Diospyros kaki (Ebenaceae): A Review

Sunity Singh¹ and Himanshu Joshi²

¹Shoolini University of Biotechnology and Management, Solan, H.P.

²Nitte Gulabhi Shetty Memorial Institute of Pharmaceutical Sciences, Paneer, Mangalore India.

*Corresponding Author E-mail: visitdj@gmail.com

ABSTRACT:

The present review article is an effort to compile all the Phytochemical and Pharmacological investigations regarding the plant Diospyros kaki (Ebenaceae). The plant is traditionally used to treat various ailments like gonorrhoea, leucorrhoea, menorrhoea, diabetes, cough and also in the treatment of herpes. Several phytoconstituents has been isolated and identified from the different parts of the plant belonging to the category of glycosides, flavonoids, tannins, saponins, sterols and triterpenoids. A review of chemical constituents present and their pharmacological activities are given in the present article.

KEYWORDS: Diospyros kaki, Ebenaceae, Japenese persimmon.

INTRODUCTION:

Diospyros kaki is a deciduous tree measuring to 12 m in height and 7 m in diameter. It belongs to family Ebenaceae. Its common name is Japanese persimmon and the country of origin is Japan (Gilman and Watson, 1993). The plant prefers light (Sandy), medium (loamy) and heavy (clay) soil and well drained soil. It flowers from July to August and the seeds ripen in November. The flowers are dioecious. It can grow in semi shade (light woodland) or no shade. It requires moist soil (plants for a future database). D. kaki needs a subtropical to mild-temperate climate. It may not fruit in tropical lowlands. In Brazil, the tree is considered suitable for all zones favorable to citrus, but those zones with the coldest winters induce the highest yields. The atmosphere may range from semi-arid to one of high humidity. Propagation is by seed, root suckers or grafting onto wild rootstocks (Sastry, 1952).

Geographic distribution:

D. kaki is native to China, India, Japan and Myanmar. It is exotic to Afghanistan, Algeria, Australia, Brazil, Egypt, France, Indonesia, Israel, Italy, Korea, Republic of, Palestine, Philippines, Russian Federation, Union of Soviet Socialist Republic (Former), United States of America and Vietnam.

Uses of various parts of plants:

Food: Fully ripe fruits are usually eaten out-of-hand. The flesh may be added to salads, blended with ice cream mix or yoghurt, used in pastries, puddings or made into jam or marmalade. Ripe fruits can be frozen whole or pulped. Drying is commonly practised. Roasted seeds have served as a coffee substitute. Tea can also be made from fresh or dried leaves. D. kaki is high in vitamin and a moderate source of ascorbic acid.

Timber: Wood fairly hard and heavy, black with streaks of orange-yellow, salmon, brown or grey; close-grained; takes a smooth finish and is prized in Japan for fancy inlays, though it has an unpleasant odour. Tannin from unripe fruits has been employed in brewing sake, also in dyeing and as a wood preservative.

Other uses: Fruit may be converted into molasses, cider, beer and wine. Juice of small, inedible wild fruits, calyx and seeds is diluted with water and painted on paper or cloth as an insect and moisture-repellent medicine. It is a handsome ornamental tree with drooping leaves and branches that give it a languid, rather tropical appearance. Trees can be planted as a hedge or as a screen if pruned heavily.

Traditional uses:

The stem bark is astringent and styptic. The fruit is said to have different properties depending on its stage of ripeness, though it is generally antitussive, astringent, laxative, nutritive and stomachic. The fresh fully ripe fruit is used raw in the treatment of constipation and haemorrhoids and when cooked is used to treat diarrhea. The dried fruit is used in the treatment of bronchial complaints, whilst when ground into powder it is used to treat dry coughs. Juice from the unripe fruit is used in the treatment of hypertension. The fruits are considered to be antifebrile, antivininous and demulcent. The peduncle is used to treat coughs and hiccups and the calyx is used to treat hiccups.

BIOLOGICAL AND PHARMACOLOGICAL ACTIVITIES:

Homeopathic medicine ‘Creveld’ had been developed from D. kaki (Creveld, 2001). The remedy has been used for patients suffering severe physical, psychological and mental complaints due to post-traumatic stress. D. kaki has been much used during chemotherapy and radiotherapy in which it substantially reduced the side effects caused by primary therapy. In some cases, the tumours or metastases disappeared (during or after treatment) sooner than one would normally expect.

