![GC-MS chromatogram (TIC) of Myrcianthes storkii leaf essential oil [1. α-pinene; 2. myrcene; 3. pcymene; 4. limonene; 5. 1,8-cineole; 6. linalool; 7. α-copaene; 8. (E)-caryophyllene; 9. α-humulene; 10. ciscalamenene; 11. 1-epi-cubenol; 12. cubenol].](https://www.researchgate.net/publication/376388587/figure/fig1/AS:11431281210891856@1702213588615/GC-MS-chromatogram-TIC-of-Myrcianthes-storkii-leaf-essential-oil-1-a-pinene-2_Q320.jpg)
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UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
Chemical profile of essential oils of the Costa Rican native tree Myrcianthes
storkii (Myrtaceae)
Carlos Chaverri1,2 & José F. Cicció1,2
1. Universidad de Costa Rica, Escuela de Química, 11501-2060 San José, Costa Rica; cachaverri@gmail.com,
jfciccio@gmail.com
2. Universidad de Costa Rica, Centro de Investigaciones en Productos Naturales (CIPRONA), 11501-2060 San José, Costa
Rica.
Received 10-VII-2023 ● Corrected 08-IX-2023 ● Accepted 11-IX-2023
https://doi.org/10.22458/urj.v16i1.4863
ABSTRACT. Introduction: The genus Myrcianthes ranges
from southern Florida to Chile, including the Caribbean,
and the species Myrcianthes storkii is a shrub or tree
found in Costa Rica and western Panama, in wet to very
rainy, cloud, and oak forests (altitude 1300-3150m).
Objective: To identify the chemical composition of
essential oils from leaves, floral buds, and twigs of M.
storkii of Costa Rica. Methods: We obtained the essential
oils through hydrodistillation in a Clevenger-type
apparatus. The chemical composition of the oils was done
by GC/FID and GC/MS, using the retention indices on DB-
5 and Carbowax types of capillary columns in addition to
mass spectra. Results: The oils consisted mainly of
terpenoids (55,45-87,75%). A total of 281 compounds
accounted for 91,27-74,56% of the total amount of oils.
The major constituents from the leaf oil were myrcene
(17,44%), cis-calamenene (12,60%), α-pinene (5,48%), (E)-
caryophyllene (5,16%), limonene (3,91%), p-cymene
(3,71%), 1,8-cineole (2,80%), and α-humulene (2,80%).
The floral bud essential oil consisted mainly of α-pinene
(15,23%), cis-calamenene (12,70%), myrcene (8,59%), 1,8-
cineole (4,26%), germacrene B (3,65%), α-humulene
(3,55%), and (E)-caryophyllene oxide (2,93%). The major
components of twig oil were cis-calamenene (11,31%),
palmitic acid (7,99%), (E)-caryophyllene (4,68%), 𝛿-
cadinene (3,28%), cubenol (3,24%), and (Z)-caryophyllene
oxide (2,94%). Conclusion: The presence of a significant
quantity of myrcene and cis-calamenene seems to be
characteristic of this species.
Keywords: Myrcianthes storkii, essential oils, cis-
calamenene, myrcene, α-pinene, 1,8-cineole.
RESUMEN. “Perfil químico de los aceites esenciales del
árbol nativo costarricense Myrcianthes storkii
(Myrtaceae)”. Introducción: El género Myrcianthes se
extiende desde el sur de Florida hasta Chile, incluyendo el
Caribe, y la especie Myrcianthes storkii es un arbusto o
árbol que se encuentra en Costa Rica y el oeste de
Panamá, en bosques húmedos, muy lluviosos, de neblina
y robles (altitud de 1300 a 3150 m). Objetivo: Identificar
la composición química de los aceites esenciales de las
hojas, yemas florales y ramas de M. storkii de Costa Rica.
Métodos: Obtuvimos los aceites esenciales mediante
hidrodestilación en un aparato de tipo Clevenger.
Determinamos la composición química de los aceites
mediante cromatografía de gases con detector de
ionización de llama (GC/FID) y cromatografía de gases
acoplada a espectrometría de masas (GC/MS). Usamos los
índices de retención en columnas capilares de tipos DB-5
y Carbowax, además de espectros de masas. Resultados:
Los aceites están compuestos principalmente por
terpenoides (55,45-87,75%). Identificamos 281
compuestos, que representaron el 91,27-74,56% de la
cantidad total de los aceites. Los principales
constituyentes del aceite de hoja fueron mirceno
(17,44%), cis-calameneno (12,60%), α-pineno (5,48%), (E)-
cariofileno (5,16%), limoneno (3,91%), p-cimeno (3,71%),
1,8-cineol (2,80%) y α-humuleno (2,80%). El aceite
esencial de las yemas florales consistió principalmente en
α-pineno (15,23%), cis-calameneno (12,70%), mirceno
(8,59%), 1,8-cineol (4,26%), germacreno B (3,65%), α-
humuleno (3,55%) y óxido de (E)-cariofileno (2,93%). Los
componentes principales del aceite de las ramas fueron
cis-calameneno (11,31%), ácido palmítico (7,99%), (E)-
cariofileno (4,68%), δ-cadineno (3,28%), cubenol (3,24%)
y óxido de (Z)-cariofileno (2,94%). Conclusión: La
presencia de una cantidad significativa de mirceno y cis-
calameneno parece ser característica de esta especie.
Palabras clave: Myrcianthes storkii, aceites esenciales,
cis-calameneno, mirceno, α-pineno, 1,8-cineol.
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
The Myrtaceae is a pantropical family that comprises 17 tribes, about 144 genera, and over
5500 species (Wilson, 2011; Vasconcellos et al., 2017) distributed through southern regions of the
world (with a few representatives in Africa). This family is composed mainly of shrubs and trees with
most genera occurring in Australia and tropical and subtropical America. One of the characteristics
of this family is the presence of oil glands that produce essential oils, mainly constituted by
terpenoids.
Myrcianthes O. Berg is a genus composed of 39 recognized species ranging from southern
Florida and Mexico to Bolivia and northern Argentina, Uruguay and north-central Chile and the
Caribbean (McVaugh, 1963; Tucker et al., 1992; Tucker et al., 2002, World Flora Online [WFO],
2023). Myrcianthes storkii (Standl.) McVaugh [Synonyms: Eugenia rigidissima Cufod.; E. storkii
Standl.; Myrcianthes rigidissima (Cufod.) W.D. Stevens] is a native shrub or tree of about 4 to 30m
tall, with a distributional range from Costa Rica and western Panama. In Costa Rica, it is distributed
in wet to very rainy, cloud, and oak forests, from 1300 to 3150m of elevation and it is known
vernacularly as ‘guayabillo’ (Barrie, 2007). These forests can be found on mountain slopes, varying
in the intensity of rainfall. The leaves are elliptic or obovate to broadly elliptic or broadly obovate,
coriaceous, and glabrous on both sides. When the leaves are crushed, they give off a scent with
aromatic flavor. Young twigs are coarsely sericeous.
Many studies on the chemical composition of essential oils of diverse species of Myrcianthes
have been reported. Some of these studies are summarized in Table 1 in Appendix. The species and
the morphological part from which the studied essential oil was isolated, the location, and the major
compounds that constitute the oils are indicated. In general terms, the studied oils are constituted
mainly of terpenes and terpenoids.
There is no information about possible traditional uses of M. storkii.
To the best of our knowledge, no previous reports on the chemical composition of essential
oils of this species have been published.
MATERIALS AND METHODS
Plant materials: We collected leaves, floral buds, and twigs of Myrcianthes storkii from a
single tree in the locality of Pacayas de Alvarado, Province of Cartago, Costa Rica (09°55'03"N
83°48'29"W, at an elevation of 1 700m). A voucher specimen is Luis J. Poveda Álvarez 4915 (F).
