Articles

Excoecaria agallocha

Synonyms

Commia cochinchinensis, Excoecaria camettia, Excoecaria affinis, Stillingia agallocha [1]

Vernacular Names:

Malaysia

Bebuta, Buta-buta, Pokok Buta [2]

English Blinding Tree [7]
Thailand

Tatum, Tatum Thale (Central); Bu-to (Malay-Pattani)

Philippines

Ali, Alipata, Buta, Buta-buta, Dila-dila, Himbabao [3]

India

Kampetti, Tillai, Agil Ambala-vrksham (Tamil); Gevaa, Huraa (Maharashtra); Gangawaa [8]

Tonga

Feta’anu [9]

General Information

Description

Excoecaria agallocha has trees of up to 15m high, monoecious. The stipules measure 3-5.5 by about 3mm. The leaves are opposite while the petiole measure 1.2-1.4cm long; blade elliptic, 7-18 by 2-5cm, length/width ratio 3.4-3.6, coriaceous, symmetric, base cuneate, margin crenate, apex acute to shortly acuminate; nerves 14-20 till apex. The staminate inflorescences and flowers seen only very young and bracts with 2 large glandular areas. The pistillate flowers in separate racemes of up to 13cm long,  measuring 1-1.5mm diameter, up to more than 20 flowers per inflorescence; bracts broadly ovate, measuring 1-1.2 by around 0.8mm, with large glandular areas. The pedicel is absent and the sepals broadly ovate measure around 2 by 1.8mm. The ovary measures around 1.8 by 1.8mm, style measures 1-1.3 mm long, longitudinally grooved, apically with abscission zones. The stigmas measure around 2.5mm long, recurved. The fruits not lobed, globose, measure around 4 by 4cm high. The seeds measure 9.5 by 9.5mm. [34]

Plant Part Used

Leaves, bark [4][9].

Chemical Constituents

(13R,14S)-ent-8a,13;14,15-diepoxy-13-epi-labdan-3-one; (13R,14R)-ent-8a,13;14,15-diepoxy-13-epi- labda-3beta-ol; (15R, 16S)-ent-15,16-epoxybeyeran-3-one; (24R)-24-ethylcholesta-4,22-dien-3-one; 2a,3a,18-trihydroxy-3b,20-epoxybeyer-15-ene; 2-acetoxy-1,15-beyeradiene-3,12-dione (5); 2-hydroxy-1,15-beyeradiene-3,12-dione (6); 3,5,7,3',5'-pentahydroxy-2R,3R-flavanonol; 3-O-a-L-rhamnopyranoside; 3a, 1a,14a-trihydroxyisopimara-7,15-diene;  3a,11b-dihydroxy-ent-isopimara-8(14),15-dien-2-one; 3a,18-dihydroxy-3b,20-epoxybeyer-15-ene; 3b,20-epoxy-3 a lpha-hydroxybeyer-15-ene; 3b,20:15R,16S-diepoxy-3 a lpha-beyeranol; 3b,20-epoxy-3 a lpha,6 a lpha-dihydroxy-18-nor-beyer-15-ene; 3b-[(2E,4E)-6-oxo-decadienoyloxy]-olean-12-ene;

3-oxo-ent-13epi-8(13)-epoxy-15-chloro-14-hydroxylabdane; 6a,14a,17-trihydroxy-7,15-isopimaradien-3-one;  8,13-epoxy-3-nor-2,3-seco-14-epilabden-2,4-olide (5); 11a,14a-dihydroxy-7,15-isopimaradien-3-one; 12-deoxyphorbol 13-(3E,5E-decadienoate); acetylaleuritolic acid; agallochaol K-P;  agallochaol Q; b-amyrin acetate;

