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Ximenynic acid: A versatile lead molecule for drug development

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Review Article Natural chemistry
International Journal of Pharma and Bio Sciences
Ph.D research scholar, JJT university, Jhunjhunu, Rajasthan, India.
Dr. D. Y. Patil institute of Pharmaceutical research and sciences, Pimpri, India.
Vice president clinical research, Mprex healthcare, Pune, India
With the growing concern over the unhealthy consequences of using chemical preservatives like sodium
benzoate, benzoic acid the food industry, investigation towards natural and herbal substances has
been increasing. Ximenynic acid (or Santalbic acid) is one of the few acetylenic fatty acids predominantly
exists in the seed oil of Santalaceae, Olacaceae, and Opiliaceae families. A number of in vitro and in vivo
studies have revealed therapeutic effects of ximenynic acid against various diseases. In general,
ximenynic acid exhibits many biological activities and pharmacological effects, including antibacterial,
antifungal, anti-inflammatory activities. However, a detailed analysis of the pharmacology, phytochemistry
and analytical methods for characterisation of ximenynic acid is scarce. The aim of present review is to
coherently discuss some of the most important applications of ximenynic acid and unites the results
obtained from several studies reporting the biological properties of this molecule. .The present review
paper reveals new perspective for investigations of biological properties of ximenynic acid and developing
novel formulations.
Ximenynic acid, Santalaceae, Pharmacological activities, Phytochemistry, Bioavailability.
Received on: 19-08-2019
Revised and Accepted on: 03-10-2019
Creative commons version 4.0
Ph.D research scholar, JJT university, Jhunjhunu, Rajasthan, India.
Int J Pharma Bio Sci 2019 Oct; 10(4): (P) 93-99 ISSN 0975-6299
This article can be downloaded from
Fatty acids turn out to be building blocks of a huge
group of natural substances called lipids.
In foods,
they are generally present as triacylglycerols (fats and
oils) and glycerophospholipids. To an extent, fatty acids
are also established in the appearance of partial
acylglycerols (Mono and diacylglycerols). They also
occur as esters with other hydroxy compounds (e.g.
sterols), amides (sphingolipids), and free compounds.
Acetylenic acids, are a class of fatty acids having one or
more triple bonds . They are found in plants, fungi,
microbes, and marine organisms.
They have been
accounted to hold a miscellany of pharmacological
properties, including antibacterial, antifungal,
antiparasitic, and antitumor activities.
The set of the
acetylenic fatty acids with a chain length of seventeen
and twenty-one carbon atoms are very huge. Fourty of
the one hundred and thirty-six specified compounds
occur are natural, others are synthetic. Almost all of the
naturally occurring acetylenic fatty acids were identified
in higher plants but a few of the C
and C
acids were
found in mosses
and microorganisms. Chemically
they have maximum three double or four triple bonds
but overall not more than five unsaturated bonds are
present per molecule.
Santalbic acid (or ximenynic
acid), octadeca-11-trans-en-9-ynoic acid, is one of the
few acetylenic fatty acids occurring at higher levels in
plant seed oils.
Similar to the numerous unusual fatty
acids, ximenynic acid is a distinguishing component of
the seed oils of only a few closely connected plant
families. It crops up in the angiosperm order Santalales,
i.e. in the conventional ‘‘santalalean’ plant families
Santalaceae, Olacaceae and Opiliaceae, and has not
been found outside the Santalales
. In the most recent
two decades, however, these original families have
been divided and numerous novel plant family names
and circumscriptions have been projected.
With few
exceptions, plants with ximenynic acid in their seeds
originate frequently on those continents that were
formed after the break-up of the old Gondwanaland
In certain plants, ximenynic acid can
attain up to 95.0 % of the total seed oil fatty acids
pretty often levels above 70 % of total fatty acids have
been found. Since ximenynic acid holds a chemically
fascinating reactive conjugated enyne group, it could be
of significance as a raw material for the chemical
industry. In addition to this, seed oil fatty acids with
unusual functional groups are also of significant curiosity
in plant chemotaxonomy and plant evolution (Table 1).
While the demand for ximenynic acid has a growing
trend, it is essential to review the most current
biosynthesis methods of this ximenynic acid. The aim of
this article is to provide an outline of the current
methods for the extraction, identification, and purification
of ximenynic acid, as well as the current findings
regarding its pharmacological activities and the different
approaches carried out to boost the use of ximenynic
acid in diverse formulations.
Table 1
Physico-chemical properties of ximenynic acid
Chemical Names
Santalbic acid; Trans
ynoic acid
2 Molecular Formula C
3 CAS Number 557-58-4
4 Molecular Weight 278.436 g/mol
6 Boiling Point 416.79 °C.
7 Density 0.9±0.1 g/cm
8 Vapour Pressure 0.0±2.1 mmHg at 25°C
9 Index of Refraction 1.484
Molar Refractivity 85.1±0.3 cm
LogP 6.76
Flash Point 200.0±18.7 °C
Polar Surface Area
Polarizability 33.7±0.5 10
Surface Tension 37.5±3.0 dyne/cm
logP (o/w) 6.254 (est)
Soluble in water, 0.04157 mg/L
Nickrentet al.(2010)proposed a revised classification of plants belonging to Santalaceae and Olacaceaefamilies.
number of plants mentioned in Table2can currently be considered to be members of a new plant family.