Extraction of essential oils: We isolated the oils from fresh plant material by
hydrodistillation at atmospheric pressure, for 3 h using a Clevenger-type apparatus. The distilled oils
were collected and dried over anhydrous sodium sulfate, filtered, and stored between 0°C and 10°C
in the dark, until further analysis. The essential oil yields (v/w) were 0,05% (leaves), 0,09% (floral
buds), and (0,01% twigs).
Gas chromatographic analyses (GC-FID): We analyzed the essential oils of M. storkii by
capillary gas chromatography with a flame ionization detector (GC/FID) using a Shimadzu GC-2014
gas chromatograph. Data have been collected on a poly (5% diphenyl/95% dimethylsiloxane) fused
silica capillary column (30m x 0,25mm; film thickness 0,25μm), (MDN-5S, Supelco). The GC
integrations were performed with LabSolutions, Shimadzu GCsolution™ Chromatography Data
System software, version 2.3. Operating conditions used were carrier gas N2, flow 1,0mL/min; oven
temperature program: 60 to 280°C at 3°C/min, 280°C (2 min); sample injection port temperature
250°C; detector temperature 280°C; split 1:60.
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
Gas chromatography-mass spectrometry (GC-MS): GC-MS analyses were performed with a
Shimadzu GC-2010 Plus gas chromatograph coupled with a GCMS-QP2010 SE apparatus and with
GCMSsolution™ software (version 4.20), with NIST and Wiley 139 computerized databases. The
analyzes were performed with two fused-silica-capillary columns with stationary phases of different
polarities: 1,4-bis(dimethylsiloxy) phenylene dimethylpolysiloxane and polyethylene glycol. The
data were obtained with a non-polar SLB™-5ms (Supelco) fused silica column (30m x 0,25mm; film
thickness 0,25μm). Operating conditions were: carrier gas He, flow 1,4 mL min-1 with constant
pressure; oven temperature was programmed linearly from 60°C to 280°C at 3°C min-1; sample
injection port temperature 250°C; interface temperature 260°C; ionization voltage: 70 eV; ionization
current 60μA; scanning speed 0,30s over 35 to 400 amu range; split 1:70. Also, the data were
obtained with a second polar Supelcowax™10 (Supelco) fused silica column (30m x 0,25mm; film
thickness 0,2 μm). Operating conditions were carrier gas He, flow 1,4mL min-1; oven temperature
program: 60–220°C at 3°C min-1; sample injection port temperature 240°C; transfer line
temperature 230°C; ionization voltage: 70 eV; ionization current 60 μA; scanning speed 0,30s over
acquisition mass range, 35 to 400 amu; split 1:70.
Compound identification: We identified the essential oil constituents by comparison of
their linear retention indices which were calculated in relation to a homologous series of n-alkanes,
on a poly (5% diphenyl/95% dimethylsiloxane) type column (van den Dool & Kratz, 1963) and on
polyethylene glycol capillary column and, by comparison of their mass spectra with those published
in the literature (Adams, 2007), or those of our own homemade MS library, or comparing their mass
spectra with those available in the computerized databases (NIST 107 and Wiley 139) or in a web
source (Wallace, 2021). To obtain the retention indices for each peak, 0,1 μL of an n-alkane mixture
(Sigma, C8–C32 standard mixture) was co-injected under the same experimental conditions reported
above. Integration of the total chromatogram (GC/FID), expressed as area percent, without
correction factors, has been used to obtain quantitative compositional data.
RESULTS
The essential oils from different parts of Myrcianthes storkii presented a complex mixture
of compounds. The constituents identified, their experimental retention indices on two columns of
diverse polarity, their relative percentage concentrations, and the methods used for their
identification are presented in Table 2 in Appendix. The constituents are listed in order of elution
on a non-polar poly-(5% phenyl 95% dimethylsiloxane) type column and for comparison purposes,
previously published values of the retention indices are included (Adams, 2007; Wallace, 2021).
Myrcianthes storkii gave essential oils that were predominantly terpenoid in nature. The
leaf and floral bud oils were dominated by monoterpenoids (42,66% and 38,63%, respectively) and
sesquiterpenoids (44,67% and 44,69%, respectively), whereas twig oil was dominated by
sesquiterpenoids (46,45%) and aliphatic compounds (18,77%). From the hydrodistilled oils, a total
of 281 compounds were identified using GC/FID and GC/MS, accounting for 91,27% (leaves), 86,65%
(floral buds), and 74,56% (twigs) of the total composition of the essential oils.
The leaf essential oil consisted largely of monoterpene hydrocarbons (36,98%) and
sesquiterpene hydrocarbons (34,06%) with minor amounts of oxygenated derivatives. The main
constituents were myrcene (17,44%), cis-calamenene (12,60%), α-pinene (5,48%), (E)-caryophyllene
(5,16%), limonene (3,91%), p-cymene (3,71%), 1,8-cineole (2,80%), α-humulene (2,80%), cubenol
(2,45%), α-copaene (2,22%), α-cubebene (2,10%), linalool (2,05%), (E)-caryophyllene oxide (2,04%),
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
and β-phellandrene (2,00%). [See the total ion chromatogram (TIC) in Fig 1]. The chemical structures
of some of these compounds are shown in Fig. 3.
Fig. 1. GC-MS chromatogram (TIC) of Myrcianthes storkii leaf essential oil [1. α-pinene; 2. myrcene; 3. p-
cymene; 4. limonene; 5. 1,8-cineole; 6. linalool; 7. α-copaene; 8. (E)-caryophyllene; 9. α-humulene; 10. cis-
calamenene; 11. 1-epi-cubenol; 12. cubenol].
The composition of the floral bud essential oil also was dominated by sesquiterpene
hydrocarbons (32,36%), and monoterpene hydrocarbons (30,75%) with α-pinene (15,23%), cis-
calamenene (12,70%), myrcene (8,59%), 1,8-cineole (4,26%), germacrene B (3,65%), α-humulene
(3,55%), (E)-caryophyllene oxide (2,93%), α-copaene (2,24%), hinesol (2,16%), and α-cubebene
(2,14%) as main constituents.
The twig essential oil was constituted mainly of sesquiterpenoids (46,45%) and aliphatic
compounds (18,77%), with a minor quantity of monoterpenoids (6,84%). The major compounds
found were cis-calamenene (11,31%), hexadecanoic acid (7,99%), (E)-caryophyllene (4,68%), 𝛿-
cadinene (3,28%), cubenol (3,24%), (Z)-caryophyllene oxide (2,94%), 1-epi-cubenol (2,45%), α-
humulene (2,38%), and α-copaene (2,19%). The aliphatic mixture of compounds was constituted of
acids (palmitic acid as the main compound), aldehydes, alcohols, esters, and hydrocarbons. [See the
total ion chromatogram (TIC) in Fig 2].
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
Fig. 2. GC-MS chromatogram (TIC) of Myrcianthes storkii twig essential oil [1. α-pinene; 2. myrcene; 3. p-
cymene; 4. limonene; 5. α-copaene; 6. (E)-caryophyllene; 7. α-humulene; 8. δ-cadinene; 9. cis-calamenene;
10. (E)-caryophyllene oxide; 11. cubenol; 12. palmitic acid; 13. (E)-phytol].
Fig. 3. Structures of some constituents of the essential oils of Myrcianthes storkii from Costa Rica.
DISCUSSION
Analyzing the data in Table 1, the chemical composition of essential oils obtained from
leaves of Myrcianthes is very varied. However, there seem to be some common, widespread
compounds, such as the monoterpenes α-pinene, β-pinene, p-cymene, and limonene; the
sesquiterpenes (E)-caryophyllene and α-humulene, and the terpenoids 1,8-cineole, linalool,
terpinen-4-ol, α-terpineol, and (E)-caryophyllene oxide. Some of them are ubiquitous natural
products that display ecological roles such as assisting in pollinator attraction, deterrent action
against certain herbivores, and antimicrobial or allelopathic activities (Anaya et al., 2001;
Gershenzon & Dudareva, 2007; Yazaki et al., 2017; Boncan et al., 2020; Escobar-Bravo et al., 2023).
