Bioscience, Biotechnology, and Biochemistry

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Antimicrobial constituents of peel and seeds of

camu-camu (Myrciaria dubia)

Tai Kaneshima, Takao Myoda, Kazuki Toeda, Takane Fujimori & Makoto
Nishizawa

To cite this article: Tai Kaneshima, Takao Myoda, Kazuki Toeda, Takane Fujimori &
Makoto Nishizawa (2017) Antimicrobial constituents of peel and seeds of camu-camu
(Myrciaria�dubia), Bioscience, Biotechnology, and Biochemistry, 81:8, 1461-1465, DOI:
10.1080/09168451.2017.1320517

To link to this article: https://doi.org/10.1080/09168451.2017.1320517

Published online: 05 May 2017.

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Bioscience, Biotechnology, and Biochemistry, 2017
Vol. 81, No. 8, 1461–1465

Antimicrobial constituents of peel and seeds of camu-camu (Myrciaria dubia)

Tai Kaneshima, Takao Myoda*, Kazuki Toeda, Takane Fujimori and Makoto Nishizawa
Department of Food and Cosmetic Science, Tokyo University of Agriculture, Abashiri, Japan

Received May 16, 2016; accepted April 9, 2017

https://doi.org/10.1080/09168451.2017.1320517

Various antimicrobial constituents of camu-camu
fruit were isolated. Acylphloroglucinol (compound 1)
and rhodomyrtone (compound 2) were isolated from
the peel of camu-camu (Myrciaria dubia) fruit, while
two other acylphloroglucinols (compounds 3 and 4)
were obtained from camu-camu seeds. The structures
of the isolated compounds were characterized by
spectrophotometric methods. Compounds 1 and 4
were confirmed to be new acylphloroglucinols with
different substituents at the C7 or C9 position of 2,
and were named myrciarone A and B, respectively.
Compound 3 was determined to be isomyrtucommu-
lone B. This is the first report of the isolation of 3
from a natural resource. The antimicrobial activities
of compounds 1, 3, and 4 were similar to those of 2,
and the minimum inhibitory concentrations were
either similar to or lower than that of kanamycin.
These results suggest that the peel and seeds of
camu-camu fruit could be utilized for therapeutic
applications.
Key words: Camu-camu; Myrciaria dubia;
acylphloroglucinol; antimicrobial activity
Camu-camu (Myrciaria dubia) is a bushy riverside
tree that belongs to the family Myrtaceae, and is found
in the upper Amazon rainforest. The fruits of the tree
are also called camu-camu, and are commonly culti-
vated and harvested in Peru. Camu-camu has attracted
attention because it contains large amounts of vitamin
C,1) and a number of studies have reported on its vari-
ous constituents, carotenoids,2,3) anthocyanins,4) and
other volatile compounds.5,6) Recently, many processed
foods derived from camu-camu, such as juice and vine-
gar, have become commercially available in advanced
countries, and the cultivation area of camu-camu has
expanded from Peru to neighboring counties, such as
Brazil, Venezuela, and Colombia.7) Concomitant with
the increase in the amount of camu-camu production,
the residue of juice production, peel and seeds, which
is often discarded as industrial waste, has also
increased. The residual peel and seeds amounts to
nearly 40% of the fresh fruit, yet they have not yet
been utilized for other potential applications. The
development of efficient uses for the residues may be
beneficial to the industry of camu-camu juice produc-
tion and cultivation of camu-camu fruit. To this end,
we have investigated the constituents of camu-camu
peel and seeds, and revealed strong antioxidant activi-
ties associated with the polar portions of the extracts of
peel and seeds, as well as antimicrobial activities asso-
ciated with the non-polar portions.8)
Our previous studies investigating the antioxidant
activities of camu-camu resulted in the isolation of
C-glycosidic ellagitannins, such as castalagin and ves-
calagin, and their confirmation as the constituents
responsible for the antioxidant activities.9,10) We also
previously reported the isolation of rhodomyrtone, an
acylphloroglucinol, as a potent antimicrobial constituent
in the camu-camu peel.11) Our successive investigation
demonstrated the presence of related antimicrobial
acylphloroglucinols, including two new compounds, in
the peel and seeds of camu-camu. Herein, we report
the structures and antimicrobial activities of these pre-
viously isolated compounds.
Materials and methods
Materials and chemicals. Dried powder of the peel
and seeds obtained from camu-camu juice production
was obtained from Empresa Agroindustrial del Peru
S.A. (Peru). These samples were used after drying at
room temperature.
Kanamycin and aureobasidin were purchased from
Wako Pure Chemicals (Osaka, Japan) and Takara Bio
Inc. (Ohtsu, Japan), respectively. All other chemicals
were purchased from Kanto Chemicals (Tokyo, Japan).
Nuclear magnetic resonance (NMR) spectra were mea-
sured with an Agilent MR-400 NMR spectrometer in
deuterated chloroform (CDCl3). Chemical shifts were
determined by using tetramethylsilane (TMS) as the

