Excoecaria agallocha L.

Last updated: 24 Aug 2016

Scientific Name

Excoecaria agallocha L.

Synonyms

Commia cochinchinensis Lour., Excoecaria affinis Endl., Excoecaria agallocha var. camettia (Willd.) Müll.Arg., Excoecaria agallocha var. lancifolia Pax & K.Hoffm., Excoecaria agallocha var. orthostichalis Müll.Arg., Excoecaria agallocha var. ovalis (Endl.) Müll.Arg., Excoecaria camettia Willd., Excoecaria ovalis Endl., Excoecaria sphaerosperma F.Muell. ex Pax [Illegitimate], Stillingia agallocha (L.) Baill. [1]

Vernacular Name

Malaysia Bebuta, buta-buta (buta means blindness), bomo, dari, kajaoe mata boeta, pohun [2]
English Blind-your-eye mangrove, blind-your-eyes, blind-your-eyes mangrove, blinding tree, blinding tree of Ceylon, milky mangrove, poison mangrove, river poison tree [2]
India Gangu, geneo, gengwa, geo-gheria, goma, guan [2]
Indonesia Kayu betah, kayu buta-buta, menengan [2]
Thailand Bu-to, buu-to, ta-thum-tha-le, tatum, tatum thale [2]
Myanmar Kayaw taway [2]
Philippines Buta-buta, lipata [2]
Vietnam Gi[as], tr[af] m[ur] [2]
Japan Metubushi-no-ki, miishi-kuki, Okinawa-jinkô, shima-shiraki, shimashiraki [2]
Papua New Guinea Sisimet, sismet, su, te’eria [2].

Geographical Distributions

Excoecaria agallocha is distributed along the coasts of southern India and Sri Lanka to Burma (Myanmar), Indo-China, China, Taiwan, the Ryukyu Islands, Thailand, throughout the Malaysian region, northern Aus­tralia and the Pacific. [3]

Botanical Description

E. agallocha is a member of the family Euphorbiaceae. It is a shrub or tree that can reach up to 15(-20) m tall. [3]

The leaves are spirally arranged, ovate or elliptical, measure 3-9 cm x 2-5 cm, shortly blunt acuminate at apex while the margins are crenulate-serrate. [3]

The inflorescence is unisexual, with the male inflorescence densely spike-like and almost cat­kin-like when young. [3]

The fruit is a capsule, tricoccous, lobed, about 1 cm in diametre and borne in short racemes. [3]

Cultivation

E. agallocha is common in mangrove forests, tidal thick­ets and freshwater swamp forests up to 100(-400) m altitude. [3]

Chemical Constituent

E. agallocha has been reported to contain β-sitostenone, β-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-3β,20-epoxy-3a, 6α-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, excoecarins N, excoagallochaols A-D, ent-labda-8(17),13E-diene-3β,15-diol, excoecarins R1, excoecarins R2, excoecarins S, excoecarins T1, excoecarins T2, excoecarins V1-V3, ent-kauran-16 b-ol-3-one, labda-8(17),13E-diene-3b,15-diol, ribenone, taraxerone, taraxero, (13R,14S)-ent-8a,13, 14,15-diepoxy-13-epi-labdan-3-one, (13R,14R)-ent-8a,13, 14,15-diepoxy-13-epi- labda-3β-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, 2-hydroxy-1,15-beyeradiene-3,12-dione, 3,5,7,3',5'-pentahydroxy-2R,3R-flavanonol, 3-O-a-L-rhamnopyranoside, 3α,1α,14α-trihydroxyisopimara-7,15-diene, 3α,11β-dihydroxy-ent-isopimara-8(14),15-dien-2-one, 3α,18-dihydroxy-3β,20-epoxybeyer-15-ene, 3β,20-epoxy-3α-hydroxybeyer-15-ene, 3β,20:15R,16S-diepoxy-3α-beyeranol, 3β,20-epoxy-3α,6α-dihydroxy-18-nor-beyer-15-ene, and 3β-[(2E,4E)-6-oxo-decadienoyloxy]-olean-12-ene. [4][5][6][7][8][9]

Hexane extract of E. agallocha roots has been reported to contain 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, 11a,14a-dihydroxy-7,15-isopimaradien-3-one, 12-deoxyphorbol 13-(3E,5E-decadienoate), acetylaleuritolic acid, agallochaol K-P, agallochaol Q, β-amyrin acetate. [5]

Plant Part Used

Leaves, bark. [10][11]

Traditional Use

The Fijian and the Indians had advocated the use of E. agallocha 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 [12][13]. Decoction of the leaves is used for treatment of epilepsy and ulcers [14]. The juice boiled in oil is used to treat rheumatism and paralysis [12].

