1. Journal of Ethnopharmacology 97 (2005) 293–299
Antibacterial activity of crude extracts from Mexican medicinal
plants and purified coumarins and xanthones
Kakuko Yasunakaa,∗, Fumiko Abeb, Ariaki Nagayamaa, Hikaru Okabeb,
Lucio Lozada-P´erezc, Edith L´opez-Villafrancod, Elizabeth Estrada Mu˜nize,
Abigail Aguilarf, Ricardo Reyes-Chilpae
a Department of Microbiology and Immunology, School of Medicine, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
b Faculty of Pharmaceutical Sciences, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan
c Department of Biology, Faculty of Science, National University of Mexico, Ciudad Universitaria, 04510 Mexico, Mexico
d Herbarium IZTA, National University of Mexico, Campus Iztacala, Tlalnepantla, Estado de Mexico 54090, Mexico
e Institute of Chemistry, National University of Mexico, Ciudad Universitaria, 04510 Mexico, Mexico
f Herbarium IMSSM, Mexican Institute for Social Security, National Medical Center S. XXI, Cuahtemoc 330, 06725 Mexico, D.F. Mexico
Received 30 November 2003; received in revised form 1 November 2004; accepted 15 November 2004
Available online 12 January 2005
Abstract
Thirty-two extracts from 22 Mexican medicinal plants of 15 different families were assayed to determine their antibacterial activity against
Escherichia coli and Staphylococcus aureus. Seventeen plants showed antibacterial activity, while five plants showed no activity against
both bacteria. All of the extracts showed higher activity against Staphylococcus aureus (methicillin-sensitive and methicillin-resistant) than
against Escherichia coli, except one. Among the plants examined, Bursera simaruba (L.) Sarg. (Burseraceae), Haematoxylum brasiletto
H. Karst. (Fabaceae), Calophyllum brasiliense Cambess. (Clusiaceae), and Mammea americana L. (Clusiaceae) were highly active against
Staphylococcus aureus. Coumarins (mammea A/BA and mammea A/AA) and xanthones, namely jacareubin and 1,3,5,6-tetrahydroxy-2-(3,3-
dimethylallyl) xanthone, were isolated as the principle compounds from the last two plants.
© 2004 Elsevier Ireland Ltd. All rights reserved.
Keywords: Antibacterial activity; Mexican medicinal plants; Coumarins; Xanthones; Escherichia coli; Staphylococcus aureus
1. Introduction
Many plants or their components are used as folk
medicines in many parts of the world to cure various in-fectious
diseases such as urinary tract infections, bronchi-tis,
diarrhea, cutaneous abscesses and parasitic diseases. On
the other hand, antibiotics have dramatically reduced the
incidence of many infectious diseases. Nevertheless, many
problems remain unresolved due to occasional serious side
effects and the appearance of antibiotic-resistant mutant bac-teria.
Methicillin-resistant Staphylococcus aureus (MRSA),
for example, is one of the main species of bacteria that cause
∗ Corresponding author. Tel.: +81 92 801 1011; fax: +81 92 801 9390.
E-mail address: kakuko@fukuoka-u.ac.jp (K. Yasunaka).
nosocomial infections in hospitals worldwide (Ichiyama et
al., 1991; Yasunaka and Kono, 1999; Takeda et al., 2000).
In recent years, the emergence of MRSA has become a seri-ous
problem because of its resistance against numerous an-tibiotics.
Although many studies on antimicrobial activity of
medicinal plants have been made over the past 30 years (Khan
et al., 1980; Samy et al., 1998; Essawi and Srour, 2000), a
large number of plants still have not been studied. In this con-text,
we examined the antibacterial properties of medicinal
plants from Mexico.
It has been estimated that nearly 3103 higher plant species
are used in Mexican traditional medicine, of which nearly
one-third (1024) are used to treat diseases of the diges-tive
tract (Argueta-Villamar et al., 1994). The survey by the
IMSSM herbarium also indicates that Mexican medicinal
0378-8741/$ – see front matter © 2004 Elsevier Ireland Ltd. All rights reserved.
doi:10.1016/j.jep.2004.11.014

2. 294 K. Yasunaka et al. / Journal of Ethnopharmacology 97 (2005) 293–299
plants are used primarily to treat digestive (473 species),
respiratory (247 species) and skin (277 species) diseases
(Aguilar et al., 1994).
