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Bioactive Compounds of Some Malaysian Annonaceae Species

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Bioactive Compounds of Some Malaysian Annonaceae Species 4th International Conference on Advances in Biotechnology and Pharmaceutical Sciences (ICABPS'2013) Oct. 12-13, 2013 Singapore Bioactive Compounds of Some Malaysian Annonaceae Species Hairin Taha, Aditya Arya, Mustafa Ali Mohd, and A.Hamid A.Hadi Abstract—Bioactive compounds from the plants are big deal in II. PHARMACOLOGICAL PROPERTIES the nutraceutical and pharmaceutical industries. The plant based The bark, leaves and roots of some species are used in folk compounds directly or indirectly helps in the management of various disorders and thus works as a modulators. Malaysia is rich in medicines. Pharmaceutical research has found antifungal, biodiversity and have number of floras, among which Annonaceae bacteriostatic, antimalarial, and especially cytostatic capability family have vast acceptance and traditionally been used in folk of some chemical constituents of the leaves and bark. A large medicine and edible as food sources. Many studies have number of chemical compounds, including flavonoids, demonstrated that these plants possess a diverse range of alkaloids and acetogenins, have been extracted from the seeds pharmacological properties.This paper will briefly describe some of and many other parts of these plants. Flavonoids and alkaloids the bioactive compounds from the Malaysian Annonaceae species based on previous studies. have shown antibacterial properties, and have been used for treatment of medical conditions, such as skin disease, intestinal Keywords— Bioactive compounds; Annonaceae; Malaysia. worms and inflammation of the eye. Flavonoids and alkaloids contained in the leafs and bark of several species of the family I. INTRODUCTION have shown insecticidal properties . ALAYSIA is known as the richest and the oldest rain Some species of the family, such as Cananga odorata M forest in the world. At least 60% of the world’s known (ylang-ylang) also have aromatic oil and are used for perfumes species were found in the flora of Malaysia in which about or spices [2]. The strong bark is used for carrying burdens in 15,000 species of flowering plant and more than 1,170 species the Amazon Rainforest and for wooden implements, such as of ferns. The varieties of plants and flora provides tool handles and pegs. The wood is valued as firewood. Some opportunities for discovery of novel compounds, some of species are also grown as ornamental plants, especially the which could have beneficial biological activity. Malaysian Indian species Polyalthia longifolia pendula. Pharmaceutical flora is one of the oldest in the world (more than 200 million products are currently in animal and human cell-line trials. years of age) and is extremely rich in flowering plant species Acetogenins are thought to have anti-HIV and anti-cancer (15,000-20,000) with estimated 3,000 tree species. effects. A wide variety of products have been developed and Annonaceae, also called the custard apple family is a are available for cancer treatment. family of flowering plants consisting of trees, shrubs or rarely III. ARTABOTRYS lianas. With about 2300 to 2500 species and more than 130 genera, it is the largest family in Magnoliales [1]. Only five Four species of this genus have been studied: A. genera, Annona, Rollinia, Uvaria, Melodorum and Asimina grandifolius, A. maingayi , A. suaveolens , A. venustus. produce edible fruits. Its type genus is Annona. The family is Norstephalagine and atherospermidine, isolated from A. concentrated in the tropics, with few species found in maingayi, have been demonstrated to be smooth muscle temperate regions. About 900 species are Neotropical, 450 are relaxants (uterus) [3]. Afrotropical, and the other species Indomalayan. There are 38 genera, 198 described species in Malaya of which 26 genera, 131 described species are trees, more or less one-third being climbers. Hairin Taha, and A.Hamid A.Hadi are with Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia Aditya Arya is with Department of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia norstephalagine atherospermidine Mustafa Ali Mohd is with Department of Pharmacology, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia