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Articles

Swietenia macrophylla King (Meliaceae)

Synonyms

Swietenia candollei Pittier, Swietenia belizensis Lundell, Swietenia krukovii Gleason, Swietenia tessmannii Harms, Swietenia belizensis Lundell. [1],[2],[3]

Vernacular Names:

Malaysia: Cheria mahagony[3]
English: Honduras mahogany, mahogany, bigleaf mahogany, American mahogani, Baywood (GB), Bigleaf mahogany (USA), Broadleaf mahagony (USA), Large-leaved mahogany [1],[2]
Protugese(Brazil): Araputanga, caóba, cedro-í, mogno, mogno-brasileiro, aguano [1]
Spanish: Caoba, mara [1]
French: Acajou à feuille large, acajou d'Amérique, mahogany à grandes feuilles, swiéténie [2]

General Information

Description

Swietenia macrophylla is a long-lived, fast-growing, deciduous tree that can reach heights of up to 50 m with a trunk measuring 3-4 m in girth found in both ever-wet and seasonally dry tropical rainforests and thrives in a very wide range of soil conditions. It is native to tropical America, Mexico and South America.  A monoecious specie with an as yet unknown primary pollinator.  The fruits are large woody capsules, measuring 10-20 cm long which split open when ripe to release about 50 large winged seeds. The seedlings require overhead light for growth but not for survival. [4]  The leaves 15-35 cm long. The leaflets in 6-12 pairs, lanceolate, 7-15 cm long, 2.5-7 cm wide, inequilateral at base, acuminate at apex, petioluled, entire, coriaceous, glabrous; panicles 9-20 cm long; bracts and bracteoles orbicular or nearly so, deciduous; calyx cup 2-2.5 mm wide, lobes rounded; petals obovate to spatulate, 5-6 mm long, 2-3 mm wide. The capsule ovoid, 12-15 cm long, 7-7.5 cm wide, acute to acuminate apically. The seeds 7.5-8.5 cm long, the wing about twice as long as body, reddish brown. [5]

Plant Part Used

Seeds, barks. [4],[15]

Chemical Constituents

The seeds contain tetranortriterpenoids, swietenine, swietenine acetate and swietenolide (a bitter principle], swietenolide tiglate, swietenolide diacetate, augustineolide, 8, 30-epoxy swietenine acetate and 3b-6-dihydroxydihydrocarapin,[6],[7],[8],[9],[10]  3,6-Di-O-acetylswietenolide 0.25-hydrate was isolated from the ethyl acetate extract of the seeds. [11]  Other tetranortriterpenoids isolated from the seeds were methyl 3b-tigloyloxy-2,6-dihydroxy-1-oxo-meliac-8(30)-enate, methyl 3b-tigloyloxy-2-hydroxy-1-oxo-meliac-8(30)-enate, methyl 3b-tigloyloxy-2-hydroxy-8a,30a-epoxy-1-oxo-meliacate, methyl 3b-acetoxy-2,6-dihydroxy-8a,30a-epoxy-1-oxo-meliacate and methyl 3b-isobutyryloxy-2,6-dihydroxy-8a,30a-epoxy-1-oxo-meliacate [7] and 3b,14-dihydroxymexicanolide, 3-O-tigloylswitenolide, febrifugina, 3,6-di-O,O-acetylswietenolide. [12]

The terminal shoots, and mature and senescent leaves of the S. macrophylla contained essential oils which largely consisted of sesquiterpenes. The compounds that have been identified were a-copaene, b-bourbonene, b-cubebene, b-elemene, b-caryophyllene, b-gurjunene, allo-aromadendrene, g-himachalene, germacrene D, germacrene A, b-ionone, bicyclogermacrene, a-bisabolene, b- bisabolene, g- bisabolene, 7-epi-a-selinene, cadina-1,4-diene, hexadecanoic acid and ethyl hexadecanoate. Oils from the terminal shoots (212 mg, 0.053% w/w), mature leaves (193 mg, 0.048% w/w), and senescent (188 mg, 0.047%) leaves contained 19, 16, and 13 components, respectively.  All samples contained germacrene D as the major constituent (58.5–66.5%).  The oils all contained g-himachalene, germacrene A, cadina-1,4-diene, hexadecanoic acid, and ethyl hexadecanoate, although in different proportions.  The oils from mature and senescent leaves were most similar and contained 10 similar compounds. [13]

