Tunjuk langit Seed
Swietenia macrophylla King
Meliaceae
Figure 1 :Swietenia macrophylla. (a) Tree habit; (b) leaves; (c) bark; (d) brown fruit, cross section of fruit (insert); (e) seed and wing; (f) seed capsule; (g) seed coat (h) seed. (Photos courtesy of FRIM, 2016)
DEFINITION
Tunjuk langit seed consists of the powder of dried seeds of Swietenia macrophylla King (Meliaceae).
SYNONYM
Swietenia belizensis Lundell, Swietenia candollei Pittier, Swietenia macrophylla Kingvar. marabaensis Ledoux et Lobato, Swietenia tessmannii Harms [ 1 ].
VERNACULAR NAMES
Big-leaf mahogany, broad-leafed mahogany, American mahogany, Honduras mahogany, sky fruit (English); Tunjuk langit, mahogani (Malay); Xiang tian guo (Chinese); Tettankottai (Tamil) [ 2 , 3 ].
CHARACTER
IDENTIFICATION
Plant Morphology
Swietenia macrophylla is an evergreen tree, up to 30–35 m tall. Bark is grey and smooth when young, turning dark brown, ridged and flaky when old. Leaves up to 35–50 cm long, alternate, glabrous with 4–6 pairs of leaflets; leaflet 9–18 cm long, stalked and shortly acuminate. Inflorescence an axillary panicle 10–20 cm long, consisting of small cymes. Flowers small and white, fragrant. Fruits capsular, oblong or ovoid, 11.6–38.7 cm length, 6.7–12.0 cm diameter and light grey to brown with 4–5 valves, each fruits contains 22–71 developed seeds. Seeds dark brown, samaroid, woody, glossy, bulky at their base, 7–12 cm long and 2–2.5 cm wide including the wing, posses wing-like structure at the base that aids its dispersion by wind [ 5 , 6 , 7 ].
Microscopy
Powdered material consists of fragment of epidermis cells with straight to curved anticlinal wall. The abundant starch granules are mostly simple, rounded to oval in shape and usually found in group, also associated with oil globules [ 8 ].
Figure 2 : Microscopic characters of Swietenia macrophylla dried seeds powder of 0.355 mm size. (a) & (b) Epidermis cells (magnification 20x); (c) starch granules (red arrow) associated with oil globules (yellow arrow) (magnification 40x); (d) oil globules (magnification 10x). [Scale bars: a, b, e = 50 µm; c = 20 µm; d = 100 µm]
Chemical Tests
Observation of solution after treatment with reagent :
| Test for the presence of triterpenes | Dark red |
Thin Layer Chromatography (TLC)
Figure 3 : TLC chromatogram of swietenolide (S) at Rf: 0.26 min and ethanol extract of Swietenia macrophylla dried seeds powder (L) observed under (a) UV at 366 nm after spraying with 10% sulphuric acid reagent and heat at 105°C for 3 min and (b) visible light after spraying with 10% sulphuric acid reagent and heat at 105°C for 3 min
| Test Solutions | Weigh about 0.5 g of S. macrophylla dried seeds powder of 0.355 mm size in a 7 mL screw-capped vial. Add 5 mL of ethanol and sonicate for 15 min. Filter the solution, dry under reduced pressure and reconstitute in 5 mL methanol. Filter the solution through filter paper. Use the filtrate as test solution. |
| Standard solution | Dissolve swietenolide (CAS no.: 3776-48-5) in methanol to produce 1.0 mg/mL solution. |
| Stationary Phase | HPTLC silica gel pre-coated plate 60 F254, 10 x 10 cm |
| Mobile phase | Hexane : ethyl acetate (1 : 1) (v/v) |
| Application |
|
| Development distance | 8 cm |
| Drying | Air drying |
| Detection |
|
High Performance Liquid Chromatography (HPLC)
| Test solution | Weigh about 0.5 g of S. macrophylla dried seeds powder of 0.355 mm size in a 14 mL screw-capped vial. Add 5 mL of ethanol and sonicate for 15 min. Filter the solution, dried under reduced pressure and reconstitute in 5 mL methanol. Filter the mixture with 0.45 µm syringe filter into a 7 mL screw-capped vial. Use the filtrate as test solution. | |||||||||||||||
| Standard solution | Dissolve swietenolide (CAS No.: 3776-48-5) in methanol to produce 1.0 mg/mL solution. | |||||||||||||||
| Chromatographic system |
Detector: PDA 230 nm Column: C18 (5 µm, 4.6 mm i.d. x 250 mm) (Luna C18, Phenomenex if necessary) Column oven temperature: Ambient Flow rate: 1.0 mL/min Injection volume: 10 µL |
|||||||||||||||
| Mobile Phase (gradient mode) |
|
|||||||||||||||
| System suitability requirement |
Perform at least five replicate injections of the standard solutions (1.0 mg/mL). The requirements of the system suitability parameters are as follow:
|
|||||||||||||||
| Acceptance criteria |
|
(a)
(b)
Figure 4 : Whole HPLC chromatogram of (a) swietenolide standard solution (1.0 mg/mL) at tr= 5.963 min and (b) ethanol extract of Swietenia macrophylla dried seeds powder showing peak corresponding to swietenolide standard solution at tr= 5.967 min.
