A review on genus Osyris: Phytochemical constituents and traditional uses
Correspondence Address: DOI: 10.4103/2229-5119.102747
Osyris is the evergreen shrubs or trees belonging to the sandal wood family, Santalaceae and is distributed in the tropical and temperate zone. The majority of plants are partially parasitic on other plants. Most of the plants belonging to the Santalaceae family have strong characteristic fragrance and are known for its volatile constituents. The leaves are used as a wild herbal tea and the plants are used traditionally to treat varieties of health problems like gynecological disorder and adjusting of cracked bones, etc. The genus Osyris consists of various classes of compounds, which include hexyl and hexenyl derivatives, sesquiterpenes, dihydro-β-agarofuran sesquiterpenes, phenolic acids, flavonoids, pyrrolizidine and quinolizidine alkaloids, lignans, β-carboline alkaloids, iridoids, norisoprenoids, phenylpropanoids, long chain hydrocarbons, carbohydrates, aminoacids, and halogenated pyrimidine alkaloids. The review of phytochemical constituents isolated from genus Osyris is presented here with its traditional uses. Keywords: Gynecological disorder, herbal tea, Osyris, phytochemicals
The genus Osyris comprises of the evergreen shrubs or trees belonging to the sandal wood family, Santalaceae. The majorities of plants are partially parasitic on other plants and are widely distributed in the tropical and temperate region. The genus Osyris includes more than 34 species. [1] The fruit is a nut or a drupe and brightly colored. The fruit is relatively small (up to 1 cm), usually with rudimentary perianth at apex or with only rudimentary disk, exocarp fleshy, endocarp crustaceous. Inflorescences are axillary, male ones cymose; bisexual and female ones often 1-flowered; bracts and bracteoles on male inflorescences caduceus. Flowers are unisexual (when plants dioecious) or are bisexual. The bisexual flowers have perianth tube mostly connate to ovary, lobes 3 (or 4), triangular or ovate, with a tuft of hair adaxially. Short stamens are 3 (or 4) on the base of lobes. Anthers are ovoid; cells are distinct, parallel, and dehiscence longitudinal. Disks are nearly flat and sinuate at margin. Ovary is inferior, 1-loculed, and 2-4 ovules. Styles are needle-shaped. Stigmas are 3 (or 4) parted. The male flower has stamens slightly longer than the bisexual flower and ovary is rudimentary. Female flowers have prominent bracteoles and perianth tube shorter. Seeds are globose. The branches of Osyris are usually 3-ridged or -angled. Leaves are alternate, ± sessile, elliptic-lanceolate or elliptic-ovate. Leaves are usually ± leathery, pinnately veined and lateral veins inconspicuous. [2] Scientific classification Kingdom: Plantae Phylum: Tracheophyta Class: Magnoliopsida Subclass: Rosidae Order: Santalales Family: Santalaceae Genus: Osyris
The genus Osyris is widely distributed in the tropical and temperate region of southern Europe, northern Africa, and southwest Asia. Leaves, roots, barks, fruits, and woods of the shrub are used for different purposes by ethnic groups of different region of Asia, Africa, and Europe. Leaves The fresh leaves of O. compressa are used to tan the leather with light brown color, while the bark was used to tan the leather with dark brown color. A decoction of fresh leaves is used to tan cotton to make them more durable, in the days before nylon. [3] The Tamangs and Newars of Kavre, central part of Nepal, use leaves of O. wightiana as a substitute of tea. The leaves of plant are dried and its infusion in hot water is consumed as tea. O. wightiana is locally known as 'Nundhiki' in Kavre district of Nepal. The tea made from the leaves of O. wightiana stimulates the flow of breast milk and also acts as the labor-inducing agent. [4] Two kilograms of the leaves are crushed and boiled with constant stirring in 10 l of water. When the amount is reduced to half the volume, it is stressed and the filtrate is evaporated again until a viscous sticky mass is obtained, called 'Nundhiki ko khoto'. It is cooled and preserved. The drug (Nundhiki ko khoto) is mixed with double the amount of cow's butter or Indian rapeseed oil (brassica napus) and used to massage the sprained parts twice a day for relief. [5] Immature leaves and fruits have emetic properties and contain tannins. It also contains cis-4-hydroxy-L-proline and exhibited antiviral activity. Leaf guises can be used in the veterinary purposes. [6] The leaves of O. lanceolata (Hocst and Stendel) are boiled and served orally in the traditional management of ear, nose, and throat (ENT) diseases. [7] Roots Roots and barks of O. lanceolata are used for the tea and as a tonic in the soup. The root decoction is used to treat diarrhea in Kenya. The decoction of bark and heartwood is used to treat sexually transmitted diseases and anemia in Tanzania. Extracts from the plant can cure certain