In the present paper, we describe the results of the study
on antibacterial activity of crude extracts of 22 Mexican
medicinal plants against Gram-negative Escherichia coli and
Gram-positive Staphylococcus aureus. These plants are used
in Mexican traditional medicine for the treatment of diseases
presumably caused by bacteria.We also examined the effects
of pure compounds (two coumarins, three xanthones, and a
triterpene) isolated from the active plants.
2. Materials and methods
2.1. Plant materials
Plant materials were collected during the period between
2000 and 2003 in Cuetzal´an del Progreso in the State of
Puebla, and in several localities of the State ofVeracruz. Calo-phyllum
brasiliense Cambess. (Clusiaceae) was collected in
Santa Marta and Los Tuxtlas of the State of Veracruz. Plant
materials were also purchased at “Sonora Medicinal Plant
Market” in Mexico City, or from surplus herbarium spec-imens.
Taxonomic identification was performed and con-firmed
by three of us (A. Aguilar, E. L´opez-Villafranco,
and L. Lozada-P´erez) based on voucher specimens that had
been deposited in the IMSSM herbarium of the Mexican In-stitute
for Social Security, and IZTA and MEXU herbaria
of the National University of Mexico. The ethnobotanical
literature of the States of Puebla and Veracruz in particu-lar
(L´opez-Villafranco, 1988; Mart´ınez-Alfaro et al., 1995;
Cano-Asseleith, 1997; Mendoza-M´arquez, 2000) and other
references on Mexican medicinal plants (Aguilar et al., 1994;
Soto-Nu˜nez and Sousa, 1995; Reyes-Chilpa et al., 2003) were
also consulted. Investigated plant materials and their appli-cations
in Mexican traditional medicine are listed in Table 1.
2.2. Preparation of plant extracts
Plant extracts were prepared according to the procedures
of Abe et al. (2002). Each dried plant part was extracted with
organic solvents (mainly with methanol). Fresh plant parts
and other solvents used in this study are shown in Table 2.
The solvent of each extractwas dried in vacuo and the residue
was then dissolved in dimethyl sulfoxide (DMSO) to produce
a final concentration of 100 mg/ml.
2.3. Preparation of coumarins, xanthones and a
triterpene
Coumarin mammea A/BA (1) and triterpene friedelin (6)
were extracted from the leaves of Calophyllum brasiliense,
collected in Santa Marta of the State of Veracruz (Reyes-
Table 1
Plants examined and their ethnomedical applicationsa
Family Scientific name Local name Ethnomedical applicationb
Annonaceae Annona cherimola Mill. Chirimoya Diarrhea, fever, anthelmintic, cough, emetic
Annona muricata L. Guan´abana Diarrhea, dysentery, leprae
Aristolochiaceae Aristolochia taliscana Hook. et Arn. Guaco Cutaneous disease
Asteraceae Piqueria trinervia Cav. Hierba de San Nicol´as Dysentery, fever
Bixaceae Bixa orellana L. Achiote Dysentery, measles, mouth pimples
Burseraceae Bursera simaruba (L.) Sarg. Palo mulato Diarrhea, fever, gingivitis, cough, measles
Chenopodiaceae Chenopodium graveolens Willd. Epazote de zorrillo Diarrhea, amebiasis, stomach ache, cough
Chenopodium ambrosioides L. Epazote morado Diarrhea, stomach ache, cramps
Clusiaceae Calophyllum brasiliense Cambess. Bari Diarrhea, intestinal worms
Clusia salvinii Donn. Sm. Oreja de coyote Gonorrhea, kidney ache
Mammea americana L. Zapote Domingo Fever, cutaneous disease
Elaeocarpaceae Muntingia calabura L. P´uan, Capul´ın rojo Measles, mouth pimples, stomach ache
Euphorbiaceae Croton draco Schltdl. Sangre de grado Dysentery, pimples, sores
Fabaceae Gliricidia sepium (Jacq.) Kunth ex Walp. Cocuite Antipyretic, measles
Haematoxylum brasiletto H. Karst. Palo de Brasil Fever
Zornia thymifolia Kunth Hierba de la V´ıbora Fever
Malvaceae Malvaviscus arboreus Cav. Azocopacle, manzanita Dysentery, stomach ache, sores, cough
Piperaceae Piper amalago L. Cordoncillo Fever
Piper auritum Kunth Acuyo Fever, skin infections
Polypodiaceae Phlebodium aureum (L.) J. Sm. Lengua de ciervo Fever, kidney diseases, ulcer
Rubiaceae Hamelia patens Jacq. Balletilla Pimples, malaria, sores
Verbenaceae Aloysia triphylla Royle T´e cedr´on Diarrhea, stomach ache
a See Table 2 for voucher herbarium specimens.