Observing the data provided in Table 1, differences are found in the composition of the
essential oils of samples of the same species that grow in different places. The oils of M. fragrans
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
from Jamaica (Tucker et al., 1992) and Cuba (Pino et al., 2000) were rich in limonene, α-pinene, α-
terpineol, and 1,8-cineole, whereas the essential oil from Venezuela (Mora et al., 2009) was rich in
myrcene, β-caryophyllene, and other sesquiterpenoids. The oil from Ecuador (Armijos et al., 2018)
differed from all the other samples and species in that it contained large amounts of geranial and
neral. The two Costa Rican samples of this species gave oils with the unique fact of presenting as
main compounds the benzenoid 1,3,5-trimethoxybenzene and (E)-methyl isoeugenol (Cole et al.,
2008) and the phenylpropanoid ester, methyl (E)-cinnamate (Chaverri & Cicció, 2017).
The essential oil of M. storkii leaves is mainly constituted of terpenoids (87,75%) and small
amounts of aliphatic compounds (2,55%) and benzenoids (0,91%). This oil is characterized by the
dominant compounds myrcene (17,44%) and cis-calamenene (12,60%). In the studies conducted to
date, only the oils of M. rhopaloides and M. leucoxyla from Colombia (Silva et al., 2016; Quijano-
Célis et al., 2016), and M. fragrans from Venezuela (Mora et al., 2009) presented myrcene in
significant quantities (17,7%, 17,4% and 8,9% respectively). Myrcene possesses sedative and
anxiolytic properties (Rao et al., 1990), anti-inflammatory (Rufino et al., 2015), as well as antioxidant
and cytoprotective properties (Xanthis et al., 2021); it also has anti-aging properties (Surendran et
al., 2021) and anti-invasive activity on a human breast cancer epithelial cell line, MDA-MB-231 (Lee
et al., 2015). This compound is a valuable renewable material for the industrially sustainable
synthesis of many fine chemical products, which have high added value and are used in multiple
applications (Behr & Johnen, 2009).
cis-Calamenene appears to be a distinctive compound in the essential oils of M. storkii from
Costa Rica, accompanied by a large amount of myrcene. Of the studied species, only M. rhopaloides
from Costa Rica (Cole et al., 2008) and M. myrsinoides from Ecuador (Montalván et al., 2018)
presented significant amounts of the diastereoisomer, trans-calamenene (2,5% and 15,9%
respectively). The cis-calamenene, an aromatic cadinene, is a major constituent (2,1-9,1%) of the
essential oil of Cupressus bakeri Jeps. (Cupressaceae) foliage (Rafii et al., 1992; Kim et al., 1994) and
is present in the commercial Baccharis dracunculifolia DC. essential oil (1,0%) (Weyerstahl et al.,
1996). Also, this compound was identified in cuticular waxes of the stingless bees Nannotrigona
testaceicornis and Plebeia droryana (Pianaro et al., 2009).
In summary, we have shown, for the first time, the chemical composition of Myrcianthes
storkii essential oil from different morphological parts (leaves, flower buds, and twigs). The presence
of a high amount of myrcene and cis-calamenene in the essential oils seems to be characteristic of
this species.
ACKNOWLEDGEMENTS
The authors are grateful to Vicerrectoría de Investigación (UCR) for financial support
(Project No. 809- B 9-170) and to Luis J. Poveda Álvarez (earlier in Herbarium JVR) for his help in the
collection and identification of the species. The authors also thank the anonymous reviewers for
their critical reading and valuable suggestions.
ETHICAL, CONFLICT OF INTEREST AND FINANCIAL STATEMENTS
The authors declare that they have fully complied with all pertinent ethical and legal
requirements, both during the study and in the production of the manuscript; that there are no
conflicts of interest of any kind; that all financial sources are fully and clearly stated in the
Acknowledgements section; and that they fully agree with the final edited version of the article. A
signed document has been filed in the journal archives.
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
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UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
APPENDIX
TABLE 1
Major compounds present in some Myrcianthes spp. essential oils.
Species
Country, location
Essential oil constituents (>2,0%)
Biological
observations
References
M. callicoma
McVaugh
Argentina
α-Pinene, limonene, and 1,8-
cineole.
Carmen et al.,
1972
M. cisplatensis
(Camb.) Berg
Argentina
1,8-Cineole (13,5%), and geraniol
(8,4%).
Taher et al.,
1983
M. cisplatensis
(Camb.) Berg
Argentina,
Catamarca.
(Air-dried leaves)
(0,15%)
1,8-Cineole (40,7%), limonene
(22,1%), α-terpineol (7,7%),
linalool (4,8%), and α-pinene
(4,3%).
Zygadlo et al.,
1997
M. cisplatensis
(Camb.) Berg
Uruguay, ‘Cerros
pelados’,
Canelones.
(Air-dried leaves)
1,8-Cineole (53,8%), α-pinene
(16,6%), α-terpineol (4,2%),
limonene (4,1%), and thujopsan-
4α-ol (2,0%).
Lorenzo et al.,
2001
M. cisplatensis
Camb.) Berg
Brazil, Alegrete,
Rio Grande do Sul.
(Fresh leaves)
(0,2%)
1,8-Cineole (29,8%), limonene
(10,9%), β-caryophyllene (10,8%),
α-pinene (8,9%), α-terpineol
(5,7%), guaiol (4,9%), globulol
(4,8%), α-selinene (2,7%),
aromadendrene (2,5%), and α-
humulene (2,0%).
Apel et al., 2006
M. cisplatensis
(Camb.) Berg
Argentina
(Dried leaves)
1,8-Cineole (45,7%), limonene
(27,1%), α-terpineol (7,7%),
linalool (4,8%), α-pinene (4,3%),
and δ-cadinene (2,3%).
Fumigant and
repellent properties
against permethrin-
resistant head lice.
Toloza et al.,
2006
M. coquimbensis
(Barnèoud) L.R.
Landrum & Grifo
Chile, La Serena.
(Air-dried leaves)
Limonene (14,5%), carvone
(8,7%), α-pinene (7,2%), β-pinene
(5,7%), p-cymene (5,3%), trans-
carveol (4,9%), cis-pinocarveol
(4,3%), linalool (4,1%), trans-
linalool oxide (furanoid) (3,6%),
myrtenal (3,4%), pinocarvone
(3,2%), verbenone (2,9%), cis-
linalool oxide (furanoid) (2,8%),
and myrtenol (2,2%).
Tucker et al.,
2002
M. discolor
(Kunth) McVaugh
Ecuador, Loja-
Chuquiribamba
Road, Loja.
(Fresh leaves)
(0,08%)
β-Caryophyllene (29,40%),
bicyclogermacrene (7,45%), β-
elemene (6,93%), α-cubebene
(6,06%), α-humulene (3,96%), 𝛿-
cadinene (3,2%), limonene
(2,63%), and amorpha-4,7(11)-
diene (2,28%).
Strong inhibitory
effect against
acetylcholinesterase
(AChE) and
moderate
antiradical effect.
Romero et al.,
2023
M. fragrans (Sw.)
McVaugh
Jamaica, Douglas
Castle, St. Ann.
(Air-dried leaves)
Limonene (56,0%), α-terpineol
(10,9%), 1,8-cineole (7,1%), α-
pinene (6,9%), and β-pinene
(2,0%).
Tucker et al.,
1992
M. fragrans (Sw.)
McVaugh
Cuba, Pinar del
Río.
(Leaves and stalks)
(1,4%)
α-Pinene (41,8%), limonene
(30,0%), 1,8-cineole (6,5%), α-
terpineol (5,7%), and cis-piperityl
acetate (2,1%).
Pino et al., 2000
M. fragrans (Sw.)
McVaugh
Costa Rica,
Monteverde.
(Fresh leaves)
(See Cole et al., 2008).
Cytotoxic to Hep G2
and SK-Mel-28 cells.
Werka et al.,
2007
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
M. fragrans (Sw.)
McVaugh
Costa Rica,
Monteverde.
