Glycosmis pentaphylla (PROSEA)

Plant Resources of South-East Asia Introduction

List of species

Glycosmis pentaphylla (Retz.) A.DC.

Protologue: Prodr. 1: 538 (1824).

Family: Rutaceae

Chromosome number: 2n= 18

Synonyms

• Limonia pentaphylla Retz. (1788),
• Glycosmis arborea (Roxb.) A.DC. (1824),
• Glycosmis cochinchinensis auct.

Vernacular names

• Indonesia: gongseng (Sundanese), jerukan, totoan (Javanese)
• Malaysia: merapi, nerapi, terapi
• Philippines: gingging (Tagalog), linauin (Iloko)
• Cambodia: dom phlang
• Laos: som sum, om chune
• Vietnam: cơm rượu, bưởi bung.

Origin and geographic distribution

G. pentaphylla is found from India and Sri Lanka eastward to Burma (Myanmar), Thailand, southern China and Indo-China, possibly the Philippines, Peninsular Malaysia, Sumatra and Java and also cultivated elsewhere.

Uses

In Java (Indonesia), a decoction of the roots of G. pentaphylla is taken to treat bilious attacks. A decoction of roots and leaves is taken for intestinal trouble. In Vietnamese folk medicine the leaves are considered appetitive, stomachic and an infusion of roasted leaves is prescribed for women after delivery as an appetizer. In Peninsular Malaysia, Glycosmis (e.g. G. parviflora (Sims) Little, G. puberula Lindley ex Oliv., G. pentaphylla) is an ingredient of various medicinal mixtures. An infusion of leaves and roots is given after childbirth as a protective medicine. In traditional Indian medicine G. pentaphylla is used to treat diarrhoea, coughs, rheumatism, anaemia, and jaundice. Juice of the leaves is used in fever, liver complaints and as a vermifuge. A paste of the leaves mixed with ginger is applied for eczema and skin affections. A decoction of the roots is given for facial inflammation. The pale wood is sometimes used for tool handles.

Production and international trade

G. pentaphylla is only used on a local scale.

Properties

Chemical investigations in Glycosmis have generally focused on 3 species, i.e. G. pentaphylla, G. parviflora and G. mauritiana (Lamk) Tanaka. The extracts from the leaves, stems, and roots were mainly characterized by different classes of alkaloids. Quinoline-, acridone-, carbazole-, and quinazoline-type were the most widespread structural groups. Recently a naphthaquinone alkaloid has been added to this list. Amides also represent an important and characteristic chemical character of Glycosmis. Some of the amides in Glycosmis are derived from anthranilic-, isovaleric-, and senecioic-acid. The most characteristic group of amides, however, are the sulphur-containing derivatives of (E)- or (Z)-3-(methylthio)-propenoic acid: about 45 have so far been isolated and identified. They are mainly accumulated in the leaves, and to a lesser extent in stem and root bark.

In general, the majority of Glycosmis species contain varying amounts of different sulphur-containing amides, with the exception of G. pentaphylla. However, G. pentaphylla is particularly characterized by the accumulation of quinazolines in the leaves.

Biological activity of the sulphur-containing amides was investigated using spore suspensions of the test fungus Cladosporium herbarum, as well as germ tube inhibition test using different phytopathologic fungi including Alternaria, Botrytis, Fusarium and Pyricularia. The bioassays were also extended to assess toxicity towards insects: the activity of the compounds against the polyphagous pest insect Spodoptera littoralis was tested for contact toxicity, growth inhibition, and survival rate against neonate larvae.

Results revealed that all amides derived from methylthio-propenoic acid linked with styryl (phenylethenyl) amine moieties (methylillukumbin A, illukumbin B, methylillukumbin B) showed higher antifungal activity than those linked with phenethyl amine (sinharin, methylsinharin). By contrast, amines without a linkage to an aromatic system (penangin, isopenangin) showed no activity against the tested fungi at all. The same was true for the series of amides derived from methylsulphonyl-propenoic acid, which differ from their related methylthio-propenoic acid derived compounds through a different oxidation state of the sulphur atoms. Furthermore, it is interesting to note that, with respect to insect toxicity, also the styryl or phenethyl amine part was found to be essential.