b L´opez-Villafranco (1988), Aguilar et al. (1994); Mart´ınez-Alfaro et al. (1995), Soto-Nu˜nez and Sousa (1995), Cano-Asseleith (1997), Mendoza-M´arquez,
(2000), and Reyes-Chilpa et al. (2003).

3. K. Yasunaka et al. / Journal of Ethnopharmacology 97 (2005) 293–299 295
Table 2
Plants examined and their antibacterial activities
Family Scientific name Herbarium and
register number
Parta (solvent)b MICc (g/ml)
Escherichia
coli C600
Staphylococcus
aureus 209P
Annonaceae Annona cherimola IZTA 879 Seeds (M) 1024 512
Annona muricata IMSSM 14760 Seeds, S (M) 1024 1024
Aristolochiaceae Aristolochia taliscana IMSSM 14718 R (M) 1024 1024
Asteraceae Piqueria trinervia IZTA 880 G (M) 1024 1024
Bixaceae Bixa orellana IMSSM 14759 Seeds (M) 1024 128
Burseraceae Bursera simaruba IZTA 868 L, T (M) fresh 1024 8
Bursera simaruba IZTA 868 S (M) fresh 1024 64
Chenopodiaceae Chenopodium graveolens IMSSM 14751 G (M) 512 256
Chenopodium ambrosioides IZTA 881 G (M) 1024 1024
Clusiaceae Calophyllum brasiliensed IMSSM 14439 L (H)e 512 32
Calophyllum brasiliensed IMSSM 14439 L (A)e 1024 2
Calophyllum brasiliensed IMSSM 14439 L (last M)e 1024 32
Calophyllum brasiliensef IMSSM 14425 L (M) 1024 16
Calophyllum brasiliensed IMSSM 14754 H (M+A) 128 8
Clusia salvinii IMSSM 14434 L (M+C) 1024 128
Mammea americana IMSSM 14420 P (H) 1024 8
Mammea americana IMSSM 14420 P (AcOEt insol) 1024 256
Mammea americana IMSSM 14420 P (AcOEt) 512 16
Mammea americana IMSSM 14420 P (A) 512 4
Mammea americana IMSSM 14420 Seeds (M) 256 2
Elaeocarpaceae Muntingia calabura IZTA 870 F (M) fresh 1024 256
Muntingia calabura IZTA 870 L (M) fresh 512 128
Euphorbiaceae Croton draco IZTA 871 L (M) fresh 1024 64
Fabaceae Gliricidia sepium IZTA 25146 L (M) 1024 64
Haematoxylum brasiletto IMSSM 14726 S (M) 128 16
Zornia thymifolia IMSSM 14725 L (M) 1024 128
Malvaceae Malvaviscus arboreus IMSSM 14726 L (M) fresh 1024 256
Piperaceae Piper amalago FECME 85564 L (M) fresh 512 1024
Piper auritum IZTA 872 L (M) 1024 1024
Polypodiaceae Phlebodium aureum IMSSM 14727 Whole (M) 1024 512
Rubiaceae Hamelia patens IZTA 28222 L, T (M) 1024 256
Verbenaceae Aloysia triphylla IMSSM 14754 L (M) fresh 1024 64
a F, fruits; G, ground parts; H, heartwoods; L, leaves; P, fruit peels; R, roots; S, stems; T, twigs; fresh, fresh plant parts.
