Annona muricata L.

Last updated: 01 Jun 2016

Scientific Name

Annona muricata L.

Synonyms

Annona bonplandiana Kunth, Annona cearaensis Barb.Rodr., Annona macrocarpa Wercklé, Guanabanus muricatus M. Gómez [1]

Vernacular Name

Malaysia Durian belanda, durian benggala, durian Makkah [2], durian Europa, nangka Belanda, seri kaya Belanda [3]
English Soursop [2], graviola, paw paw [4]
China 刺果番荔枝 (Ci guo fan li zhi) [5]
India Fofi, jeuto, lakshmana phalamu, mam phal, mamaphal, mulcita, mullu raama phala, mulluccita, mutcitamaram, pulippala, vilattinuna [3]
Indonesia Sirsak, nangka belanda (Javanese); nangka seberang [2]
Thailand Thurian-thet, thurian-khaek, rian-nam [2], ma-thu-rian [3]
Laos Khan thalot, khièp thét [2]
Philippines Guayabano (Tagalog); atti (Ibanag); llabanos (Bisaya) [2]
Cambodia Tiep banla, tiep barang [2]
Vietnam Mang câù xiêm [2]
Papua New Guinea Saua sap [2], sow sap [3]
France Corossol épineux [2].

Geographical Distributions

Annona muricata is native to tropical America where it is an important fruit crop. It was one of the first fruit trees introduced to the old world after Columbus discovered America. The Spaniards brought it to the Philippines at an early date and it can be found in most tropical countries. [2]

Botanical Description

A. muricata is a member of the Annonaceae family. It is a shrub or small tree which is 3-10 m tall, conforms to Troll's architectural model and branches from near the base. [2]

The leaves are oblong-obovate, measuring 8-16 cm x 3-7 cm and short acuminate at the apex. The petiole is 3-7 mm long. [2]

The flowers are regular, 1-2-flowered inflorescences and greenish-yellow. The pedicel is up to 2.5 cm long. There are 3 sepals which are triangular, persistent and about 4 mm long. There are 6 petals in 2 rows where the outer 3 are broadly ovate, measuring 3-5 cm x 2-4 cm while the other inner 3 measure 2-4 cm x 1.5-3.5 cm and with short claws at the base. The stamens are numerous, borne on a raised torus in many rows, measure 4-5 mm long while the filaments are densely pubescent. The ovaries are numerous, densely pubescent and confluent afterwards. [2]

The ripe fruit is a pseudocarp, broadly ovoid or ellipsoid, measuring up to 10-20 cm x 15-35 cm, dark green and covered with soft spines 6 mm long and with fleshy and juicy white pulp. The blackish-brown shiny seeds are numerous, obovoid and measuring 2 cm x 1 cm. [2]

Cultivation

A. muricata  is the least hardy of the Annona species, which requires a warm and humid tropical climate. It grows at elevations up to 1000 m and as far as 25°S in sheltered sites. Growth and fruiting are set back severely by cold spells, and light frosts kill the tree. A dry season enhances leaf fall and synchronises extension growth and flowering to some extent. Yields may be higher under these conditions, provided that high humidity prevails during the period of fruit set; there are indications that, as for other Annona species, both very high and low humidities may be detrimental to fruit set. Where humidity tends to be low, a sheltered site is recommended to limit transpiration (also because the tree is shallow-rooted). Most soils are suitable for cultivation, but drainage should be good because the tree does not tolerate waterlogging. [2]

