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Family Leguminosae
Jatoba
Hymenaea courbaril L.
STINKING TOE
Luan ye dou

Scientific names Common names
Hymenaea animifera Stokes Jatoba (Phil.)
Hymenaea candolleana Kunth Courbaril (Engl.)
Hymenaea courbaril L. Courbril locust (Egl.)
Hymenaea multiflora Kleihoonte Flour tree (Engl.)
Hymenaea resinifera Salisb. Kerosene tree (Engl.)
Hymenaea retusa Hayne Locust tree (Engl.)
Inga megacarpa M.E.Jones Stinktoe (Engl.)
  West Indian locust (Engl.)
Hymenaea courbaril L. is an accepted name. The Plant List

Other vernacular names
BRAZIL: Abati, Copal-do-brasil, Jatahai, Jatel, Cuebra machado.
CHINESE: Luan ye dou.
CUBA: Algarrobo, Curbaril, Quiebra hacha.
El SALVADOR: Copinol.
FRENCH: : Bois de Courbaril, Caroubier de Guyane.
GERMANY: Heuschreckenbaum, Sudamerikanische.
GUATEMALA: Copinol, Cuapinol, Guapinol, Hoja de cuchillo, Pac, Pacay, Pacoj.
INDONESIA: Kobari, Locus.
COUNTRY: Copinol.
SPANISH: Guapinol.
VENEZUELA: Algarrobo, Corobore.

Botany
Jatoba is an evergreen, medium-sized tree, growing 25 or more meters tall. Bole is 1 meter or more in diameter. Bark is smooth, 2.5 cm or more thick, gray to pinkish brown. Leaves are alternated, bifoliolate, glossy green above, gland dotted. Petiole is 1-2 cm long, petiolules twisted, 2 to 4 mm long, leaflet blade falcate, rarely oblong or obovate, 4-10 cm by 2-5 cm, coriaceous, base asymmetrical and rounded, margin entire, apex short to long acuminate. Inflorescence if terminal, densely corymbose-paniculate, 8 to 15 cm long and wide,. Flowers are large, buds p to 3.5 cm long; open flower 3 cm in diameter; calyx campanulate, 4-merous, gray-green, tube 6 mm long, lobes ovate to elliptical, 15 to 18 mm by 8 mm. Fruit is a compressed cylindrical pod, 8 to 20 cm by 4 to 8 cm, smooth or rough, dark-brown, indehiscent, containing 6 to 12 seeds embedded in pale, yellow, unpleasant smelling fruit flesh. Seed is ellipsoidal, flattened, 2 to 3 cm long, dark red. (In the Philippines large nodules with a rough surface have been observed on the roots.) (2)

Distribution
- Introduced.
- Native to the American tropics.
- Distributed in the West Indies, Central and South American from southern Mexico to Brazil.
- Now found in Malesia, particularly Peninsular Malaysia, Sabah, and Java. (2)