(Fresh leaves)
(0,03%)
1,3,5-Trimethoxybenzene
(15,7%), α-cadinol (10,4%), (Z)-
hex-3-en-1-ol (10,0%), eudesma-
4(15),7-dien-1β-ol (9,0%),
caryophyllene oxide (7,8%),
spathulenol (7,5%), muurola-
4,10(14)-dien-1β-ol (4,7%),
caryophylla-4(12),8(13)-dien-5β-
ol (4,2%), humulene epoxide II
(3,9%), τ-muurolol (3,5%), α-
muurolol (3,2%), and (E)-
methylisoeugenol (2,5%).
Cole et al., 2008
M. fragrans (Sw.)
McVaugh
Venezuela, Aldea
Llanetes, Táchira.
(Fresh leaves)
(0,08%)
β-Caryophyllene (11,5%),
myrcene (8,9%), phellandrene/
limonene (8,7%), α-humulene
(6,7%), α-copaen-8-ol (6,7%),
globulol (4,9%), viridiflorol (4,7%),
bicyclogermacrene (4,4%), α-
copaene (3,5%), δ-cadinol (2,8%),
δ-cadinene (2,6%), linalool (2,3%),
and τ-cadinol (2,1%).
Mora et al.,
2009
M. fragrans (Sw.)
McVaugh
Costa Rica, Santo
Domingo, Heredia
(Fresh leaves)
(0,5%)
Methyl (E)-cinnamate (39,6%),
limonene (34,6%), α-pinene
(6,8%), linalool (6,8%), and
heptan-2-ol (2,0%).
Chaverri &
Cicció, 2017
M. fragrans (Sw.)
McVaugh
Ecuador, Cerro
Villonaco, Loja.
(Aerial parts)
(0,28-0,38%)
Geranial (23,6-31,1%), neral
(17,8-24,3%), β-pinene (3,9-
7,5%), α-pinene (2,8-5,9%),
(2E,6E)-farnesal (3,2-8,0%),
(2Z,6E)-farnesal (3,0-6,7%), and
geraniol (2,5-3,1%).
Antimicrobial
activity against
Klebsiella
pneumoniae,
Candida albicans,
and Saccharomyces
cerevisiae
Armijos et al.,
2018
M. gigantea (D.
Legrand) D.
Legrand
Brazil, Espumoso,
Rio Grande do Sul.
(Fresh leaves)
(0,1%)
Spathulenol (28,9%), iso-
spathulenol (9,5%, α-cadinol
(7,0%), caryophyllene oxide
(6,7%), limonene (4,5%), α-pinene
(3,5%), β-pinene (2.8%), globulol
(2,8%), α-copaene (2,6%), β-
selinene (2,5%), and (Z)-hex-3-en-
1-ol (2,4%).
Apel et al., 2006
M. leucoxyla
(Ortega)
McVaugh
Colombia,
Pamplona,
Santander.
(Dried leaves)
(0,3%)
α-Pinene (28,4%), 1,8-cineole
(15,7%), β-caryophyllene (8,8%),
spathulenol (3,3%), guaiol (3,1%),
β-humulene (3,0%), and
caryophyllene oxide (3,0%).
Antimicrobial
activity against
Staphylococcus
aureus.
Antioxidant activity.
Yáñez et al.,
2013.
Granados et al.,
2014
M. leucoxyla
(Ortega)
McVaugh
Colombia,
Andean Plateau,
Sabana de Bogotá
(Fresh leaves)
(0,1%)
Caryophyllene oxide (21,7%), α-
terpineol (8.0%), linalool (7,8%),
1,8-cineole (6,3%), geraniol
(5,1%), epi-globulol (3,4%),
geranyl acetate (3,2%),
germacrene D (3,2%), 2-carene
(2,9%), and τ-cadinol (2,7%).
Antimicrobial
activity against
Pseudomonas
aeruginosa and
Salmonella
typhimurium.
Pombo et al.,
2016
M. leucoxyla
(Ortega)
McVaugh
Colombia,
Bogotá
(Young fresh
leaves)
(0,1%)
Limonene (21,2%), myrcene
(17,4%), spathulenol (7,1%), β-
pinene (8,4%), α-pinene (5,4%),
caryophyllene oxide (2,7%),
linalool (2,4%), α-terpineol (2,3%),
Quijano-Célis et
al., 2016
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
terpinen-4-ol (2,2%), and α-
cadinol (2,2%).
M. myrsinoides
(Kunth) Grifo
Venezuela,
Mérida.
(Leaves)
(0,5%)
Terpinen-4-ol (32,2%), o-cymene
(8,2%), spathulenol (7,6%),
caryophyllene oxide (7,1%), α-
terpineol (4,1%), β-oplopenone
(3,9%), limonene (3,8%),
isoaromadendrene epoxide
(3,8%), humulene epoxide II
(3,0%), and τ-muurolol (2,5%).
Antimicrobial
activity against
Bacillus cereus, B.
subtilis, and
Staphylococcus
epidermidis.
Araujo et al.,
2017
M. myrsinoides
(Kunth) Grifo
Ecuador,
Gonzanamá, Loja.
(Fresh leaves)
(0,3%)
Caryophyllene (16,6%), trans-
calamenene (15,9%), 1,8-cineole
(10,4%), spathulenol (6,2%),
limonene (5,3%), trans-cadina-
1,4-diene (3,5%), cis-muurola-
4(14),5-diene (2,6%), α-pinene
(2,5%), α-copaene (2,1%),
germacrene D (2,1%), and α-
terpineol (2,0%).
Montalván et
al., 2018
M. osteomeloides
(Rusby) McVaugh
Bolivia,
Cochabamba.
(Fresh leaves)
(0,6%)
1,8-Cineole (55,7%), α-pinene
(17,9%), α-terpineol (8,5%), β-
pinene (4,6%), and limonene
(4,1%).
López et al.,
2005
M. pseudo-mato
(D. Legrand)
Mc.Vaugh
Argentina, Oran,
Salta.
(Dried leaves)
(0,3%)
1,8-Cineole (32,5%), β-
caryophyllene (18,9%), sabinene
(6,6%), α-pinene (6,5%),
aromadendrene (5,4%), τ-
muurolol (4,5%), (E)-nerolidol
(3,5%), τ-cadinol (3,4%),
spathulenol (3,3%), α-terpineol
(2,7%), β-eudesmol (2,3%), and α-
humulene (2,1%).
Antimicrobial
activity against
Staphylococcus
aureus, Bacillus
cereus and
Micrococcus luteus.
Demo et al.,
2002
M. pseudo-mato
(D. Legrand)
Mc.Vaugh
Bolivia,
Cochabamba.
(Fresh leaves)
(0,1%)
1,8-Cineole (24,4%), α-pinene
(17,1%), linalool (11,7%),
limonene (8,5%), γ-terpinene
(7,3%), p-cymene (3,9%), and α-
terpineol (2,4%).
López et al.,
2005
M. pungens
(Berg) D. Legrand
Argentina
(Leaves)
1,8-Cineole (13,5%), pulegone
(9,4%), farnesol (9,0%), nerol
(5,4%), and geraniol (4,5%).
Ubiergo et al.,
1986
M. pungens
(Berg) D. Legrand
Argentina,
Catamarca.
(Air-dried leaves)
(0,2%)
1,8-Cineole (45,9%), limonene
(17,3%), α-terpineol (8,1%), α-
pinene (3,3%), linalool (3,0%), and
globulol (2,8%).
Zygadlo et al.,
1997
M. pungens (O.
Berg) D. Legrand
Brazil, Viamão, Rio
Grande do Sul.
(Fresh leaves)
(0,1%)
β-Caryophyllene (10,1%),
spathulenol (9,7%), β-elemene
(9,1%), α-cadinol (8,0%),
bicyclogermacrene (6,9%),
globulol (6,2%), epi-globulol
(4,7%), β-bisabolene (3,3%), (E)-γ-
bisabolene (3,3%), β-selinene
(3,1%), 1,8-cineole (2,7%),
caryophyllene oxide (2,3%), α-
pinene (2,1%), τ-muurolol (2,1%),
α-humulene (2,0%), and δ-
cadinene (2,0%).
