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Brief Review on the Genus Diospyros: a Rich Source of Naphthoquinones

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Asian J. Adv. Basic Sci.: 2017, 5(2), 34-53 ISSN (Print): 2454 – 7492 ISSN (Online): 2347 – 4114 www.ajabs.org Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones Venu Sharma School of Biotechnology, University of Jammu, Jammu & Kashmir, INDIA * Correspondance: E-mail: [email protected] (Received 01 Sept, 2017; Accepted 14 Sept, 2017; Published 21 Sept, 2017) ABSTRACT: Diospyros genus (Ebenaceae) comprises about 500 species. A number of them are used for their multiple pharmacological activities. Ethano-phramacologically various plant parts are formulated and prescribed in the form of extracts and the decoctions for remedy of different diseases in many tribes. These activities are due to presence of bioactive secondary metabolites in the plant. Systematic and detailed investigation on the composition and pharmacological significance of medicinal plants should be conducted to standardize the formulations, based on ingredients. In the present review, naphthoquinone, naphthalene and naphthol derivatives isolated from Diospyros species are documented here with the pharmacologically important species of the genus. Keywords: Diospyros genus; species; Ebenaceae; pharmacological activities; naphthoquinones. INTRODUCTION: Diospyros genus belongs to the retic, laxative and stypic. Its dried flowers are reported to family Ebenaceae. The plants of Ebenaceae are wide be used in urinary, skin and blood diseases. A dilute ex- spread in tropics and sub tropics, occasionally into tem- tract is used as an astringent lotion for eyes5. Heartwood perate areas. According to Hegnaeur1 the family consists of D.mollis has been found to be active against hook- of seven genera, namely Diospyros, Euclea, Maba, worms but less active against tapeworms14. Oncothea, Rhaphidanthe, Royena and Tetraclis. However Stem of D.maritima Blume is used to treat rheumatic at present Maba, Rhaphidanthe, Royena and Tetraclis are diseases in Taiwan15. D.morrisiana bark has been shown included under Diospyros and Oncotheca is included as a to exhibit antibiotic activity16, known as "Shan Hung monotypic family2. Thus most of the botanists consider Shih" in herbal medicine of Taiwan. Bark of D.nigra is that it is composed of the three genera Diospyros, Euclea antirheumatic17 and is also used in swellings, the fruits and Lassiocarpa. The genus Diospyros Linn. is by far the are antidysentric and the leaves are laxative, styptic and largest with 500 species3 out of which 50 species are antileucorrhoeic18. Bark of D.peregrina Gurke is used in found in India4, mostly in the evergreen forests of Deccan, the treatment of dysentry and intermittent fevers19. Its Assam and Bengal. A few of them occur in N. India also5. ethanolic extract has been claimed to possess anti Medicinal impotence of the Diospyros Species: protozoal activity against Entamoeba histolitica, antiviral Chemical examination of Ebenaceae generally confined activity against Ranikhet disease virus and hypoglycemic to the genus Diospyros. A number of Diospyros species activity in albino rats8. Leaves of D.quaesita Thw are are reputed for their local herbal medicinal uses6,7. In the used for treatment of asthma20. In bark extract of treatment of asthma, abdominal pains, dysentry, leprosy, D.tomentosa hyposensitive activity was confirmed21. D. whopping cough, menstrual troubles and as antibiotics tricolor is reported to be efficaciuos in leprosy. several parts of the plant have been used since a long A purified extract of persimmon fruits has been shown to time. 50% Ethanol extract of D. montana and exhibit a strong detoxifying activity on various snake D.pereqrina were found to have weak antiprotozoal8, venom but not against bee venom22. The antibacterial, antiviral and hypoglycemic activity. The common antifungal and antiallergic properties of Diospyros have persimmones are the edible fruits of D.kaki and been attributed to the presence of naphthoquinones23. The D.discolar. Naphthoquinones and other related quinonoid most interesting is their biological activity against parasit- compounds are one of the major natural product classes ic protozoa namely Leishmania, Trypnosoma and Plas- with varied biological activities9-11. The medicinal proper- modium. Plumbagin and other related quinones have been ties of some of the Diospyros species are as follow; A active against Leishmania spp., while diospyrin was found decoction of D.candolleana bark is used in rheumatism to be active against Leishmania donovani24. and swellings12. Barks of D.exsculpta and D.malabarica are used as a remedy for dysentry5. The bark extract of The heartwood of this genus has considerable economic D.ferrea Bakh, Willd syn. Mababuxifolia is found to have importance as a source of timbers and also as edible antitumour activity13. Leaves of D.malanoxylon are diu- fruits25,26. The heartwood of D.ebenum (ebony tree) is 34 [(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones] extremely hard, durable and resistant to seasonal changes5. naphthol. Naphthols being sensitive to