Chemical Constituent

A. muricata  has been reported to contain acetaldehyde, amylcaproate, amyloid, annomonicin, annomontacin, cis-annomuricin-D-one, trans-annomuricin-one, annomuricine A – C, annonacin A, cis-annonacin, 2-4 trans-iso-annonacin, iso-annonacin, annonacin, cis- annonacin-10-one, neo-iso-annonacin-10-one, iso-annonacin-10-one, neo-annonacin-10-one, annonacin-10-one, annonacinone, annonain, annonaine, annopentocin A, annopentocin B, annopentocin C, anomuricine, anomurine, anoniine, anonol, arginine, arianacin, ascorbic acid, asimilobine, atherospermine, atherosperminine, b-carotene, b-sitosterol, caffeic acid, campesterol, caproic acid methyl ester, caprylic acid methyl ester, carbohydrate, cellobiose, cholesterol, citric acid, citrulline, (+)coclaurine, cohibins C, cohibins D, corepoxylone, (-)coreximine, (+)coreximine, coronin, corossolin, corossolone, deacetyl uvaricin, dextrose, D-sucrose, epomuricenin A, epomuricenin B, epoxy murin A, epoxy murin B, ethanol, folic acid, fructose, galactomannan, gamma amino butyric acid, gentisic acid, geranyl caproate, gigntetrocin A, gigantetrocin  B, gigantetrocin, gigantetronenin, glucose, cis-goniothalamicin, goniothalamicin, HCN, hex-trans-2-en-1-ol, howiicin A 4-deoxy howiicin B, howiicin B, howiicin F, howiicin G, Iron, isocitric acid, javoricin, lignoceric acid, longifolicin, malic acid, mericyl alcohol, methanol, methyl-hexanoate, montanacin, montecristin, diepoxy-muricanin, muricapentocin, muricatacin, muricatalicin, muricatalin, muricatetrocin A, muricatetrocin B, muricatocin A, muricatocin B, muricatocin C, muricin A, muricin B, muricin C, muricin D, muricin E, muricin F, muricin G, muricine, muricinine, muricoreacin, murihexocin C, murihexol, murisolin, myricyl alcohol, myristic acid, nornuciferine, oleic acid, ornithine, palmitic acid, cis-panatellin, paraffin, p-coumaric acid, potassium chloride, procyanidin, resin, cis-reticulatacin, reticulatacin-10-one, (+)reticuline, reticuline, rolliniastatin 1, rolliniastatin 2, scyllitol, cis-solamin, solamin, stearic acid, stepharine, stigmasterol, tannin, cis-i-uvariamicin, cis-iv-uvariamicin, and xylosyl cellulose. [6]

Plant Part Used

Seeds, leaves, barks, fruits [4][7]

Traditional Use

The leaves of A. muricata is believed to have lactagogue, sedative and tranquilizing properties [6][8]. It has been used for viral and bacterial fevers [4]. It has been recorded that in Malaysia, the Caribbean and South America the decoction of the leaves is a remedy for cough, cold and fevers [9][10]. In Malaysia the leaves are macerated in water and the infusion is used to sponge down high fever [10]. Hot water extract of dried leaves can be used to treat ringworm [6].

Crushed leaves of A. muricata  are used to treat scabies, head lice and other skin diseases of children [7][10]. It also are applied over abscesses as an aid to resolving the inflammation [7][11][12][13]. In the Cooks Island the scent from crushed leaves of A. muricata is used to treat vertigo and fainting spells while in Caracoa the hot water extract of the leaves is taken orally with Citrus aurantium every morning to relieve nervousness. In the British Guyana the crushed leaves in water together with lime juice is rubbed on to the head of a drunkard to render him instantaneously sober [6][14]. It can act as an anticonvulsant when the leaves are given in a decoction form [15].

A poultice of the pulp is used to remove chiggers by applying it for for three days. [14][16]

Juice of the fruit of A. muricata is considered a diuretic and is a remedy for haematuria and urethritis [14]. The heart of the fruit and fruit juice is also used for worms and parasites [8][12][15][17]. It has been used to getting rid of head lice by applying the juice of the fruit on the head [10]. A decoction of the fruit is given for high fever [17].  The fruit and the fruit juice is taken for diarrhea and dysentery [8]. In Malaysia a decoction of the unripe fruit is a remedy for jaundice and diarrhea [17].