Int J Pharma Bio Sci 2019 Oct; 10(4): (P) 93-99 ISSN 0975-6299
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Table 2
Occurrence of santalbic acid in various seed oils
Santalum album Santalaceae
84.00 GLC-area-% Morris LJ 1966
Santalumobtusifolium Santalaceae
71.50 GLC-area-% Vickery JR 1984
Exocarpossparteus Santalaceae
69.70 GLC-area-% SundarRao K 1992
Exocarposaphyllus Santalaceae
67.50 GLC-area-% SundarRao K 1992
Olaxbenthamiana Olacaceae 63.00 GLC-area-% Aitzamuller K 1996
Osyris alba Santalaceae
57.10 GLC-area-% Mikolajczak KL
Cansjerarheedii Opiliaceae 55.40 GLC-area-% Aitzamuller K 1996
Exocarposcupressiformis Santalaceae
53.20 GLC-area-% Aitzamuller K 1996
Santalumacuminatum Santalaceae
52.50 GLC-area-% Aitzamuller K 1996
Santalummurrayanum Santalaceae
45.00 GLC-area-% Hatt HH 1956
Comandrapallida Santalaceae
43.00 GLC-area-% Mikolajczak KL
Santalumspicatum Santalaceae
37.27 GLC-area-% Liu Y 1995
Ximeniaamericana Olacaceae 26.50 GLC-area-% Rovesti Paolo 1979
Ximeniacaffra Olacaceae 24.30 GLC-area-% Ligthelm SP 1954
Ximenia spp. Olacaceae 24.00 GLC-area-% Ligthelm SP 1952
Ximeniacaffra var. natalensis Olacaceae 22.00 GLC-area-% Ligthelm SP 1954
Olacaceae 21.90 GLC-area-% Ligthelm SP 1954
Jodinarhombifolia Santalaceae
20.30 GLC-area-% Spitzer V 1994
Leptomeriaaphylla Santalaceae
19.50 GLC-area-% Hatt HH 1960
Agonandrabrasiliensis Opiliaceae 18.80 GLC-area-% Aitzamuller K 2000
Exocarposcupressiformis Santalaceae
16.70 GLC-area-% Badami RC 1981
Pyrulariapubera Santalaceae
10.00 GLC-area-% Badami RC 1981
Agonandraexcelsa Opiliaceae 8.90 GLC-area-% Aitzamuller K 1997
Agonandrasilvatica Opiliaceae 7.60 GLC-area-% Aitzamuller K 2000
Opiliaamentacea Opiliaceae 7.60 GLC-area-% Aitzamuller K 1996
Heisteriaacuminata Olacaceae 7.50 GLC-area-% Aitzamuller K 1999
Agonandraexcelsa Opiliaceae 5.00 GLC-area-% Aitzamuller K 2000
Agonandrasilvatica Opiliaceae 4.80 GLC-area-% Aitzamuller K 2000
Heisteriasilvanii Olacaceae 3.49 GLC-area-% Spitzer V 1997
Pyrulariaedulis Santalaceae
1.40 GLC-area-% Zhang JY 1989
Ongokea gore Olacaceae 1.00 GLC-area-% Morris LJ 1963
Acanthosyrisspinescens Santalaceae
1.00 GLC-area-% Powell RG 1966
Malaniaoleifera Olacaceae 0.17 GLC-area-% Aitzamuller K 1992
Bulocket al(1963), in their study on “Acetylenic Fatty
Acids in Seeds and Seedlings of Sweet Quandong”
have obtained stones of the fruit of Santalum
acuminatum from the Human Nutrition Unit, University of
Sydney. These stones have a diameter of about 1 cm
and look like small peach stones. A stone was busted
and the kernel was ground which was further extracted
with chloroform and methanol to yield oil. The oil was
saponified with 80% methanolic potassium hydroxide
(0.5 mol/l) for 2 h at 70°C. After acidification with
aqueous sulphuric acid, the free fatty acids were
extracted with light petroleum and diethyl ether. A fatty
acids comprising of ximenynic acid, oleic acid and
some minor other fatty acids were obtained. As the
methyl esters of ximenynic acid and oleic acid could not
be separated by reverse phase, purification was
performed on a straight phase , with hexane/isopropanol
as the mobile phase. This resulted crude methyl ester
mixture. After saponification, ximenynic acid with a
purity of 95%, containing 5% eicosenoic acid was
Yandi et al (1996), in their study on
“separation and identification of ximenynic acid isomers
in the seed oil of Santalum spicatumR Br. as their 4,4-
dimethyloxazoline derivatives” extracted seed oil from
the mature seeds of S. spicatum by grinding seed
samples and extracting with hexane in a Soxhlet
apparatus for 2 h. Anhydrous sodium sulfate was used
to dry the solution followed by removal of the solvent
using the Buchi rotatory evaporator under reduced
pressure at 60°C to yield a viscous, pale yellow oil.
Isolation of trans ximenynic acid was done by refluxed a
sample of the oil with potassium hydroxide in 95%
ethanol (200 mL) for 1 h. The mixture was cooled and
acidified with 6 M HCI to pH 1. Ximenynic acid was
obtained by crystallization from hexane.
Recrystallization from hexane gave trans-ximenynic acid
as white flakes. The seed oil of Santalum spicatumwas
found to contain a significant amount of ximenynic acid,
a long-chain acetylenic fatty acid, as a major component
(34%). The identity of trans-ximenynic acid was
confirmed after isolation by ultraviolet, infrared,
H and
C nuclear magnetic resonance (NMR) spectroscopy
and gas chromatography/ mass spectrometry (GC/MS).
The cis isomer of ximenynic acid was also found (<1%)
in some samples. The cis and trans isomers were
Int J Pharma Bio Sci 2019 Oct; 10(4): (P) 93-99 ISSN 0975-6299
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characterized by GC/MS comparison of their methyl
esters and 4,4-dimethyloxazoline derivatives.
Ximenynic acid has shown a wide range of
pharmacological applications due to its significant
antioxidant properties. The Patent filing of formulations
containing ximenynic acid has increased over the past
few years. Conventionally, ximenynic acid is used as
antimicrobial, antifungal, and antiallergic agents. Current
research has shown its pharmacological benefits for the
treatment of various chronic diseases such as cancer,
skin diseases, hair loss, and hypercholesterolemia. Add
Anti-proliferation activities of Ximenynic acid were
evaluated by Fang et al. (2016) in HepG2 human
hepatoma cell line and the underlying mechanisms.