Apel et al., 2006
M. pungens (O.
Berg) D. Legrand
Brazil, Pelotas, Rio
Grande do Sul.
β-Caryophyllene (32,7%),
germacrene D (14,2%),
Marín et al.,
2008
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
(Cultivated, fresh
edible, and ripped
fruits)
bicyclogermacrene (11,2%), β-
eudesmol (8,1%), furfural (7,7%),
epi-globulol (3,9%), elemol (3,8%),
α-humulene (3,3%), γ-eudesmol
(2,5%), and α-eudesmol (2,5%).
M. pungens (O.
Berg) D. Legrand
Brazil,
Maringá.
(Dried leaves)
(0,2%)
β-Caryophyllene (11,7%), 1,8-
cineole (10,1%),
bicyclogermacrene (7,9%), 5-epi-
neointermedeol (6,0%),
caryophyllene oxide (5,2%),
limonene (3,5%), β-selinene
(3,4%), (E)-β-ocimene (3,3%), β-
elemene (3,0%), δ-cadinene
(3,0%), α-cubebene (2,8%),
germacrene A (2,3%), and
germacrene B (2,2%).
Antimicrobial
activity against
Staphylococcus
aureus and Bacillus
cereus.
de Jesús et al.,
2021
M. rhopaloides
(Kunth) McVaugh
Ecuador, Cerro el
Villonaco, Loja.
(Fresh leaves)
(0,3%)
Geranial (33,7%), neral (25,0%), β-
pinene (9,0%), α-pinene (6,9%),
geranyl acetate (3,0%), and
geraniol (2,3%).
Malagón et al.,
2003
*M. rhopaloides
(Kunth) McVaugh
Costa Rica,
Chomogo,
Monteverde.
(Fresh leaves)
(See Cole et al., 2008).
Cytotoxic to SK-Mel-
28 cells.
Werka et al.,
2007
*M. rhopaloides
(Kunth) McVaugh
Costa Rica,
Chomogo,
Monteverde.
(Fresh leaves)
(0,02%)
Linalool (17,7%), α-cadinol
(14,4%), spathulenol (11,1%), τ-
cadinol (9,6%), 1-epicubenol
(6,9%), α-muurolol (5,5%),
cyclocolorenone (4,9%), α-
terpineol (3,5%), eudesma-
4(15),7-dien-1β-ol (3,4%),
caryophyllene oxide (3,3%),
tetradecan-1-ol (3,3%), trans-
calamenene (2,5%), and δ-
cadinene (2,2%).
Cole et al., 2008
*M. rhopaloides
(Kunth) McVaugh
Costa Rica,
Brillante,
Monteverde.
(Fresh leaves)
(E)-Hex-2-enal (46,1%), 1,8-
cineole (12,5%), linalool (9,1%), α-
cadinol (6,7%), α-terpineol (4,4%),
τ-muurolol (2,6%), and terpinen-
4-ol (2,0%).
Cole et al., 2008
M. rhopaloides
(Kunth) McVaugh
Colombia,
Macheta,
Cundinamarca
(Fresh leaves)
(0,28%)
Citronelal (27,3%), myrcene
(17,7%), citronelol (15,5%),
neoisopulegol (6,6%), α-pinene
(4,2%), β-pinene (4,2%), β-
caryophyllene (2,5%), isopulegol
(2,3%), and α-farnesene (2,2%).
Silva et al., 2016
M. sp. nov. ‘black
fruit’
Costa Rica,
Monteverde.
(Fresh leaves)
1,8-Cineole (52,8%), α-pinene
(11,8%), α-terpineol (11,7%),
heptan-2-ol (11,1%), β-pinene
(8,4%), and limonene (4,3%).
In vitro citotoxic
activity against Hep-
G2 and SK-Mel-28
human tumor cell
lines.
Setzer et al.,
1999
M. sp. nov. ‘black
fruit’
Costa Rica,
Monteverde.
(Fresh leaves)
1,8-Cineole (38,3%), α-terpineol
(21,2%), heptan-2-ol (15,5%),
terpinen-4-ol (4,2%), and β-
pinene (3,8%).
Cole et al., 2008
* According to Manual de Plantas de Costa Rica, vol. 6, M. rhopaloides (Kunth) McVaugh does not inhabit Costa Rica, and
this name could probably have been used instead of M. storkii (?) (Barrie, 2007, p. 770).
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
TABLE 2
Chemical constituents of the essential oils of Myrcianthes storkii from Costa Rica
aCompound
bRILit
cRIExp
dSw10Exp
Class
(L) Leaf
(%)
(F) Floral
buds (%)
(T) Twigs
(%)
eIM
3-Methylbut-2-enal
790
1 206(F)
A
ftr
2;3
Hexanal
801
1 084(L,F)
A
tr
tr
tr
2;3
(E)-Hex-2-enal
846
841
1 222(L)
A
0,10
0,01
1;2;3
(Z)-Hex-3-enol
850
850
1 384(F)
A
0,65
0,08
1;2;3
(E)-Hex-2-enol
854
853
A
tr
1;3
Hexan-1-ol
863
863
1 352(L,F)
A
0,11
0,02
0,03
1;2;3;4
2-Butyl furan
885
882
Misc.
tr
1;3
Heptan-2-one
889
888
A
tr
1;3
Nonane
900
900
A
0,02
1;3
Bornylene (2-Bornane)
908
1 512(T)
M
tr
2;3
Heptanal
901
900
1 189(T)
A
0,04
tr
0,02
Anisole
913
914
B
0,03
1;3
Tricyclene
921
920
M
0,02
1;3
Cumene
924
924
1 177(L)
B
tr
1;2;3
α-Thujene
924
926
M
0,15
0,16
0,02
1;3
3,5-Dimethylene-1,4,4-
trimethylcyclopentene
931
1 179(F)
IT
tr
2;3
α-Pinene
932
933
1 029(L,F,T)
M
5,48
15,23
1,57
1;2;3;4
α-Fenchene
945
944
1 056(L,F)
M
0,04
tr
1;2;3
Camphene
946
945
1 068(L,F)
M
tr
0,13
1;2;3
(E)-Hept-2-enal
947
946
A
0,03
tr
1;3
Thuja-2,4(10)-diene
953
953
1 128(L,F)
M
tr
0,03
1;2;3
Isobutyl butanoate
958
961
1 159(F)
A
tr
1;2;3
Sabinene
969
972
1 123(F)
M
0,11
1;2;3
Oct-1-en-3-one
972
973
A
0,03
tr
1;3
β-Pinene
974
977
1 112(L,F,T)
M
0,64
0,88
0,15
1;2;3;4
Octan-3-one
979
979
A
tr
1;3
2-Pentylfuran
984
984
1 232(L,T)
Misc.