diseases, including the killer Hepatitis B. In central parts of Nepal, the root paste and bark of O. wightiana, is used to plaster around the fractured bone after adjusting it properly. About 100 g of bark is boiled in 3 l of water for an hour to obtain a gelatinous mass and is applied around the dislocated bone. The plaster in then wrapped in a cloth. The whole structure is kept together with the help of thin bamboo-splints. [8] The root bark is boiled in water for about 10 min, cooled, and stressed; this liquid, about 10 tea spoons three times a day, is given to women after childbirth to stop bleeding and to boost energy, which helps in contraction of uterine muscles. [9] The roots are used in case of tingling (Jham garne in Nepali) or neurological problems. [10] The roots of O. quadripartite are used for the treatment of cancer in Tanzania. [11] O. alba is used for making brooms in Italy. The root fibers are also used to make baskets. [3] Barks The barks of the stem and roots of O. compressa are used in the manufacture of aromatic oils that are used in making expensive perfumes, quality lotions, rare soaps, and sweet smelling candles. The wood yields between 4 and 10% oil when distilled. The boiled concoction of the bark, together with other herbs, is reputed to be useful in improving blood circulation, digestive, and respiratory and nervous systems. The boiled product is given to women after giving birth to boost their appetite. The oils and paste derived from the bark is used to treat skin diseases such as infectious sores, ulcers, acne, and rashes. The tree is also known to be a disinfectant and a sedative. It is effective against the killer hepatitis B. The bark when boiled produces a dark color solution, which is used to flavor the tea. [3] The bark is boiled in water, stressed, and boiled again to form a gelatinous mass that is applied in the eyes to relieve inflammation. About 1 teaspoon of this preparation, three times a day, is given to persons suffering from blood dysentery. The juice of bark, and in some places a paste of fruit, is applied to forehead to relieve headache. The juice of bark, about 4 teaspoons three times a day, is given in cases of indigestion. [12] An infusion of the bark is emetic. Decoction of the bark is taken to treat diarrhea. [13] Fruits The fruits of O. compressa are edible and are an important food of early inhabitants of the South African cape. The powdered fresh/dry fruit of O. quadripartite, mixed with water, is given orally for 3 days and applied topically on the infected body part of livestock in Wonago Woreda of Ethiopia. [14] Wood The heart wood scent is used in sacred ceremonies and to purify holy places. Incense sticks from the wood are burned in temples and houses. The wood is heavy and fine grained, suitable for curving ornaments, and small utensils like pestles. [3] The heart wood is faintly fragrant and reported to be used for adulterating sandalwood. In Tanzania, the decoction of O. lanceolata (locally called Mdunula) is drunk to cure cough. [15] O. abussinica and O. compressa are burned and pregnant women are supposed to sit in the smoke to ease the pregnancy. [16] The plant part of O. lanceolata is burned and the smoke is directed to either the vagina or the vulva for gynecological complaints of menorrhagia and infertility in South Africa [17],[18] Less frequently, O. lanceolata is also used for the management of malaria in central Kenya. [19] Hexenyl derivatives suggested the possible insect attract function. [20] Some Jordanian traditional healers claim the successful use of this plant in the treatment of amoebic dysentery. [21] The extract of small shoots of O. tenuifolia are used for antipyretic agent by the Massai people for cattle. [22] In Ethiopia, O. quadripartite, is used as toothbrush sticks for maintaining oral hygiene. [23]
The crude extracts of O. alba screened for cytotoxicity on the lymphoma cell-line U937-GTB with the survival index for the tested concentration 20, 200, and 2000 μg/ml are ≥100, ≥100, and 1, respectively.[24] The root bark of O. lanceolata was screened for its antioxidant potential using three variations of the Diphenylpicrylhydrazyl (DPPH) radical scavenging method, namely, aTLC autographic assay, a semi quantitative TLC assay, and a spectrophotometric assay. The radical scaveniging power of the five extracts correlated positively with the total phenolic content. The radical scavenging ability, as measured by IC 50 values, were found to be 48.4 (±) 0.4 and 49.5 (±) 1.9 μg/ml for the 90% methanol/water and methanol extract, respectively, while those of the chloform, n-hexane, and SFE extracts were found to be >250 μg/ml. [25] The dihydro-β-agarofuran polyesters and pentacyclic triterpenoids isolated from O. lanceolata displayed antifungal activity against Candida albicans. It also showed the positive antibacterial activity against Gram-positive Bacillus subtilis  and