They demonstrated the anti-proliferation and pro-
apoptosis activities of ximenynic acid by cell viability
assay and flow cytometry analysis. The results revealed
that ximenynic acid blocked G1/S phase transition by
inhibiting the protein expression of the cell cycle
associated protein general control of amino acid
synthesis yeast homolog like 2 (GCN5L2), and the
mRNA expression of cyclin D3 and cyclin E1. They
found that ximenynic acid may inhibit the growth of
HepG2 cells by selective inhibition of COX-1 expression,
which leads to cell cycle arrest, and alters the apoptosis
pathway and expression of angiogenic factors.
Dhanushka et al. (2012) isolated ximenynic acid from S.
acuminatum. Their studies revealed that ximenynic acid
exhibited anti- inflammatory properties on several rat
peritoneal leukocytes. Further studies on ximenynic acid
revealed that it alters the cytochrome P-450 enzyme in
rats, indicating a pharmacological change in the hepatic
In 2017, Gautam and his co-workers assessed the
antimicrobial screening of petroleum ether and ethanol
extracts of Santalum album seeds by disc diffusion
method on two gram-positive bacteria, Bacillus subtilis,
Staphylococcus aureus, gram negative Pseudomonas
aeruginosa, Escherichia coli and the fungus Candida
albicans. The results of the investigations indicated
possible high potency of petroleum ether extract due to
ximenynic acid which could serve as chemotherapeutic
Jones et al. (1995) determined the degree of
antimicrobial activity of ximenynic acid, which is a major
constituent of the oil. They also found that ximenynic
acid was an inhibitor of Gram-positive bacteria and a
number of pathogenic fungi in standardized
Misra and Dey (2012) evaluated the
antibacterial properties of the five extracts and
compared with sandalwood oil by screening against nine
Gram-negative and five Gram-positive bacterial strains
by disc diffusion, agar spot, and TLC bioautography
methods. Bioautography results indicated the presence
of potential antimicrobial constituents in somatic embryo
extracts and sandalwood oil.
According to Mavundza et al. (2016), ximenynic acid
exhibited larvicidal activity against laboratory-reared
larvae of An. arabiensis mosquitoes, a potent malaria
vector in South Africa. A dose response bioassay was
performed for pure compounds to determine the EC50
Croft et al. (1987) tested the effects of ximenynic acid on
leukotriene B4 and thromboxane B2 production in rat
peritoneal leukocytes and compared them with non-
acetylenic compounds, linoleic and ricinoleic acids.
Ximenynic acid exhibited significant dose dependent
inhibition of leukotriene B4, thromboxane B2 and 6-
ketoprostaglandin F1 alpha production. These results
indicate that ximenynic acid differentially inhibits the
cyclooxygenase and lipoxygenase products of
stimulated leukocytes and that at high doses of these
fatty acids the effect on these products may be partially
due to inhibition of phospholipase A2.
In another study undertaken by Jones et al. in 1994 on
ximenynic acid in hepatic cytochrome P-450, it was
found that the Hepatic microsomal cytochrome P-450
activity in animals fed for 20 days was significantly
higher (P < 0.05) than in controls. Histopathological
examination did not reveal any lesions in the tissues of
any animal fed quandong oil. The fact that ximenynic
acid was readily absorbed and widely distributed in
tissues was associated with an elevated level of hepatic
cytochrome P-450.
Nugteren and Christ in 1987 pinpointed a number of
fatty acids having moderate inhibitory potency, viz.
ximenynic acid, crepenynic acid, columbinic acid and
timnodonic acid (the precursor of prostaglandin E3).
Yandi and Robert designed the study to obtain basic
information on changes in tissue fatty acid composition
and on the metabolic fate of ximenynic acid in mice fed
with sandalwood seed oil (SWSO)-enriched diet. They
reported that the fatty acid composition of liver and
adipose tissue were markedly altered by dietary fats,
and mice fed on an SWSO-enriched diet were found to
contain ximenynic acid but only in low concentration
(0.3–3%) in these tissues. Ximenynic acid was not
detected in brain.
Dhanushka et al. (2012) further investigated that a
highly purified ximenynic acid increases cellular
detoxification, anti-oxidation capacity. It leads to a
strengthening of the extracellular matrix (ECM),
increases dermal strength and improves skin elasticity.
Int J Pharma Bio Sci 2019 Oct; 10(4): (P) 93-99 ISSN 0975-6299
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Nugteren and Christ (1987), studied the effect of
Ximenynic acid on prostaglandin biosynthesis. It was
found that acetylenic acids with unsaturated eighth and
tenth positions demonstrate a sixteen fold higher
potency in inhibiting prostaglandins than acetylenic fatty
acids with ninth and eleventh position unsaturation.
Thus ximenynic acid is considered a moderate
In addition, Sun et al. proposed that
plant derived acetylenic fatty acids block lipoxygenase
more than cyclooxygenase, and the capacity of
inhibition depends upon the chain length and the
positioning of unsaturation.
Sok et al. (1982) also
reported that acetylenic fatty acids inhibit leukotriene
activity more efficiently than prostaglandins.
findings substantiate that disruption of the eicosanoid
pathway by acetylenic fatty acids including ximenynic
acid acts differently to non-steroidal anti-inflammatory
drugs (NSAIDs). Croft et al (1987) have reported that
ximenynic acid inhibits leukotriene B4, thromboxane B2,
and 6-ketoprostaglandin F1α - prostaglandins of the
sheep vascular tissue. Based on these studies, the
authors proved that ximenynic acid produced a
vasodilative effect and increased blood circulation.