Preclinical Data

Pharmacology

Tumourpromoting 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 1.2 μg/mL of the plant extract in cell culture. [15]

Antitumour promoting activity

Contrary to the above findings Konishi et al. 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) [16]. 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 significant antitumour-promoting effects in the mouse two-stage carcinogenesis test [17].

Antiviral activity

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. [16]

Antioxidant activity

Masuda et al. 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. [8]

Anti-inflammatory activity

Li et al. 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. [18]

Toxicity

No documentation

Clinical Data

Clinical findings

No documentation

Precautions

No documentation

Side effects

No documentation

Pregnancy/Breast Feeding

No documentation

Age limitation

No documentation

Adverse reaction

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 [19]. It is said that the sap is so poisonous that even the smoke from the burning branches affects the eyes with insufferable pain [20]. 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 [21][22].

Interaction & Depletion

No documentation

Contraindications

No documentation

Dosage

No documentation

Poisonous Management

No documentation

Line drawing

161

Figure 1: The line drawing of E. agallocha. [3]

References

  1. The Plant List. Ver 1.1. Excoecaria agallocha L. [homepage on the Internet]. c2013 [updated 2012 Mar 23; cited 2016 Aug 24]. Available from: http://www.theplantlist.org/tpl1.1/record/kew-83292
  2. Quattrocchi U. CRC world dictionary of medicinal and poisonous plants: Common names, scientific names, eponyms, synonyms, and etymology. Volume III E-L. Boca Raton, Florida: CRC Press, 2012; p. 203
  3. van Valkenburg JLCH. Excoecaria agallocha L. In: van Valkenburg JLCH, Bunyapraphatsara N, editors. Plant Resources of South-East Asia No. 12(2): Medicinal and poisonous plants 2. Leiden, Netherlands: Backhuys Publishers, 2001; p. 264.
  4. Konishi T, Takasaki M, Tokuda H, Kiyosawa S, Konoshima T. Anti-tumor-promoting activity of diterpenes from Excoecaria agallocha. Biol Pharm Bull. 1998;21(9):993-996.
  5. Anjaneyulu ASR, Rao VL. Five diterpenoids (agallochins A-E) from the mangrove plant Excoecaria agallocha Linn. Phytochem. 2000;55:891-901.
  6. Erickson KL, Beutler JA, Cardellina JH 2nd, McMahon JB, Newman DJ, Boyd MR. A novel phorbol ester from Excoecaria agallocha. J Nat Prod. 1995;58(5):769-772.
  7. Kumarasinghe SP, Seneviratne R. Skin and eye injury due to latex of Excoecaria agallocha. Australas J Dermatol. 1998;39(4):275-276.
  8. Masuda T, Yonemori S, Oyama Y, et al. Evaluation of the antioxidant activity of environmental plants: activity of the leaf extracts from seashore plants. J Agric Food Chem. 1999;47(4):1749-1754.
  9. Konishi T, Konoshima T, Fujiwara Y, Kiyosawa S. Excoecarins D, E, and K, from Excoecaria agallocha. J Nat Prod. 2000;63(3):344-346
  10. Bloomfeild SF. Illness and cure in Tonga: Traditional and modern practice. Nuku’alofa, Tonga: Vava’u Press, 2002; p. 145.
  11. 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 species 1. Planta Med. 1985;51(5):368-3671.
  12. Seemann B. Vegetable productions of the Feejee Islands. Am J Sci. Hayes New Heaven. 1863;35:447.
  13. Khare CP. Indian medicinal plants: An illustrated dictionary. Berlin: Springer-Verlag, 2007; p. 257.
  14. Sahoo S, Ramesh DB, Rao YR, Debata BK, Misra VN, editors. Conservation and utilization of medicinal and aromatic plants. New Delhi: Allied Publishers Limited, 2001; p. 49.
  15. Norhanom AW, Yadav M. Tumour promoter activity in Malaysian Euphorbiaceae. Br J Cancer. 1995;71(4):776-779.
  16. Erickson KL, Beutler JA, Cardellina JH 2nd, McMahon JB, Newman DJ, Boyd MR. A novel phorbol ester from Excoecaria agallocha. J Nat Prod. 1995;58(5):769-772.
  17. 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;24(12):1440-1442.
  18. 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;71(17-18):2124-2131.
  19. Chin WY, Gopalakrishnakone P. A colour guide to dangerous plants. Singapore: Singapore University Press; 1990. p. 33.
  20. Somerville M. Molecular and microscopic science. Volume 1. London: John Murray Publisher, 1869; p. 426.
  21. 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;51(5):368-371.
  22. 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;60(4):351-355.