(a)
(b)
Figure 5 : HPLC chromatogram highlighting the elution region of swietenolide in (a) swietenolide standard solution (1.0 mg/mL) and (b) ethanol extract of Swietenia macrophylla dried seeds powder showing peak corresponding to swietenolide standard solution at tr= 5.967 min.
Figure 6 : UV spectrum of swietenolide standard solution (1.0 mg/mL) and ethanol extract of Swietenia macrophylla dried seeds powder.
PURITY TESTS
The purity tests, except foreign matter test, are based on S. macrophylla dried seeds powder of 0.355 mm particle size.
| Foreign Matter |
| Not more than 2% |
| Ash Contents | |
| Total ash | Not more than 4% |
| Acid-insoluble ash | Not more than 0.1% |
| Water-soluble ash | Not less than 0.5% |
| Loss on Drying |
| Not more than 5% |
| Extractive Values | |
| Water-soluble extracts | |
| Hot method | Not less than 11% |
| Cold method | Not less than 7% |
| Ethanol-soluble extracts | |
| Hot method | Not less than 30% |
| Cold method | Not less than 25% |
SAFETY TESTS
The safety tests are based on S. macrophylla dried seeds powder of 0.355 mm particle size.
| Heavy Metals | |
| Arsenic | Not more than 5.0 mg/kg |
| Mercury | Not more than 0.5 mg/kg |
| Lead | Not more than 10.0 mg/kg |
| Cadmium | Not more than 0.3 mg/kg |
| Microbial Limits | |
| Total bacterial count | Not more than 105 cfu/g |
| Total yeast and mould count | Not more than 104 cfu/g |
| Bile-tolerant gram negative | Not more than 104 cfu/g |
| Specific Pathogens | |
| Salmonella spp. | Absent in 25 g |
| Escherichia coli | Absent in 1 g |
| Staphylococcus aureus | Absent in 1 g |
| Pseudomonas aeruginosa | Absent in 1 g |
CHEMICAL CONSTITUENTS
Methanol extract of S. macrophylla seeds was found to contain limonoids (e.g. febrifugin, humilinolide F, khayasin T, swietenine, swietenine acetate, swietemacrophin, swietemahonin E, 6-O-acetyl-3’-demethylswietephragmin E, 3,6-O,O-diacetylswietenolide, 3-O-tigloylswietenolide, 3-O-tigloyl-6-O-acetylswietenolide, 6-O-acetylswietemahonin G and methyl 3β-tigloyloxy-2-hydroxy-8α,30α-epoxy-oxo-meliacate), coumarin (e.g. scopoletin), steroids (e.g. β-sitostenone, 3β-hydroxystigmast-5-en-7-one, β-sitosterol and stigmasterol) and fatty acid ester (e.g. stearic acid methyl ester) [ 9 , 10 ].
Ethanol extract of S. macrophylla seeds was found to contain limonoids (e.g. andirobin, febrifugin, khayasin T, proceanolide, swietenine, swietenolide, swietenine acetate, swielimonoids A – F, swietemahonin, swietemahonin E, swietemahonin F, swietemahonolide, 7-deacetoxy-7α-hydroxygedunin, methyl angolensate, 3-O-tigloylswietenolide, 6-O-acetylswietenolide, 3,6-O,O-diacetylswietenolide, 3-O-acetylswietenolide, 6-O-acetylswietemahonin G, 7-deacetoxy-7-oxogedunin and seco-mahoganin) [ 11 ].
Acetone extract of S. macrophylla seeds was found to contain limonoids (e.g. andirobin, augustineolide, khayasin T, proceranolide, swietenine, swietenine C, swietenolide, swietemahonin E swietemahonin F, swietemahonin G, 2-hydroxyswietenine, 7-deoxyswietenine, 3,6-O,O-diacetylswietenolide, 6-O-acetylswietenolide, 3β,6-dihydroxydihydrocarapin, methyl 3β-tigloyloxy-2-hydroxy-1-oxo-meliac-8(30)-enate and methyl 3β-tigloyloxy-2-hydroxy-8α,30α-epoxy-1-oxo-meliacate) [ 12 , 13 ].
