH [3]
comp-10 [11]
FASI [11]
 comp-410 [3]
(robustaol A)
AM [3]
 robustaol A [6]
AM [6]
CHO at C5
IC50 : 25.4 ± 1.4 [11]
 CH3 at C5
 OCH3 at C6
COCH(CH3)2
COCH2CH(CH3)2
COCH2CH(CH3)2
 comp-491 [3]
 prenyl at C5
 OCH3 at C4
 CH3 at C5
 OCH3 at C4
 CH3 at C5
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 CH3 at C5
COCH3
COCH3
COCH2CH2CH3
COCH2CH2CH3
COCH2CH(CH3)2
 prenyl at C5
0.11.0g/ml [3]
CHO
 CH3 at C5
 OCH3 at C6
Compounds with two acylphloroglucinol moieties, one in fully enol form and the other with the OH at C2 replaced by a keto O
COCH3
COCH3
COCH3
 pyranoid ring
fused at C5C6
(chromene unit),
with two CH3 in 
 two CH3 at C5
 pyranoid ring
 comp-426 [3]
AB [3]
CT [3]
 comp-427 [3]
AB [3]
e
fused at C5C6
(chromene unit),
with two CH3 in 
 CH3 and prenyl at C5
 O-prenyl at C4
 CH3 and prenyl at C5
 prenyl at C5
 CH3 and prenyl at C5
 pyranoid ring
fused at C5C6
(chromene unit),
with two CH3 in 
 two CH3 at C5
 pyranoid ring
fused at C5C6
(chromene unit),
with two CH3 in 
 two CH3 at C5
 prenyl at C5
 two CH3 at C5
 pyranoid ring
fused at C5C6
(chromene unit),
with two CH3 in 
 CH3 and prenyl at C5
 CH3 at C5
COCH3
COCH3
COCH3
COCH3
COCH3
COCH3
COCH2CH3
COCH2CH3
COCH2CH3
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH2CH2CH3
COCH3
COCH2CH2CH3
COCH3
COCH2CH2CH3
COCH3
 two CH3 at C5
 CH3 at C5
 two CH3 at C5
COCH2CH2CH3
COCH2CH3
COCH2CH2CH3
 CH3 at C5
 two CH3 at C5
 CH3 at C5
COCH2CH3
 two CH3 at C5
COCH2CH2CH3
COCH2CH2CH3
COCH(CH3)2
 CH3 at C5
 OCH3 at C6
 two CH3 at C5
CH3 at C5
COCH(CH3)CH2CH3
COCH(CH3)CH2CH3
 two CH3 at C5
CH3 at C5
COCH(CH3)CH2CH3
 two CH3 at C5
 two CH3 at C5
 CH3 at C5
 two CH3 at C5
CT [3]
 comp-428 [3]
 comp-429 [3]
 comp-425 [3]
AB [3]
CT [3]
AB [3]
CT [3]
AB [3]
CT [3]
 comp-424 [3]
AB [3]
CT [3]
 uliginosin A [24]
AB1 [24]
 comp-434 [3]
AB [3]
 comp-436 [3]
(saroaspidin A)
AB [3]
 flavaspidic acid-AB
[11]
 norflavaspidic acidAB [11]
 flavaspidic acid PB
(2) [22]
FASI [11]
AB [11]
FASI [11]
IC50 : 28.7 ± 1.4 [11]
LPOI [22]
(DPPH)RS [22]
(SO)RS [22]
 flavaspidic acid-PB
[11]
 flavaspidic acid PB
(1) [22]
FASI [11]
AB [11]
LPOI [22]
(DPPH)RS [22]
(SO)RS [22]
IC50 : 13.1  M TBA [22]
IC50 : 76.3 M FTC [22]
IC50 : 64.4 M [22]
NBTR [22]
IC50 : 23.1 ± 1.4 [11]
 aspidin-BB [11, 23]
FASI [11, 23]
AB [11, 23]
 comp-437 [3]
(saroaspidin B)
AB [3]
 comp-438 [3]
(saroaspidin C)
AB [3]
0.2g (TLC)BA [24]
IC50 : 29.7 ± 1.1 [11]
IC50 : 12.9  M TBA [22]
IC50 : 71.7 M FTC [22]
IC50 : 58.6 M [22]
NBTR [22]
IC50 : 32.6 ± 3.0 [11, 23]
Compounds with two acylphloroglucinol moieties, both of them having the OH at C2 replaced by a keto O
COCH2CH3
COCH3
COCH2CH3
COCH2CH3
COCH2CH2CH3
COCH2CH3
COCH(CH3)2
COCH(CH3)2
 two CH3 at C5
 two CH3 at C5
 two CH3 at C5
 two CH3 at C5
 two CH3 at C5
 two CH3 at C5
 two CH3 at C5
 two CH3 at C5
 albaspidin-AP [11]
FASI [11]
IC50 : 71.7 ± 3.9 [11]
 albaspidin-PP [11]
FASI [11]
AH [3]
FASI [11]
AH [3]
AB1 [24]
IC50 : 60.2 ± 3.5 [11]
 albaspidin-PB [11]
 japonicin A [24]