Constituents
- Dried fruit pulp per 100 g yields: 309 calories, 14.6 g water, 5.9 g protein, 2.2 g fat, 75.3 g total carbohydrate, 13.4 g fiber, 2.0 g ash, 28 mg calcium, 143 mg phosphorus, 3.2 mg iron, trace of ß-carotene equivalent, 0.23 mg thiamine, 0.14 mg riboflavin, 4.1 mg niacin, and 11 mg ascorbic acid. (4)
- Phytoconstituents include alpha-copaene, alpha-cubebene, alpha-himachalene, alpha-humulene, alpha-muurolene, alpha-selinene, astilibin, beta-bisabolene, beta-bourbonene, beta-copaene, beta-cubebene, beta-gurjunene, ß-humulene, ß-selinene, ß-sitosterol, calarene, carboxylic acids, caryophyllene, catechins, clerodane diterpenes, communic acids, copacamphene, copalic acid, cubebene, cyclosativene, cyperene, delta-cadinene, gamma-muurolene, gamma-cadinene, halimadienoic acids, heptasaccharides, kovalenic acid, labdadiene acids, octasaccharides, oligosaccharides, ozic acids, polysaccharides, selinenes, and taxifolin. (6)
- Study of seeds isolated two new biscoumarins from H. courbaril, namely:. hymenain 7-O-b-glucopyranosyl- (1'''--> 2'')-O-a-apiofuranosyl-(1''''--> 2''')-O-α-galactopyranoside (1) and hymenain 7-O-b-glucopyr- anosyl-(1''' --> 2'')-O-α-apiofuranoside (2). (14)
- Study of H. courbaril essential oil showed main compounds of trans-caryophyllene (46.24%), oxide caryophyllene (14.67%) and α-humulene (9.19%). (see study below) (16)
- GC and GC-MS study of pods ripe fruit for essential oil yielded main constituents of sesquiterpene a-copaene (11.1%), spathulenol (10.1%), and ß-selinene (8.2%) while unripe fruits yielded germacrene-D (31.9%), ß-caryophyllene (27.1%) and bicyclogermacrene (6.5%). (see study below) (17)
- Bioactivity-guided fractionation of methanol extract yielded three new diterpenoids: (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid   (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). (see study below) (18)

Properties
- All parts contain a resin..
- Even when the tree's life cycle is completed and the tree dies, the wood of the Jatoba tree does not rot, a property that underscores therapeutic potential. (13)
- Considered anodyne, antiseptic, astringent, laxative, pectoral, purgative, sedative, stimulant, tonic, vermifuge. (
4)
- Studies have suggested antifungal, antibacterial, anti-inflammatory, lipid peroxidation inhibition, antioxidant, myorelaxant, larvicidal properties.

Parts used
Bark, leaves, fruit.

Uses

Edibility
- Fruit, raw or cooked. Used for making custards and ice-cream.
- Pulp around the seed is edible, although with a peculiar or unpleasant smell. (2)
- In Brazil, fruit pulp used as carbohydrate source for making alcoholic beverage.
- In South America, the pulp is dried and powdered for making snacks; also, mixed with water to prepare a drink called 'atole.' (19)
Folkloric
- Bark decoction used as respiratory and urinary tonic by indigenous people of the Amazon basin. (3)
- Decoction used to treat cough, back pains, stomach problems. Externally, use for athlete's foot. (3)
- Leaves used to treat cystitis, hepatitis, prostatitis and cough. Resin and sap used for treating fresh wounds. (3)
- Fruit is a mild laxative;
- In traditional medicine in Panama, fruit used to treat mouth ulcers. Leaves and wood used for treatment of diabetes. (6)
-Used for beri-beri, blenorrhagia, bronchitis, catarrh, cultists, emphysema. Bark infusion used as depurative stomachic in exanthema. Smoke from rosin used for headaches and rheumatism. (4)
- In traditional Brazilian folk medicine, used for anemia, kidney problems, sore throat, bronchitis and asthma
(15)
- In Suriname, infusion of stem bark used for treatment of hypertension.
(19)
Others
- Wood: Wood is valuable and resembles mahogany; hard, durable, used for construction, door and window frames, furnitures, ship building, paneling and parquet flooring.
Bark is so thick it us used by Indians for making canoes. (2) Even when the tree's life cycle is completed and the tree dies, the wood of the Jatoba tree does not rot. (13)
- Fuel: Wood can be used as firewood and the pods for alcohol generation.
- Tannin: Bark yields tannin.
- Agroforestry: Used as nitrogen fixing tree to rehabilitate degraded and marginal soils. (2)
- Honey: Flowers attract beens and used for honey production. (2)
- Resin: A source of copal. Brazil is the main source of the resin. International trade is reportedly small or negligible. "Recent copal" obtained from tapping is exported to India and China, where it is made into coarse varnish. (2) Sticky resin called "anime" with its pleasant fragrance can be used for making incense, perfume, and varnish. Also, the indigenous peoples of the Amazon have used the resin for centuries to preserve the colors of their pottery. (19)
- Crafts: In El Salvador, hard reddish-brown seeds are used by artisans to create jewelry and miniature paintings on the inside surface of cut seeds. (5)

