Articles

Glycosmis pentaphylla (Retz.) DC.

Synonyms

Limonia pentaphylla Retz.

Vernacular Names:

Malaysia: Napan, Nerapan [1], Merapi [2]
English: Ash Sheora, Orangeberry, Rum Berry, Gin Berry [3]
Chinese: Shan Xiao Jie, Shi Ling Jiu [4]
Thailand: Khoei Tai, Luk Khoei Tai [4]

General Information

Description

Glycosmis pentaphylla is a small, evergreen tree or shrub, belonging to the Rutaceae family which grows to a height of 5m measures. It is widely distributed in tropical forests at low altitudes, spanning from India, south China, Thailand, peninsular Malaysia, Indonesia and to the Philippines islands. [2]

Plant Part Used

Leaf, stem, root. [2]

Chemical Constituents

The dried stem bark of G. pentaphylla from Papua New Guinea was extracted with methanol-dichloromethane. After separation followed by subsequent purification a novel naphthoquinone, and a new acridone alkaloid called glycoquinone and glycocitrine-III were isolated. Twelve known alkaloids; noracronycine, des-N-methyl-noracronycine, des-N-methylacronycine, citracridone-I, arborinine, 5-hydroxyarborinine, acrifoline, skimmianine, kokusaginine, avicenol-B, avicequinone-C, and avicenone were also isolated. [5]

Four hydroquinone diglycoside acyl esters, glypentosides A-C and seguinoside F were isolated from the stems of G. Pentaphylla. [6]

More recently six new apiosyl-(1®6)-glucosyl isoflavones: 3’,7-dihydroxy-4’,5,6-trimethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-β-D-apiofuranosyl-(1®6)-β-D-glucopyranoside, 2’,7-dihydroxy-4’,5’,5,6-tetramethoxyisoflavone 7-O-(5-O-trans-p-coumaroyl)-β-apiofuranosyl-(1®6)-β-D-glucopyranoside, 2’,7-dihydroxy-4’,5’,5,6-tetramethoxyisoflavone 7-O-β-D-apiofuranosyl-(1®6)-β-D-glucopyranoside, 7-hydroxy-4’,8-dimethoxyisoflavone 7-O-β-D-apiofuranosyl-(1®6)-β-D-glucopyranoside, 7-hydroxy-4’,6-dimethoxyisoflavone 7-O-β-D-apiofuranosyl-(1®6)-β-D-glucopyranoside, 4’,5-dihydroxy-3’,7-dimethoxyisoflavone 4’-O-β-D-apiofuranosyl-(1®6)-β-D-glucopyranoside were isolated from the stems of G. Pentaphylla. [7]

The root bark contains alkaloids skimmianine, g-fagarine, dictamine, arborine, carbazole, 3-methoxycarbazole, homoglycosolone, homoglycolone, glycolone, glycozoline, and glycozolicine, and β-sitosterol. The roots yield carbazoles glycozoline, glycozolidine, dictamine, arborine and skimmianine, while the leaves contain arborinine, mupamine, and triterpene arborinone. Flowers are found to contain glycophymine, glycosolone, glycophymoline, and an amide glyomide. Vitexin, 7-methoxy apigenin, p-hydroxybenzoic acid, vanillic acid, syringic acid and ferulic acid are other compounds present in the leaves. [8]

Arborine [2-benzyl-1-methyl-4(1H)-quinazolone] was isolated as the major compound from the ethyl acetate soluble fraction of leaf extract of G. Pentaphylla. [9]

Traditional Use:

In Malaysia, an infusion of the leaves and roots is prescribed to mothers during confinement. In Java, a decoction of the roots and leaves is taken to treat intestinal ailments. In India, the herb is used to treat diarrhoea, coughs, rheumatism, anaemia, and jaundice. The juice from the leaves is used to treat fever, liver problems and also as anthelmintic. A paste prepared from the leaves of the herb and ginger can be used for the treatment of eczema and other skin infections. [2]

Pre-Clinical Data

Pharmacology

Antitumor activity

An acridone alkaloid called arborinine obtained from G. pentaphylla showed significant inhibition of crown gall tumours in a simple potato disc bioassay. The arborinine has the potential as an anticancer agent, hence further in vitro assay using cancer cell lines are needed to confirm this activity. [10]