Traditional Use:

A most valued tropical hardwood as its timber is easily worked, durable and has a rich red colour. [4]

The seeds are chewed or pounded and swallowed by the natives and the common people of Malaysia to treat high blood pressure. [6] The seeds are traditionally used by the local healers of East Midnapore, West-Bengal, India to cure diarrhoea. [14]

The Mosetene indians of Andean Piedmont, Bolivia, drink a decocotion of the crushed seeds to induce abortion.  To heal wounds and skin problems including skin allergy in children, the crushed seeds are mixed with Attalea phalerata seed oil and applied onto the skin as a poultice. The Mosetenes also used the bark as a dying agent.  Previous research showed a strong correlation between the dying properties of species and its antimalarial activity.   It is also used to dye cotton thread, brown. A decoction of the seeds is used to treat malaria in Indonesia. [15] and in India, where it is also used to treat diabetes and hypertension. [10]

Pre-Clinical Data

Pharmacology

Antimicrobial activity

The antimicrobial activity of a methanol extract of S. macrophylla bark was examined against selected gram positive and gram negative bacteria (20 strains) and fungi (4 strains).  The methanol extract of S. macrophylla bark showed high sensitivity against Escherichia coli strains while all Shigella strains showed resistance.  The extract was effective against Candida albicans but least effective against Penicillium sp.. [16]

Antiprotozoan activity

A lectin isolated from the leaves of S. macrophylla (molecular weight=295 kDa) was cytotoxic aginst Acanthamoeba sp. (a corneal keratitis-causing amoeba) and Tetrahymena pyriformis (a ciliate) indicating its potential as an antiparasitic agent.  S. macrophylla lectin showed cytotoxicity against Acanthamoeba sp. and against Tetrahymena pyriformis at concentrations as low as 25 ppm and 10 ppm, respectively.  The mechanism could involve interaction of the lectin with sugars present in the protozoans. [17]

Antimalarial activity

The bark extract of S. macrophylla showed good in vivo activity (73% inhibition of the rodent malaria Plasmodium vinckei petteri at 250 mg/kg) and in vitro activity (78% inhibition of chloroquine resistant Plasmodium falciparum strains (Indo) at 100 µg/mL against malarial.  The standard antimalarial drugs for the in vitro assay were Cinchona calisaya stem bark extract (0.4 µg/mL produced 100% inhibition) and chloroquine (100% inhibition at 148 ng/mL).  For the in vivo assay, Cinchona calisaya bark extract produced 91% inhibition at 250 mg/kg/day while chloroquine (5 mg/kg/day) inhibited 100% of the parasite growth. [15]

The water extract of S. macrophylla seeds strongly inhibited the growth of Plasmodium falciparum and Babesia gibsoni with inhibition rates of almost 100% and more than 85%, respectively. Babesia gibsoni is a canine intra-erythrocytic parasite that causes anemia.  Its life cyle is similar to that P. falciparum and both produce similar disease symptoms. [18]

Anti-inflammatory, antimutagenic and antitumor-promoting activity

The crude ethanol extract of the seeds S. macrophylla (1 mg/g body weight] showed anti-inflammatory activity as it reduced carrageenan-induced inflammation in mice by 79% . [19]  The solvent fractions of the ethanol extract, i.e. hexane, CCl4 and methanol fractions showed less anti-inflammatory activity.  The methanol fraction elicited the highest inhibition (60%) while the hexane fraction produced a low inhibition of 23%.  The ethanol extract  (0.02 mg/g body weight) showed antimutagenic effects by the micronucleus test as it reduced the number of micronucleated polychromatic erythrocytes induced by the mutagen mitomycin C, by almost 50%.  The ethanol crude extract and its solvent fractions showed significant antitumor-promoting activity as they inhibited Epstein-Barr early-antigen (EBV-EA) activation using 12-0 tetradecanoylphorbol-13-acetate (TPA) as the tumor promoter. [19]