Also the methylthio-carbonic acid derived amides, which may be regarded as products of chain shortening of methylthio-propenoic acid derived compounds, are highly bioactive. The antifungal activity of dehydroniranin B was comparable to the activity of methylillikumbin A, with an ED₅₀ value of 5.5 μg/ml in the germ tube inhibition test towards C. herbarum. In all insect toxicity tests the most active compounds were the methylthiocarbonic acid derivatives niranin, dehydroniranin B and ritigalin. As an example the values for niranin were LC₅₀ = 0.03 μmol/dm² in the contact toxicity test, and EC₅₀ = 0.25 μmol/g for the growth inhibition, and LC₅₀ = 0.81 μmol/g for the lethality of the larvae in the feeding tests. By contrast, the corresponding methylpropenoic acid amides e.g. methylillikumbin A, only showed moderate activity against S. littoralis. In general, from the results available, it became clear that derivatives elongated with prenyl chains or carrying oxidized sulphur (sulphones) have considerably less insect and fungitoxic activities.

Several alkaloids and amides, isolated from G. pentaphylla, are reported to have biological activities. For instance glycozolidol, a carbazole alkaloid isolated from the roots of G. pentaphylla, is active against some gram-positive and gram-negative bacteria. Furthermore, arborinine, an acridone alkaloid, exhibited significant inhibition of crown gall tumours produced by Agrobacterium tumefaciens in a potato disk bioassay.

Additionally, leaf extracts of G. pentaphylla exhibited a high degree of nematicidal action against the adults and larvae of the nematode Radopholus similis. The leaf extracts inhibit the juvenile hormone III-biosynthesis in vitro of corpora allata from 3-day-old females of the field cricket Gryllus bimaculatus. The bio-active compound responsible for this activity was identified as the quinazolone alkaloid arborine. This alkaloid also showed larvicidal activity against the mosquito Culex quinquefasciatus.

Roots of G. pentaphylla were furthermore shown to inhibit the growth and survival of larvae of the citrus root weevil Diaprepes abbreviatus, when incorporated in their diet. This assay was used to guide fractionation of an active acetone extract, which led to the identification of dehydrothalebanin B (an amide) as the active compound.

Biological activities of extracts included effects of leaf- (250, 500 and 750 mg/kg body weight) and stem bark- (100, 200 and 400 mg/kg body weight) extracts of G. pentaphylla, which were studied on CCl₄ (1 mg/kg body weight) induced hepatic injury in albino rats. Parameters studied were plasma ALAT, ASAT, ALP, total bilirubin and tissue histopathology. Recovery of hepatic tissue was indicated using the highest dose (750 mg/kg body weight) of the leaf extract. The therapeutic dose range was devoid of toxic effects; toxicity was only observed histopathologically at and above 2.5 g/kg body weight of this extract.

Petroleum ether, chloroform, ethanol and aqueous extracts of root bark of G. pentaphylla were evaluated for their effect on experimentally-induced diarrhoea in albino rats. In general, all extracts exhibited significant activity. The ethanol extract, however, was found to be very effective at low dosages (100 and 200 mg/kg). Acute toxicity tests on rats and mice revealed no toxicity at doses up to 5000 mg/kg, except for the petroleum ether extract where symptoms such as CNS excitement followed by depression, and 25% mortality in mice were observed at a dose of 1000 mg/kg.

The petroleum ether extract of the root of G. pentaphylla was lethal to the larvae of Culex quinquefasciatus, C. sitiens, Aedes aegypti and Anopheles stephensi with LC₉₀ values of 54.20, 42.66, 57.14 and 43.85 mg/l, respectively. The column chromatographic fraction isolated from the crude extract showed promising biological activity with LC₉₀ values of 20.42, 16.98, 21.87 and 19.95 mg/l against C. quinquefasciatus, C. sitiens, Aedes aegypti and Anopheles stephensi, respectively.

Finally, a steam distillate of G. pentaphylla leaves showed high antifungal activity against Cladosporium cladosporioides, but no activity against Staphylococcus aureus or Escherichia coli. The essential oils from the bark, leaves and seeds of this species were also analysed using high-resolution gas chromatography. Substantial differences in the composition of the oils from the three plant parts were noticed. The bark and leaf oils were rich in aliphatic ketones (about 80% and 47%, respectively) while the seed oil contained a high percentage of aliphatic (26%) and monocyclic (24%) terpene alcohols.

Adulterations and substitutes

Amides are also found in Clausena, another member of the tribe Clauseneae.