Bombardelli et al. (1994) first reported the microvascular
kinetic activity of ximenynic acid. This activity was first
evaluated on patients suffering from cellulitis or venous
Subsequently, the microvascular kinetic
activity of ximenynic ethyl ester (a semi-synthetic
derivative of natural ximenynic acid) was patented in
1992 as a treatment for cellulitis, hair loss and erectile
Bombardelli et al. (1994) demonstrated
that the application of ximenynic acid ester increased
microvascular blood flow and capillary density. Patients
experienced significant reduction symptoms without any
marked adverse reactions recorded; more over the
dermal appeal at the site of application has increased
Commercial patents have claimed that
formulations containing ximenynic acid improved lipid
metabolism and also skin appeal when incorporated to
Messenger and Rundegren (2004), reported that neither
ximenynic acid nor other acetylenic fatty acids have
been reported to show any anti-androgenic
Inhibition of leukotrienes and thromboxane
would also result in a reduction of intracellular calcium
ions by inhibiting the activation of the IP3 receptor, but
the result would produce a similar vasodilatory effect.
Ximenynic acid ethyl ester (and its vasoactive
properties) was patented as a treatment and prevention
of hair loss by Bombardelli et al. (1997).
According to
Glynn et al,a topical formula with ximenynic acid
together with several other natural ingredients is used
for modulation and re-growth of hair.
The present review provides information about isolation,
biological and pharmacological activities of ximenynic
acid which can be used as an excipient or an active in
novel formulations. Ximenynic acid is acetylenic fatty
acids, that are consumed in fruits, vegetables, and plant
derived beverages. Additionally, there are fewer
formulations in the market containing ximenynic acid in
different dosage forms either alone or in combination
with other active ingredients. Both conventional and
innovative methods have been reported for the
extraction of ximenynic acid from natural sources.
Accurate comparison between procedures is not
straightforward because of the variance in the plant
materials. However, current trends in the extraction
process have been focused on the discovery and design
of green and sustainable extraction techniques to
optimize the extraction of ximenynic acid. Numerous
studies have reported diverse pharmacological activities
of ximenynic acid, including antioxidant, anti-
inflammatory, anticancer, and antimicrobial and skin
disorder.However, the observed pharmacological effects
do not always translate into the clinic because of the
poor bioavailability, less information of ximenynic acid.
To overcome this barrier, researchers have proposed
different strategies thatwill enhance bioavailability and
ultimately give health benefits. The present review
provides information about ximenynic acid. One major
challenge that the food and pharmaceutical industry
faces is toprovide basic-applied research and
technology innovations (e.g. ximenynic acid delivery
systems, synthesis of ximenynic acid derivatives) into
safe products providing health benefits for the
Mr.Shivatare R conceptualized and gathered the data
with regard to this Review. Dr.Nagore D, Dr.Ganu G,
and Dr.Chitlange S ranalyzed these data and necessary
inputs were given towards the designing of the
manuscript. All authors discussed the introduction,
isolation and pharmacological action to the final
Conflict of interest declared none.
1. Akoh CC, Min DB, ed. Food Lipids. 3rd ed. New
York: CRC Press; 2008. Available from:
2. Velíšek J, Cejpek K. Biosynthesis of food
constituents: Lipids. 2. Triacylglycerols,
glycerophospholipids, and glyceroglycolipids
&amp;ndash; a review. Czech J Food Sci.
DOI: 10.17221/3321-cjfs
3. Velíšek J CK. Biosynthesis of food constituents:
Lipids. 1. Fatty acids and derived compounds—A
review. Czech J food Sci. 2006;24(5):193–216.
DOI: 10.17221/3317CJF
Int J Pharma Bio Sci 2019 Oct; 10(4): (P) 93-99 ISSN 0975-6299
This article can be downloaded from
4. Bohlmann F. Chemistry and biology of naturally
occurring acetylenes and related compounds.
(NOARC). In: Lam. J, ed. Bioactive Molecules,
Amsterdam, New York; 1988. 1–19 p.
5. Xu T, Tripathi SK, Feng Q, Lorenz MC, Wright
MA, Jacob MR, et al. A Potent Plant-Derived
Antifungal Acetylenic Acid Mediates Its Activity by
Interfering with Fatty Acid Homeostasis.
Antimicrob Agents Chemother. 2012;56(6):2894–
DOI: 10.1128/AAC.05663-11
6. Carballeira NM. New advances in fatty acids as
antimalarial, antimycobacterial and antifungal
agents. Prog Lipid Res. 2008;47(1):50–61.
DOI: 10.1016/j.plipres.2007.10.002
7. Siddiq A, Dembitsky V. Acetylenic Anticancer
Agents. Anticancer Agents Med Chem. 2008 Feb
DOI: 10.2174/187152008783497073
8. Jamieson GR, Reid EH. Lipids of Fontinalis
antipyretica. Phytochemistry. 1976;15(11):1731–
9. Vierengel A, Kohn G, Vandekerkhove O,
Hartmann E. 9-octadecen-6-ynoic acid from
Riccia fluitans. Phytochemistry. 1987;26(7):2101–
10. Kohn G, Vandekerkhove O, Hartmann E,
Beutelmann P. Acetylenic fatty acids in the
ricciaceae (hepaticae). Phytochemistry.
11. Kohn G, Demmerle S, Vandekerkhove O,
Hartmann E, Beutelmann P. Distribution and
chemotaxonomic significance of acetylenic fatty
acids in mosses of the dicranales. Phytochemistry
[Internet]. 1987 Jan;26(8):2271–5.
DOI: 10.1016/S0031-9422(00)84699-3
12. Kohn G, Hartmann E, Stymne S, Beutelmann P.
Biosynthesis of Acetylenic Fatty Acids in the Moss
Ceratodon purpureus (Hedw.) Brid. J Plant
Physiol. 1994;144(3):265–71.
DOI: 10.1016/S0176-1617(11)81185-5
13. Diedrich M, Henschel K-P. The natural
occurrence of unusual fatty acids Part 3.
Acetylenic fatty acids. Food / Nahrung.