Chloroform extract of S. macrophylla seeds was found to contain limonoids (e.g. methyl 3β-tigloyloxy-2,6-dihydroxy-1-oxo-meliac-8(30)-enate, methyl 3β-acetoxy-2,6-dihydroxy-8α,30α-epoxy-1-oxo-meliacate, 3β-isobutyryloxy-2,6-dihydroxy-8α,30α-epoxy-1-oxo-meliacate and humilin B) [ 12 ].
MEDICINAL USES
Uses described in folk medicine, not supported by experimental or clinical data
Traditionally, the seeds are used to lower blood sugar level and relieve pain [ 14 ]. The seeds are also used to heal various ailments of the skin due to parasitic diseases through external application of the mashed seeds [ 15 ].
Biological and pharmacological activities supported by experimental data
Antidiabetic activity
Aqueous extract of S. macrophylla seeds (2 g/kg) administered orally to streptozotocin-induced diabetic Wistar albino rats (6 – 8 weeks) daily for a duration of 30 days significantly (p < 0.05) decreased the blood glucose levels (98.66 ± 9.26 mg/dL) compared to diabetic rats treated with metformin (67 ± 9.23 mg/dL) [ 16 ].
Aqueous extract of S. macrophylla seeds (200 mg/kg) was administered orally to streptozotocin-induced diabetic Wistar rats (180 – 240 g) daily for a duration of 30 days. The extract decreased the blood glucose level (3.72 ± 0.01 mmol/L) compared to diabetic rats treated with metformin (5.48 ± 0.03 mmol/L) [ 21 ].
Methanol extract of S. macrophylla seeds (300 mg/kg) administered orally to streptozotocin-induced diabetic Wistar albino rats (2 – 3 months) daily for a duration of 12 days significantly (p < 0.01) decreased the blood glucose level (119.17 ± 2.81 mg/dL) comparable to diabetic rats treated with glibenclamide (113.00 ± 2.77 mg/dL) [ 17 ].
Methanol extract of S. macrophylla seeds (300 mg/kg) administered orally to streptozotocin-induced diabetic Wistar albino rats (150 – 200 g) daily for a duration of 12 days significantly (p < 0.01) decreased the fasting blood glucose level (8.19 ± 0.01 mg/dL) compared to diabetic rats treated with glibenclamide (9.48 ± 0.01 mg/dL) [ 18 ].
Methanol extract of S. macrophylla seeds (300 mg/kg) administered orally to alloxan- induced diabetic Wistar albino rats (200 – 240 g) daily for a duration of 10 days significantly (p < 0.001) decreased the blood glucose level (172.83 ± 3.7 mg/dL) compared to diabetic rats treated with glibenclamide (168.00 ± 3.6 mg/dL) [ 19 ].
Ethanol extract of S. macrophylla seeds (100.00 mg/kg) administered orally to streptozotocin-induced diabetic male albino rats (9 weeks) daily for a duration of 45 days significantly (p < 0.05) decrease the blood glucose level (131.13 ± 8.08 mg/dL) compared to diabetic rats treated with glibenclamide (98.58 ± 6.84 mg/dL) [ 22 ].
Swietenine isolated from S. macrophylla seeds (50 mg/kg) administered orally to neonatal-streptozotocin induced diabetic Wistar albino rats (aged three days old) daily for a duration of 5 days significantly (p < 0.01) decreased the fasting blood glucose level (121.32 ± 5.12 mg/dL) compared to diabetic rats treated with glibenclamide (115.17 ± 6.34 mg/dL) [ 20 ].
Antimicrobial activity
Methanol extract of S. macrophylla seeds (50 µg/mL) inhibited the growth of Bacillus cereus with inhibition zone of 24.10 mm, Staphylococcus aureus (28.00 mm) and Escherichia coli (29.60 mm) compared to streptomycin (32 mm, 30 mm and 29 mm, respectively) using disc diffusion assay [ 23 ].
Methanol extract of S. macrophylla seeds (50 mg/mL) inhibited the growth of Cryptococcus albidus with inhibition zone of 36.33 mm, Aspergillus flavus (23.46 mm), A. niger (29.68 mm) and Candida albicans (31.32 mm) compared to fluconazole (28 mm, 21 mm, 22 mm and 25 mm respectively) using disc diffusion assay [ 23 ].