Antidiarrhoeal activity

The petroleum ether extract of S. macrophylla seeds (25, 50 & 100 mg/kg body weight, p.o.) showed antidiarrhoeal activity in castor oil-induced diarrhoea in rats, indicating its potential for development as an antidiarrhoeal drug . [14] The extract of S. macrophylla produced a reduction in the rate of defecation and improved the consistency of faeces, effects that were comparable to those produced by the standard anti-diarrhoeal drug, diphenoxylate (50 mg/kg).  The maximum effects were seen with 100 mg/kg body weight of S. macrophylla seed extract.  The mechanism may involve increased reabsorption of water due to decreased intestinal motility as the petroleum ether seed extract elicited a profound decrease in intestinal transit and significantly inhibited castor oil-induced entero-pooling (intestinal fluid accumulation), effects which were comparable to those produced by atropine sulphate and a drug that produced gastrointestinal hypomotility.  The extract was equally effective at preventing or curing diarrhoea. [14]

Toxicities

Antifeedant activity

The antifeedant property of the seed extracts of S. macrophylla were investigated using the fall armyworm (FAW), Spodoptera frugiperda (J. E. Smith) and the striped cucumber beetle (SCB), Acalymma vittatum (F.). The seed extracts were highly deterrent (feeding ratios of 0.02 and 0.18 for the ethanol and hexane extracts, respectively) in the FAW bioassay.  The feeding ratio was defined as the percentage of an extract-treated leaf disk consumed/percentage of control disk consumed.  The feeding ratio of 1.0 indicated no deterrency as equal quantities of treated and control leaf disks were eaten.  The extracts were non lethal since 20 % mortality was seen with the ethanol extract while no mortality occurred with the hexane extract.  However, none of the insects pupated while the larvae were all small. The antifeedant activity was also exhibited against SCB although S. macrophylla seed extract was not as potent as the other plant extracts that were also screened. [20]

 

Brine shrimp lethality activity

In the 24 h brine shrimp (Artemia salina Leach) bioassay, the ethanol and hexane extracts of S. macrophylla seeds elicited 22 and 44% mortality, respectively while at 48 h, the mortality were 48 and 76%, respectively. [20]

The crude methanol extracts of the stem barks and leaves of S. macrophylla elicited LC50 values of >1000 and 704.83 µg/mL, respectively, in the brine shrimp lethality bioassay.  The positive control for this assay was the crude extract of the stem bark of Annona squamosa which showed an LC50 value of 6.5 µg/mL. [21]

Haemorrhagic activity

The seeds of Swietenia species and the bark of S. mahagony have been reported to induce uterine haemorrhage which can lead to death. [15]

Genotoxicities and Mutagenicity Studies

No documentation

Clinical Data

Clinical Trials

No documentation

Adverse Effects in Human:

The allergic contact dermatitis, rhinitis and conjunctivitis in joiners who were exposed to Honduras mahogany dust. [22] The contact dermatitis due to S. macrophylla has also been described elsewhere 2, 6-Dimethoxy-p-benzoquinone, is a relatively good sensitizer in guinea pigs.  It was isolated in small amounts from S. macrophylla.  It is recommended that 2,6-dimethoxy-p-benzoquinone be used in patch tests in in cases of suspected contact dermatitis to S. macrophylla. [23]

Use in Certain Conditions

Pregnancy / Breastfeeding

No documentation

 

Age Limitations

Neonates / Adolescents

No documentation

 

Geriatrics

No documentation

Chronic Disease Conditions

No documentation

Interactions

Interactions with drugs

No documentation

Interactions with Other Herbs / Herbal Constituents

No documentation

Contraindications

Contraindications

No documentation

Case Reports

Two men, a 45- and a 54-year-old, who have been working for a long time in their occupations as joiners experienced occupational allergic contact dermatitis and reacted to Honduras mahogany dust on patch testing. [22] They also presented with rhinitis, conjunctivitis.  The allergen of Honduras mahogany is not known.