DOI: 10.1002/food.19910350214
14. Aitzetmüller K, Matthäus B, Friedrich H. A new
database for seed oil fatty acids the database
SOFA. Eur J Lipid Sci Technol. 2003
15. II A. An update of the Angiosperm Phylogeny
Group classification for the orders and families of
flowering plants: APG II. Bot J Linn Soc. 2003
16. III A. An update of the Angiosperm Phylogeny
Group classification for the orders and families of
flowering plants: APG III. Bot J Linn Soc. 2009
DOI: 10.1111/j.1095-8339.2009.00996.x
17. Nickrent DL, Malécot V, Vidal-Russell R DJ. A
revised classification of Santalales. Taxon.
DOI: 10.2307/25677612
18. Gunstone FD, Russell WC. Fatty acids. Part III.
The constitution and properties of santalbic acid.
J Chem Soc. 1955;3782.
19. Aitzetmüller K. Capillary GLC fatty acid
fingerprints of seed lipids—a tool in plant
chemotaxonomy? J High Resolut Chromatogr.
1993 Aug;16(8):488–90.
DOI: 10.1002/jhrc.1240160809
20. Aitzetmüller K. Fatty acid patterns of
Ranunculaceae seed oils: phylogenetic
relationships. In: Systematics and Evolution of the
Ranunculiflorae. Vienna: Springer Vienna; 1995.
p. 229–40.
21. Wolff RL, Lavialle O, Pédrono F, Pasquier E,
Deluc LG, Marpeau AM, et al. Fatty acid
composition of pinaceae as taxonomic markers.
Lipids. 2001 May;36(5):439–51.
DOI: 10.1007/s11745-001-0741-5
22. Aitzetmüller K. Santalbic acid in the plant
kingdom. Plant Syst Evol. 2012 Nov
DOI: 10.1007/s00606-012-0678-5
23. Nugteren DH, Christ-Hazelhof E. Naturally
occurring conjugated octadecatrienoic acids are
strong inhibitors of
prostaglandin biosynthesis. Prostaglandins.
DOI: 10.1016/0090-6980(87)90022-0
24. Ximenynic acid, CID=5312688 [Internet]. National
Center for Biotechnology Information: PubChem
Database;2019 [cited 2019 Sept 19]. Available
nynic-acid 9]
25. Ximenynic acid [Internet]. TGSC Information
System; 2019 [cited 2019 Sept 19] Available
26. MFCD00210569 [Internet]. ChemSpider; 2019
[cited 2019 Sept 19] Available from:
Structure.4472113.html l
27. Bu’Lock JD, Smith GN. Acetylenic fatty acids in
seeds and seedlings of sweet quandong.
Phytochemistry. 1963;2(3):289–96.
28. Liu YD, Longmore RB, Fox JED. Separation and
identification of ximenynic acid isomers in the
seed oil of Santalum spicatum R.Br. as their 4,4-
dimethyloxazoline derivatives. J Am Oil Chem
Soc. 1996;73(12):1729–31.
DOI: 10.1007/BF02517979
29. Lie Ken Jie MSF, Pasha MK, Ahmad F.
Ultrasound-assisted synthesis of santalbic acid
and a study of triacylglycerol species inSantalum
album (Linn.) seed oil. Lipids. 1996;31(10):1083–
DOI: 10.1007/bf02522466
30. Cai F, Li J, Liu Y, Zhang Z, Hettiarachchi DS, Li
D. Effect of ximenynic acid on cell cycle arrest
and apoptosis and COX-1 in HepG2 cells. Mol
Int J Pharma Bio Sci 2019 Oct; 10(4): (P) 93-99 ISSN 0975-6299
This article can be downloaded from
Med Rep. 2016 Dec;14(6):5667–76.
DOI: 10.3892/mmr.2016.5920
31. Hettiarachchi DS, Liu Y, Jose S, Boddy MR, Fox
JED, Sunderland B. Assessment of Western
Australian sandalwood seeds for seed oil
production. Aust For. 2012;75(4):246–50.
DOI: 10.1080/00049158.2012.10676409
32. Vadnere GP, Usman MR, Lodhi S, Patil V.
Phytochemical investigation and in vitro
antimicrobial screening of santalum album seeds
extracts. Int J Pharm Pharm Sci. 2017;9(11):117-
33. Jones GP, Rao KS, Tucker DJ, Richardson B,
Barnes A, Rivett DE. Antimicrobial Activity of
Santalbic Acid from the Oil of Santalum
acuminatum (Quandong). Int J Pharmacogn.
DOI: 10.3109/13880209509055210
34. Misra BB, Dey S. Comparative phytochemical
analysis and antibacterial efficacy of in vitro and
in vivo extracts from East Indian sandalwood tree
(Santalum album L.). Lett Appl Microbiol.
DOI: 10.1111/lam.12005
35. Mavundza EJ, Chukwujekwu JC, Maharaj R,
Finnie JF, Van Heerden FR, Van Staden J.
Identification of compounds in Olax dissitiflora
with larvacidal effect against Anopheles
arabiensis. South African J Bot. 2016;102:1–3.
DOI: 10.1016/j.sajb.2015.06.013
36. Croft KD, Beilin LJ, Ford GL. Differential inhibition
of thromboxane B2 and leukotriene 84
biosynthesis by two naturally occurring acetylenic
fatty acids. Biochim Biophys Acta - Lipids Lipid
Metab. 1987;921(3):621–4.
DOI: 10.1016/0005-2760(87)90091-9
37. Jones GP, Birkett A, Sanigorski A, Sinclair AJ,
Hooper PT, Watson T, et al. Effect of feeding
quandong (santalum acuminatum) oil to rats on
tissue lipids, hepatic cytochrome P-450 and tissue
histology. Food Chem Toxicol. 1994;32(6):521–5.