Description

• An evergreen shrub or small tree, 1-5 m tall; branches glabrous, unarmed, young parts finely rusty puberulent.
• Leaves alternate, imparipinnate with (1-)3-5(-7) leaflets; petiole 2.5-5.5 cm long; stipules absent; leaflets narrowly elliptical or oblong-elliptical, 6-24 cm × 2-7 cm, base acuminate, apex acuminate, margin entire or minutely to distinctly crenulate-serrate, lateral veins 6–12 pairs; petiolules 3-8 mm long.
• Inflorescence axillary, paniculate, elongated up to 8 cm long, narrow, tri-pinnate, branches short, ascending, axes and bracteoles rusty puberulent.
• Flowers mostly 5-merous, about 5 mm long, fragrant; sepals broadly ovate to rotund, 1-1.5 mm long, margin ciliolate; petals obovate to elliptical, 5 mm × 2.5 mm, glabrous, white; stamens up to 3.5 mm long; ovary ovoid, up to 2.5 mm long, coarsely pustular-glandular, usually 5-celled, style scarcely distinct.
• Fruit a berry, subglobose, white to pink or crimson, 10-13.5 mm in diameter, 1(-3)-seeded, edible.
• Seed round to plano-convex, suboblong, green.

Growth and development

The fragrant flowers attract bees that most probably effect pollination. G. pentaphylla can be found flowering and fruiting throughout the year.

Other botanical information

Glycosmis is a difficult and taxonomically confusing genus, that is badly in need of a critical taxonomic and nomenclatural review. However, the genus as such can be easily distinguished from the closely related other members of the subtribe Clauseninae: Clausena and Murraya. Glycosmis comprises some 40-50 species and occurs from India and Sri Lanka eastward to southern China and Taiwan, throughout South-East Asia to northern Australia; in Malesia some 25 species occur. The name G. pentaphylla has often been incorrectly applied to other species and forms, including G. parviflora, further adding to the confusion. The species has often been confused in India and western South-East Asia with another highly variable species: G. mauritiana (Lamk) Tanaka. As medicinal uses in South-East Asia almost exclusively refer to G. pentaphylla, the information has been grouped under this name here. G. parviflora (synonym G. citrifolia (Willd.) Lindley), native to southern China and Indo-China, is cultivated as an ornamental and naturalized in various parts of the tropics. In Taiwan, it is used in folk medicine for the treatment of skin itch, scabies, boils and ulcers.

Ecology

G. pentaphylla prefers relatively dry habitats from sea-level up to 1000 m altitude, and is commonly encountered in secondary thickets.

Propagation and planting

G. pentaphylla can be propagated by seed or semi-ripe cuttings.

Husbandry

G. pentaphylla should preferably be grown in a fertile, moisture-retentive, but well-drained medium that is rich in organic matter, with full sun to partial shade.

Harvesting

Leaves and roots of G. pentaphylla are collected whenever the need arises.

Handling after harvest

Roots of G. pentaphylla can be chopped in smaller pieces to be dried and stored for future use.

Genetic resources and breeding

G. pentaphylla has a large area of distribution, either naturally or as a result of cultivation, and does not seem to be at risk of genetic erosion.

Prospects

Alkaloids, amides and especially the sulphur-containing amides of G. pentaphylla show a range of interesting biological activities, mainly in the field of phytopathology and insect control. They might be of great interest for future development of new crop protection agents, and as such merit further research. As a spin-off of this research, an evaluation should take place to find out if extracts might have potential as a local source of protectants in rural communities.

Literature

• Hofer, O. & Greger, H., 2000. Sulfur-containing amides from Glycosmis species (Rutaceae). In: Herz, W., Falk, H., Kirby, G.W. & Moore, R.E. (Editors): Fortschritte der Chemie organischer Naturstoffe. Vol. 80. Springer Verlag, Vienna, Austria & New York, United States. pp. 187-223.
• Jayarama, M., Seifert, K., Hoffmann, K.H. & Lorenz, M.W., 1999. Inhibition of juvenile hormone biosynthesis in Gryllus bimaculatus by Glycosmis pentaphylla leaf compounds. Phytochemistry 50(2): 249-254.
• Latha, C. & Ammini, J., 1999. Evaluation of the larvicidal potential of Glycosmis pentaphylla against four important mosquito species of Kerala, India. International Pest Control 41(2): 50-51.
• Pillai, N.R., 1992. Anti-diarrhoeal activity of Glycosmis cochinchinensis root barks in experimental animals. Fitoterapia 63(4): 323-326.
• Shapiro, J.P., Bowman, K.D. & Lapointe, S.L., 2000. Dehydrothalebanin: a source of resistance from Glycosmis pentaphylla against the citrus root weevil Diaprepes abbreviatus. Journal of Agricultural and Food Chemistry 48(9): 4404-4409.
• Stone, B.C., 1994. Additional notes on the genus Glycosmis Correa (Rutaceae). The Gardens’ Bulletin Singapore 46(1): 113-119.

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Authors

• L.S.L. Chua & J.L.C.H. van Valkenburg