*Corresponding author. Email: t1myouda@bioindustry.nodai.ac.jp

Abbreviations: NMR, nuclear magnetic resonance; TMS, tetramethylsilane; ESI, electrospray ionization; HPLC, high performance liquid chro-
matography; TLC, thin layer chromatography; MIC, minimum inhibitory concentration; MHB, Mueller-Hinton broth; DMSO, dimethylsulfoxide;
COSY, correlation spectroscopy; HSQC, hetero-nuclear single quantum coherence; HMBC, hetero-nuclear multiple-bond connectivity; NOESY,
NOE correlated spectroscopy; MRSA, methicillin resistant Staphylococcus aureus.

© 2017 Japan Society for Bioscience, Biotechnology, and Agrochemistry

1462 T. Kaneshima et al.
internal reference. Mass spectra were measured with an
Agilent 6540 QTOF spectrometer in positive electro-
spray ionization (ESI) mode. Optical rotations were
measured on a JASCO P-2100 polarimeter. UV-vis
spectra were measured with a Shimadzu UV-1700 spec-
trophotometer. Gradient HPLC chromatograms were
obtained with a JASCO LC-2000 Plus HPLC system
equipped with a MD-2010 Plus photodiode array detec-
tor and an Atlantis T3 column (3 μm, 4.6 mm i.d. ×
150 mm, Waters, Milford, MA, USA). The mobile
phase for gradient elution was as follows: solvent A
was 5% acetonitrile containing 0.2% formic acid, and
solvent B was 100% acetonitrile. The gradient condi-
tion was as follows: 0 min, 0% B; 5 min, 60% B;
15 min, 70% B; 25 min, 80% B; 35–40 min, 100% B;
41 min, 0% B. Preparative HPLC was performed with
a Shimadzu LC-8A pump, a Hitachi L-4200 detector
with a prep cell (2 mm) and an Inertsil ODS-4 column
(20 mm i.d. × 250 mm, GL Sciences, Tokyo, Japan).
The mobile phase was composed of 75% acetonitrile
containing 0.1% of acetic acid.
Extraction and isolation. Dried peel of camu-camu
(431.4 g) was extracted with n-hexane (1000 mL) three
times at room temperature. The combined extract was
concentrated under reduced pressure at 40 °C to dry-
ness to obtain n-hexane extract (31.4 g). The n-hexane
extract (500 mg) was dissolved in n-hexane (10 mL)
and was subjected to countercurrent partition with 90%
acetonitrile (acetonitrile:water = 9:1 v/v, 10 mL) three
times, and the resultant n-hexane layer (187.1 mg) and
90% acetonitrile layer (231.4 mg) were obtained. The
90% acetonitrile layer was dissolved in 75% acetoni-
trile, and the soluble portions were subjected to prepar-
ative HPLC, which yielded two fractions (Fr. A and
B). Fr. A was pure (compound 1), but Fr. B was shown
to be a mixture, and was further fractionated by prepar-
ative TLC (PLC silica gel 60 F254, 2 mm, MERCK,
developed with ethyl acetate : benzene : acetic
acid = 1:9:0.1) to yield compound 2. From 1.0 g of
crude peel extract, 2.0 mg of compound 1 and 5.0 mg
of compound 2 were obtained.
Dried camu-camu seeds (400.2 g) were also
extracted using the procedure described above to
obtain n-hexane extract (9.9 g). The n-hexane extract
was purified by preparative HPLC to yield compounds
3 and 4. From 1.0 g of crude seed extract, 1.6 mg of
compound 3 and 1.2 mg of compound 4 were
obtained.
Compound 1 (6,8-dihydroxy-2,2,4,4-tetramethyl-7-
(2-methyl-1-oxopropyl)-9-(2-methylpropyl)-4,9-dihydro-
1H-xanthene-1,3(2H)-dione, myrciarone A). A light