b-sitostenone; b-sitosterol;  cycloart-22-ene-3b, 25-diol; ellagic acid; ent-2,3-secokaur-16-en-2,3-dioic acid; ent-3,4-seco-16a-hydroxyatis- 4(19)-en -3-oic acid;  ent-3b-hydroxybeyer-15-ene-2,12-dione; ent-3 b,20-epoxy-3 a,6 a-dihydroxykaur-16-ene; ent-3-oxo-13-epi-manoyl oxide; ent-3b-hydroxy-13-epi-manoyl oxide; ent-3b-hydroxy -15-beyeren-2-one; ent-3b-hydroxykaur-16-en-2-one; ent-11b-hydroxy-8(14),15-isopimaradien-3-one; ent-12-oxo-2,3-secobeyer-15-ene-2,3-dioic acid;  ent-15-epoxy-beyerane-3alpha-ol;  ent-15-chloro-13,14-dihydroxylabd-8(9)-en-3-one; ent-15-chloro-labd-8(9)ene-3alpha,13,14-triol; ent-15-hydroxylabda-8(17),13E-dien-3-one; ent-15-hydroxy-labda-8(17),13E-dien-3-one; ent-16-hydroxy-3-oxo-13-epimanoyl oxide; ent-16-hydroxy-3-oxo-13-epi-manoyloxide,  ent-16a-hydroxy-atisane-3,4-lactone; ent-16a-hydroxy-atisane-3-one; ent-atisane-3b,16a-diol; excoecarins M and N; excoagallochaols A-D; ent-labda-8(17),13E-diene-3beta,15-diol; excoecarins R1and R2; excoecarins S, T1, and T2; excoecarins V1-V3; ent-kauran-16 b-ol-3-one; labda-8(17),13E-diene-3b,15-diol; ribenone; taraxerone; taraxero. [14-19] [21-32]

Traditional Used:

E. agallocha is known to be poisonous and most mangrove dwelling societies avoid its use as medicine. However, when needed it is being sought after for specific conditions.

Infectious diseases

The Fijian and the Indians had advocated the use of this plant to treat leprosy by way of fumigation. It is the latex that is found to be effective treatment for this condition. In Fiji the smoke of the burning wood is applied over the lesion. In India the juice boiled in oil is applied instead. [6][8]

Other uses

Decoction of the leaves is used for treatment of epilepsy and ulcers. [4] The juice boiled in oil is used to treat rheumatism and paralysis. [6] The bark is said to induce abortion. [9]

Pre-Clinical Data

Pharmacology

Tumour-promoting activity

It was found that E. agallocha were amongst the extracts of 48 species of commonly used herbs of the Euphorbiaceae family to have a potent cancer-promoting activity. The EBV-inducing activity was observed to be as low as o.2 to 1.2micrograms/ml of the plant extract in cell culture. [12]

Anti-tumour promoting activity

Contrary to the above findings Konishi et al. [15] found that extracts of the resinous wood of of E. agallocha contained at least 4 diterpene compound exhibiting significant inhibitory effects on the EBV activation induced by the tumour promoter, 12-O-tetradecanoylphorbol-13-acetate (TPA). These diterpenes are ent-16-hydroxy-3-oxo-13-epi-manoyloxide, (13R,14R)-ent-8alpha,13;14,15-diepoxy-13-epi- labda-3beta-ol, ent-3beta-hydroxy-15-beyeren-2-one and ent-15-hydroxy-labda-8(17),13E-dien-3-one. Further to this, they isolated 8 new diterpenoids and found the secolabdane-type diterpenoid identified as compound 7 had remarkable inhibitory effects on the EBV early antigen induction and a significant anti-tumour-promoting effects in the mouse two-stage carcinogenesis test. [20]

Antimicrobial activity

Antiviral

A novel phorbol ester 12-deoxyphorbol 13-(3E,5E-decadienoate) was isolated from the leaves and stems of E. agallocha of Northwest Australia. This compound was found to be the anti-HIV principle of this plant. It was also found that this compound is a potent displacer of [3H]-phorbol dibutyrate from rat brain membranes.[15]

Antioxidant activity

Masuda et al. [17] found that extracts of leaves of E. agallocha had potent antioxidant activity as compared to 38 other plants they investigated. It was determined that the antioxidant activity was due to the presensce of ellagic acid.

Anti-inflammatory activity

Li et al. [32] isolated 15 compounds from the stems and twigs of E. agallocha. Of these 7 were found to show anti-inflammatory potency to suppress expression of NF-kappaB and AP-1 targeted genes including TNF-alpha and IL-6 induced by lipopolysaccharide (LPS) in mouse macrophages Raw 264.7 cells. They were also found to block NF-kappaB activation and AP-1 activation dramatically.

