R.Mogana et al. / Journal of Pharmacy Research 2011,4(8),2482-2489 Review Article Available online through ISSN: 0974-6943 http://jprsolutions.info Canarium L. : A Phytochemical and Pharmacological Review R.Mogana1* and C.Wiart2 1School of Pharmacy, Faculty of Science, University of Nottingham(Malaysia Campus), Jln Broga, Semenyih, 43500, Selangor Darul Ehsan, Malaysia 2School of Biomedical Science, Faculty of Science, University of Nottingham(Malaysia Campus), Jln Broga, Semenyih, 43500, Selangor Darul Ehsan, Malaysia Received on: 17-05-2011; Revised on: 12-06-2011; Accepted on:16-07-2011 ABSTRACT The genus Canarium L. consists of 75 species of aromatic trees which are found in the rainforests of tropical Asia, Africa and the Pacific. The medicinal uses, botany, chemical constituents and pharmacological activities are now reviewed. Various compounds are tabulated according to their classes their structures are given. Traditionally Canarium L. species have been used to treat a broad array of illnesses. Pharmacological actions for Canarium L. as discussed in this review include antimicrobial, antioxidant, anti-inflammatory, hepatoprotective and antitumor activity. Keywords: Canarium L., Burseraceae, antibacterial, antioxidant, pharmacology, secondary metabolites INTRODUCTION Canarium L. belongs to the family of Burseraceae Kunth. in the order Sapindales the bark of Canarium luzonicum Miq. or Canarium commune L. which has Juss. ex Bercht. & J. Pearl. This family consists of 18 genera and about 700 been used in the form of an ointment as a stomach stimulant and as an expec- species of tropical trees[1]. The word Canarium L. derives from the Malay torant [8]. The barks of Canarium indicum L. has been used for chest pains name ‘kanari’[2]. Canarium L. species often produce edible kernels, called where else the oil has been patented for treatment of arthritis pain and the canarium nut of commercial interest: Canarium indicum L., Canarium oleoresin of the tree is applied as a poultice for ulcerated wounds. The resin of solomonense B.L.Burtt, Canarium harveyi Seem, Canarium odontophyllum Canarium tonkinense Engl. has been used as a stimulant, rubefacient and anti- Miq. and Canarium album L. Another economical interest of Canarium L. rheumatic when applied externally. The oleoresin has been applied as oint- species, is the production of resins used in foods (Canarium luzonicum Miq.), ment for ulcers [9]. in the making of incense and varnishing. The dried fruit of chinese olive or Canarium album (Lour.) Raeusch. is used in In spite of these commercial potentials of Canarium L., little attention has China and used to treat bacterial and viral infections, inflammation, poisoning been given to the collection and conservation of Canarium L. species [3]. and for detoxification [10]. In Chinese folk medicine, the dried fruits of The genetic diversity thus derogates at an alarming rate. Canarium album (Lour.) Raeusch have been used for treatment of angina, dysentery, snake bites, cough-hematemesis, enteritis, diarrhoea, toxicosis from BOTANICAL DESCRIPTION swellfish and alcohol [11]. The genus Canarium L. probably originated from the North American conti- nent, not Gondwanaland [1]. This clade embraces 75 species of trees which are Canarium schweinfurthii Engl. is used by traditional healers as a remedy for mainly found in tropical Asia and the Pacific, and a few species in tropical diabetes mellitus in southern Senegal [12] while in Congo and Central African Africa [2]. About 9 species were found in the Philippines [2]. The geographi- Republic the plant is used in fever, as stimulant, emollient, in post-partum cal centre of their genetic diversity is the Molucca Islands of eastern Indone- pain, constipation, malaria, diarrhoea, sexual infections and rheumatism [13]. sia, but their centre of cultivated diversity is undoubtedly western Melanesia. In Indonesia, the bark of Canarium littorale Bl. is used to make a decoction Twenty to 25 species are found in the South Pacific, of which 21 are in Papua taken to heal haemorrhoids [3]. New Guinea [4], eight in the Solomon Islands [5] and 3 or 4 in Vanuatu [6]. The members of the genus Canarium L. consist of medium to large buttressed CHEMICAL CONSTITUENTS trees up to 40-50m tall, or rarely a shrub. The barks are greenish grey, fawn or Isolation and structure elucidations of secondary metabolites in Canarium L. light yellow brown that are usually smooth, scaly or dippled with many small has been carried out since the 50s [14] Majority of investigations include the lenticels. Outer bark are thin while the inner barks are pinkish brown or resin and the fruit of the species. reddish brown, laminated, soft and aromatic with a clear sticky or rarely oily exudate. The stems are usually terete. To date about 99 compounds have been isolated from 9 species, which are Canarium schweinfurthii Engl., Canarium boivinii Engl., Canarium The leaves are pinnate, spiral and