yellow amorphous powder. λmax 299 nm, ½a18
D + 7.5°
(c = 0.24, CHCl3), HR-MS; m/z 429.2282 [M + H]+
(calcd. for C25H33O6, 429.2268). NMR spectrum see
Table 1. H-H correlations in COSY: H9-H1′′, H2′-2′
Me, and H2′′-2′′Me. C-H long-range correlations in
HMBC: C1-2Me, C2-2Me, C3-2Me and 4Me, C4-4Me,
C4a-4Me, C6-H5, C7-H5, C8a-H5 and H9, C9-H1′′
and H2′′, C9a-H9, C10a-H5, C2Me-2Me, C4Me-4Me,
C1′-H2′ and 2′Me, C2′-2′Me, C2′Me-H2′ and 2′Me,
C1′′-H9 and 2′′Me, C2′′-H9 and 2′′Me, C2′′Me-2′′Me.
Compound 2 (rhodomyrtone). See reference11).
NMR spectrum see Table 1.
Compound 3 (isomyrtucommulone B). A light yel-
low amorphous powder. λmax 301 nm, ½a18D + 48.6°
(c = 0.07, CHCl3), HR-MS; m/z 415.2119 [M + H]+
(calcd. for C24H31O6, 415.2112). NMR spectrum see
Table 1.
Compound 4 (6,8-dihydroxy-2,2,4,4-tetramethyl-7-
(3-methyl-1-oxobutyl)-9-(2-methylpropyl)-4,9-dihydro-
1H-xanthene-1,3(2H)-dione, myrciarone B). A light
yellow amorphous powder. λmax 301 nm, ½a18 D + 67.5°
(c = 0.04, CHCl3), HR-MS; m/z 429.2270 [M + H]+
(calcd. for C25H33O6, 429.2268). NMR spectrum see
Table 1. H-H correlations in COSY: H9-H1′′, H2′-2′
Me, H3′-3′Me, and H1′′-1′′Me. C-H long-range correla-
tions in HMBC: C1-2Me, C2-2Me, C3-2Me and 4Me,
C4-4Me, C4a-H9 and 4Me, C6-H5, C7-H5, C8a-H5
and H9, C9-1′′Me, C9a-H9, C10a-H5 and H9, C2Me-
2Me, C4Me-4Me, C1′-H2′, H3′ and 2′Me, C2′-H3′, 2′
Me and 3′Me, C3′-H2′, 2′Me and 3′Me, C2′Me-H2′
and H3′, C3′Me-H2′ and H3′, C1′′-H9 and 1′′Me, and
C1′′Me-H9 and 1′′Me.
Antimicrobial activities. Micro-well dilution broth
susceptibility assays were used to determine the mini-
mum inhibitory concentrations (MICs). Test solutions
of the isolated compounds and fractions were prepared
in DMSO (1.0 mg/mL). Aqueous solutions of kanamy-
cin and aureobasidin (1.0 mg/mL) were prepared as
positive controls.
Antimicrobial activities were tested against follow-
ing microorganism; Bacillus subtilis JCM 1465, Strep-
tococcus mutans JCM 5175, Escherichia coli O157
JCM 18426, Pseudomonas aeruginosa JCM 5962, and
Candida albicans JCM 2085 were purchased from
Riken BioResource Center (Ibaraki, Japan), Bacillus
cereus NBRC 3457, Micrococcus luteus NBRC
12708, Staphylococcus epidermidis NBRC 100911,
and Salmonella typhimurium NBRC 12529 were
obtained from Biological Resource Center (National
Institute of Technology and Evaluation, Chiba, Japan),
Staphylococcus aureus NRIC 1135 and Saccharomyces
cerevisiae NRIC 1410 were provided by Nodai
Research Center (Tokyo University of Agriculture,
Japan). Mueller-Hinton broth medium (MHB, 23.1 g/
L, 90 μL) and the test solutions (10 μL) were added
to the first well of a 96-well plate. Aliquots (50 μL)
of the mixtures in the first column were transferred to
the second column, and were diluted with 50 μL of
MHB (21.0 g/L). The procedure was repeated to the
11th column. Inoculum (5 μL) of each microorganism
prepared having an OD of 0.132–0.257 at 600 nm
was added, and incubated at 25, 30, or 37 °C for
18 h. Bacterial growth was megascopically deter-
mined, and MIC values were determined.
 Antimicrobial Constituents of Camu-camu Peel and Seeds 1463
Table 1. NMR spectra data of compounds 1–4.