Hexane and diethyl ether extract of S. macrophylla seeds (1000 µg/mL) inhibited the growth of Salmonella typhi with inhibiton zone of 22 mm and 21 mm, respectively comparable to streptomycin (22.5 mm) using disc diffusion assay [ 24 ].
Antinociceptive activity
Ethanol extract of S. macrophylla seeds (200 mg/kg) was administered orally to albino mice (18 – 25 g) one hour before induction of acetic acid. The extract showed significant (p < 0.01) reduction in the number of writhings (24.8 ± 2.31) comparable to acetylsalicyclic acid (21.3 ± 4.22) using acetic acid-induced writhing test [ 25 ].
Ethanol extract of of S. macrophylla seeds (200 mg/kg) was administered orally to albino mice (18 – 25 g) one hour before tested with hot plate test. The extract showed significant (p < 0.01) effect in the reaction time (21.63 ± 3.50 s) compared to morphine (28.16 ± 2.2 s) [ 25 ].
Analgesic activity
Ethanol extract of S. macrophylla seeds (200 mg/kg) was administered orally to albino mice (18 – 25 g) one hour before tested with tail immersion test. The extract showed significant (p < 0.01) effect in the reaction time (3.15 ± 0.30 s) compared to morphine (5.20 ± 0.46 s) [ 25 ].
Antidiarrhoeal activity
Petroleum ether extract of S. macrophylla seeds (100 mg/kg) was administered orally to Swiss albino rats (150 – 180 g) 30 minutes after induction of castor oil to induce diarrhoea. After six hours, the extract significantly (p < 0.001) decreased the total number of diarrhoeal faeces (5.2 ± 1.30) with percentage of inhibition (71.12%) compared to diphenoxylate treated group (5.9 ± 1.30, 67.23%) [ 26 ].
Cytotoxicity activity
Swielimonoid B, swietenolide, swietenine acetate and methyl angolensate isolated from S. macrophylla seeds showed cytotoxicity activity against human liver cancer cell line (Huh-7) with half-maximal effective concentration (EC50) values of 7.2 ± 1.33, 3.5 ± 0.34, 6.3 ± 1.12 and 4.3 ± 2.31 μM, respectively compared to ribavirin (12.6 ± 1.1 µM) using MTT assay [ 11 ].
Clinical studies
Information and data have not been established.
SAFETY INFORMATION
Preclinical studies (Toxicology studies)
14-days toxicity study
S. macrophylla seeds powder suspended in olive oil (2 g/kg) was administered orally at a single dose to male and female Sprague Dawley rats (aged eight week old; 150 – 220 g) and were observed for 14 days. No sign of toxicity was observed with lethal dose at 50% (LD50) > 2 g [ 27 ].
Others (Adverse reactions, contraindications, side effects, warning, precautions)
Information and data have not been established.
DOSAGE
Information and data have not been established.
STORAGE
Store below 30°C. Protect from light and moisture.
REFERENCES
- The Plant List Database. [Internet]. Swietenia macrophylla King; 2012. [cited on 14 Jun 2016]. Available from: http://www.theplantlist.org/tpl1.1/record/kew-2601504.
- National Park Flora and Fauna Web. [Internet]. Swietenia macrophylla King; 2013. [cited on 11 July 2017]. Available from: https://florafaunaweb.nparks.gov.sg/Special-Pages/plant-detail.aspx?id=3150
- Botanical Plant Names Singhala Plant Names Database. [Internet]. Swietenia macrophylla King; 2011. [cited on 11 July 2017]. Available from: http://dh-web.org/bot2sinhala.html.
- Arumugasamy K, Latha KV, Sathish Kumar NH. Studies on some pharmacognostic profile of Swietenia macrophylla King. Acient Science of Life. 2004; XXIV (2): 1-5.
- Soerianegara I, Lemmens RHMJ. Plant Resources of South-East Asia 5(1): Timber Trees: Major Commercial Timbers. Wageningen, Netherlands. Pudoc Scientific Publishers. 1993.
- Wiart C. Medicinal Plants of the Asian Pasific; Drug for the Future?. Singapore: World Scientific Publishing CO. Pte. Ltd. 2009; p.154.
- Louppe D, Oteng-Amoako AA, Brink M. Plant Resources of Tropical Africa. Vol. 7 (1) Timber 1. Leiden, Netherlands: Backhuys Publishers. 2008; p.523-524.
- Esau K. Anatomy of Seed Plants. India: John Wiley & Sons, Inc. 1960; p.321-335.