Read More

  1)  Botanical Info

  2)  Western Herbs

References

Normal 0 false false false EN-US X-NONE X-NONE MicrosoftInternetExplorer4

  1. NPGS-GRIN. Taxon: Swietenia macrophylla King  http://www.ars-grin.gov/cgi-bin/npgs/html/taxon.pl?35955. . [Accessed on 12 Nov 2007]
  2. MMPND – Sorting Swietenia names.  http://www.plantnames.unimelb.edu.au/Sorting/Swietenia.html. . [Accessed on 12 Nov 2007]
  3. AgroForestryTree Database.  http://www.worldagroforestrycentre.org/SEA/Products/AFDbases/AF/asp/SpeciesInfo.asp?SpID=1566. [ Accessed on 12 Nov 2007]
  4. Brown N, Jennings S, Clements T.  The ecology, silviculture and biogeography of mahogany (Swietenia macrophylla): a critical review of the evidence.  Perspectives in Plant Ecology, Evolution and Systematics. 2003; 6(1,2): 37-49 
  5. PIER – Swietenia macrophylla King.  http://www.hear.org/pier/species/swietenia_macrophylla.htm.. [Accessed on 12 Nov 2007]
  6. Chan KC, Tang TS, Toh HT.  Isolation of swietenolide diacetate from Swietenia Macrophylla.  Phytochemistry. 1976;15:429-430. 
  7. Kojima K, Isaka K, Ogihara Y.  Tetranortriterpenoids from Swietenia macrophylla. Chem. Pharm. Bull. 1998; 46(3):523-525.
  8. Taylor ARH and Taylor DAH.  Limonoid extractives from Swietenia macrophylla.  Phytochemistry. 1983; 22(12): 2870-2871. 
  9. Mootoo BS, Ali A, Motilal R, Pingal R, Ramlal A, Khan A, Reynolds WF, McLean S.  Limonoids from Swietenia macrophylla and S. aubrevilleana.  J Nat Prod. 1999; 62(11):1514-1517. 
  10. Solomon KA, Malathi R, Rajan SS, Narasimhan S, Nethaji M.  Swietenine.  Acta Cryst. 2003;59: 1519-1521. 
  11. Fowles RG, Mootoo BS, Ramsewak R, Reynolds W, Lough AJ.  3,6-Di-O-acetylswietenolide 0.25-hydrate.  Acta Crystallographica. 2007; 63: 660–661. 
  12. Schefer AB, Braumann U, Tseng LH, Spraul M, Soares MG, Fernandes JB, da Silva MFGF, Vieira PC, Ferreira AG.  et al. Application of high-performance liquid chromatography–nuclear magnetic resonance coupling to the identification of limonoids from mahogany tree (Switenia macrophylla, Meliaceae) by stopped-flow 1D and 2D NMR spectroscopy.  Journal of Chromatography A. 2006; 1128: 152-163. 
  13. Soares MG, Batista-Pereira LG, Fernandes JB, Correâ AG, da Silva MFGF, Vieira PC, Filho ER, and Ohashi OS.  et al. Electrophysiological responses of female and male Hypsipyla grandella (Zeller) to Swietenia macrophylla essential oils.  Journal of Chemical Ecology. 2003; 29(9): 2143- 2151. 
  14. Maiti A, Dewanjee S, Mandal SC.  In Vivo Evaluation of Antidiarrhoeal Activity of the Seed of Swietenia macrophylla King (Meliaceae).  Tropical Journal of Pharmaceutical Research. 2007; 6(2): 711-716. 
  15. Munõz V, Sauvain M, Bourdy G, Callapa J, Rojas I, Vargas L, Tae A, Deharo E.  The search for natural bioactive compounds through a multidisciplinary approach in Bolivia. Part II. Antimalarial activity of some plants used by Mosetene indians.  Journal of Ethnopharmacology. 2000; 69: 139-155. 
  16. Dewanjee S, Kundu M, Maiti A, Majumdar R, Majumdar A, Mandel S.C. In Vitro Evaluation of Antimicrobial Activity of Crude Extract from Plants Diospyros peregrina, Coccinia grandis and Swietenia macrophylla.  Tropical Journal of Pharmaceutical Research. 2007; 6(3): 773-778. http://www.ajol.info/viewarticle.php?id=34886. . [Accessed on 12 Nov 2007]
  17. Endriga MA, Mojica ERC, Merca FE, Lacsamana MS, Deocaris CC.  Evaluation of some lectins as anti-protozoal agents.  J. Med. Sci. 2005; 5(1): 31-34.
  18. Murnigsih T, Subeki, Matsuura H, Takahashi K, Yamasaki, M, Yamato O, maaede Y, Katakura K, Suzuki M, Kobayashi S, Chairul, Yoshihara T.  Evaluation of the inhibitory activities of the extracts of Indonesian traditional medicinal plants against Plasmodium falciparum and Babesia gibsoni.  J.Vet. Med. Sci.2005 67(8):829-831.
  19. Guevara A.P, Apilado A, Sakurai H, Kozuka M, Tokuda H. Normal 0 false false false EN-US X-NONE X-NONE MicrosoftInternetExplorer4 Anti-inflamatory, Antimutagenicity and Antitumor-promoting Activities of Mahogany Seeds, Swietenia macrophylla (Meliaceae). 1996;  PJS, 125(4). http://www.stii.dost.gov.ph/pjsweb/data/mahogany.htm. [Accessed on 12 Nov 2007]
  20. Mikolajczak KL and Reed DK.  Extractives of seeds of the Meliaceae: Effects on Spodopterafrugiperda (J.E. Smith), Acalymma vittatum (F.), and Artemia salina Leach.  Journal of Chemical Ecology. 1987; 13(1): 99-111.
  21. Pisutthanan S, Plianbangchang P, Pisutthanan N, Ruanruay S, Muanrit O. Brine shrimp lethality sctivity of Thai medicinal plants in the family Meliaceae.  Naresuan University Journal. 2004; 12(2): 13-18. http://www.nu.ac.th/nu_journal/pdf/journal/12(2)13-18.pdf.. [Accessed on 12 Nov 2007]
  22. Estlander T, Jolanki R, Alanko K, Kanerva L.  Occupational allergic contact dermatitis caused by wood dusts.  Contact Dermatitis. 2001; 44: 213-217.
  23. Hausen BM.  Sensitizing capacity of naturally occurring quinones.  V. 2.6-Dimethoxy-p-benzoquinone: Occurrence and significance as a contact allergen.  Contact Dermatitis,. 1978; 4: 204-213.
Normal 0 false false false EN-US X-NONE X-NONE MicrosoftInternetExplorer4