Fig. 1 5 4th International Conference on Advances in Biotechnology and Pharmaceutical Sciences (ICABPS'2013) Oct. 12-13, 2013 Singapore IV. FISSISTIGMA VII. MONOCARPIA Bioassay-guided fractionation led to the isolation of a Two compounds were isolated, monocarpin [7], a known chalcone, pedicin 6 (IC50 = 300 mM) which was active cycloartane triterpene, is bioactive, and a nitrogenous pigment, on tubulin assembly, and the dihydro analog, which is inactive. monomargine . Monomargine exhibits cytotoxic activity on Two new condensed chalcones, fissistin and isofissistin KB cells (IC50 = 0.7 mg/m1) and on P388 leukemia (IC50 = exhibited cytotoxicity against KB cells but no activity on 0.7mg/ml) [8]. tubulin assembly [4]. Pedicin Fissistin/ Isofissistin Fig. 2 Fig. 5 V. PSEUDUVARIA VIII. PHAEANTHUS Pseuduvarine A and Pseuduvarine B, isolated from Pseuduvaria rugosa showed significant and potent cytotoxicity 4’, 5-diformyl-2-methoxydiphenylether, doryphornine and selectivity towards the tested cells, with Pseuduvarine A methyl ether, (+)-vietnamine, (+)-phecrassipine A, (-)- being the most toxic against breast cells (MC7) at IC50 value phecrassipine B, (-)-limacine and (+)-limacusine isolated from of 0.9 µM and Pseuduvarine B being the most toxic and Phaeanthus crassipetalus showed relaxant effects against the selective on human promyelocyctic leukemia (HL-60) cell contraction induced by NE [9]. This finding supports the earlier report where Phaeanthus crassipetalus has been used in lines (IC50 12.4 µM) [5]. the treatment high blood pressure by people in Borneo. Pseuduvarine A Pseuduvarine B Fig. 3 Fig. 6 EFERENCES VI. MITRELLA R [1] Leboeuf, M.; Cavé, A.; Bhaumik, P. K.; Mukherjee, B.; Mukherjee, R., Desmosdumotin C, a chalcone isolated from Mitrella kentii The phytochemistry of the annonaceae. Phytochemistry 1980, 21 (12), [6] demonstrated gastroprotective effects on gastric ulcer 2783-2813. models in rat. [2] Benini, C.; Ringuet, M.; Wathelet, J.-P.; Lognay, G.; du Jardin, P.; Fauconnier, M.-L., Variations in the essential oils from ylang-ylang (Cananga odorata [Lam.] Hook f. & Thomson forma genuina) in the H3C CH3 3" Western Indian Ocean islands. Flavour and Fragrance Journal 2012, 27 H CO O 3 5' 6' (5), 356-366. H 2" 4" 1' [3] Cortes, D.; Torrero, M. Y.; Pilar D'Ocon, M.; Luz Candenas, M.; Cave, 2 A.; Hadi, A. H., [Norstephalagine and atherospermidine: two smooth 5" 4' 2' 1" muscle relaxant aporphines from Artabotrys maingayi]. J Nat Prod H3C 3' 1 3 6" 1990, 53 (2), 503-8. O OH H [4] Alias, Y.; Awang, K.; Hadi, A. H.; Thoison, O.; Sevenet, T.; Pais, M., An antimitotic and cytotoxic chalcone from Fissistigma lanuginosum. J Fig. 4 Desmosdumotin C Nat Prod 1995, 58 (8), 1160-6. [5] Taha, H.; Hadi, A. H.; Nordin, N.; Najmuldeen, I. A.; Mohamad, K.; Shirota, O.; Nugroho, A. E.; Piow, W. C.; Kaneda, T.; Morita, H., 6 4th International Conference on Advances in Biotechnology and Pharmaceutical Sciences (ICABPS'2013) Oct. 12-13, 2013 Singapore Pseuduvarines A and B, two new cytotoxic dioxoaporphine alkaloids from Pseuduvaria rugosa. Chemical & pharmaceutical bulletin 2011, 59 (7), 896-7. [6] Sidahmed, H.; Azizan, A.; Mohan, S.; Abdulla, M.; Abdelwahab, S.; Taha, M.; Hadi, A.; Ketuly, K.; Hashim, N.; Loke, M.; Vadivelu, J., Gastroprotective effect of desmosdumotin C isolated from Mitrella kentii against ethanol-induced gastric mucosal hemorrhage in rats: possible involvement of glutathione, heat-shock protein-70, sulfhydryl compounds, nitric oxide, and anti-Helicobacter pylori activity. BMC Complementary and Alternative Medicine 2013, 13 (1), 183. [7] Mahmood, K.; Pais, M.; Fontaine, C.; Ali, H. M.; Hamid, A.; Hadi, A.; David, B.; Guittet, E., Monocarpin, a new cycloartane from Monocarpia marginalis. Tetrahedron Letters 1992, 33 (26), 3761-3764. [8] Mahmood, K.; Païs, M.; Fontaine, C.; Ali, H. M.; Hamid, A.; Hadi, A.; Guittet, E., Monomargine, a nitrogenous cytotoxic pigment from Monocarpia marginalis. Tetrahedron Letters 1993, 34 (11), 1795-1796. [9] Zaima, K.; Takeyama, Y.; Koga, I.; Saito, A.; Tamamoto, H.; Azziz, S.; Mukhtar, M.; Awang, K.; Hadi, A. H.; Morita, H., Vasorelaxant effect of isoquinoline derivatives from two species of Popowia perakensis and Phaeanthus crassipetalus on rat aortic artery. J Nat Med 2012, 66 (3), 421-427 7.
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