The crushed seeds are considered more potent remedy for worms and parasites. [4]

The oil of the leaves and unripe fruit mixed with olive oil is a remedy for neuralgia for the Brazilians in the Amazon [8]. The leaves and barks are used to ease difficult labour and their lotion are used for treating asthma, influenza and cough [6][7].  Tea made from the leaves and also fruit juice can be used for liver problems including cholecystosis [16].  In the Peruvian Amazon the bark, roots and leaves are used to treat diabetes [8]. The astringent properties of various parts of the plant especially the bark and the half ripe fruit renders them useful in the treatment of diarrhea, a remedy for distention and dyspepsia [4][7][8]

Preclinical Data

Pharmacology

Antidiabetic activity

Diabetes mellitus contribute amongst the various uses of A. muricata in traditional medicine. Two studies on the hypopglycaemic effects of various extracts of A. muricata were conducted. In the first study [18] they demonstrated the ability of methanolic extract of A. muricata to reduce blood glucose level significantly in streptozotocin-induced diabetic Wistar rats. Another study showed that the aqueous extract of the leaves was able to stimulate the secretion of insulin [19].

Antioxidant activity

Ethanol extract of A. muricata leaves (500 mg/mL) exhibited antioxidant activity showed maximum scavenging acitivity of 2,2-azinobis-(3-ethylbenzothizoline-6-sulphonate (90.05%), followed by scavenging of hydroxyl radical (85.88%) and nitric oxide (72.60%) at the same concentration. There was only moderate lipid peroxidation inhibition activity. [20] 

Aqueous extracts of the A. muricata leaves showed that this extract was able to increase antioxidant enzymes activities significantly. [19] 

Cytotoxic activity

The cytotoxic activity of A. muricata is attributed to the presence of many Annonaceous acetogenins. These array of compounds are found in most of the Annonaceae family of plants. Listed are the annonaceous acetogenins found in A. muricata:

Annomuricin C, muricatocin C are active against the A-549 human lung and the MCF-7 human breast solid tumour cell lines [20]; gigantetronenin. [21]

Annomutacin, (2,4-trans)-10R-annonacin-A-one, (2,4-cis)-10R-annonacin-A-one are active against the human A-549 lung tumour cell line. [22]

Cis-annonacin, cis-annonacin-10-one, cis-goniothalamicin, arianacin, javoricin where annomutacin selectively cytotoxic to colon adenocarcinoma cells (HT-29). [23]

Annomuricine, muricapentocin showed significant cytotoxicities against sixt types of human tumours with selectivities to the pancreatic carcinoma (PACA-2) and colon adenocarcinoma (HT-29) cell lines. [24]

Annopentocins A, B, C, cis-annomuricin-D-ones, trans-annomuricin-D-one where annopentocin A is selectively cytoxic to pancreatic carcinoma cells (PACA-2), annopentocin B and C are selectively cytotoxic to lung carcinoma cells (A-549) and mixture of cis- and trans-annomuricin-D-ones are selectively cytotoxic to lung (A-549), colon (HT-29) and pancreatic (PACA-2) cell lines. [25]

Muricoreacin, murihexocin showed significant cytotoxicities among six human tumour cell lines with selectivities to the prostate adenocarcinoma (PC-3) and pancreatic carcinoma (PACA-2) cell lines. [26]

Annonacin, annonacin A and annomuricin A showed cytotoxic activity against cell line U-937. [27]

Muricatetrocin A and B, longifolicin, corossolin, corossolone showed significant selectivite cyctotoxicities towards human hepatoma cell lines Hep G(2) and 2,2,25. [28]

Muricatenol, 2,4-cis-gigantetrocinone and 2-4-trans-gigantetrocinone, 2,4-trans-isoannonacin-10-one, 2,4-trans-isoannonacin, gigantetrocin A, B, annomontacin, gigantetronenin. In this study the CHCl3 fraction of the seed extract showed strong anti-tumour activities. [29]