(albaspidin iBiB)
Compounds with three phloroglucinol moieties, all in fully enol form
IC50 : 56.1 ± 2.6 [11]
0.5 g (TLC)BA [24]
COCH(CH3)2
 OCH3 at C6
 CH3 at C5
 comp-540 [3]
AM [3]
AB[3]
 comp-541 [3]
AM [3]
AB[3]
 comp-542 [3]
AM [3]
AB[3]
 comp-543[3]
AM [3]
AB[3]
 comp-544 [3]
AM [3]
AB[3]
 comp-545 [3]
AM [3]
AB[3]
 comp-546 [3]
AM [3]
AB[3]
 comp-554
CT [3]
AH [3]
COCH(CH3)CH2CH3
COCH(CH3)2
COCH2CH2CH3
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
COCH(CH3)CH2CH3
COCH2CH2CH3
COCH2CH2CH3
COCH2CH2CH3
COCH2CH2CH3
COCH(CH3)2
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
COCH(CH3)CH2CH3
COCH3
COCH3
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
COCH(CH3)CH2CH3
COCH3
COCH3
COCH2CH2CH3
COCH2CH2CH3
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C6
 CH3 at C5
 OCH3 at C2
 OCH3 at C6
 CH3 at C5
Compounds with three phloroglucinol moieties,
the middle one in fully enol form and the side ones with the OH at C2 replaced by a keto O
COCH2CH3
COCH2CH2CH3
COCH3
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
 two CH3 at C5
 two CH3 at C5
 two CH3 at C5
 filicinic acid-ABP
[11]
FASI [11]
AB [11]
AH [3]
IC50 : 31.0 ± 2.7 [11]
 japonicin IV [3]
 two CH3 at C5
Compounds with more complex structures
COCH(CH3)2
COCH(CH3)2
 pyranoid ring
fused at C5C6
(chromene unit),
with a prenyl and a
CH2CH2CHC(CH3)2
attached
 pyranoid ring
fused at C5C6
(chromene unit),
with attached a
CH2CH2CHC(CH3)2
 comp-1 [26]
 comp-3 [26]
AB [26]
MIC : 864 g/ml
CT [26]
IC50 : 6.515.7 g/ml CTA
[26]
AB [26]
MIC : 28 g/ml
CT [26]
IC50 : 8.520.0 g/ml CTA
[26]
DD [26]
DD [26]
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
 pyranoid ring
fused at C4C5
(chromene unit)
 two CH3 at C5
 pyranoid ring
fused at C4C5, in
turn fused to
cyclopentane
 two CH3 at C5
 prenyl at C3
 6-member ester ring
fused at C4C5, from
esterification of a
CHPhCHCOOH at C5
with OH at C4
 CH(CH(CH3)2Y at
C3, with Y derived
 isouliginosin B [24]
AB1 [24]
MIC : 0.16 g (TLC)BA
[24]
 hyperbrasilol A [24]
AB1 [24]
MIC : 0.32 g (TLC)BA
[24]
 comp-1 [27]
AB3 [27]
MIC : 2–8 g/ml AD [27]
 semimyrtucommulone
[14]
AIa [14]
AIb [14]
AB [3]
IC50 : 29 μM [14]
IC50 10 μM [14]
MIC : 32–64g/ml
 myrtucommulone [14,
23]
AIa [14]
AIb [14]
AO
AB [23]
AB [3]
IC50 : 17 μM [14]
IC50 : 1.8 μM [14]
IC50 : 13.6162 μM [14]
1335 mm PD [23]
MIC : 0.5–2 g/ml
 comp-1b [27]
AB2 [27]
MIC : 2–8 g/ml AD [27]
 comp-2 [27]
AB2 [27]
MIC : 4–128 g/ml AD
[27]
IC50 : 2.74  0.45 g/ml MA'
[27]
from a phloroglucinol
moiety with two OH
replaced by keto O
COCH(CH3)2
COCH2CH(CH3)2
COCH(CH3)CH2CH3
COCH(CH3)CH2CH3
COCH(CH3)CH2CH3
COCH(CH3)CH2CH3
COCH(CH3)CH2CH3
COCH(CH3)2
 CH3 at C5
 CH(CH(CH3)2Y at
C3 and C5, with Y
derived from a
phloroglucinol
moiety with two OH
replaced by keto O
 prenyl at C3
 6-member ester ring
fused at C4C5,
from esterification
of a CHPhCHCOOH
at C5 with OH at C4
 CH2CHC(CH3)CH2
CH2CHC(CH3)2 at
C3
 6-member ester ring
fused at C4C5,
from esterification
of a CHPhCHCOOH
at C5 with OH at C4