DOI: 10.1016/0278-6915(94)90108-2
38. Liu Y, Longmore RB. Dietary sandalwood seed oil
modifies fatty acid composition of mouse adipose
tissue, brain, and liver. Lipids. 1997
DOI: 10.1007/s11745-997-0125-x
39. Sun FF, McGuire JC, Morton DR, Pike JE,
Sprecher H, Kunau WH. Inhibition of platelet
arachidonic acid 12-lipoxygenase by acetylenic
acid compounds. Prostaglandins.
DOI: 10.1016/0090-6980(81)90151-9
40. Sok D-E, Han C-Q, Pai J-K, Sih CJ. Inhibition of
leukotriene biosynthesis by acetylenic analogs.
Biochem Biophys Res Commun.
DOI: 10.1016/0006-291x(82)91675-8
41. Bombardelli E, Guglielmini G, Morazzoni P, Curri
SB, Polinelli W. Microvascularkinetic activity of
ximenynic acid ethyl ester. Fitoterapia.
42. Bombardelli E, Cristoni A, Morazzoni P.
Combinations of vasoactive substances with fatty
acids to prevent hair loss. 1997; U.S. Patent No.
43. Bombardelli E, Sergio BC. Polyunsaturated acids
having isokinetic action and pharmaceutical and
cosmetic formulations containing them 1992; U.S.
Patent No. 5,104,655.
44. Bombardelli E. Combinations of vasoactive
agents and their use in the treatment of sexual
dysfunctions 2012; U.S. Patent No. 8,092,844.
45. Eggink M, Stam W, Schmid U, Koenen C, Rogers
J, Peilow A, Bosley J. Ximenynic acid
compositions, methods for their production and
uses thereof 2004; U.S. Patent No.
46. Messenger AG, Rundegren J. Minoxidil:
mechanisms of action on hair growth. Br J
Dermatol. 2004;150(2):186–94.
DOI: 10.1111/j.1365-2133.2004.05785.x
47. Glynn, K.M., Duvel, L.A, Flower, D.M. Methods
and compositions for modulating hair growth or
regrowth. U.S. Patent Application 11/500,704.
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... Acid with the molecular formula C11H21NO3. The fatty acid [5][6][7] ximenynic acid, commonly known as santalbic acid, is the conjugated enzyme form of the compound. This substance's chemical name is octadeca-11-trans-en-9-ynoic acid. ...
Full-text available
A novel analytical technique and validation study were developed to determine the concentration of ximenynic acid (XMA) in semisolid dosage formulations (SDF) such as cream, gel, lotion, etc. The procedure makes use of reverse-phase high-performance liquid chromatography (HPLC). A Phenomenex Luna Column 5 (4.6 x 250 mm) was used for the analysis, using acetonitrile as the mobile phase, sodium dihydrogen phosphate monohydrate as the stationary phase, and 229 nm detection at 30 degrees Celsius. In spite of the presence of additional compounds, their presence had no effect on the detection of XMA in SDF. As part of validating this HPLC technique, a number of tests were performed to evaluate its specificity, linearity, accuracy, precision, and durability. International Conference on Harmonization standards were used to determine whether the method was adequate (ICH). Because it is simple to implement and produces reproducible results, the presented HPLC approach has the potential to be utilized in industry to standardize herbs and Phytomedicines. Because XMA has the potential to be a game-changing method of treating ageing, its advancement may benefit the pharmaceutical and cosmetics sectors.
A new analytical approach and validation study were developed to assess the quantity of ximenynic acid (XMA) in Santalum album Linn. extract. High-performance liquid chromatography (HPLC) in reverse phase is the technique that is used in this procedure. The anti-aging properties of the medicine were tested using enzymes that inhibit hyaluronidase and elastase, respectively, in order to gather information and findings. Methanol and water were used as the mobile phase for the analysis, which was carried out using a ZORBAX SB-C18 column with a size 5 µ (4.6 x 250 mm) column size. During the course of this HPLC method validation, a number of different tests that were pertinent to specificity, linearity, accuracy, precision and robustness were carried out. The technique was tested to see whether or not it would be able to fulfill the prerequisites set out by the International Conference on Harmonization (ICH). Research conducted on anti-aging found that XMA was much more efficient than catechin at decreasing the activities of elastase and hyaluronidase. Because of its use, speed and reliability, the HPLC method that was described has the potential to be effectively utilized in industry for the standardization of herbs and phytomedicines. Because XMA has the potential to be a breakthrough anti-aging treatment, the pharmaceutical and cosmetics industries may benefit from its development.
Full-text available
A novel HPTLC analytical technique and validation study were developed to determine the concentration of ximenynic acid (XMA) in semisolid dosage formulations (SDF) such as cream, gel, lotion, etc. The procedure makes use of reverse-phase high-performance liquid chromatography (HPLC). This study presents the first report of sensitive, selective, precise and robust HPTLC method, which has been developed and validated for quantification of the XMA from pharmaceutical formulation. The chromatographic development was carried out on HPTLC plates precoated with silica gel 60 F254 using a mixture of Toluene: Ethyl Acetate: Methanol: Formic acid (5:4:0.5:0.5 v/v/v/v) as mobile phase. Detection was carried out densitometrically at 254 nm. The Rf value of XMA were found at Rf about 0.3 ± 0.01. The method was validated as per ICH guideline with respect to linearity, accuracy, precision, robustness etc. The method is new, simple and economic for routine estimation of XMA in bulk, preformulation studies and pharmaceutical formulation to help the industries as well as researchers for their sensitive determination of XMA rapidly at low cost in routine analysis. Because XMA has the potential to be a game-changing method of treating ageing, its advancement may benefit the pharmaceutical and cosmetics sectors. Ximenynic acid; Skin Care Medicinal Formulation; HPTLC; Validation
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This review article gives a survey of the principal biosynthetic pathways that lead to the most important food glycerolipids, i.e. triacylglycerols, glycerophospholipids, and glyceroglycolipids as reported in recently published papers. Glycerophospholipids are further subdivided to phosphatides, lysophosphatides, and plasmalogens. The subdivision of the topics is predominantly via biosynthesis. Reaction schemes, sequences, and mechanisms with the enzymes involved are extensively used as well as detailed explanations based on chemical principles and mechanisms.
