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Chemistry of Some Species Genus Lantana

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Chemistry of Some Species Genus Lantana Pak. J. Bot., 43: 51-62, Special Issue, December, 2011 (Medicinal Plants: Conservation & Sustainable use) CHEMISTRY OF SOME SPECIES GENUS LANTANA HIDAYAT HUSSAIN1*, JAVID HUSSAIN1,2*, AHMED AL-HARRASI1 AND ZABTA KHAN SHINWARI3 1Department of Biological Sciences and Chemistry, College of Arts and Sciences, University of Nizwa, Birkat Al-Mouz, Nizwa 616, Sultanate of Oman 2Department of Chemistry, Kohat University of Science and Technology, Kohat, Pakistan 3Department of Biotechnology, Quaid-i-Azam University, Islamabad, Pakistan *Corresponding author e-mail: [email protected] (H. Hussain) [email protected] (J. Hussain) Abstract This review presents the currently known phytochemical constituents of the genus Lantana; a total of 160 natural compounds have been included. Lantana is free from diterpenoids and rich in essential oils. Monoterpenes, triterpenes, flavones coumarin, steroids, iridoid glycosides, and caffeic acid derivatives are reported from Lantana. Triterpenes and flavones are the more common secondary metabolites in Lantana. Lantana plants are used in folk medicine in many parts of the world. The genus Lantana also produces a number of metabolites in high quantities and some have been shown to possess useful biological activities. The ethnopharmacology, phytochemistry and toxicity of Lantana are considered. The biological activities exhibited by some of the metabolites are discussed and the results of recent studies on the triterpene inhibitors of human α-thrombin discovered in this plant are presented. H H O Introduction H The genus Lantana (Verbenaceae), as described by H H H H 1 2 4 Linnaeus in 1753, contained seven species, six from South OH 3 America and one from Ethiopia (Munir, 1996). Lantana H (from .the Latin lento, to bend) probably derives from the ancient Latin name of the genus Viburnum, which it 6 resembles a little in foliage and inflorescence. Lantana is 5 7 8 mostly native to subtropical and tropical America, but a few taxa are indigenous to tropical Asia and Africa. It now occurs in approximately 50 countries, where several species CO H are cultivated under hundreds of cultivar names. The 2 CO2H recorded number of Lantana species varies from 50 to 270 HO O specific and subspecific entities, but it appears that a better R estimate is 150 species (Atkin, 2004). The genus is a 10 R = Me difficult one to classify taxonomically since species are not 11 R = CH2OH 13 stable and hybridisation is widespread, the shape of inflorescence changes with age, and flower colours vary Fig. 1. Compounds 1-13 isolated from of L. indica. with age and maturity (Munir, 1996). In this review, the ethnopharmacology, phytochemistry and toxicity of Lantana involucrata: In a study of novel antitumor agents Lantana species are considered. The biological activities from rainforest plants, three new isopropenylfurano-β- exhibited by some of the metabolites are discussed and the naphthoquinones, designated lantalucratins A (14), B (15), results of recent studies on the triterpene inhibitors of and C (16), and three new isoprenyl-α-naphthoquinones, human α-thrombin discovered in this genus are presented. designated lantalucratins D (17), E (18), and F (19), were isolated from L. involucrata (Fig. 2). Lantalucratins A (14) Lantana indica: L. indica Roxb. is a shrub native to India, and B (15) showed cytotoxic activities against various where it has been used as a sudorific, intestinal antiseptic, human tumor cell lines, including drug-resistant variants, diaphoretic and in the treatment of tetanus, rheumatism and with IC50 values of 1.0-4.9 μM (Hayashi et al., 2004). malaria in the Ayurvedic system of medicine (Singh et al., 1991). Steam distilled essential oil obtained from the leaves R1 O of L. indica was analyzed by capillary gas chromatography R2 R2 OMe (GC) and gas chromatography mass spectrometry O (GC/MS). These chemical compounds identified from the R1 R oil were trans-caryophyllene (1), α-selinene (2), globulol 3 O R4 O (3), trans-caryophyllene oxide (4), α-guaiene (5), valencene HO (6), humulene (7), and β-eudesmene (8) (Fig. 1) (Akhtar et O 14 R1 = OMe, R2 = H al., 2006). Antifungal activity of the following triterpenoids 17 R1 = OMe, R2 = R3 = R4 = H 15 R1 = OH, R2 = H from L indica root was studied: oleanolic acid (9), 3- 18 R1 = OMe, R4 = OH, R2 = R3 = H 16 R1 = H, R2 = OH ketooleanolic acid (10), (+)-24-hydroxy-3-oxoolean-12-en- 19 R2 = OMe, R3 = R4 = OH, R1 = H 28-oic acid (11), 3β,24-dihydroxyolean-12-en-28-oic acid Fig. 2. Compounds 14-19 isolated from L. involucrata. (12), and 3,24-dioxo-olean-12-en-28-oic acid (13) (Fig. 1) (Verma et al., 1998; Singh et al., 1990; Singh et al., 