 prenyl at C3
 6-member ester ring
fused at C4C5,
from esterification
of a CHPhCHCOOH
at C5 with OH at C4
 CH2CHC(CH3)CH2
CH2CHC(CH3)2 atC3
 6-member ester ring
fused at C4C5,
from esterification
of a CHPhCHCOOH
at C5 with OH at C4
 pyranoid ring
fused at C5C6
(chromene unit),
with a prenyl and a
CH2CH2CHC(CH3)2
chain attached
 pyranoid ring
fused at C5C6
(chromene unit),
with attached a
CH2CH2CHC(CH3)2
 C2 and C6 replaced
AM [27]
 comp-3 [27]
AB2 [27]
MIC : 2–64 g/ml AD [27]
 comp-4 [27]
AB2 [27]
MIC : 2– >128 g/ml AD
[27]
IC50 : 11.21  5.40 g/ml
MA' [27]
AM [27]
 comp-2 [26]
AB [26]
CT [26]
 comp-4 [26]
 hyperforin [28, 29]
MIC : 3264 g/ml DD
[26]
IC50 : 715.3 g/ml CTA
[26]
AB [26]
MIC : 232 g/ml DD [26]
CT [26]
IC50 : 6.215.6 g/ml
[26]
SIRT1 [28]
IC50 : 15  0.5g/ml [28]
CTA
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
by keto O
 5-member ring joint
at C1 an C3, with
attached a prenyl and
CH2CH2CHC(CH3)2
 prenyl at C3 and C5
 C2 and C6 replaced
by keto O
 5-member ring joint
at C1 an C3, with
attached a prenyl and
CH2CH2CHC(CH3)2
 prenyl at C3 and
C5
 OCH2COOH at C4
 C2 and C6 replaced
by keto O
 5-member ring joint
at C1 an C3, with
attached a prenyl and
CH2CH2CHC(CH3)2
 prenyl at C3 and C5
 OCO-pyridine atC4
 C2 and C6 replaced
by keto O
 5-member ring joint
at C1 an C3, with
attached a prenyl and
CH2CH2CHC(CH3)2
 prenyl at C3 and C5
 OCH3 at C4
 C2 and C6 replaced
by keto O
 5-member ring joint
at C1 an C3, with
attached a prenyl and
CH2CH2CHC(CH3)2
 prenyl at C5
 furan ring fused at
C3C4 with
SIRT2 [28]
CT [28]
PI [28]
AM [28]
IC50 : 28  0.2g/ml [28]
IC50 : 1.3  0.2g/ml [28]
IC50 : 1.15  0.1g/ml [28]
2.1g/ml [28]
 aristoforin [28]
SIRT1 [28]
SIRT2 [28]
CT [28]
PI [28]
IC50 : 7  0.2g/ml [28]
IC50 : 21  1g/ml [28]
IC50 : 4.9  0.1g/ml [28]
IC50 : 0.59  0.09g/ml [28]
 hyperforin nicotinate
[29]
AM [29]
IC50 : 4.8g/ml [29]
 7-OMe hyperforin
[29]
AM [29]
IC50 : 7.8g/ml [29]
 furohyperforin [29]
AM [29]
IC50 : 1.7g/ml [29]
 hyperforin hemiacetal
[29]
AM [29]
IC50 : 2.0g/ml [29]
 comp-433 [3]
AB [3]
C(CH3)2OH ortho to O
COCH(CH3)2
COCH(CH3)2
COCH(CH3)2
 C2 and C6 replaced
by keto O
 5-member ring joint
at C1 an C3, with
attached a prenyl and
CH2CH2CHC(CH3)2
 ether O bridging C2
and C5
 6-member ether ring
fused at C4C5,
with a 5-member
ring fused
 keto O at C2
 two CH3 at C5
compounds with one acylphloroglucinol moiety and one non-acylated phloroglucinol moiety
COCH(CH3)2
non-acylated
phloroglucinol
derivative f
 prenyl at C5
 CH2COCH(CH3)2
and prenyl at C1,
keto O at C4 and
CH3 at C5
 comp-435 [3]
AB [3]
 guttiferone G [28]
SIRT1 [28]
SIRT2 [28]
CT [28]
IC50 : 9  0.2g/ml [28]
IC50 : 22  0.5g/ml [28]
IC50 : 5.3  0.2g/ml [28]
PI [28]
IC50 : 0.6  0.1g/ml [28]
notes:
a
Substituents different from acyl chains are denoted by R if attached at C3 and by R if attached at C5. For conciseness sake,
the symbol  is used to identify the formula of R; the formula is reported only for R  H. Similarly, the formula of R is
reported only for R  H.