1.     NPGS-GRIN. Taxon: Swietenia macrophylla King  http://www.ars-grin.gov/cgi-bin/npgs/html/taxon.pl?35955. . [Accessed on 12 Nov 2007]

2.     MMPND – Sorting Swietenia names.  http://www.plantnames.unimelb.edu.au/Sorting/Swietenia.html. . [Accessed on 12 Nov 2007]

3.     AgroForestryTree Database.  http://www.worldagroforestrycentre.org/SEA/Products/AFDbases/AF/asp/SpeciesInfo.asp?SpID=1566. [ Accessed on 12 Nov 2007]

4.     Brown N, Jennings S, Clements T.  The ecology, silviculture and biogeography of mahogany (Swietenia macrophylla): a critical review of the evidence.  Perspectives in Plant Ecology, Evolution and Systematics. 2003; 6(1,2): 37-49

5.     PIER – Swietenia macrophylla King.  http://www.hear.org/pier/species/swietenia_macrophylla.htm.. [Accessed on 12 Nov 2007]

6.     Chan KC, Tang TS, Toh HT.  Isolation of swietenolide diacetate from Swietenia Macrophylla.  Phytochemistry. 1976;15:429-430.

7.     Kojima K, Isaka K, Ogihara Y.  Tetranortriterpenoids from Swietenia macrophylla. Chem. Pharm. Bull. 1998; 46(3):523-525.

8.     Taylor ARH and Taylor DAH.  Limonoid extractives from Swietenia macrophylla.  Phytochemistry. 1983; 22(12): 2870-2871.

9.     Mootoo BS, Ali A, Motilal R, Pingal R, Ramlal A, Khan A, Reynolds WF, McLean S.  Limonoids from Swietenia macrophylla and S. aubrevilleana.  J Nat Prod. 1999; 62(11):1514-1517.

10.  Solomon KA, Malathi R, Rajan SS, Narasimhan S, Nethaji M.  Swietenine.  Acta Cryst. 2003;59: 1519-1521.

11.  Fowles RG, Mootoo BS, Ramsewak R, Reynolds W, Lough AJ.  3,6-Di-O-acetylswietenolide 0.25-hydrate.  Acta Crystallographica. 2007; 63: 660–661.