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Objective: Present study aimed phytochemical evaluation and antimicrobial screening of petroleum ether and ethanol extracts of Santalum album seeds.Methods: Petroleum ether and ethanol extracts were screened for presence of chemical constituents. Petroleum ether extract was investigated detail by using chromatographic and spectroscopic methods. In vitro antimicrobial activity of both extracts were investigated using disc diffusion method on two gram-positive bacteria, Bacillus subtilis, Staphylococcus aureus, gram negative Pseudomonas aeruginosa, Escherichia coli and fungus Candida albicans.Results: Santalbic acid was identified in petroleum ether extract and content determined by HPTLC was 4.7%w/w. It was seen that petroleum ether extract have MIC value for B. subtilis, P. aeruginosa, E. coli and C. albicans were 78.125 µg/ml, 19.331 µg/ml, 625 µg/ml & 39.062 µg/ml respectively while MBC was 39.062 µg/ml, 4.882 µg/ml, 312.5 µg/ml & 9.765 µg/ml, respectively. Petroleum ether extract showed MIC and MBC values for S. aureus was similar as 156.25µg/ml. So, the petroleum ether extract showed significant antimicrobial activity against both gram positive, gram negative and fungal strain.Conclusions: The results of present investigations were indicative of possible high potency of petroleum ether extract due to santalbic acid which could serve as chemotherapeutic agent.
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A revised and updated classification for the families of flowering plants is provided. Many recent studies have yielded increasingly detailed evidence for the positions of formerly unplaced families, resulting in a number of newly adopted orders, including Amborellales, Berberidopsidales, Bruniales, Buxales, Chloranthales, Escalloniales, Huerteales, Nymphaeales, Paracryphiales, Petrosaviales, Picramniales, Trochodendrales, Vitales and Zygophyllales. A number of previously unplaced genera and families are included here in orders, greatly reducing the number of unplaced taxa; these include Hydatellaceae (Nymphaeales), Haptanthaceae (Buxales), Peridiscaceae (Saxifragales), Huaceae (Oxalidales), Centroplacaceae and Rafflesiaceae (both Malpighiales), Aphloiaceae, Geissolomataceae and Strasburgeriaceae (all Crossosomatales), Picramniaceae (Picramniales), Dipentodontaceae and Gerrardinaceae (both Huerteales), Cytinaceae (Malvales), Balanophoraceae (Santalales), Mitrastemonaceae (Ericales) and Boraginaceae (now at least known to be a member of lamiid clade). Newly segregated families for genera previously understood to be in other APG-recognized families include Petermanniaceae (Liliales), Calophyllaceae (Malpighiales), Capparaceae and Cleomaceae (both Brassicales), Schoepfiaceae (Santalales), Anacampserotaceae, Limeaceae, Lophiocarpaceae, Montiaceae and Talinaceae (all Caryophyllales) and Linderniaceae and Thomandersiaceae (both Lamiales). Use of bracketed families is abandoned because of its unpopularity, and in most cases the broader circumscriptions are retained; these include Amaryllidaceae, Asparagaceace and Xanthorrheaceae (all Asparagales), Passifloraceae (Malpighiales), Primulaceae (Ericales) and several other smaller families. Separate papers in this same volume deal with a new linear order for APG, subfamilial names that can be used for more accurate communication in Amaryllidaceae s.l., Asparagaceace s.l. and Xanthorrheaceae s.l. (all Asparagales) and a formal supraordinal classification for the flowering plants.
Ximenynic acid is a conjugated enyne fatty acid, which is currently of interest due to its anti-inflammatory activity. Due to the association between inflammation and cancer, the present study was designed to investigate the anti‑cancer activity of ximenynic acid in the HepG2 human hepatoma cell line and the underlying mechanisms. The current study demonstrated the anti‑proliferation and pro‑apoptosis activities of ximenynic acid by cell viability assay and flow cytometry analysis. The expression of anti‑apoptosis protein silent information regulator T1 (SIRT1) was significantly suppressed by ximenynic acid. Furthermore, ximenynic acid blocked G1/S phase transition by inhibiting the protein expression of the cell cycle‑associated protein general control of amino acid synthesis yeast homolog like 2 (GCN5L2), and the mRNA expression of cyclin D3 and cyclin E1. Furthermore, ximenynic acid suppressed the expression of angiogenesis‑associated genes, including vascular endothelial growth factor (VEGF)‑B and VEGF‑C. Finally, ximenynic acid significantly inhibited the expression of cyclooxygenase‑1 (COX‑1) mRNA and protein, however COX‑2 expression was not reduced. The results of the present study suggested that ximenynic acid may inhibit growth of HepG2 cells by selective inhibition of COX‑1 expression, which leads to cell cycle arrest, and alters the apoptosis pathway and expression of angiogenic factors. The current study aimed to investigate whether ximenynic acid might be developed as novel anticancer agent.
In this preliminary study, the tolerability and the efficacy of ximenynic acid ethyl ester on the microcirculatory maldistribution present in cellulitis have been investigated. The product, included in a O/W emulsion, has been administered topically in a single dose (tolerability test) to healthy subjects and for 60 consecutive days (efficacy test) to subjects with cellulitis. Since these subjects presented also signs of preclinical venous insufficiency, some parameters linked with this particular status were investigated by means of different techniques. The results obtained demonstrated that ximenynic acid ethyl ester is endowed with an interesting vasokinetic activity which suggests its possible use both in the cosmetic and therapeutic fields.