Compound 1 Compound 211) Compound 3 Compound 4

δC δH (mult., JHZ) δC δH (mult., JHZ) δC δH (mult., JHZ) δC δH (mult., JHZ)

1 197.5 197.5 197.7 196.7
2 56.1 56.1 56.1 56.1
3 212.1 212.1 212.2 212.2
4 47.1 47.1 47.3 47.3
4a 166.8 166.8 167.8 167.8
5 94.5 6.07 (1H, s) 94.8 6.08 (1H, s) 94.9 6.10 (1H, s) 95.0 6.10 (1H, s)
6 158.0 158.3 158.6 158.5
7 106.7 107.5 107.9 107.4
8 158.0 162.5 162.1 162.2
8a 106.7 106.7 104.9 105.0
9 25.2 4.24 (1H, t, 5.9) 25.1 4.25 (1H, t, 5.9) 31.9 4.29 (1H, d, 3.5) 32.0 4.29 (1H, d, 3.5)
9a 114.2 114.2 111.8 111.8
10a 155.6 155.6 156.4 156.4
1′ 210.9 206.3 211.0 210.9
2′ 39.8 3.88 (1H, m, 6.6) 53.2 2.95 (1H, dd, 15.8, 6.6) 38.9 3.89 (1H, m, 6.6) 46.4 3.75 (1H, m, 6.6)
3.01 (1H, dd, 15.8, 6.6)
3′ 25.1 2.28 (1H, m, 6.7) 26.8 1.42 (1H, obscure)
1.85 (1H, m, 7.3)
1′′ 45.9 1.44 45.9 1.42 34.5 1.98 (1H, m, 3.5) 34.5 1.99 (1H, m, 3.5)
1.41 (2H, obscure) 1.45 (2H, dd, obscure)
2′′ 25.1 1.46 25.1 1.42
1.42 (1H, obscure) 1.46 (1H, dd, obscure)
2Me 24.2 1.36 (3H, s) 24.1 1.37 (3H, s) 23.9 1.36 (3H, s) 23.9 1.36 (3H, s)
24.5 1.39 (3H, s) 24.5 1.40 (3H, s) 25.1 1.42 (3H, s) 24.6 1.42 (3H, s)
4Me 24.6 1.42 (3H, s) 24.6 1.43 (3H, s) 24.6 1.41 (3H, s) 24.6 1.41 (3H, s)
24.7 1.54 (3H, s) 24.7 1.55 (3H, s) 25.1 1.58 (3H, s) 25.1 1.58 (3H, s)
2′Me 19.1 1.20 (3H, d, 6.6) 19.1 1.21 (3H, d, 6.6) 16.4 1.19 (3H, d, 6.6)
19.2 1.19 (3H, d, 6.6) 19.2 1.20 (3H, d, 6.6)
3′Me 22.8 0.98 (6H, d, 6.7) 11.9 0.92 (3H, t, 7.3)
1′′Me 19.2 0.78 (6H, t, 7.2) 18.8 0.78 (3H, d, 7.0)
19.3 0.78 (3H, d, 7.0)
2′′Me 23.1 0.83 (3H, d, 6.0) 23.1 0.83 (3H, d, 6.0)
23.5 0.87 (3H, d, 6.0) 23.5 0.87 (3H, d, 6.0)