- Chen JJ, Huang SS, Liao CH, Wei DC, Sung PJ, Wang TC, Cheng MJ. A new phragmalin-type limonoid and anti-inflammatory constituents from the fruits of Swietenia macrophylla. Food Chemistry. 2010;120:379-384.
- Chen LC, Liao HR, Chen PY, Kuo WL, Chang TH, Sung PJ, Wen ZH, Chen JJ. Limonoids from the seeds of Swietenia macrophylla and their anti-inflammatory activities. Molecules. 2015;20:18551-18564.
- Cheng YB, Chien YT, Lee JC, Tseng CK, Wang HC, Lo IW, Wu YH, Wang SY, Wu YC, Chang FR. Limonoids from seeds of Swietenia macrophylla with inhibitory activity against dengue virus 2. Journal of Natural Products. 2014;77:2367-2374.
- Kojima K, Isaka K, and Ogihara Y. Tetranortriterpenoids from Swietenia macrophylla. Chemical and Pharmaceutical Bulletin. 1998;46(3):523-525.
- Mootoo BS, Ali A, Motilal R, Pingal R, Ramlal A, Khan A, Reynolds WF and McLean S. Limonoids from Swietenia macrophylla and S. aubrevilleana. Journal of Natural Products. 1999;62:1514-1517.
- Goh BH, Kadir A. In vitro cytotoxic potential of Swietenia macrophylla King seeds against human carcinoma cell lines. Journal of Medicinal Plants Research. 2011;5:1395-1404.
- Bourdy G, De Walt SJ, Chavez De Michel LR, Roca A, Deharo E. Medicinal plant uses of the tacana, an amazonian bolivian ethnic group. Journal of Ethnopharmacology. 2000;70:80-109.
- Dutta M, Biswas UK, Chakraborty R, Banerjee P, Kumar P, Raychaudhuri U. Reduced erythrocyte carbonic anhydrase activity by Swietenia macrophylla seeds in diabetic rats. Journal of diabetic, Metabolic Disorders and Control. 2015;2(2):1-5.
- Maiti A, Dewanjee S, Kundu M, Mandal SC. Evaluation of antidiabetic activity of the seeds of Swietenia macrophylla in diabetic rats. Journal of Pharmaceutical Biology. 2009;47(2):132-136.
- Maiti A, Dewanjee S, Jana G, Mandal SC. Hypoglycemic effect of Swietenia macrophylla seeds against type II diabetes. International Journal of Green Pharmacy. 2008;2(4):224-227.
- Maiti A, Dewanjee S, Mandal SC. Effect of Swietenia macrophylla seeds on normal and alloxan-induced diabetic rats. Oriental Pharmacy and Experimental Medicine. 2007;7(4):363-371.
- Dewanjee S, Maiti A, Das AK, Mandal AC, Dey SP. Swietenine: A potential oral hypoglycemic from Swietenia macrophylla seed. Fitoterapia. 2009;80:249-251.
- Dutta M, Biswas UK, Chakraborty R, Banerjee P, Raychaudhuri U, Kumar A. Evaluation of plasma H2S levels and H2S synthesis in streptozotocin induced Type-2 diabetes-an experimental study based on Swietenia macrophylla seeds. Asian Pacific Journal of Tropical Biomedicine. 2014;4(1):S483-S487.
- Kalaivanan K, Pugalendi KV. Antihyperglycemic effect of the alcoholic seed extract of Swietenia macrophylla streptozotocin-diabetic rats. Pharmacognosy Research. 2011;3(1):67-71.
- Maiti A, Dewanjee S, Mandal SC, Annadurai S. Exploration of antimicrobial potential of methanol and water extract of seeds of Swietenia macrophylla (Family: Meliaceae), to substantiate folklore claim. Iranian Journal of Pharmacology and Therapeutics. 2007; 6: 99-102.
- Mohammed SB, Azhari NH, Mashitah YM, Abdurahman NH, Mazza AS. Physiochemical characterization and antimicrobial activity of Swietenia macrophylla King seed oil. International Journal of Engineering Research and Technology. 2014;3(3):1787-1792.
- Das A, Sunilson JAJ, Gopinath R, Radhamani S, Nilugal K. Anti-nociceptive activity of the fruits of Swietenia macrophylla King. Journal of Pharmacy Research. 2009;2(9):1367-1369.
- 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.
- Balijepalli MK, Suppaiah V, Chin A, Buru AS, Sagineedu SR, Pichika MR. Acute oral toxicity studies of Swietenia macrophylla seeds in Sprague Dawley rat. Pharmacognosy Research. 2015;7(1):38-44.
