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Chemical composition of volatiles

from Opuntia littoralisOpuntia ficusindica, and Opuntia prolifera growing
on Catalina Island, California
a

Cynthia R. Wright & William N. Setzer

Department of Chemistry, University of Alabama in Huntsville,

Huntsville, AL35899, USA
Published online: 20 Dec 2013.

To cite this article: Cynthia R. Wright & William N. Setzer , Natural Product Research (2013):
Chemical composition of volatiles from Opuntia littoralisOpuntia ficus-indica, and Opuntia prolifera
growing on Catalina Island, California, Natural Product Research: Formerly Natural Product Letters,
DOI: 10.1080/14786419.2013.867345
To link to this article: http://dx.doi.org/10.1080/14786419.2013.867345

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Natural Product Research, 2013

http://dx.doi.org/10.1080/14786419.2013.867345

SHORT COMMUNICATION
Chemical composition of volatiles from Opuntia littoralis, Opuntia cusindica, and Opuntia prolifera growing on Catalina Island, California
Cynthia R. Wright and William N. Setzer*
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA

Downloaded by [Moskow State Univ Bibliote] at 07:19 11 January 2014

(Received 13 August 2013; nal version received 10 November 2013)

The essential oils from the cladodes of Opuntia littoralis, Opuntia cus-indica and
Opuntia prolifera growing wild on Santa Catalina Island, California, were obtained by
hydrodistillation and analysed by gas chromatography-mass spectrometry (GC MS).
Terpenoids were the dominant class of volatiles in O. littoralis, with the two main
components being the furanoid forms of cis-linalool oxide (10.8%) and trans-linalool
oxide (8.8%). Fatty acid-derived compounds dominated the essential oil of O. cusindica with linoleic acid (22.3%), palmitic acid (12.7%), lauric acid (10.5%) and
myristic acid (4.2%) as major fatty acids. O. prolifera oil was composed of 46.6%
alkanes and the primary hydrocarbon component was heptadecane (19.2%). Sixteen
compounds were common to all the three Opuntia species.
Keywords: Cactaceae; essential oil composition; linalool oxide; lauric acid; palmitic
acid; linoleic acid; (9Z)-tricosene

1. Introduction
Opuntia littoralis (Engelm.) Cockerell, Opuntia cus-indica (L.) Mill. and Opuntia prolifera
Engelm. are species of cactus family (Cactaceae) and are distributed on the coastal slopes of the
Pacic Ocean from Southern California to Northern Mexico (Baldwin et al. 2012). O. littoralis
and O. prolifera are native to the coastal slopes of the California Channel Islands, including
Santa Catalina Island (Baldwin et al. 2012).
The at, eshy pads of O. littoralis and O. cus-indica were split and used by Native
Americans to bind wounds and burns (Nobel 1994). The Chumash people had used O. littoralis
as a poultice for wounds (Adams et al. 2010). O. cus-indica is a popular herbal medicine in
Mexico where it is used for diabetes, hypercholesterolaemia, obesity, alcohol-induced hangover,
colitis, diarrhoea, benign prostatic hypertrophy and atherosclerosis (Rodriguez-Fragoso et al.
2008). Extracts of O. cus-indica have also been used to treat ulcers (Galati et al. 2001). The
pharmacological activities of O. cus-indica have been reviewed (Kaur et al. 2012). Although
there is a rich ethnobotanical history of Opuntia use, to our knowledge, there has been only
limited study of the volatiles of these plants. The oral volatiles of O. cus-indica from Italy (De
Leo et al. 2010) and from Tunisia (Ammar et al. 2012), and the fruit essential oils of cultivated
O. cus-indica from Catania, Italy (Arena et al. 2001) and Sicily (Zito et al. 2013) have been
reported. In this work, we present the chemical compositions of the essential oils from the
cladodes of O. littoralis, O. cus-indica and O. prolifera growing wild on Santa Catalina Island,
California.