Bioassay-guided fractionation of the dichloromethane extract of Olax dissitiflora bark has led to the isolation of santalbic acid and a mixture of two closely related compounds (exocarpic acid and octadec-9,11-diynoic acid). The isolated compounds were then evaluated for their larvicidal activity against laboratory-reared larvae of An. arabiensis mosquitoes, a potent malaria vector in South Africa. The mixture of exocarpic acid and octadec-9,11-diynoic acid exhibited the highest larvicidal activity with an EC50 value of 17.31μg/ml compared to ximeninic acid which had an EC50 value of 62.17μg/ml.
In a time of diminishing resources, a better knowledge of nature's biodiversity is important. The plant kingdom contains lipids with an astonishing variety of structures, particularly so in angiosperm seed oils. Lipids as natural products are an exciting field of research. Over many years, the Institute for Chemistry and Physics of Lipids in Münster has collected seed oil fatty acid composition data, which were sorted by plant botanical name. Although this collection contained numerous examples for the occurrence, distribution, and content of fatty acids with unusual structures in various concentrations, they could not be searched for manually. This data collection has now been transferred into an electronically searchable database, offering a variety of search routines. Currently it contains about 110, 000 individual data in 17, 500 sets, relating to more than 7, 000 different plant species. About 500 different fatty acids are listed. The database permits searches for plant species, genera and families, for individual fatty acids and combinations of fatty acids in their seed oils, and for their percentage contents in form of fatty acid composition tables. It also contains literature references and close to 1, 000 unpublished data from analyses carried out by GLC analysis between 1986 and 2002 in the Institute for Chemistry and Physics of Lipids. Most interestingly, fatty acid partial structures or functional groups can also be searched for, yielding the percentage contents of relevant fatty acids, using a specially developed “Delta-Notation” system. The data on occurrence and distribution of unusual fatty acids in the plant kingdom will be useful in chemistry, botany, search for renewable resources, plant breeding, gene technology or gene transfer and indirectly also for enzyme design. A number of examples for “search” and find operations are given and may help to illustrate the usefulness of the new database.
Following our previous review on Pinus spp. seed fatty acid (FA) compositions, we recapitulate here the seed FA compositions of Larix (larch), Picea (spruce), and Pseudotsuga (Douglas fir) spp. Numerous seed FA compositions not described earlier are included. Approximately 40% of all Picea taxa and one-third of Larix taxa have been analyzed so far for their seed FA compositions. Qualitatively, the seed FA compositions in the three genera studied here are the same as in Pinus spp., including in particular the same Δ5-olefinic acids. However, they display a considerably lower variability in Larix and Picea spp. than in Pinus spp. An assessment of geographical variations in the seed FA composition of P. abies was made, and intraspecific dissimilarities in this species were found to be of considerably smaller amplitude than interspecific dissimilarities among other Picea species. This observation supports the use of seed FA compositions as chemotaxonomic markers, as they practically do not depend on edaphic or climatic conditions. This also shows that Picea spp. are coherently united as a group by their seed FA compositions. This also holds for Larix spp. Despite a close resemblance between Picea and Larix spp. seed FA compositions, principal component analysis indicates that the minor differences in seed FA compositions between the two genera are sufficient to allow a clear-cut individualization of the two genera. In both cases, the main FA is linoleic acid (slightly less than one-half of total FA), followed by pinolenic (5,9,12-18:3) and oleic acids. A maximum of 34% of total Δ5- olefinic acids is reached in L. sibirica seeds, which appears to be the highest value found in Pinaceae seed FA. This apparent limit is discussed in terms of regio- and stereospecific distribution of Δ5-olefinic acids in seed triacylglycerols. Regarding the single species of Pseudotsuga analyzed so far (P. menziesii), its seed FA composition is quite distinct from that of the other two genera, and in particular, it contains 1.2% of 14-methylhexadecanoic (anteiso-17:0) acid. In the three genera studied here, as well as in most Pinus spp., the C18 Δ5-olefinic acids (5,9-18:2 and 5,9,12-18:3 acids) are present in considerably higher amounts than the C20 Δ5-olefinic acids (5,11-20:2 and 5,11,14- 20:3 acids).
The occurrence and distribution of santalbic acid in the plant kingdom are reported and discussed. This conjugated acetylenic fatty acid, octadeca-11-trans-en-9-ynoic acid (in “Delta Notation” 18:2Δ9a,11t), occurs in members of the santalalean plant families, mostly in tropical and subtropical areas. The range is from only traces up to 95.0 % of total fatty acids in the seed oil. However, some caution is required during the analysis, so the presence of this acid may have been overlooked sometimes. This fatty acid may be toxic to humans, but may be of interest for technical purposes because of a reactive functional group.
Protonema Cells Of The Moss Ceratodon Purpureus Accumulate Triacylglycerols With Two Acetylenic Acids, 9,12-Octadecadien-6-Ynoic Acid (18:2A) And 9,12,15-Octadecatrien-6-Ynoic Acid (18:3A), As Main Components. By Following The Incorporation Of The [14C]-Precursors (Acetate, Linoleate, γ-Linolenate, α-Linolenate, Stearidonate And 18:2A) Into 18:3A In Triacylglycerol Accumulating Cells, The Pathway For Acetylenic Acids Could Be Established. 18:2A And 18:3A Could Be Synthesized By A Second Desaturation Of The Δ 6 Double Bond Of Linolenate And Stearidonate, Respectively. However The Major Pathway For 18: 3A synthesis was via a Δ 15 desaturation of 18:2A. Since 18:2A was found exclusively in the triacylglycerols of the cell, the triacylglycerols in Ceratodon purpureus can act either as a direct substrate for the Δ 15 desaturation or, alternatively, the 18:2A has to be detached, desaturated and reincorporated into triacylglycerols. These results, as well as recent results from developing sunflower seeds by Garces et al. (1994, in press), present evidence that, in contrast to the general believe, plant triacylglycerols are not metabolic inert molecules during the cell stage of triacylglycerol deposition.