Staphylococcus aureus and Gram-negative Escheria coli and Pseudomonas aeruginos. [26] Osyrisine (37), catechin (86), and catechin-3-O-α-L-rhamnopyranoside (88) exhibited a significant level of antiparasitic activity against two parasites, Entamoeba histolytica and Giardia intestinalis. [21] A methanolic extract of O. quadripartite, with the high content of flavonoids, is found to be effective in reducing the increased capillary permeability, induced in rats by various chemical mediators involved in the inflammatory process. [27] The α-amylase inhibitory activity IC 50 value of crude extract of O. alba was found to be 0.08 mg/ml. [28] During screening of some medicinal plants of Ethiopia for antibacterial and antifungal properties, the methanolic extract of leaves and stem barks of O. quadripartite showed positive test for polyphenols and unsaturated steroid/triterpenes. These extracts found to have in vitro antibacterial and antifungal properties. [29] On analysis of O. wightiana by bioassay guided fractionation method, the ethyl acetate fraction showed antioxidant and antiglycating properties. On further analysis of the ethyl acetate fraction, Kaempferol-3-O-rutinoside (78) was isolated and found to be a potent antiglycating agent. [30]
The widespread uses of different parts of genus Osyris in traditional medication system have resulted in considerable chemical analysis of the plant and their active principles. The phytochemical investigation of genus Osyris has resulted in 108 compounds with varying structural patterns [Table 1] and [Figure 1],[Figure 2],[Figure 3],[Figure 4],[Figure 5],[Figure 6],[Figure 7],[Figure 8],[Figure 9],[Figure 10],[Figure 11],[Figure 12],[Figure 13],[Figure 14] and [Figure 15]. Most of the plants belonging to the family, Santalaceae have strong characteristic fragrance and are known for its volatile constituents. The analysis of volatile constituents of genus Osyris showed the presence of hexyl and hexenyl derivatives, sesquiterpenes, longchain hydrocarbons, and fattyacids. Besides the volatile constituents, other major classes of compounds, triterpenes, dihydro-β-agarofuran sesquiterpenes, flavonoids, phenolic acids and phenyl propanoids, pyrrolizidine and quinolizidine alkaloids, norisoprenoids, lignans, and β-carboline alkaloids are also present in the genus.
Hexyl and hexenyl derivatives The gas chromatography- mass spectrometric (GC-MS) analysis of volatile constituents from O. alba, isolated by applying headspace solid-phase micro extraction techniques, hexyl and hexenyl derivatives were identified. The GC-MS analysis resulted in the characterization of 13 compounds, representing with (Z)-3-hexenyl acetate (2) (56.0%), (Z)-3-hexen-l-ol (5) (12.2%), 1-hexanol (3) (8.2%), and (Z)-3-hexenyl-2-methylbutyrate (12) (7.0%) as main constituents. [20] Long chain hydrocarbons and fatty acids The seed oils of Santalaceae species are rich in the acetylenic fattyacids, and the presence of a particular acid may constitute a useful chemotaxonomic character. The major components, 7-hydroheptadeca-trans-10,16-diene-8-yonic acid (17) and santalbinic acid or ximimenic acid (18) are isolated from the petroleum ether of O. alba and the acids longer than C-18 are also present. [31],[32],[33] Dotriacontanoic acid (14) and 2-octanoic acid (15) are isolated from O. alba of Jordanian origin. [21] 1-Octacosanol (16) was isolated from the aerial parts of O. wightiana, collected from Nepal. [30] Pyrrolizidine and quinolizidine alkaloids The investigation of the alkaloid extracts of hemiparasitic plant, O. alba, collected from southern France, revealed the concomitant presence of both pyrrolizidine and quinolizidine alkaloids. [34],[35] They were identified using its retention index and mass fragmentation pattern. Le Scao Bogaert has also reported the presence of quinolizidine alkaloid. [35] The eight quinolizidine alkaloids identified were sparteine (38), N-methyl cytosine (19), cytosine (20), methyl-12-cytisine acetate (21), hydroxyl-N-methylcytisine (23), N-formylcytisine (24), lupanine (22), and anagyrine (25). The seven pyrrolizidine alkaloids detected are chysin A (26), chysin B (28), 1-carboxypyrrolizidine-7-olide (27), senecionine (32), integerrimine (33), retrorsine (34), senecivernine (35), and a new alkaloid janfestine (29). These alkaloids were isolated by the preparative thin layer chromatography (TLC). The simultaneous presence of these two alkaloids indicates that Osyris have tapped more than one host plant concomitantly. Osyrisine (37) was isolated as a new compound from the butanolic fraction of O. alba.