12.  Schefer AB, Braumann U, Tseng LH, Spraul M, Soares MG, Fernandes JB, da Silva MFGF, Vieira PC, Ferreira AG.  et al. Application of high-performance liquid chromatography–nuclear magnetic resonance coupling to the identification of limonoids from mahogany tree (Switenia macrophylla, Meliaceae) by stopped-flow 1D and 2D NMR spectroscopy.  Journal of Chromatography A. 2006; 1128: 152-163.

13.  Soares MG, Batista-Pereira LG, Fernandes JB, Correâ AG, da Silva MFGF, Vieira PC, Filho ER, and Ohashi OS.  et al. Electrophysiological responses of female and male Hypsipyla grandella (Zeller) to Swietenia macrophylla essential oils.  Journal of Chemical Ecology. 2003; 29(9): 2143- 2151.

14.  Maiti A, Dewanjee S, Mandal SC.  In Vivo Evaluation of Antidiarrhoeal Activity of the Seed of Swietenia macrophylla King (Meliaceae).  Tropical Journal of Pharmaceutical Research. 2007; 6(2): 711-716.

15.  Munõz V, Sauvain M, Bourdy G, Callapa J, Rojas I, Vargas L, Tae A, Deharo E.  The search for natural bioactive compounds through a multidisciplinary approach in Bolivia. Part II. Antimalarial activity of some plants used by Mosetene indians.  Journal of Ethnopharmacology. 2000; 69: 139-155.

16.  Dewanjee S, Kundu M, Maiti A, Majumdar R, Majumdar A, Mandel S.C. In Vitro Evaluation of Antimicrobial Activity of Crude Extract from Plants Diospyros peregrina, Coccinia grandis and Swietenia macrophylla.  Tropical Journal of Pharmaceutical Research. 2007; 6(3): 773-778. http://www.ajol.info/viewarticle.php?id=34886. . [Accessed on 12 Nov 2007]

17.  Endriga MA, Mojica ERC, Merca FE, Lacsamana MS, Deocaris CC.  Evaluation of some lectins as anti-protozoal agents.  J. Med. Sci. 2005; 5(1): 31-34.

18.  Murnigsih T, Subeki, Matsuura H, Takahashi K, Yamasaki, M, Yamato O, maaede Y, Katakura K, Suzuki M, Kobayashi S, Chairul, Yoshihara T.  Evaluation of the inhibitory activities of the extracts of Indonesian traditional medicinal plants against Plasmodium falciparum and Babesia gibsoni.  J.Vet. Med. Sci.2005 67(8):829-831.

19.  Guevara A.P, Apilado A, Sakurai H, Kozuka M, Tokuda H. Anti-inflamatory, Antimutagenicity and Antitumor-promoting Activities of Mahogany Seeds, Swietenia macrophylla (Meliaceae). 1996; PJS, 125(4). http://www.stii.dost.gov.ph/pjsweb/data/mahogany.htm. . [Accessed on 12 Nov 2007]

20.  Mikolajczak KL and Reed DK.  Extractives of seeds of the Meliaceae: Effects on Spodopterafrugiperda (J.E. Smith), Acalymma vittatum (F.), and Artemia salina Leach.  Journal of Chemical Ecology. 1987; 13(1): 99-111.

21.  Pisutthanan S, Plianbangchang P, Pisutthanan N, Ruanruay S, Muanrit O. Brine shrimp lethality sctivity of Thai medicinal plants in the family Meliaceae.  Naresuan University Journal. 2004; 12(2): 13-18. http://www.nu.ac.th/nu_journal/pdf/journal/12(2)13-18.pdf.. [Accessed on 12 Nov 2007]

22.  Estlander T, Jolanki R, Alanko K, Kanerva L.  Occupational allergic contact dermatitis caused by wood dusts.  Contact Dermatitis. 2001; 44: 213-217.

23.  Hausen BM.  Sensitizing capacity of naturally occurring quinones.  V. 2.6-Dimethoxy-p-benzoquinone: Occurrence and significance as a contact allergen.  Contact Dermatitis,. 1978; 4: 204-213.