Insecticidal and Larvicidal activity

A study to identify (i) the active principle in the leaf extract of G. pentaphylla and (ii) the structure of at least one of the effective compounds using in vitro bioassay which measures the rate of juvenile hormone biosynthesis in the corpora allata of insects.  The ethanolic acetate fraction of G. pentaphylla leaf extract inhibits the juvenile hormone biosynthesis in the corpora allata from 3 day old females of the field cricket Gryllus bimaculatus in a dose-dependent manner. The bioactive compound was identified as the alkaloid arborine. This alkaloid was also found to contain strong insecticidal activity against dipteran species as well as showing larvicidal activity against the mosquito Culex quinquefasciatus. [9]

Hepatoprotective activity

The effects of leaf extracts and stem bark of G. pentaphylla were studied on CCl4 induced hepatic injury in albino rats. The parameters studied include plasma liver enzymes (ALT, AST and ALP), total bilirubin and tissue histopathology. The recovery of hepatic tissues was demonstrated with the highest dose of leaf extract at 750mg/kg body weight and at this therapeutic dose, there was no toxic effect shown. At and above the dose of 2.5g/kg body weight, toxicity of leaf extract was observed as shown by the tissue histopathology. [11]

Another study on the hepatoprotective activity of extracts from the stem bark of G. pentaphylla and the whole plant of Phyllanthus fratermus was evaluated against CCl4-induced jaundice in rats. The extracts were administered orally for 7 days. On the 3rd and 6th days, the rats were given CCl4 and olive oil subcutaneously in 50:50 ratio. The blood samples were taken on the 8th day and serum liver enzymes such as ALP, ALT, ALT, g-GT and total bilirubin were analysed. The results of the study showed the crude extracts of G. pentaphylla and P. fratermus demonstrated the ability to prevent hepatic injury/liver necrosis in the preventive group and showed enhanced regeneration on the curative group. [12]

Toxicities

The leaf extract of G. Pentaphylla showed toxicity level to be at and above 2.5g/kg body weight as was histopathologically observed in tissues of albino rats. [11]

Clinical Data

Clinical Trials

No documentation

Adverse Effects in Human:

No documentation

Use 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

No documentation

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  1)  Botanical Info

References

    1. Burkill, I.H. A Dictionary of the Economic Products of Malay Peninsular, Ministry of Agriculture Malaysia. 1935; pp 1086.
    2. Samy, J., Sugumaran, M. and Lee, K.L.W. Herbs of Malaysia. Federal Publications Sdn. Berhad, Shah Alam. 2005; pp 114-115.
    3. TopTropicals–Rare plants for home and garden http://toptropicals.com/catalog/uid/glycosmis_pentaphylla.htm. Accessed on 15 Dec 2007.
    4. Multilingual Multiscript Plant Name Database–Sorting Citrus Relatives  http://www.plantnames.unimelb.edu.au/Sorting/Citrus_3.html#Glycosmis. Accessed on 15 Dec 2007.
    5. Ito, C. et al. Chemical constituents of Glycosmis pentaphylla. Isolation of a novel napthoquinone and a new acridone alkaloid. Chem. Pharm. Bull. 1999; 47:1579-1581.
    6. Wang, J. et al. Hydroquinone diglycoside acyl esters from the stems of Glycosmis pentaphylla. Phytochemistry. 2006; 67:486-491.
    7. Wang, J. et al. Isoflavone Diglycosides from Glycosmis pentaphylla. J. Nat. Prod. 2006; 69:778-782.
    8. Daniels, M. Medicinal Plants: Chemistry and Properties. Science Publishers, Enfield, USA. 2005; pp 43.
    9. Muthukrishnan, J. et al. Inhibition of juvenile hormone biosynthesis in Gryllus bimaculatus by Glycosmis pentaphylla leaf compounds. Phytochemistry.1999; 50:249-254.
    10. Quader, M.A., Nutan, M.T.H. and Rashid, M.A. Antitumor alkaloid from Glycosmis pentaphylla, Fitoterapia.1999; 70:305-307.
    11. Mitra, S. & Sur, R.K. Hepatoprotection with Glycosmis pentaphylla (Retz). Indian J. Exp Biol. 1997; 35:1306-1309.
    12. Borah, R.C., Mohan, P., Choudhury, B.H. and Barua, I.C. Hepatoprotective activity of Phyllanthus fratermus L. and Glycosmis pentaphylla (Retz) correa used against jaundice in N.E. India in Borah, R.C. et al. (Editors). Bioprospecting of commercially important plants:Proceedings of the national symposium on “Biochemical approaches for utilization and exploitation of commercially important plants”, Jorhat, India. 2004; 12-14 Nov 2003.