Results and discussion Compound 1 was obtained as a light yellow amor-

The n-hexane extracts of the peel and seeds of
camu-camu exhibited strong antimicrobial activities
against Gram-positive bacteria,8) and both of the
n-hexane and 90% acetonitrile layers obtained by coun-
tercurrent partition of the n-hexane extracts exhibited
strong activities.9) As shown in Table 2, the compounds
in the n-hexane extract that exhibited antimicrobial
activities were divided between the n-hexane layer and
the 90% acetonitrile layers. The activities of those in
the n-hexane layers were slightly higher than those of
the 90% acetonitrile layers, but the presence of large
amounts of lipids in the n-hexane layers made it
difficult to isolate the active compounds. Therefore, we
first attempted to isolate active compounds in the 90%
acetonitrile layers.
Two compounds (1 and 2) were isolated from the
90% acetonitrile layer of peel, and two (3 and 4) from
the seeds. Compound 2 was characterized as an
acylphloroglucinol isolated from Rhodomyrtus
tomentosa,12) as previously reported. Compound 3
was identified as an acylphloroglucinol, isomyrtucom-
mulone B. Appendino et al. reported that isomyrtucom-
mulone B is an isomer of myrtucommulone B, and was
a thermal degradation product of a trimeric
acylphloroglucinol, myrtucommulone A.13) This is the
first report of the isolation of isomyrtucommulone B
(3) from a natural resource.
phous powder, and its HR-MS indicated a molecular
formula of C25H32O6. The molecular weight of 1 was
14 mass units lower than that of 2. The 13C-NMR
spectrum of 1 suggested the presence of three carbonyl
carbons, eight methyl carbons, two quaternary carbons,
and six olefinic or aromatic carbons, along with a
methylene and two methine carbons. The COSY spec-
trum indicated the presence of one 2-methylpropyl
group and one 1-methylethyl group, instead of two 2-
methylpropyl groups as in 2. The HSQC and HMBC
spectra indicated that the 2-methylpropyl group was
attached to a methine carbon and the 1-methylethyl
group to a carbonyl carbon. These data suggested that
1 was an analog of 2, and that the 3-methyl-1-oxobutyl
group at the C7 position of 2 was replaced by a
2-methyl-1-oxopropyl group. The position of the
2-methyl-1-oxopropyl group was confirmed at C7
because a cross peak was observed between the methyl
protons at the C4 position and the aromatic proton at
the C5 position in the NOESY spectrum of 1. Thus,
the structure of 1 was identified as 6,8-dihydroxy-
2,2,4,4-tetramethyl-7-(2-methyl-1-oxopropyl)-9-(2-methyl
propyl)-4,9-dihydro-1H-xanthene-1,3(2H)-dione. As the
[α]D value of 1 was positive, as is the case for 2, the
orientation of the 2-methylpropyl group at the C9 posi-
tion was assumed to be the same as that of 2. Taken
together, compound 1 is a new compound and was
appropriately named myrciarone A.
1464 T. Kaneshima et al.
Compound 4 was obtained as a light yellow amor- a 3-methyl-1-oxobutyl group as in 2, respectively. The
phous powder, and its HR-MS indicated a molecular presence of these groups was confirmed by 2D-NMR
formula of C25H32O6. The molecular weight of 4 was experiments. The NOESY spectrum of 4 also con-
14 mass units lower than that of compound 2. The 1H- firmed that the 2-methyl-1-oxobutyl group was located
and 13C-NMR spectra of 4 were similar to those of 2, at the C7 position. The orientation of the 1-methylethyl
however, the 1H-NMR spectrum of 4 indicated that the group and the stereochemistry of the 2-methyl-1-oxobu-
presence of a 2-methylethyl group and a 2-methyl-1- tyl group have not yet been dissolved, and further stud-
oxobutyl group, instead of a 2-methylpropyl group and ies are needed. However, compound 4 is a new
compound and was appropriately named myrciarone B.
The antimicrobial activities of acylphloroglucinols
(1–4) isolated from the n-hexane extracts of the peel
and seeds of camu-camu fruit against six Gram-positive
9a
bacteria, three Gram-negative bacteria, and two yeast
1 9 8a
7 were tested, and the MIC values are shown in Table 2.
3
4a 10a
The activities of compounds 1, 3 and 4 were nearly the
5
same as those of 2. These acylphloroglucinols and all
R1 R2 fractions showed antimicrobial activities against Gram-
positive bacteria, but no activities against Gram-nega-
Myrciarone A (1)
tive bacteria and fungi. These data are consistent with
1′ 1′′ the results of Limusuwan et al.14) who reported that
rhodomyrtone (2) exhibited potent antimicrobial activi-
ties against Gram-positive bacteria, such as Bacillus,
Rhodomyrtone (2) Micrococcus, Staphylococcus, and Streptococcus spp.,
while no activities were observed against Gram-
negative bacteria and fungi. The MIC values against
the Gram-positive bacteria listed in Table 2 are similar
Isomyrtucommulone B (3) to or lower than those of kanamycin used as a positive
control, and were comparable to those reported by
Limusuwan et al.14) As kanamycin is active against
both Gram-positive and Gram-negative bacteria, the
Myrciarone B (4) mechanism of antimicrobial action of these
acylphloroglucinols must therefore be different from
that of kanamycin. Sianglum et al. reported that
Fig. 1. Structure of compounds 1–4.
rhodomyrtone exhibited potent antimicrobial activity