1991). Lantana montevidensis: The flavonoid fraction from the They concluded that these compounds had no antifungal leaves of L. montevidensis (Spreng.) Briq., showed antiproliferative activity against human gastric activity. adenocarcinoma (MK-1, GI50: 12 μg/ml), human uterus 52 HIDAYAT HUSSAIN ET AL., carcinoma (HeLa, 5 μg/ml), and murine melanoma flavones, luteolin (31) 7, 3'-dimethoxy- (32) and 7, 3', 4'- (B16F10, 5 μg/ml) cells In vitro. Bioactivity-guided trimethoxyluteolin (33), from L. montevidensis (Fig. 3). chemical investigation of the fraction resulted in the isolation of apigenin (20) and ten 5, 6, 7-oxygenated Lantana tiliifolia: L. tiliifolia Cham. is the most common flavones: cirsilineol (21), eupatorin (22), 5, 4'-dihydroxy- Lantana in Brazil, but it is not considered a weed because 6, 7, 3' ,5'-tetramethoxyflavone (23), 5, 6-dihydroxy-7, 3', it is controlled by a complex of natural predators such as 4'-trimethoxyflavone (24), 5, 6, 4'-trihydroxy-7, 3', 5'- insects and fungi (Rwangabo et al., 1988). A new trimethoxyflavone (25), 5, 6, 3'-trihydroxy-7, 4'- triterpene, 24-hydroxy-3-oxours-12-en-28-oic acid (34), dimethoxyflavone (26), 5, 3', 4'-trihydroxy-6, 7, 5'- was reported together with the known triterpenes ursonic trimethoxyflavone (27), cirsiliol (28), hispidulin (29), and acid (35), oleanonic acid (10), ursolic acid (36), and eupafolin (30) (Nagao et al., 2002). Similarly, oleanolic acid (9) (Johns et al., 1983a) (Fig. 4). Wollenweber et al., (1997) reported another three OMe OH OH MeO O MeO O OH OMe HO O MeO MeO OH O OH O 22 OH O 21 OMe 20 OMe OH OH OMe MeO O OMe MeO O MeO O OMe OMe HO MeO HO OH O 25 OH O OH O 23 24 OH OH OH OMe OH MeO O MeO O MeO O OH OMe MeO HO MeO OH O OH O OH O 28 26 27 OH OH OH HO O HO O HO O OH OH MeO MeO OH O OH O OH O 29 30 31 OH OH MeO O OMe MeO O OMe OH O 32 OH O 33 Fig. 3. Compounds 20-33 isolated from L. montevidensis. Lantana × hybrida: A compound, 1-caffeylrhamnose (37), was isolated from the flowers of L. hybrida and after alkaline hydrolysis yielded caffeic acid and L-rhamnose (Imperato et al., 1975). Another sugar derivative, 1-(3- CO H 2 CO2H glucosyloxy-4-hydroxycinnamyl)glucose (38) was isolated from L. × hybrida (Imperato, 1976) (Fig. 5). O HO Lantana achyranthifolia: Aerial parts of L. R R achyranthifolia Desf. produced two flavonoids 34 R = CH2OH 36 (Dominguez et al., 1983), penduletin (39) and 35 R = CH3 chrysosplenetin (40), and the roots produced a new furano-1,4-naphthoquinone named diodantunezone (41) Fig. 4. Compounds 34-36 isolated from L. tiliifolia. (Abeygunawardena et al., 1991) (Fig. 6). CHEMISTRY OF SOME SPECIES GENUS LANTANA 53 CH2OH HO OO2CCH=CH OH O O OH O HO O OH OH HOH2C OH 37 OH O 38 OH OH OH OH Fig. 5. Compounds 37 and 38 isolated from L. × hybrida. OH OH O MeO O MeO O OMe O MeO OMe MeO OMe OH O OH O OH O 39 40 41 Fig. 6. Compounds 39-41 isolated from L. achyranthifolia. Lantana lilacina: A new acyclic monoterpene glucosyl name of the plant. The structure was established as 5- ester named β-D-glucopyranose, 1-[(2E, 6S)-6-hydroxy-2, hydroxy-6, 7, 3', 4', 5'-pentamethoxyflavone (Rwangabo 6-dimethyl-2, 7-octadienoate] (42) was isolated from the et al., 1988). Umuhengerin (43) exhibited In vitro leaves of L. lilacina Desf. (Takeda et al., 1998) (Fig. 7). antibacterial and antifungal properties in concentrations up to 200 µg/ml against various pathogens, including Lantana trifolia: L. trifolia L. is a species used in the folk Staphylococcus aureus, Salmonella typhimurium, medicine of Rwanda (Johns et al., 1983a). From the Candida tropicalis, Aspergillus niger, Aspergillus MeOH extract of the dried leaves of L. trifolia, a new, fumigatus, Trichophyton mentagrophytes, and antimicrobially active, polymethoxylated flavone was Mucrosporum canis (Rwangabo et al., 1988) (Fig. 8). isolated and named umuhengerin (43) after the Rwandese O OMe OMe O HO HO MeO O O OMe OH HO MeO OH OH O 42 43 Fig. 7. Compound 42 isolated from L. lilacina. Fig. 8. Compound 43 isolated from L. trifolia. Lantana camara: The plant L. camara L. is native to outbreeder weed that has invaded vast expanses of tropical and subtropical America. Dutch explorers pastures, orchards and forest areas in many tropical and introduced it into the Netherlands from Brazil in the late subtropical regions. It has been estimated that 4 million 1600s and later explorers from other countries brought hectares in Australia (Munir, 1996; Ross, 1999) and seeds to Europe, Great Britain and North America. 160,000 in Hawaii (Ross, 1999), have been invaded by Following its introduction into Hawaii as a garden flower, this plant. Apart from its popularity as a garden plant, L. it soon spread to the islands of the Pacific, Australia and camara is said to form a useful hedge and to provide a southern Asia.
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