stipulated. The rachis is terete flattened to odontophllum Miq., Canarium manii King., Canarium album (Lour) Raeusch, channeled swollen at base, and bears 5-21 folioles. The folioles are oblique at Canarium zeylanicum (Retz.) Blume, Canarium commune L., Canarium base, entire, dentate or serrate at margin, often thick and acuminiate at apex. muelleri F.M. Bailey and Canarium bengalense Roxb. The extensively re- The secondary nerves are arching and joined near margin. The tertiary nerves searched species are Canarium schweinfurthii Engl. and Canarium album are reticulate. The infloresence is an axillary or terminal panicle. (Lour.) Raeusch [10,11,15-17] The calyx is cupular. The corolla includes 3 creamy petals. The androecium Among the secondary metabolites isolated from members of the genus comprises a whorl of 6 stamens. The disc within the stamens is 6 lobed. The Canarium L. are terpenes (monoterpenes, triterpenes, tetraterpenes like caro- gynaecium consist of 3 carpels united into a 3 lobular ovary. The drupes are tenoids, sesquiterpenes, cyclohexane and sterols), carboxylic acids, coumarins, seated on a persistent enlarged calyx and enclose a woody stone [7]. furans, lipids and phenols (flavonoids, tannins, phenolic acids). The main secondary metabolites isolated so far from the genus Canarium L. consists of TRADITIONAL MEDICINAL USE terpenes with 58 compounds and flavonoids with 11 compounds. The profile Elemi (British Pharmaceutical Codex, 1934) is an oleoresin exuded through of all known secondary metabolites of Canarium L. as found in literature and their structures are included in Table 1. *Corresponding author. METHODS OF ISOLATION AND STRUCTURAL DETERMINATIONS R.Mogana The isolation and separation technique is very much dependent on the type of fractions. Essential oils are analysed with gas chromatography (GC) and mass PhD researcher, School of Pharmacy spectroscopy (MS) [13,18,19]. Other substances are separated with liquid chro- Faculty of Science, matography using different solvent mixtures with silica gel [20,21], charcoal [22], sephadex [11] and multiple column packing such as AB-8 adsorption University of Nottingham, resin, polyamide, and TSK Toyopearl HW-40(S). Other types of analytical Malaysia techniques include thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) [10,17,23-25]. Journal of Pharmacy Research Vol.4.Issue 8. August 2011 2482-2489 R.Mogana et al. / Journal of Pharmacy Research 2011,4(8),2482-2489 Table 1. Secondary metabolites of Canarium L. Compound name Species Chemical Structure Plant Reference Formula Number part Compound name Species Chemical Structure Plant Reference Formula Number part PHENOLS FLAVONOIDS CARBOXYLIC ACIDS Luteolin Canarium album (Lour.) Raeusch C 15H 10O 6 15 fruit [11] Octyl acetate Canarium schweinfurthii Engl. C H O 1 resin,oil [13] Luteolin-7-O-ß-D-glucoside Canarium album (Lour.) Raeusch C 21H 20O 11 16 fruit [11] 10 20 2 Quercetin Canarium album (Lour.) Raeusch C H O 17 fruit [11] 2,5-Dimethoxytoluene Canarium schweinfurthii Engl. C 9H 12O 2 2 resin,oil [13] 15 10 7 COUMARINS Quercetin-3-O-ß-D-glucoside Canarium album (Lour.) Raeusch C 21H 19O 12 18 fruit [11] Scoparone Canarium album (Lour.) Raeusch C H O 3 fruit [38] Kaempferol Canarium album (Lour.) Raeusch C 15H 10O 6 19 fruit [11] 11 10 4 7,8,3',4'-tetrahydroxyflavanoneCanarium album (Lour.) Raeusch 20 fruit [11] Scopoletin Canarium album (Lour.) Raeusch C 10H 8O 4 4 fruit [38] HETEROCYCLIC 3,5,7,3'-tetrahydroxy-4'- Canarium album (Lour.) Raeusch 21 fruit [11] COMPOUNDS- FURANS methoxyflavanonol 2-acetylfuran Canarium schweinfurthii Engl. C H O 5 resin,oil [13] Hyperin/Quercetin-3- Canarium album (Lour.) Raeusch C 21H 20O 12 22 dried stem, [27],10] 6 6 2 galactoside leaf,fruit n-octanol Canarium schweinfurthii Engl. C 8H 18O 6 resin,oil [13] LIPIDS Kaempferol-3-glucoside Canarium album (Lour.) Raeusch C 21H 20O 11 23 fruit [10] Hexadecanoic acid Canarium schweinfurthii Engl. C H O 7 fruit,oil [39] Amentoflavone Canarium album (Lour.) Raeusch C 30H 18O 10 24 fruit [10] 16 32 2 Agathisflavone Canarium manii King. C H O 25 stem,bark [21] 9-octadecenoic acid Canarium schweinfurthii Engl. C 18H 34O 2 8 fruit,oil [39] 30 18 10 6,9-octadecadienoic acid Canarium schweinfurthii Engl. C H O 9 fruit,oil [39] PHENOLIC ACIDS 18 32 2 Sinapic acid Canarium album (Lour.) Raeusch C H O 26 fruit [17] 9,12,15-octadecatrienoic acid Canarium schweinfurthii Engl. C 18H 32O 4 10 fruit,oil [39] 11 12 5 Oleic acid(cis-C18:1n9) Canarium schweinfurthii Engl. C H O 11 fruit,oil [40] Corilagin Canarium album (Lour.) Raeusch C 27H 22O 18 27 fruit [10] 18 34 2 Gallic acid Canarium album (Lour.) Raeusch C H O 28 fruit [38],[10] Linoleic acid(cis-C18:2n6) Canarium schweinfurthii Engl. C 18H 32O 2 12 fruit,oil [40] 7 6 5 n-decanol Canarium schweinfurthii Engl. C H O 13 resin, oil [13] Ellagic acid Canarium album (Lour.) Raeusch C 14H 6O 8 29 dried [27] 10 22 stem,leaf n-dodecanol Canarium schweinfurthii Engl.