tr
tr
1;2;3
6-Methylhept-5-en-2-one
987
985
1 337(F)
A
tr
1;2;3
Myrcene
988
990
1 168(L,T)
M
17,44
8,59
1,78
1;2;3
Octanal
998
995
1 292(L,T)
A
0,18
0,06
1;2;3
δ-2-Carene
1 001
1 001
1 138(F)
M
tr
1;2;3
(E)-Hex-3-enyl acetate
1 001
1 000
A
0,06
1;3
α-Phellandrene
1 002
1 006
1 175(T)
M
0,46
0,63
0,13
1;2;3
p-Mentha-1(7),8-diene
1 003
1 172(L,F)
M
tr
tr
2;3
δ-3-Carene
1 008
1 011
1 149(L,F,T)
M
0,66
0,45
0,12
1;2;3
α-Terpinene
1 014
1 017
1 182(L,T)
M
0,13
0,14
0,05
1;2;3
m-Cymene*
1 020
1 021
1 272(L,F,T)
M
tr
tr
0,43
1;2;3
p-Cymene*
1 022
1 024
M
3,71
1,59
1;3
Limonene
1 024
1 029
1 204(L,F,T)
M
3,91
0,10
0,87
1;2;3;4
β-Phellandrene
1 025
1 030
1 212(L,T)
M
2,00
0,10
0,37
1;2;3
1,8-Cineole
1 026
1 031
1 211(L)
OM
2,80
4,26
0,09
1;2;3;4
(Z)-β-Ocimene
1 032
1 035
1 235(L,T)
M
0,94
1,50
0,18
1;2;3
Phenyl acetaldehyde
1 041
1 041
B
0,05
1;3
(E)-β-Ocimene
1 044
1 045
1 252(L,T)
M
0,43
0,22
0,09
1;2;3
(E)-Oct-2-enal
1 049
1 427(L)
A
tr
2;3
Isopentyl butanoate
1 052
1 056
1 270(L,F)
A
tr
tr
1;2;3
γ-Terpinene
1 054
1 058
1 245(L,T)
M
0,44
0,32
0,19
1;2;3
(E)-Oct-2-en-1-ol
1 060
1 064
A
tr
1;3
Octan-1-ol
1 063
1 065
1 559(L,F)
A
0,02
0,02
0,05
1;2;3
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
cis-Linalool oxide
(Furanoid)
1 067
1 439(F)
OM
tr
2;3
p-Cresol
1 071
1 071
B
0,02
1;3
4-Pentenyl butanoate
1 076
1 075
1 341(L)
A
tr
0,32
1;2;3
m-Cymenene
1 082
1 083
1 420(L,F)
M
tr
tr
1;2;3
trans-Linalool oxide
(Furanoid)
1 084
1 468(F)
OM
tr
2;3
p-Mentha-2,4(8)-diene
1 085
1 085
M
0,02
tr
1;3
Terpinolene
1 086
1 089
1 1282(T)
M
0,48
0,51
0,20
1;2;3
Methyl benzoate
1 088
1 091
B
tr
1;3
p-Cymenene
1 089
1 091
1 484(L,F)
M
0,03
tr
0,05
1;2;3
6,7-Epoximyrcene
1 090
1 410(L,F)
OM
tr
tr
2;3
Linalool
1 095
1 097
1 552(L,F,T)
OM
2,05
2,65
0,37
1;2;3;4
Undecane
1 100
1 100(L)
A
tr
2;3;4
Nonanal
1 100
1 104
1 394(L,T)
A
0,22
tr
0,80
1;2;3
Perillene
1 102
1 105
1 420(L,T)
Misc.
tr
0,10
0,05
1;2;3
1,3,8-Menthatriene
1 108
1 218(F)
M
tr
2;3
3-Methyl-3-butenyl
isovalerate
1 112
1 114
A
0,06
1;3
exo-Fenchol
1 118
1 120
OM
0,05
1;3
cis-p-Menth-2-en-1-ol
1 118
1 120
OM
tr
1;3
α-Campholenal
1 122
1 487(F)
OM
tr
2;3
trans-Pinocarveol
1 135
1 646(F)
OM
tr
2;3
trans-p-Menth-2-en-1-ol
1 136
1 139
1 624(L)
OM
tr
0,04
1;2;3
cis-Verbenol
1 137
1 650(F)
OM
tr
2;3
(E)-Epoxy-ocimene
1 137
1 486(L)
OM
tr
2;3
cis-p-Menth-1,8-diene-1-ol
1 138
1 667(F)
OM
tr
2;3
neo-allo-Ocimene
1 140
1 144
M
0,06
1;3
trans-Verbenol
1 140
1 672(F)
OM
tr
2;3
Veratrol
1 141
1 726(F)
OM
tr
2;3
p-Menth-3-en-8-ol
1 145
1 146
OM
tr
1;3
Citronellal
1 148
1 158
OM
0,01
1;3
(E)-Non-2-enal
1 157
1 159
1 531(L,F,T)
A
0,51
0,01
0,24
1;2;3
Pinocarvone
1 160
1 166
1 555(F)
OM
0,01
1;2;3
1,3-Dimetoxybenzene
1 165
1 167
B
0,05
1;3
Ethyl benzoate
1 169
1 170
1 658(F)
B
0,09
1;2;3
Nonan-1-ol
1 172
1 171
A
0,05
1;3
Terpinen-4-ol
1 174
1 178
1 597(L,F)
OM
0,37
0,27
0,05
1;2;3;4
Naphthalene
1 178
1 183
1 721(L)
B
0,43
1;2;3
m-Cymen-8-ol
1 176
1 846(F)
OM
tr
2;3
p-Cymen-8-ol
1 179
1 846(L,F)
OM
tr
tr
2;3
Cryptone
1 183
1 185
IT
0,06
tr
1;3
Methyl salicylate
1 190
1 191
1 760(L,F)
B
0,29
0,37
0,16
1;2;3
α-Terpineol
1 192
1 195
1 693(F)
OM
0,16
0,15
0,07
1;2;3
Myrtenal
1 195
1 614(F)
OM
tr
2;3
trans-p-Menthan-2-one
1 199
1 198
OM
0,15
1;3
Decanal
1 201
1 206
1 497(T)
A
0,04
tr
0,61
1;2;3
Verbenone
1 204
1 688(F)
OM
tr
2;3
trans-Piperitol
1 207
1 209
OM
0,02
0,07
1;3
Octyl acetate
1 211
1 214
A
0,07
1;3
trans-Carveol
1 215
1 219
1 831(F)
OM
tr
1;2;3
(E,E)-2,4-Nonadienal
1 220
1 221
A
0,06
tr
1;3
1-p-Menth-9-al
1 221
1 222
OM
tr
1;3
β-Cyclocitral
1 225
1 222
IT
tr
1;3
cis-Carveol
1 226
1 861(F)
OM
tr
2;3
Nerol
1 227
1 230
OM
0,11
0,02
tr
1;3
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
Cumin aldehyde
1 238
1 237
OM
0,01
1;3
Carvone
1 239
1 719(F)
OM
tr
2;3
(Z)-Dec-3-en-1-ol
1 242
1 245
A
0,04
0,02
0,05
1;3
Geraniol
1 249
1 248
OM
0,06
0,04
0,06
1;3;4
(E)-Dec-4-en-1-ol
1 259
1 252
A
0,03
1;3
Pent-4-enyl hexanoate
1 260
1 254
1 534(F)
A
tr
1;2;3
(E)-Dec-2-enal
1 260
1 261
1 638(L,T)
A
0,19
0,07
0,41
1;2;3
trans-Ascaridole glycol
1 266
2 086(F)
OM
tr
2;3
Ethyl salicylate
1 266
1 261
1 796(L)
B
tr
0,06
1;2;3
Nonanoic acid
1 267
1 266
A
0,05
1;3
Dodecanol
1 271
1 271
A
0,50
1;3
Dihydro-linalool acetate
1 272
1 269
OM
tr
1;3
p-Menth-1-en-7-al
(Phellandral)
1 280
1 283
OM
0,02
0,12
1;3
Car-2-en-10-al
1 289
1 281
OM
tr
1;3
p-Cymen-7-ol (Cumic
alcohol)
1 289
2 093(F)
OM
tr
2;3
(2Z,4Z)-Deca-2,4-dienal
1 292
1 292
A
tr
0,05
1;3
Undecan-2-one
1 293
1 293
1 598(T)
A
0,05
1;2;3
Carvacrol
1 298
1 296
OM
0,05
1;3
2-Methylnaphthalene