Toxicities

No documentation

Clinical Data

Clinical Trials

No documentation

Adverse Effects in Human:

The milky juice causes blisters on the skin of people sensitive to it. On contact with the eyes it can cause intense pain and temporary blindness. [2] It is said that the sap is so poisonous that even the smoke from the burning branches affects the eyes with insufferable pain. [5] There are two types of irritant factors forming the skin and eye irritants identified in the latex of E. agallocha i.e. cryptic and free Excoecaria factors. The cryptic irritants had been identified as polyfunctional diterpene esters which are aliphatic polyunsaturated 9,13,14-orthoesters of the daphnane-type parent alcohol 5b-hydrocyresiniferonol-6a,7a-epoxide, esterified simultaneously in their 20-position with aliphatic saturated homologous n-carboxylic acids. Per se they are non irritant and required to be activated to generate mixtures of the highly irritant factors. It was found that by alkaline transesterification the highly irritant factors were released. This comprise of a mixture of the highly irritant Excoecaria factor A1/A2/A3 (OH-20 deacylated) and three other mixtures of still unkown Excoecaria factors A4/A5, A6/A7 and A8/A9. [10-11]

An instant remedy for the temporary blinding effects of the latex of E. agallocha is to drop into the eyes the juice of the shoot of the fern Achrosticum aureum Linn. [33]

Used 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

A report of sever skin and eye injury due to exposure to latex of E. agallocha was published by Kumarasinghe et al. [16]