b A, acetone; C, dichloromethane; AcOEt, ethyl acetate; H, hexane; M, methanol; insol, insoluble fraction.
c Minimum inhibitory concentration.
d Corrected in Santa Marta, State of Veracruz.
e Extracted with firstly hexane, secondly acetone, lastly methanol.
f Corrected in Los Tuxtlas, State of Veracruz.
Chilpa et al., 2004). Coumarin mammea A/AA (2) was ex-tracted
with hexane at room temperature from the fruit peels
(421 g) of Mammea americana L. (Clusiaceae). The extract
spontaneously yielded yellow crystals, which were recrystal-lized
from hexane/CH2Cl2 (6 g). Xanthones jacareubin (3),
1,3,5,6-tetrahydroxy-2-(3,3-dimethylallyl) xanthone (4) and
6-deoxyjacareubin (5) were extracted from the heartwood of
Calophyllum brasiliense (Reyes-Chilpa et al., 1997). In the
isolation process, each of these extracts was subjected to var-ious
chromatographies to yield pure product. The structural
determination of pure compounds was carried out using 1H
and 13C nuclear magnetic resonance, infrared and ultraviolet
spectroscopies, and mass spectrometry. For bioassay, each
pure compound was dissolved in DMSO to produce a final
concentration of 20 mg/ml.
2.4. Bacteria and media
Antibacterial evaluations were performed against Es-cherichia
coli K12 strain C600, methicillin-sensitive Staphy-lococcus
aureus (MSSA) strain FDA 209P and two
methicillin-resistant Staphylococcus aureus (MRSA) strains:
no. 3208 and no. 80401. These two MRSA strains were
clinically isolated in Fukuoka City, Japan, and clearly de-termined
to be MRSA (Yasunaka and Kono, 1999). Strain
no. 3208 did not produce any -lactamase but no. 80401

4. 296 K. Yasunaka et al. / Journal of Ethnopharmacology 97 (2005) 293–299
did produce -lactamase. All the bacterial strains were kept
at −80 ◦C until used. Brain heart infusion agar (BHI agar)
and Mueller–Hinton broth (MH broth) were purchased from
the Nippon Becton Dickinson Co., Tokyo, Japan. Oxacillin
was purchased from Sigma-Aldrich Co., Tokyo, Japan. -
Lactamase production was detected according to the manu-facturer’s
instructions using cefinase disks (the Nippon Bec-ton
Dickinson Co., Tokyo).
2.5. Antibacterial activity assay: evaluation of minimum
inhibitory concentration (MIC)
MIC evaluations were performed by the micro-dilution
method. MH broth was used as the dilution and incuba-tion
broth. Bacteria grown on BHI agar plates for 16 h were
suspended in MH broth. The bacterial cell numbers were
adjusted to approximately 3–6×106 cfu (colony forming
unit)/ml. Plant extracts (100 mg/ml of DMSO) or pure com-pounds
(20 mg/ml of DMSO) were subjected to serial two-fold
dilution. Each 80 l of the bacterial suspensions was
added to 20l of each serial two-fold dilution of the test ma-terial
in a 96-well dish plate and thenwas mixed. The bacteria
were incubated at 37 ◦C for 24 h, and growth or no-growth
was assessed by the naked eye, then MIC was determined.
DMSO solutions that did not contain any test material or
only contained oxacillin were used as controls. All assays
were performed three times for each plant extract against
Escherichia coli C600 and Staphylococcus aureus 209P, but
only one time against eachMRSAstrains. The assays for pure
compounds were performed three times against all these four
bacteria. MIC values were shown as a mean value of each
assay. An MIC value at ≤64g/ml was judged to show high
activity, while 128–512 and ≥1024g/ml were considered
to show moderate and no antibacterial activity, respectively.