Studies
Biochemical Analysis Under Heat Stress:
Study investigated the differential expression of proteins and lipids produced by the tree under heat stress conditions. Several volatiles, isoprene, 2-methyl butanenitrile, ß-ocimene and a number of sesquiterpenes were produced under heat stress. Heat stress proteins, including heat shock proteins, histone proteins, oxygen evolving complex, and photosynthetic proteins were believed to play key roles in imparting thermotolerance. (7)
Antifungal / Cytotoxicity / Fisetin / Fresh Xylem Sap: Study evaluated the cytotoxicity of fresh xylem sap of Hymenaea courbaril and fisetin against 3T3-A31 cells of Balb/c and for bioactivity against fungi Cryptococcus neoformans species complex and dermatophytes. Fisetin was filtered from the fresh xylem sap. The filtrate was a moisture of fistinediol, fustin, 3-O-methyl-2,3-trans-fustin and taxifolin. Results showed in vitro antifungal activity and low toxicity on animal cells. The xylem sap inhibited the growth of dermatophytes and C. neoformans with MIC of <256 µg/mL while fisetin showed MIC <128 µg/mL. Fisetine showed lower toxicity IC50 of 158 µg/ml compared to fresh xylem sap IC50 109 µg/ml. (8)
Terpenoids / COX-2 and Lipid Peroxidation Enzyme Inhibition / Fruits: Study of fruit powder yielded sucrose and linolenic acid as major compounds. Pods yielded labdane diterpenoids. Total amounts of the terpenoids in the fruit was about 0.1% (w/w) of the dried fruit. Compound 3 and 4 showed selective COX-2 enzyme inhibition. Compounds 1, 2 and 5 inhibited lipid peroxidation by 46%, 48%, and 75%, respectively at 100 ppm. (see constituents above) (9)
Antimicrobial / Fruit: Study evaluated the antimicrobial activity of H. courbaril against four bacteria, E. coli, S. aureus, B. subtilis and P. aeruginosa and fungi C. albicans and Saccharomyces cerevisiae and A. niger. The dichloromethane extract showed antimicrobial activity against Staphylococcus aureus with 1.47% inhibition. No inhibitory activity was seen against fungi. (10)
Ultrasound-Assisted Extraction of Polyphenols / Increase Antioxidant Capacity / Bark: Study reports on the ultrasound assisted extraction of polphenols from bark. Water with S/F of 20 was the best solvent for extraction of phenolic compounds. Results showed a statistically significant (p<0.005) effect with approximately 15% increase in total phenolic compounds content when using maximum power. DPPH analysis confirmed the high antioxidant capacity of the ultrasound extracts. (11)
Synergism with S. adstringens against -Assisted Extraction of Polyphenols / Increase Antioxidant Capacity / Bark: Study investigated the in vitro antimicrobial activities of H. courbaril and Stryphnodendron adstringens against clinical bacterial isolated. The crude extracts of both vegetal species showed bacteriostatic activity against almost all bacteria evaluated, with MIC ranging from 135-1250 µg/ml. The combination exhibited potent synergistic antimicrobial activity with MICs of 31.25 µg/ml against Acinetobacter baumannii, E. coli, and S. aureus. The synergism against resistant bacteria suggests potential for the development of new drugs. (12)
Glycosylated Biscoumarins / Seeds: Study of seeds isolated two new biscoumarins from H. courbaril seeds. This was the first study for the purpose of identifying seed molecules. (see constituents above) (14)
Myorelaxant Activity / Antioxidant / Anti-Inflammatory / Astilbin / Stem Bark: Astilbin is a flavonoid isolated from the bioactive ethyl acetate fraction of stem bark. Whole extract and some fractions strongly scavenged DPPH radical. The extract exhibited myorelaxant activity on rat trachea, with the EAF the most efficient fraction. Astilbin may be partly responsible for the myorelaxant effect of EAF. Results suggest potential antioxidant, myorelaxant and anti-inflammatory actions for the treatment of inflammatory airway disease. (15)
Anti-Inflammatory on Pterygium Fibroblasts / Essential Oil: Study evaluated the anti-inflammatory effects of essential oil in pterygium genesis. Primary cultures of pterygium fibroblasts were exposed to H. courbaril essential oil. MTT test showed α-humulene, trans-caryophyllene and both together showed cytotoxic effect in concentration of 0.5 to 5 µM. The trans-caryophyllene compound from essential oil at 25 µM showed significant anti-inflammatory effect on IL-6 production of pterygium fibroblasts. Results suggest a potential alternative adjuvant agent in the treatment of pterygium. (see constituents above) (16)
Larvicidal / Ae. aegypti / Essential Oil of Fruit Peel: GC-MS study analyzed the essential oil from peel of ripe and unripe fruits.
Tested against Aedes aegypti larvae, the essential oil shewed LC50 values of 14.8 ± 0.4 µg/ml and 28.4 ± 0.3 µg/ml for ripe and unripe fruit pod oils, respectively. (see constituents above) (17)
Diterpenoids / Weak Cytotoxicity. to Human Ovarian Cell Line and Mutant Yeast Strain: Study of methanol extract yielded three new diterpenoids. Compound 1 showed weak cytotoxicity towards 1138 mutant yeast strain and the A2780 human ovarian cancer cell line. (see constituents above) (18)