b
For conciseness sake, acronyms are utilized to denote biological activities and numbers are utilized to identify bacterial
strains.
The following acronyms are utilized for the different types of biological activity:
AB
antibacterial
AD
antidepressant
AF
antifungal
AFE
antifeedant
AH
anthelmintic
AI
anti-inflammatory
AL
antileishmanial
AM
antimalarial
AO
antioxidant
AR
antiradical
ARI
aldose reductase inhibitory activity
AT
antitumor
ATB
antituberculosis
AV
antiviral
CT
cytotoxic
(DPPH)RS
DPPH Radical Scavenging activity
EBVI
Epstein-Barr Virus inhibitory activity
FASI
mammalian Fatty Acid Synthesis FAS inhibitory activity
GI
germination inhibitory activity
H-RT+P-I
HIV-1 Reverse Transcriptase (RT) and protease inhibitory
IT
ichthyotoxic
LPOI
Lipid Peroxidation (LPO) inhibitory activity
PI
cell proliferation inhibitors
(SO)RS
Superoxide (O-2 ) Radical Scavenging activity
The following numbers are utilized to different bacteria strains and are written after the acronym denoting the type of
biological activity
bacteria strain
number
Bacillus subtilis [16, 24]
1
Staphylococcus aureus [10, 16, 24, 26]
2
Escherichia coli [10, 16, 26, 27]
3
Streptococcus pyogenes NCTC 8198 [10]
4
Streptococcus sobrinus 6715 [10]
5
Streptococcus mutans Ingbritt [10]
6
Enterococcus faecalis (VRE) [27]
7
Bacillus cereus [16]
8
Pseudomonas aeruginosa ATCC 9027 [10]
9
Klebsiella pneumoniae[16]
10
Pseudomonas aeruginosa [16, 20, 26, 27]
11
The following roman numbers are utilized to different fungal strains and appear in brackets ahead of the acronyms given to
the type of antifungal biological activity.
fungal strains
number
Candida albicans [1,3, 10, 16, 26, 27]
I
Botrytis cinera [1]
II
Phomopsis perniciosa [1]
III
T. mentagrophytes [10, 27]
IV
Cryptococcus neoformans [1, 27]
V
Trichophyton [3, 10]
VI
Fusarium[3]
VII
The following symbols are used to represent the most common cytotoxic activity
tumor strains
symbol
cytotoxic against Vero cells [1]
+
cytotoxic against LLC-PK1 cells [1]
++
c
The following acronyms are utilized for the determination methods
AD
agar dilution method
(TLC)BA
TLC bioautographic assay method
CTA
cellular test assay method
DD
doubling dilution method
DDA
disc-diffusion assays
DP
paper disk method
FTC
ferric thiocyanate method
MA
modulation assay method
MAA
Malstat assay method
NBTR
nitroblue tetrazolium (NBT) reduction method
TBA
thiobarbituric acid method
SD
serial dilutions method
TD
tube dilution method
ABA
Alamar blue assay method
CSB
Cress Seed Bioassay
INT
INT microplate method
d
For structures with two phloroglucinol moieties, the R of each moiety are indicated separately in the first column, and the
information in columns 2 and 3 refer to the moiety with the specified R (same row as the specified moiety).
To maintain consistency with the numbering of monomeric structures, for each monomer in dimeric and trimeric
acylphloroglucinols, the C atom to which the acyl chain is attached is numbered as 1, and the C atom of the benzene ring to
which the methylene bridge is attached is numbered as 3.
e
In the first column, the R of the moiety in fully enol form is indicated first.
f
Included here because of similarity of its activity with the activity of acylphloroglucinols like hyperforin and aristoforin
Reference numbering utilized in this table
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
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