3. Results
3.1. Antibacterial activity of plant extracts against
Escherichia coli and Staphylococcus aureus
To evaluate the antibacterial activity against Escherichia
coli C600 and Staphylococcus aureus 209P, the MIC of each
plant extract was assayed and the results shown in Table 2.
Nine extracts out of 32 showed moderate activity, while 23
extracts did not show any antibacterial activity against Es-cherichia
coli C600. On the other hand, many extracts ex-amined
were active against Staphylococcus aureus 209P (15
extracts, high; 11 extracts, moderate). Both acetone extract
from the leaves of Calophyllum brasiliense and methanol
extract from the seeds of Mammea americana showed
the highest antibacterial activity (MIC 2 g/ml) of all 32
extracts.
3.2. Anti-MRSA activity of plant extracts
MIC values of 15 extracts active against MSSA 209P
were further estimated against two MRSA strains (no. 3208
and no. 80401) and are shown in Table 3. All the extracts
examined showed nearly the same MIC values (1/2–2-fold
MIC) against these two MRSA strains. It is obvious that
antibacterial activity of these extracts is not influenced by
the existence of -lactamase in the bacteria, suggesting that
Table 3
Antibacterial activities of plant extracts
Plant MICa (g/ml)
Scientific name Part usedc (solvent)d MSSA 209Pb MRSA (no. 3208) MRSA (no. 80401)
Bixa orellana Seeds (M) 128 128 128
Bursera simaruba L, T (M) fresh 8 8 8
Bursera simaruba S (M) fresh 64 64 64
Calophyllum brasiliensee L (H)f 32 32 32
Calophyllum brasiliensee L (A)f 2 8 8
Calophyllum brasiliensee L (last M)f 32 32 32
Calophyllum brasilienseg L (M) 16 16 16
Calophyllum brasiliensee H (M+A) 8 16 8
Mammea americana P (H) 8 64 64
Mammea americana P (AcOEt) 16 8 16
Mammea americana P (A) 4 2 4
Mammea americana Seeds (M) 2 8 4
Croton draco L (M) fresh 64 128 64
Haematoxylum brasiletto S (M) 16 32 16
Aloysia triphylla L (M) fresh 64 64 64
a Minimum inhibitory concentration.
b MSSA, methicillin-sensitive Staphylococcus aureus; MRSA, methicillin-resistant Staphylococcus aureus.
c F, fruits; G, ground parts; H, heartwoods; L, leaves; P, fruit peels; R, roots; S, stems; T, twigs; fresh, fresh plant parts.
d A, acetone; C, dichloromethane; AcOEt, ethyl acetate; H, hexane; M, methanol; insol, insoluble fraction.
e Corrected in Santa Marta, State of Veracruz.
f Extracted with firstly hexane, secondly acetone, lastly methanol.
g Corrected in Los Tuxtlas, State of Veracruz.

5. K. Yasunaka et al. / Journal of Ethnopharmacology 97 (2005) 293–299 297
Fig. 1. Chemical structures of coumarins, xanthones, and triterpene: (1) mammea A/BA; (2) mammea A/AA; (3) jacareubin; (4) 1,3,5,6-tetrahydroxy-2-(3,3-
dimethylallyl) xanthone; (5) 6-deoxyjacareubin; (6) friedelin.
the antibacterial principles in them do not contain any -
lactam rings. From Tables 2 and 3 it was found that Bursera
simaruba (L.) Sarg. (Burseraceae), Haematoxylum brasiletto
H. Karst. (Fabaceae), Calophyllum brasiliense, and Mam-mea
americana were highly active against both MSSA and
MRSA.