Table 2. Antibacterial activities of n-hexane extracts, n-hexane layers, 90% acetonitrile layers, and acylphloroglucinols (1–4).

MIC (μg/ml)

Peel Seeds

90% 90%
n-Hexane n-Hexane Acetonitrile n-Hexane n-Hexane Acetonitorile Positive
extract11) layer 11) layer11) 1 2 11)
extract layer layer 3 4 control
Bacillus subtilis 12.50 6.25 12.50 1.56 0.78 12.50 25.00 25.00 1.56 1.56 1.56a
Bacillus cereus 6.25 6.25 6.25 1.56 0.78 3.13 1.56 3.13 0.78 1.56 6.25a
Micrococcus 6.25 6.25 12.50 1.56 0.78 25.00 – – – – 6.25a
luteus
Staphylococcus 12.50 6.25 12.50 1.56 0.78 6.25 6.25 6.25 1.56 1.56 1.56a
aureus
Staphylococcus 6.25 6.25 12.50 3.13 0.78 12.50 12.50 6.25 6.25 3.13 1.56a
epidermidis
Streptococcus 25.00 –* – 3.13 1.56 100.00 25.00 100.00 3.13 1.56 1.56a
mutans
Escherichia coli >100 >100 >100 – >100 >100 – – – – 1.56a
O157
Pseudomonas >100 >100 >100 – >100 >100 – – – – 1.56a
aeruginosa
Salmonella >100 >100 >100 – >100 >100 – – – – 6.25a
typhimurium
Saccharomyces >100 >100 >100 – >100 >100 – – – – 3.13b
cerevisiae
Candida >100 >100 >100 – >100 >100 – – – – 1.56b
albicans
a
Kanamycin.
b
Aureobasidin.
*Not tested.
 Antimicrobial Constituents of Camu-camu Peel and Seeds
against methicillin resistant S. aureus (MRSA), and
their proteome analysis indicated that a subinhibitory
concentration of rhodomyrtone affected the cellular pro-
tein expression of MRSA, such as cell wall biosynthe-
sis and cell division.15) Rhodomyrtone has also been
reported to show antimicrobial activity by reducing cell
wall strength caused by inhibition of staphyloxanthin
(yellow pigment) biosynthesis by S. aureus,16) and the
inhibition of yellow pigment biosynthesis may lead to
decreases in the resistant strain of S. aureus. Further
investigations will reveal the mechanism of antimicro-
bial activity of rhodomyrtone and related
acylphloroglucinols, and the peel and seeds of camu-
camu will be an important resource of rhodomyrtone.
Moreover, the n-hexane layer exhibited more potent
antimicrobial activity than the 90% acetonitrile layer, as
shown in Table 2, and the chromatograms of the
n-hexane and 90% acetonitrile layers suggested the
presence of other antimicrobial constituents in the peel
and seeds of camu-camu fruit. Further investigations
are needed to better elucidate the antimicrobial charac-
teristics of the peel and seeds of camu-camu fruit.
Author contributions
TK designed and performed experiments, analyzed
data and wrote the paper. TM designed the study and
wrote paper. KT developed analytical methods. TF ana-
lyzed the data. MN designed study and wrote the first
draft of the manuscript. All authors discussed the
results and implications and commented on the manu-
script at all stages.
Acknowledgments
The authors wish to express their gratitude to
Empresa Agroindustrial del Peru S.A. for the donation
of camu-camu samples, and Agilent technology Co.,
Ltd. for mass spectrometry measurements.
Disclosure statement
No potential conflict of interest was reported by the authors.
1465
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