Availability
- Wildcrafted.
- Cultivated.
- Herbal teas, tinctures, capsules, supplements in the cybermarket.

August 2020

                                                 PHOTOS / ILLUSTRATIONS
IMAGE SOURCE: Photograph | Hymenaea courbaril Flower | muroguanandi / click on image to go to source page / CC by SA 2.0 / Wikimedia Commons
IMAGE SOURCE: Photograph | Hymenaea courbaril Leaves | David J Stang / click on image to go to source page / CC by SA 4.0 / Wikimedia Commons
OTHER IMAGE SOURCE: Photograph | FLOR /courbaril Leaves | CONRADO-Trabayu propiu / click on image to go to source page / CC by SA 3.0 / Wikipedia
OTHER IMAGE SOURCE: / Illustration / Hymenaea courbaril / Ausländische Kulturpflanzen in farbigen Wandtafeln / PlantIllustrations.org

Additional Sources and Suggested Readings
(1)
Hymenaea courbaril / Synonyms / The Plant List
(2)
Hymenaea courbatil L. / PROSEA (Plant Resources of SouthEast Asia / Pl@ntUse
(3)
Hymenaea courbaril / Ken Fern: Tropical Plants Database / Useful Tropical Plants
(4)
Hymenaea courbaril / James A Duke / Handbook of Energy Corps, 1983
(5)
Courbril locust / Invasive Species Compendium / CABI
(6)
Jatoba / Tropical Plants Database / Rain-Tree