*Corresponding author. Email: wsetzer@chemistry.uah.edu

q 2013 Taylor & Francis

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C.R. Wright and W.N. Setzer

2. Results and discussion

The essential oils of O. littoralis, O. cus-indica and O. prolifera were obtained in low yields:
0.28%, 0.0012% and 0.22%, respectively. A total of 106 compounds were identied in O.
littoralis, representing 94.5% of the composition (Table S1). Sixty-ve compounds were
identied in O. cus-indica, representing 96.5% of the oil composition (Table S2). Sixty-two
compounds were identied in O. prolifera, which accounts for 94.7% of the oil composition
(Table S3).
O. littoralis oil was made up of 47.2% terpenoid-derived compounds, 29.1% fatty-acid
derived compounds, 7.6% alkanes and 10.6% furanoid and benzenoid compounds. The
compounds of greatest concentration in O. littoralis were cis-linalool oxide (10.8%), translinalool oxide (8.8%), palmitic acid (4.4%), 2-furaldehyde (3.8%), 2-hexanol (3.5%), 7,10
epoxy-2,6,10-trimethyl-2,5,11-dodecatriene (3.4%), nonanal (3.4%) and lauric acid (2.7%).
O. littoralis oil also contained small amounts of santene (0.3%), vitispirane (1.0%) and (9Z)
tricosene (0.8%). Santene is an unsaturated terpene found in East Indian sandalwood oil
(Demole et al. 1976) and black spruce needles (von Rudloff 1975). Vitispirane is a norisoprenoid
found in grapes and wine (Eggers et al. 2006). (9Z)-Tricosene (muscalure) is a sex pheromone
produced by female common houseies, Musca domestica, to attract males (Carlson & Beroza
1973). The high concentrations of furanoid linalool oxides in O. littoralis cladode essential oil
were, for us, unexpected. Linalool oxides are important fragrance components of oral
(Knudsen & Tollsten 1995; Raguso & Pichersky 1999; Pettersson et al. 2004; Maia & Andrade
2009) and fruit (Marais 1983; Heidlas et al. 1984) volatiles, including Cereus peruvianus
(Cactaceae) fruit (Ninio et al. 2003; Sitrit et al. 2004), but their presence in cactus pads seems
unusual.
Fatty acids dominated the essential oil of O. cus-indica pads with linoleic acid (22.3%),
palmitic acid (12.7%), lauric acid (10.5%) and myristic acid (4.2%) as the most abundant.
In addition to fatty acids, there were also notable quantities of (E)-phytol (8.0%), (9Z)-tricosene
(muscalure, 6.7%) and p-vinylguaiacol (3.4%). In contrast, O. cus-indica fruit grown in
Catania, Italy, was found to be primarily composed of (2E)-hexen-1-ol (54.7 58.0%) and 1
hexanol (25.2 29.5%) (Arena et al. 2001). Neither of these alcohols was detected in the O. cusindica cladode oil in this study. The fruit essential oil of a cultivar of O. cus-indica growing in
Sicily did contain large quantities of palmitic acid (33.0%) and fatty acid esters (14.0%) (Zito
et al. 2013). Fatty acids have been found to be relatively abundant in the oral essential oils of
O. cus-indica (Ammar et al. 2012). Long-chain alkanes made up a signicant portion (8.1%) of
the O. cus-indica cladode oil in this study. Large quantities of alkanes have been found in the
skin volatiles from O. cus-indica fruit (Zito et al. 2013) as well as O. cus-indica owers
(De Leo et al. 2010). O. cus-indica cladode oil contained only small quantities of linalool and
linalool oxides, in contrast to O. littoralis cladode oil (see earlier). (9Z)-Tricosene was found in
larger quantities in O. cus-indica oil than in O. littoralis oil (see earlier). Interestingly, (9Z)
pentacosene (1.4%), which is a sex pheromone of several insect species (Uebel et al. 1977;
Ginzel et al. 2003), was also found in O. cus-indica oil.
O. prolifera oil was dominated by alkanes (47.1%), and the primary component was
heptadecane (19.2%). In addition to normal alkanes, e.g. tetradecane (1.3%), pentadecane
(5.1%) and hexadecane (3.8%), there were several branched alkanes present in O. prolifera oil,
including norpristane (1.0%), pristine (1.4%) and phytane (1.0%). Fatty aldehydes (18.4%), both
saturated and unsaturated, were also common in O. prolifera oil. Another notable component in
O. prolifera was p-menth-4-en-3-one (3.5%), which has been identied in Ficus (Ogunwande
et al. 2008) and Ephedra (He et al. 2013) oils.
None of the three cactus plants examined in this work shared any major components in
similar percentages, and there were only 16 compounds found in all three cactus species.

Natural Product Research

Compounds common to all the three species were trans-linalool oxide, geranyl acetone, (E)-b
ionone, pentadecane, lauric (dodecanoic) acid, heptadecane, myristic (tetradecanoic) acid,
octadecane, nonadecane, palmitic (hexadecanoic) acid, heneicosane, (E)-phytol, docosane,
hexacosane, heptacosane and nonacosane.

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3. Conclusions
In this work, we have examined the volatile chemicals from the stems (cladodes) of three
different cactus species native to and growing wild on Santa Catalina Island, California. To our
knowledge, this is the rst study of cladode volatile chemistry, and illustrates the diversity of the
phytochemistry of the Cactaceae.
Supplementary material
Supplementary details relating to this article are available online, alongside Tables S1 S3.
Acknowledgements
The authors are grateful to Mr. Ben Coleman of the Catalina Island Conservancy for identication and
collection of the cactus specimens in this study.

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