1 298
1 299
1 830(L)
B
0,06
1;2;3
Undecanal
1 305
1 306
A
0,02
1;3
4-Hydroxy-cryptone
1 314
2 238(F)
IT
tr
2;3
(2E,4E)-Deca-2,4-dienal
1 315
1 317
A
0,10
0,05
0,27
1;3
Myrtenyl acetate
1 324
1 324
OM
tr
1;3
cis-Sabinyl acetate
1 325
1 336
OM
0,01
1;3
α-Cubebene
1 345
1 351
1 453(F,T)
S
2,10
2,14
tr
1;2;3
(E)-Undec-2-enal
1 357
1 363
A
0,20
1;3
Neryl acetate
1 359
1 364
OM
0,04
1;3
Cyclosativene
1 369
1 366
S
tr
1;3
trans-p-menth-6-en-2,8-
diol
1 371
2 314(F)
OM
tr
2;3
α-Ylangene
1 373
1 373
1 473(L,F,T)
S
0,07
0,06
0,11
1;2;3
Isoledene
1 374
1 374
S
0,04
1;3
α-Copaene
1 374
1 378
1 484(L,F,T)
S
2,22
2,24
2,19
1;2;3
Geranyl acetate
1 379
1 382
OM
0,02
1;3
β-Cubebene
1 387
1 385
1 529(L)
S
tr
0,20
1;2;3
β-Bourbonene
1 387
1 387
1 508(L,F,T)
S
0,28
0,14
0,32
1;2;3
α-Bourbonene
1 388
1 388
1 501(L)
S
0,10
1;2;3
β-Elemene
1 389
1 393
1 582(F)
S
0,38
0,41
0,18
1;2;3
Dec-9-enyl acetate
1 399
1 398
A
0,08
0,10
1;3
Tetradecane
1 400
1 400
1 400(T)
A
tr
1;2;3
(Z)-Caryophyllene
1 408
1 407
1 563(F)
S
tr
1;2;3
α-Gurjunene
1 409
1 412
1 517(L,F,T)
S
0,88
0,88
0,76
1;2;3
(E)-Caryophyllene
1 417
1 422
1 584(L,F,T)
S
5,16
0,70
4,68
1;2;3;4
(E)-α-Ionone
1 428
1 431
1 838(L)
IT
0,13
1;2;3
β-Copaene
1 430
1 578(L,F)
S
tr
tr
2;3
α-Muurolene
1 431
1 432
S
0,21
1;3
γ-Elemene
1 434
1 435
S
0,22
0,47
0,21
1;3
cis-Thujopsene
1 435
1 436
S
0,05
1;3
α-Guaiene
1 437
1 438
S
0,08
0,07
0,10
1;3
Aromadendrene
1 439
1 629(L,F,T)
S
tr
tr
tr
2;3
6,9-Guaiadiene
1 442
1 441
S
0,11
1;3
cis-Muurola-3,5-diene
1 448
1 444
S
0,42
1;3
trans-Muurola-3,5-diene
1 451
1 450
1 616(T)
S
0,05
tr
1;2;3
α-Humulene
1 452
1 456
1 674(L,F,T)
S
2,80
3,55
2,38
1;2;3;4
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
Geranyl acetone
1 453
1 457
1 857(L)
IT
0,16
1;2;3
Allo-aromadendrene
1 458
1 463
S
0,48
0,47
0,59
1;3
cis-cadina-1(16),4-diene
1 461
1 464
S
tr
0,76
1;3
cis-Muurola-4(14),5-diene
1 465
1 464
S
tr
1;3
Cabreuva oxide C
1 466
1 737(L)
OS
tr
2;3
trans-cadina-1(16),4-diene
1 475
1 475
1 648(L,T)
S
0,48
0,97
tr
1;2;3
γ-Muurolene
1 478
1 478
1 675(L,F)
S
0,21
0,10
0,31
1;2;3
α-Amorphene
1 483
1 484
S
0,12
1;3
Germacrene D
1 484
1 483
1 693(L)
S
0,80
0,75
1;2;3
(E)-β-Ionone
1 487
1 922(L)
IT
tr
2;3
β-Selinene
1 489
1 489
1 700(L,F)
S
tr
tr
0,31
1;2;3
trans-Muurola-4(14),5-
diene
1 493
1 494
1 695(L)
S
0,16
0,68
0,33
1;2;3
epi-Cubebol
1 493
1 927(L)
OS
tr
2;3
Valencene
1 496
1 718(L)
S
tr
2;3
Viridiflorene
1 496
1 680(L)
S
tr
0,31
2;3
α-Selinene
1 498
1 497
1 706(L)
S
0,32
0,32
1;2;3
Pseudowiddrene
1 498
1 661(L,F)
S
tr
tr
2;3
10,11-Epoxycalamenene
1 498
1 868(F)
OS
tr
2;3
α-Muurolene
1 500
1 500
1 712(L,T)
S
0,54
0,81
1;2;3
Cuparene
1 504
1 502
S
0,05
1;3
β-Bisabolene
1 505
1 504
S
tr
1;3
Germacrene A
1 508
1 508
S
0,43
0,18
0,17
1;3
α-Bulnesene
1 509
1 506
S
tr
1;3
(E,E)-α-Farnesene
1 509
1 509
S
tr
1;3
γ-Cadinene
1 513
1 516
1 748(F,T)
S
0,17
tr
0,14
1;2;3
Cubebol
1 514
1 515
OS
0,18
1;3
Geranyl isobutanoate
1 514
1 857(L,F)
M
tr
tr
2;3
α-dehydro-ar-Himachalene
1 516
1 888(F,T)
S
tr
tr
2;3
7-epi-α-Selinene
1 520
1 760(L)
S
tr
2;3
trans-Calamenene
1 521
1 820(F, T)
S
tr
tr
2;3
δ-Cadinene
1 522
1 524
1 742(L,T)
S
tr
3,28
1;2;3;4
cis-Calamenene
1 528
1 527
1 822(L,F)
S
12,60
12,70
11,31
1;2;3
α-dehydro-ar-himachalene
1 530
1 887(L)
S
tr
2;3
trans-Cadina-1,4-diene
1 533
1 535
1 766(L,T)
S
1,00
1,38
1,40
1;2;3
10-epi-Cubebol
1 533
1 875(L)
S
tr
2;3
α-Cadinene
1 537
1 538
1 776(L)
S
0,16
0,33
1;2;3
α-Calacorene
1 544
1 545
1 896(L,T)
S
0,40
0,41
0,63
1;2;3
cis-Muurolol-5-en-4-β-ol
1 550
1 876(F)
OS
tr
2;3
Germacrene B
1 559
1 560
1 806(L,T)
S
1,94
3,65
0,07
1;2;3
(E)-Nerolidol
1 561
1 565
2 041(L,T)
OS
0,59
0,57
1;2;3;4
β-Calacorene
1 564
1 939(L,F)
S
tr
tr
2;3
Dodecanoic acid
1 565
1 566
A
0,24
1;3
Palustrol
1 567
1 570
OS
tr
1;3
Spathulenol
1 577
2 107(L,F,T)
OS
tr
0,10
tr
2;3
(Z)-Caryophyllene oxide
1 580
1 578
1 949(L,F,T)
OS
tr
tr
tr
1;2;3
(E)-Caryophyllene oxide
1 582
1 586
1 956(L)
OS
2,04
2,93
2,94
1;2;3
Gleenol
1 586
1 587
2 024(L,F,T)
OS
tr
0,27
0,50
1;2;3
Globulol
1 590
2 056(F)
OS
tr
2;3
Viridiflorol
1 592
2 062(L)
OS
tr
2;3
Hexadecane
1 600
1 600(L,T)
A
tr
tr
2;3
Ledol (epi-Globulol)
1 602
1 607
2 005(L,F,T)
OS
0,58
0,28
0,59
1;2;3
Humulene epoxide II
1 608
1 609
2 012(L,F,T)
OS
0,92
0,48
0,93
1;2;3
1,10-di-epi-cubenol
1 618
2 038(L,T)
OS
tr
tr
tr
2;3
Junenol
1 618
1 620
2 031(L,T)
OS
0,07
0,85
0,17
1;2;3
1-epi-Cubenol
1 627
1 632
2 046(L,F,T)
OS
1,87
1,41
2,45
1;2;3
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
Muurola-4,10(14)-dien-1β-
ol
1 630
2 132(L)
OS
tr
2;3