Muricin H and I, cis-annomontacin, cis-corossolone, annocatalin, annonacin, annonacinone, solamin and corossolone. They showed significant activity in in vitro cytotoxic assays against two human hepatoma cell lines ie. HEPg(2) and 2,2,25 with annocatalin showing high selectivity against the Hep 2,2,15 cell line. [30]

Antimicrobial activity

Antiviral (HSV-1)

Ethanol extract of A. muricata in a concentration of 1 mg/mL was found to inhibit the cytopathic effect of HSV-1 (Herpes simplex virus-1) on vero cells. [31]

Antiprotozoal 

In a screening activity for antiparasitic activity of Colombina Annonaceae, Ororio et al found that the extract of Annona muricata was active against the three Leishmania spp. tested. [32] Study found that their ethyl acetate extract of the pericarp of A. muricata to be most active against Leishmania braziliensisi and Leishmania panamensis promastigotes. [27]

Toxicity

A number of potential toxic alkaloids were isolated from A. muricata. They include anonaine, anoniine, muricine and muricinine. Muricinine has a structure similar to reticuline. The bark contain high amount of hydrocyanic acid [14]. There was a report of a single fatality in a child who had over consumed tea made of the leaves of A. muricata [16].

Clinical Data

Clinical findings

No documentation.

Precautions

No documentation.

Side effects

No documentation.

Pregnancy/Breast Feeding

A. muricata has demonstrated uterine stimulant activity in an animal study (rats) and should therefore be avoided during pregnancy. [8]

Age limitation

No documentation.

Adverse reaction

The seeds contain 45% of yellow non-drying oil which is an irritant poison causing severe eye inflammation. [14]

Interaction & Depletion

No documentation.

Contraindications

Tropical myeloneuropathies

An interesting neurological syndrome, characterized by recurrent optic neuritis, cervical myelopathy from syringomyelia, paraparesis, amenorrhoea-galactorrhoea and other endocrine problems, had been described among young black women in the French West Indies. While the etiology remain obscured a possible link with Devic’s disease, actue disseminated encephalomyelitis and neurotoxicity from quinoline in A. muricata teas have been postulated. [33]

Atypical parkinsonism (Gaudeloupean Parkinson’s Disease)

The Annonaceae family of plants contained neurotoxic benzyltetrahydoisoquinoline alkaloids which had been implicated as the cause of Atypical Parkinson’s Disease found in the French West Indies. This form of Parkinson’s Disease are typically resistant to L-DOPA. It was  found that the total extract of alkaloids from A. muricata root bark and two of the most abundant subfractions, croeximine and reticuline affected the dopaminergic neurons and GAPAergic neurons by causing cell death through condensation and fragmentations of DNA in the nuclei. The effect was not excitotoxic and did not require toxin uptake by the dopamine transporter. The neurodegenation could be attenuated by increasing the concentration of glucose and toxin withdrawal after short term exposure arrested cell death. Acute treatment with totum, coreximine or reticuline reversibly inhibited dopamine uptake by a mechanism that was distinct from that causing neuronal death. It was concluded that the alkaloids can modulate the function and the survival of dopaminergic nre cells in vitro. [34]

They further isolated annonacin a major acetogenin of A. muricata and studied its effects on dopaminergic cells. They found that it was a potent killer of dopaminergic neurons and its effects was via impairment of energy production of these cells. [35][36]

It was estimated that the average fruit would contain about 15 mg of annonacin, a can of commercial nectar 36mg, and a cup of infusion or decoction of the leaves 140 mg. As an indication of its potential toxicity, an adult who consumes one fruit or can of nectar a day is estimated to ingest over 1 year the amount annonacin that could induce brain lesions in rats receiving purified annonacin by intravenous infusion. [37]

Dosage

No documentation.

Poisonous Management

No documentation.

Line drawing

81

Figure 1: The line drawing of A. muricata [2]

References

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