[21] Sesquiterpenes The lanceol was identified by Naves and Ardizio, 1954 from O. teniufolia. [36] Sequiterpenes were identified from essential oil of O. tenuifolia, by comparing their mass spectra and retention indices to mass spectral library. Four new sesquiterpenes ar-tenuifoline (53), tenuifolene (55), 2, (7Z, 10Z)-bisabolatriene-13-ol (61), and lanceoloxide (59) were isolated by preparative gas chromatography (GC) packed with different modified cyclodextrins as a chiral stationary phase and structure of the compounds was determined by nuclear magnetic resonance (NMR) spectroscopic and mass spectrometry techniques. [37] Triterpenes The crude chloroform extract of O. lanceolata, on gradually eluting with petroleum ether and CHCl 3 , pentacyclic triterpenes, 20-epikoetjapic acid (63), and octandronic acid (62) were isolated. [26] Oleanolic acid (66), ursolic acid (65), and β-sitosterol glucoside (64) were isolated from the crude aqueous methanolic extract of O. alba by silica gel column chromatography, elution with the solvent system MeOH/CHCl 3 . [21],[30] β-sitosterol (67) and β-sitosterol glucoside (64) was also isolated from chloroform fraction of O. wightiana. [30] Dihydro-β-agarofuran sesquiterpene The subfraction of CHCl 3 fraction of root barks of O. lanceolata, when subjected to silica gel column chromatography and eluted isocratically using petroleum ether/acetone, yielded three new dihydro-β-agarofuran sesquiterpene polyesters. [26] Dihydro-β-agarofuran has been reported as a component of sandalwood oil and thus can be a possible chemotaxonomic significance of the family, Santalaceae. Phenolic acids and phenyl propanoids The phenyl propanoid derivatives syringin (75) and di-O-methylcrenatin (76) were isolated from O. wightiana.[30] Protochatechuic acid (71), p-hydroxy benzoic acid (72), and p-coumaric acid (73) were isolated from O. alba. [38] Protochatechic acid (71) was also isolated during investigation of chemical constituent of O. alba by Al Jaber et al. [21] Flavonoids Three flavonol glycosides, quercetin-3-O-rutinoside (79), quercetin-3-O-β-D-glucopyranoside (80), and kaempferol-3-O-rutinoside (78) and four C-glycosylflavones, schaftoside (82), isoschaftoside (83), vitexin (81), and vicenin (84) were isolated from the aerial parts and fruits of O. alba. [39] The flavonoids were purified by sephadex LH-20 column chromatography. The quercetin-3-O-rutinoside (80) has been reported from the leaves of two other species of O. compressa and O. abyssinica. [40] Isoquercitroside (77) and rutoside (79) have been reported from O. alba. [17] The Santalaceae family mainly possess flavonols such as kaempferol and quercetin together with dihydroflavonols. Catechin (86) and kaempferol-3-O-rutinoside (78) were isolated from ethyl acetate fraction of O. wightiana as a major constituent. [30] Salvigenin (89), pachypodol (90), kumatakillin (91), penduletin (92), and kaempferol-7-methylether (93) were isolated from O. alba collected from Jordan. [21] Lignans The lignans class of compounds, (±) lyoniresinol (94), 5,5´-dimethoxylariciresinol (95), 5-methoxylariciresinol (96), and (±) syringaresinol (97) were isolated from chloroform fraction of O. wightiana. This is the first time the presence of lignans in the genus Osyris has been demonstrated. [30] Norisoprenoids Norisoprenoids are the degradation products formed by the cleavage of carotenoids. They contribute to the flavor of fruits and wine. Citroside B (98) and roseoside (99), belonging to the flavoring constituents, were isolated from the butanolic fraction of O. wightiana. [30] Halogenated pyrimidine alkaloid The author isolated the unprecedented fluorinated secondary metabolite, osanepakidine (108) from O. wightiana. It raised an intriguing question regarding the biosynthetic origin as nature has hardly evolved a biochemistry of fluoride ion and the enzymes able to form C-F bonds. [30] Miscellaneous Iridoid, 7-deoxyloganic acid (100) was obtained from the butanolic fraction by running High Pressure Liquid Chromatography (reverse phase octadecylsilane ODS L-80 column). [30] β-carboline alkaloids, harmine (101) was isolated from basic dichloromethane fraction of O. wightiana. [30] The amminoacid, cis-4-hydroxy-L-proline (107) was detected in three genera (four species) of Santalaceae. Cysteine (104), aspartic acid (105), and methionine (106) were also reported from Osyris. The presence of cis-4-hydroxy-L-proline (107) in O. arborea and in the family of Santalaceae may serve as a useful index in chemotaxonomy. [41],[42] D-Mannitol (102) and ethyl glucoside (103) were also reported from genus Osyris.[21],[30],[43]
The present review describes the phytochemical constituents isolated from genus Osyris, which is used for the various medicinal purposes. The different class of compounds isolated from the different species of genus Osyris upto September, 2011, are reviewed.
The author acknowledges the financial assistance provided by Faculty of Science, Nepal Academy of Science and Technology, Nepal.
[Figure 1], [Figure 2], [Figure 3], [Figure 4], [Figure 5], [Figure 6], [Figure 7], [Figure 8], [Figure 9], [Figure 10], [Figure 11], [Figure 12], [Figure 13], [Figure 14], [Figure 15]
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