oxidation are easily D.quaesita is well known for the quality of timber known converted to black polymeric material. These compounds as calamander or king Ebony. Furniture made from its are supposed to be derived from the oxidative coupling of timber is so highly ranked that this tree was exploited to 3-methyl - naphthalene-1,8-diol or their biogenetic equiv- near extinction during the Dutch occupation of Sri alents arising by the hydroxylations at the 2,4,5 or 7- Lanka20. In a brief study carried on the resistance of vari- positions . ous timbers of Diospyros species, the allelochemicals, Dimerisation may also take place at 2,4,5 or 7-positions22. such as quinones, flavonoids, and terpenoids possess natu- Isodiospyrin, diospyrin and mamagakinone examplify the ral repellant and toxic properties27. three ways in which the two naphthoquionones units link The wood of D.celebica was found to be highly resistant together, namely arene to arene, arene to quinone and to the subterranean termites, Reticuliterms lusi-fungus and quinone to quinone respectively36. On the basis of struc- Reticuliterms flaviceps28. The napthoquinones tural features, it has been suggested that naphthol and isodiospyrin, microphyllone and plumbagin were identi- naphthoquinone derivatives of Diospyros species are fied as major termicidal components, while diospyrin, a formed from acetate -polymelonate units. Four pathways major naphthoquinone of D.montana was not toxic to have been described for the biosynthesis of termites at the concentration tested. 7-Methyljuglone naphthoquiones in higher plants37,38. showed to be toxic at 0.100 g in 24 h while the dimer less toxic to termites29. D.montana Roxb. (Commonly known as bistendu) is a shrub of moderate size, which is distributed throughout the greater part of India. Different parts of this plant have been reported to be used in the treatment of dysentry, hiccups, urinary stones and liver disorders30. Its leaves and seeds extract exhibited antibacterial activity31. Its various parts have been reported to be efficacious in fever, dysu- ria, gravel, neuralgia, pneumonia, puerperal fever and spider bite poison32. Its bark extract has been reported to be used as anti inflammatory, antipyretic and analgesic. Alcoholic extract of its bark inhibited Ehrlich ascites car- cinoma in mice32. Its tender twigs and leaves are used as fodder33. Its crushed leaves are used by Mundas of Chhota Nagpur to poison fish34. Meliola diospyri syd. an ascomycetes fungi, is reported on the leaves of this plant. Its fruits are bitter with an unpleasant odour. They are poisonous and applied externally to boils35. Its wood is moderately hard and is used for making small articles of furniture. It is classified as a good fuel wood. Phytochemical investigation on various parts (viz., bark, Figure 1: Some examples of Diospyros species. heartwood of stem and root, mesocarp) of over forty spe- cies of Diospyros have been revealed that these species Table-1 contains a list of naphthalene, naphthol and are rich in naphthoquinones (table-1), naphthols. Flavo- naphthoquinone derivatives isolated from various noid, triterpenoid and steroid derivatives are also occur in Diospyros species. The naphthoquinone isodiospyrin high yields. Triterpenes of the lupane series viz. lupeol, isolated from stem and roots of D. morrisiana showed betulin and betulinic acid in addition to widely distributed cytotoxic activity in HCT-8 and P-388 screens77. A major β- sitosterol have proved to be good taxonomic markers of quinone diospyrin isolated from bark of D. montana ex- this genus20. This genus is however, characterized by the hibited growth inhibitory activity towards Ehrlich ascites ability to produce naphthoquinones, usually in the form of carcinoma in mice13. dimers and triterpenes of the lupane series. The Diospyros species are rich source of naphthols , di- mers of 7-methyljuglone ( 5-hydroxy-7-methyl-1 , 4- naphthoquinone ) and plumbagin ( 5-hydroxy- 2-methyl- 1, 4-naphthoquinones ). Diospyrol isolated from fresh berries of D. mollis is the only example of dimeric 35 [(Asian J. Adv. Basic Sci.: 5(2), 2017, 34-53) Brief Review on the Genus Diospyros: A Rich Source of Naphthoquinones] Molecular S. formula & Ref. Compound Source Plant part No. Melting point 39 Juglone C10H6O3 D. lycioides * O Orange needles 164-65 1. O H O 40 Plumbagin(2-Methyljuglone) C11H8O3 D. elliptifolia Bark Orange needles 75 D. gracilipes Root bark & Stem bark41 42 O D. hebecarpa Leaves & Bark 43 Me D. hoyleana Roots & Bark 44 2. D. kaki Roots 45 22 OH O D. maritima Bark , Roots & Fresh D. mespiliformis fruits 46 D. samoensis Bark47 48 Leaves 46 Droserone C11H8O4 D. maritima Fresh fruits Yellow needles 181 O 3. M e OH OH O 43 7-Methyljuglone C11H8O3 D. abloflavescens Bark, Root & Leaves Orange-red needles 124-25 D. chloroxylon Stem44, Stem bark44 & Wood45 D. ebenaster Roots46 O D. greenwayi Root bark & Stem bark47 Me D. hallierii Root bark, Stem bark & D. lotus 48 Fruit 4. D. melanoxylon 49 OH O Roots D. montana Bark, Sapwood & Eb- D. nicaraguensis ony50 D. squarrosa Bark36 D. usambarensis Wood51 Root bark & Stem bark52 Root bark53 36 [(Asian J.
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