(7)
Biochemical analysis of ‘kerosene tree’ Hymenaea courbaril L. under heat stress / Dinesh Gupta, Moustafa Eldakak, Jai S Rohila, Chhandak Basu / Plant Signaling & Behavior, 2014; 9(10): e972851 / doi: 10.4161/15592316.2014.972851 / PMCID: PMC4623024 / PMID: 25482765
(8)
Antifungal and cytotoxicity activities of the fresh xylem sap of Hymenaea courbaril L. and its major constituent fisetin / Maysa Paula da Costa, Marize Campos Valadares Bozinis,Carolina Rodriguez Costa, Lucia Kioko Jasimoto Souza et al / BMC Complement Altern Med, 2014; 14: 245 / doi: 10.1186/1472-6882-14-245 / PMCID: PMC4223399 / PMID: 25027026
(9)
Terpenoids from Stinking toe (Hymneae courbaril) fruits with cyclooxygenase and lipid peroxidation inhibitory activities / Bolleddula Jayaprakasam, Ruby Lisa Alexander-Lindo, Deborah Dewitt, Muraleedharan Gopalan Nair / Food Chemistry, Dec 2007;  105(2):485-490 / DOI:  10.1016/j.foodchem.2007.04.004
(10)
ANTIMICROBIAL ACTIVITY OF HYMENAEA COURBARIL L. FRUIT / Mariana Narvaez Correa, Oscar Eduardo Rodriguez Aguirre, Janeth del Carmen Arias Palacios / Asian Journal of Pharmaceutical and Clinical Research, June 2020, 13(6) / DOI  https://doi.org/10.22159/ajpcr.2020.v13i6.37272
(11)
Ultrasound-assisted extraction of polyphenols from jatoba (Hymenaea courbaril L. var stilbocarpa) bark. / Veggi P C, Santos D T, Fabiano-Tixier A S, Bourvellec C , Meireles M A, Chemat F / Food and Public Health, 2013; 3(3): pp 119-129 / / ISSN: 2162-9412
(12)
Synergistic activity from Hymenaea courbaril L. and Stryphnodendron adstringens (Mart.) Coville against multidrug-resistant bacteria strains / Alan Alex Aleixo, Vidyleison Neves Camargos, Karina Marjorie Silva Herrera, Ana Claudia dos Santos Pereira Andrade, Jacqueline Maria Siqueira Ferreira et al / Journal of Medicinal Plants Reserach, July 2015; 9(26): pp 741-748 / https://doi.org/10.5897/JMPR2014.5502
(13)
Fighting Fungus: Cleansing with Jatoba / Dr. Edward Group
(14)
New glycosylated biscoumarins from Hymenaea coubaril L. seeds / Hocelayne Paulino Fernandes, Adilson Paulo Sinhorin, Valeria Dornelles Gindri Sinhorin, Gerardo Magela Vieira Junior, Virgınia Cláudia Silva, Mário Geraldo de Carvalho / Phytochemistry Letters, 2015; 13: pp 413-416 / http://dx.doi.org/10.1016/j.phytol.2015.07.016
(15)
Phytochemical study guided by the myorelaxant activity of the crude extract, fractions and constituent from stem bark of Hymenaea courbaril L. / Bezerra GP, Gois RW, de BRito TS, de Lima FJ, Bandeira MA, Romero NR, Magalhaes PJ, Santiago GM / Journal of Ethnopharmacology, June 2013; 149(1): pp 62-69 / DOI: 10.1016/j.jep.2013.05.052 PMID: 23764737 
(16)
Anti-inflammatory effects of Hymenaea courbaril essential oil compounds on pterygium fibroblasts / Magda Massae Hata Hata Viveiros, Claudis Aparacida Rainho, Marcia Guimaraes Silva, Silvana A Schellini et al / Investigative Ophthalmology & Visual Science, June 2017, 58(8):
(17)
Chemical Constituents and Larvicidal Activity of Hymenaea courbaril Fruit Peel / José Cláudio D. Aguiar, Gilvandete M. P. Santiago, Patrícia L. Lavor, Helenicy N. H. Veras, Yana S. Ferreira, Michele A. A. Lima, Ângela M. C. Arriaga, Telma L. G. Lemos, Jefferson Q. Lima, Hugo C. R. de Jesus, Péricles B. Alves and Raimundo Braz-Filho / Natural Product Commuications, 2010; 5(12): pp 1977-1980
(18)
Isolation and Absolute Configuration of ent-Halimane Diterpenoids from Hymenaea courbaril from the Suriname Rain Forest / Maged Abdel-Kader, John M Berger, Carla Slebodnick, Heannine Hoch, Stan Malone, Jan J Wisse, Marga C M Werkhoven, Steven Mamber and David G I Kingston
/ Nat. Prod. 2002, 65(1): pp 11–15 / https://doi.org/10.1021/np0103261
(19)
Plant-Based Ethnopharmacological Remedies for Hypertension in Suriname / Dennis R.A. Mans, Angela Grant and Nicholaas Pinas / DOI: 10.5772/intechopen.72106

                                                                          DOI
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                                                            List of Understudied Philippine Medicinal Plants

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