Read More

  1)  Botanical Info

References

    1. P.B. Tomlinson The Botany of Mangroves Cambridge Unioversity Press Cambridge 1986 pg. 46
    2. Wee Yeow Chin, P. Gopaklakjrishnakone A Colour Guide to Dangerous Plants Singapore University Press Singapore 1990 pg. 33
    3. Elmer Drew Merrill A Dictionary of the Plant Names of the Philippine Island BiblioBazaar, LLC, Manila 2009 pgs. 14, 15, 39, 58,66
    4. S. Sahoo Conservation and Utilization of Medicinal and Aromatic Plants Allied Publishers Ltd. New Delhi 2001 pg. 49
    5. Mary Somerville On Molecular and Microscopic Science Volume 1 John Murray London 1869 pg. 426
    6. Dr. B. Seemann Vegetable Productions of the Feejee Islands, - American Journal of Science Volume 35 E. Hayes New Haven 1863 pg. 447
    7. Herbert Kenneth Airy Shaw A Dictionary of the Flowering Plants and Ferns CUP Archive 1980pg. 44
    8. C.P. Khare Indian Medicinal Plants: an Illustrated Dictionary Springer-Verlag Berlin 2007 pg. 257
    9. Siosiane Fanua Bloomfeild Illness and Cure in Tonga; Traditional and Modern Practice Vava’u Press Ltd. Nuku’alofa Tonga 2002 pg. 145
    10. Wiriyachitra P, Hajiwangoh H, Boonton P, Adolf W, Opferkuch HJ, Hecker E. Investigations of Medicinal Plants of Euphorbiaceae and Thymelaeaceae Occurring and Used in Thailand; II. Cryptic Irritants of the Diterpene Ester Type from Three Excoecaria species1. Planta Med. 1985 Oct;51(5):368-71.
    11. Karalai C, Wiriyachitra P, Opferkuch HJ, Hecker E. Cryptic and free skin irritants of the daphnane and tigliane types in latex of Excoecaria agallocha. Planta Med. 1994 Aug;60(4):351-5.
    12. Norhanom AW, Yadav M. Tumour promoter activity in Malaysian Euphorbiaceae. Br J Cancer. 1995 Apr;71(4):776-9.
    13. Erickson KL, Beutler JA, Cardellina JH 2nd, McMahon JB, Newman DJ, Boyd MR. A novel phorbol ester from Excoecaria agallocha. J Nat Prod. 1995 May;58(5):769-72.
    14. Konishi T, Takasaki M, Tokuda H, Kiyosawa S, Konoshima T. Anti-tumor-promoting activity of diterpenes from Excoecaria agallocha. Biol Pharm Bull. 1998 Sep;21(9):993-6.
    15. Erickson KL, Beutler JA, Cardellina JH 2nd, McMahon JB, Newman DJ, Boyd MR. A novel phorbol ester from Excoecaria agallocha. J Nat Prod. 1995 May;58(5):769-72.
    16. Kumarasinghe SP, Seneviratne R.  Skin and eye injury due to latex of Excoecaria agallocha. Australas J Dermatol. 1998 Nov;39(4):275-6.
    17. Masuda T, Yonemori S, Oyama Y, Takeda Y, Tanaka T, Andoh T, Shinohara A, Nakata M. Evaluation of the antioxidant activity of environmental plants: activity of the leaf extracts from seashore plants. J Agric Food Chem. 1999 Apr;47(4):1749-54.
    18. Konishi T, Konoshima T, Fujiwara Y, Kiyosawa S. Excoecarins D, E, and K, from excoecaria agallocha. J Nat Prod. 2000 Mar;63(3):344-6
    19. Anjaneyulu AS, Rao VL. Five diterpenoids (agallochins A-E) from the mangrove plant Excoecaria agallocha Linn. Phytochemistry. 2000 Dec;55(8):891-901.
    20. Konoshima T, Konishi T, Takasaki M, Yamazoe K, Tokuda H. Anti-tumor-promoting activity of the diterpene from Excoecaria agallocha. II. Biol Pharm Bull. 2001 Dec;24(12):1440-2.
    21. Anjaneyulu AS, Rao VL, Sreedhar K. ent-Kaurane and beyerane diterpenoids from Excoecaria agallocha. J Nat Prod. 2002 Mar;65(3):382-5.
    22. Konishi T, Yamazoe K, Konoshima T, Maoka T, Fujiwara Y, Miyahara K. New bis-secolabdane diterpenoids from Excoecaria agallocha. J Nat Prod. 2003 Jan;66(1):108-11.
    23. Anjaneyulu AS, Rao VL. Seco diterpenoids from Excoecaria agallocha L. Phytochemistry. 2003 Feb;62(4):585-9.
    24. Anjaneyulu AS, Rao VL, Sreedhar K. Agallochins J-L, new isopimarane diterpenoids from Excoecaria agallocha L. Nat Prod Res. 2003 Jan;17(1):27-32.
    25. Konishi T, Yamazoe K, Kanzato M, Konoshima T, Fujiwara Y. Three diterpenoids (excoecarins V1-V3) and a flavanone glycoside from the fresh stem of Excoecaria agallocha. Chem Pharm Bull (Tokyo). 2003 Oct;51(10):1142-6.
    26. Konishi T, Yamazoe K, Konoshima T, Fujiwara Y. Seco-labdane type diterpenes from Excoecaria agallocha. Phytochemistry. 2003 Oct;64(4):835-40.
    27. Kang J, Chen RY, Yu DQ. A new isopimarane-type diterpene and a new natural atisane-type diterpene from Excoecaria agallocha.  J Asian Nat Prod Res. 2005 Oct;7(5):729-34.
    28. Zou JH, Dai J, Chen X, Yuan JQ. Pentacyclic triterpenoids from leaves of Excoecaria agallocha. Chem Pharm Bull (Tokyo). 2006 Jun;54(6):920-1.
    29. Wang JD, Zhang W, Li ZY, Xiang WS, Guo YW, Krohn K. Elucidation of excogallochaols A-D, four unusual diterpenoids from the Chinese mangrove Excoecaria agallocha. Phytochemistry. 2007 Oct;68(19):2426-31. Epub 2007 Jun 21.
    30. Tian MQ, Bao GM, Ji NY, Li XM, Wang BG. [Triterpenoids and steroids from Excoecaria agallocha] Zhongguo Zhong Yao Za Zhi. 2008 Feb;33(4):405-8.
    31. Wang ZC, Lin YM, Feng DQ, Ke CH, Lin P, Yan CL, Chen JD. A new atisane-type diterpene from the bark of the mangrove plant Excoecaria agallocha. Molecules. 2009 Jan 16;14(1):414-22.
    32. Li Y, Liu J, Yu S, Proksch P, Gu J, Lin W. TNF-alpha inhibitory diterpenoids from the Chinese mangrove plant Excoecaria agallocha L. Phytochemistry. 2010 Sep 3. [Epub ahead of print]
    33. Abdul Ghani Hussain - Personal communication with dwellers of Mangrove regions of Langkawi Islands (unpublished)
    34. Flora of Thailand. http://www.nationaalherbarium.nl/thaieuph/ThEspecies/ThExcoecaria.htm [ Accessed on 22 November 2010]