3.3. Antibacterial activity of coumarins, xanthones and
a triterpene
To identify the principle compounds of Calophyllum
brasiliense and Mammea americana, we purified coumarins
1 and 2, xanthones 3–5 and triterpene 6 (Fig. 1) as described in
Table 4
Antibacterial activities of purified compounds
Compound Plant MICa (g/ml)
Scientific name Partb Escherichia
coli C600
MSSAc
209P
MRSA
(no. 3208)
MRSA
(no. 80401)
Mammea A/BA (1) Calophyllum brasiliense L 256 1 2 2
Mammea A/AA (2) Mammea americana P 256 8 8 8
Jacareubin (3) Calophyllum brasiliense H 128 4 4 4
1,3,5,6-Tetrahydroxy-2-(3,3-dimethylallyl)
Calophyllum brasiliense H 128 1 2 4
xanthone (4)
6-Deoxyjacareubin (5) Calophyllum brasiliense H 512 256 512 512
Friedelin (6) Calophyllum brasiliense L 512 512 512 512
Oxacillin 0.5 0.5 1024 512
a Minimum inhibitory concentration.
b F, fruits; G, ground parts; H, heartwoods; L, leaves; P, fruit peels; R, roots; S, stems; T, twigs; fresh, fresh plant parts.
c MSSA, methicillin-sensitive Staphylococcus aureus; MRSA, methicillin-resistant Staphylococcus aureus.

6. 298 K. Yasunaka et al. / Journal of Ethnopharmacology 97 (2005) 293–299
Section 2. MIC values of these pure compounds are shown in
Table 4. Compounds 1–4 are the compounds responsible for
the activity, since they showed higher activity against Staphy-lococcus
aureus than that of the original extract. Xanthone 5
and triterpene 6 showed no activity against Staphylococcus
aureus. Only xanthones 3 and 4 showed moderate activity
against Escherichia coli.
Various studies have previously shown the biological ac-tivities
of some coumarins and xanthones (Finnegan et al.,
1972; Sundaram et al., 1983; Iinuma et al., 1996; Reyes-
Chilpa et al., 1997; Ojala et al., 2000; Itoigawa et al., 2001;
Ito et al., 2002). However, this is the first report of antibacte-rial
activity of these six compounds against Escherichia coli
and Staphylococcus aureus (MSSA and MRSA). Calophyl-lum
brasiliense and Mammea americana contain other types
of coumarins and xanthones (Crombie et al., 1967; Finnegan
et al., 1972; Finnegan et al., 1973; Ito et al., 2002), therefore,
their antibacterial activity should be studied.
4. Discussion and conclusions
Twenty-two plants studied here are used in Mexican tra-ditional
medicine against illness such as fever, diarrhea,
malaria, dysentery, sores, and venereal diseases presumably
caused mainly by bacteria or microorganisms. Of the 22
medicinal plants assayed, seven species showed high activ-ity
againstStaphylococcus aureus and nine moderate. Only
six plants showed moderate activity against Escherichia coli.
Bursera simaruba, Haematoxylon brasiletto, Calophyllum
brasiliense, and Mammea americana showed high activ-ity
against Staphylococcus aureus. Bursera simaruba is a
widely distributed tree in the tropical area in Mexico and is
well known for its applications as water decoctions or poul-tices
made from the leaves against bacteria related diseases.
Haematoxylum brasiletto, a tree distributed in dry tropical
forests, has red heartwood. This morphological feature red
heartwood could probably be related to several medical ap-plications,
due to an association with blood or heart diseases.
Haematoxylum brasiletto is also known in certain localities
as a febrifuge (Aguilar et al., 1994; Soto-Nu˜nez and Sousa,
1995). Antibacterial compounds (1–4) isolated from the last
two species Calophyllum brasiliense and Mammea ameri-cana
would serve as promising candidates for chemothera-peutic
agents, especially against MRSA, because these com-pounds
showed much higher activity than that of oxacillin.
The results obtained in this work scientifically support
the effectiveness of medicinal plants locally and traditionally
used to treat infection-related diseases in Mexico, because of
their high antibacterial activity.
Acknowledgements
The authors are grateful to Laura Cort´es Z´arraga for her
assistance in collecting ethnobotanical data.Wewould like to
thank Dr. H. Akahane of Fukuoka University for his encour-agement
in carrying out this study. This work was supported
in part by a grant (no. 001001) from the Central Research
Institute of Fukuoka University: 2000–2001.
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