epi-α-Cadinol (tau-Cadinol)
1 638
2 156(L,T)
OS
tr
tr
tr
2;3
Caryophylla-4(12),8(13)-
dien-5α-ol
1 639
1 638
2 278(F)
OS
tr
0,16
0,48
1;2;3
Caryophylla-4(12),8(13)-
dien-5β-ol
1 639
1 641
2 272(F)
OS
0,17
1;2;3
Hinesol
1 640
1 642
OS
2,16
1;3
epi-α-Muurolol
1 640
1 643
2 172(L,F,T)
OS
tr
0,50
tr
1;2;3
α-Muurolol
1 644
1 645
2 186(L,F)
OS
tr
0,65
1;2;3
Cubenol
1 645
1 646
OS
2,45
3,24
1;3
α-Cadinol
1 652
1 658
2 216(L,F,T)
OS
1,42
1,18
0,62
1;2;3
Selin-11-en-4-α-ol
1 658
1 659
2 231(L,F,T)
OS
0,05
tr
tr
1;2;3
cis-Calamenen-10-ol
1 660
2 323(L,F)
OS
tr
tr
2;3
trans-Calamenen-10-ol
1 668
1 666
2 353(L,F)
OS
tr
0,05
1;2;3
Tetradecanol
1 671
1 676
A
1,14
1;3
Cadalene
1 675
1 678
2 198(L,F)
S
0,08
tr
0,62
1;2;3
Mustakone
1 676
2 223(F)
IT
tr
2;3
Muurola-4,10(14)-dien-1-β-
ol
1 686
1 683
OS
0,46
1;3
Eudesma-4(15),7-dien-1β-
ol
1 687
1 683
OS
0,25
0,31
1;3
Pentadecan-2-one
1 697
2 120(T)
A
tr
2;3
Eudesma-7(11)-en-4-ol
(Juniper camphor)
1 694
1 690
OS
tr
0,30
0,18
1;3
Heptadecane
1 700
1 700
A
0,09
1;3
Amorpha-4,9-dien-2-ol
1 700
1 699
2 336(L,F)
OS
0,17
tr
1;2;3
10-nor-Calamenen-10-one
1 702
2 349(F)
OS
tr
2;3
5-Hydroxy-cis-calamenene
1 713
2 325(F)
OS
tr
2;3
(2E,6Z)-Farnesol
1 714
1 712
OS
0,10
0,48
1;3
Nootkatol
1 714
1 717
2 458(L)
OS
0,05
0,30
1;2;3
Pentadecanal
1 717
1 717
A
0,05
1;3
(2Z,6E)-Farnesol
1 722
2 352(T)
OS
tr
2;3
Benzyl benzoate
1 759
1 766
2 603(L,F)
B
0,14
0,47
1;2;3
Tetradecanoic acid
1 762
1 767
2 722(T)
A
0,86
1;2;3
14-Hydroxy-α-muurolene
1 779
1 773
OS
tr
1;3
14-Hydroxy-δ-cadinene
1 803
1 806
OS
0,05
0,05
1;3
Hexadecanal
1 819
1 822
A
0,01
0,05
0,16
1;3
Hexahydrofarnesyl acetone
1 843
1 846
2 125(L)
IT
0,05
tr
0,30
1;2;3
Pentadecanoic acid
1 857
1 858
A
0,11
1;3
Benzyl salicylate
1 864
1 870
2 751(L)
B
0,05
1;2;3
Hexadecan-1-ol
1 874
1 879
2 378(T)
A
0,01
tr
0,12
1;2;3
Nonadec-1-ene
1 895
1 894
A
tr
1;3
Nonadecane
1 900
1 900
1 900(T)
A
0,40
1;2;3
Heptadecan-2-one
1 908
1 908
A
tr
1;3
(5E,9E)-Farnesyl acetone
1 913
1 906
IT
0,06
1;3
Heptadecanal
1 920
1 916
A
tr
1;3
Methyl hexadecanoate
1 921
1 923
A
tr
1;3
Isophytol
1 946
1 947
D
tr
1;3
(Z)-Hexadec-9-enoic acid
1 952
1 949
A
0,20
1;3
Geranyl benzoate
1 958
1 960
M
0,02
tr
1;3
Hexadecanoic acid
(Palmitic acid)
1 959
1 961
2 932(L,F,T)
A
tr
0,06
7,99
1;2;3;4
Ethyl hexadecanoate
1 993
1 990
2 250(T)
A
0,39
1;2;3
Eicosane
2 000
2 000
A
0,06
1;3
Manool oxide
2 009
2 002
D
0,16
1;3
UNED Research Journal, e-ISSN: 1659-441X, Vol. 16: e4863, January-December 2024 (Publicado XX-XX-2024)
Hexadecan-1-ol acetate
2 010
2 009
A
tr
1;3
(E,E)-Geranyl linalool
2 026
2 031
2 535(L,T)
D
0,05
tr
0,28
1;2;3
Heneicosane
2 100
2 100
2 100(T)
A
0,66
1;2;3
Nonadecan-2-one
2 101
2 100
A
tr
1;3
(E)-Phytol
2 107
2 612(L,F,T)
D
tr
tr
1,20
2;3
(Z)-Phytol
2 114
2 113
2 412(L)
D
0,13
0,05
1;2;3
Linoleic acid
2 134
2 132
A
0,08
0,74
1;3
Oleic acid
2 141
2 135
A
0,63
1;3
Palmitaldehyde, diallyl
acetal
2 148
2 147
A
tr
tr
1;3
Ethyl linoleate
2 155
2 162
2 518(T)
A
tr
0,43
1;2;3
Ethyl linolenate
2 169
2 169
A
tr
1;3
Nonadecan-1-ol
2 181
2 188
A
0,06
1;3
Docosane
2 200
2 200
2 200(T)
A
0,25
1;2;3;4
Eicosanal
2 219
2 220
A
tr
1;3
Tricosane
2 300
2 300
2 300(T)
A
0,53
1;2;3;4
Heneicosan-2-one
2 306
2 305
A
0,08
1;3
Tetracosane
2 400
2 400
2 400(T)
A
0,33
1;2;3;4
Pentacosane
2 500
2 500
2 500(T)
A
0,70
1;2;3;4
Hexacosane
2 600
2 600
2 600(T)
A
0,19
1;2;3;4
Heptacosane
2 700
2 700
2 700(T)
A
0,07
1;2;3;4
Octacosane
2 800
2 800
2 800(T)
A
tr
1;2;3;4
Nonacosane
2 900
2 900
2 900(T)
A
tr
1;2;3;4
TOTAL
91,29
86,65
74,56
No. of compounds
160
199
144
Compound class
Total monoterpenoids
42,66
38,63
6,84
Monoterpene
hydrocarbons (M)
36,98
30,75
6,20
Oxygenated monoterpenes
(OM)
5,68
7,88
0,64
Total sesquiterpenoids
44,67
44,69
46,45
Sesquiterpene
hydrocarbons (S)
34,06
32,36
32,84
Oxygenated sesquiterpenes
(OS)
10,61
12,33
13,61
Diterpenoids (D)
0,18
0,05
1,64
Irregular terpenoids (IT)
0,24
tr
0,52
Aliphatics (A)
2,55
2,17
18,77
Benzenoids (B)
0,91
1,01
0,29
Miscellaneous (Misc.)
tr
0,1
0,05
aCompounds listed in order of elution from poly-(5% phenyl 95% dimethylsiloxane) type column. bRILit = DB-5
(Adams, 2007; Wallace, 2021). cRIExp = Retention index relative to C8-C32 n-alkanes on the SLB™-5ms column.
dSw10Exp = Experimental retention index on Supelcowax™ 10. eIM = Identification methods: 1 = Retention
index on poly-(5% phenyl/95% methylsiloxane) type column; 2 = Retention index on Supelcowax™10; 3 = MS
spectra; 4 = Standard. ftr = Traces (<0,005%). *(Romanenko & Tkachev, 2006; Collin et al., 2010). Major
terpenoids are in boldface.