The tannins present in the fresh unripe fruits of D. kaki have very strong detoxifying activity on snake venoms of two snake species i.e. Laticauda semifasciata and Trimeresums flavoviridis (Houghton, 1993; Okonogi et al., 1979).

Fruits are known to inactivate bacterial toxins of Clostridium tetani, Diptheria, Straphylococcus alpha and Bordetella pertussis (Mallavadhani, 1998).

The leaves of Persimmon possess antithrombotic activity. It has long been used for tea in Korea since it was thought to be effective against hypertension. (Sa et al., 2005) reported a 10,000 D anticoagulant fraction has been purified from the leaves of D. kaki that inhibited thrombin-catalyzed fibrin formation with a competitive inhibition pattern.

D. kaki exhibited strong radical scavenging activity which can be attributed to the presence of catechin, epicatechin, epigallocatechin, chlorogenic acid, caffeic acid and gallic acid (Chen et al., 2007).

D. kaki peels extract possess significant cytotoxic activity against human oral squamous cell carcinoma cells (HSC-2) and human submandibular gland tumor (HSG) cells, multidrug resistance (MDR) reversal activity, anti-human immunodeficiency virus (HIV) activity and anti Helicobacter pylori activity (Kawase et al., 2002) .

The chemical constituents namely astragalin and isoquercitrin were found present in the leaves of D. kaki are responsible for its hypotensive effect, as tested on urethane anasthetized rats (Funayama, 1979) .

Persimmon peel containing high levels of dietary fibres and antioxidants with antidiabetic properties represents a potential dietary supplement for improving hyperglycemia and diabetic complications (Lee, 2006; Li et al. 2007; Hu et al., 2006) .

Polyphenols isolated from the persimmon leaf can be used as natural materials or additives for human skin owing to their beneficial biological functions, including the anti wrinkle effect and the inhibition of skin problems, for food or cosmetic compositions (An et al., 2005) .

A pharmaceutical composition for preventing and treating liver disease having liver-protecting activity, anti-oxidizing activity, anti-cancer activity, and anti-allergy contained triterpenoid compound isolated from D. kaki folium (Kyung, 2005) .

D. kaki extract and related polyphenol compounds such as catechin (C), epicatechin (EC), epicatechingallate (ECG), epigallocatechin (EGC), and epigallocatechingallate (EGCG) strongly inhibited the growth of human lymphoid leukemia Molt 4B cells in a dose-dependent manner, while C and EC inhibited the growth of the cells only moderately (Achiwa et al.,1997). Ornithine decarboxylase (ODC), a rate-limiting enzyme of polyamine biosynthesis, was inhibited by 10-20 % by these polyphenol compounds. The morphology of the Molt 4B cells indicated severe damage 3 days after treatment with PS, ECG, EGC, and EGCG. Irregular shape of the cells and DNA fragmentation were observed in PS, ECG, EGC, or EGCG-treated cells. These results suggest that PS, ECG, EGC, and EGCG induce apoptosis (programmed cell death) of Molt 4B cells.

The life span of stroke prone spontaneously hypersensitive rats was significantly prolonged on ingestion of tannins of D. kaki . Persimmon tannin was 20 times more effective than tocopherol in terms of the 50 % inhibitory concentrations (Weijian, 2005). NaoXingQing (NXQ), a novel and patented traditional Chinese medicine (TCM) drug made from the flavonoids of the leaves of D. kaki has been used for the treatment of stroke or syndrome of apoplexy in clinic to improve the outcome of ischemia stroke for years in China. Plumbagin and its derivates isolated from D. kaki roots, possess acaricidal activity (Lee and Lee, 2008) .

ANTIMICROBIAL PROPERTIES:

Fractionated extracts of persimmon peels showed a remarkable MDR reversal activity. The active compounds in persimmon leaves i.e presence of volatile oil, total flavonoid, coumarins, and organic acid are responsible for antimicrobial activities against seven food spoilage and food-borne pathogens (Lilian, 2003) . D. Kaki tannins with purity of 30 %, and oligosaccharides (non-fermentable tetra- or less- saccharides) are claimed as human intraoral pathogenic bactericidal agents (Kato et al., 2006). The isolation and identification of an antimicrobial compound kaempferol (kaempferol is an aglycon of astragalin (kaempferol 3-O-β-D-glucopyranoside) against Streptococcus mutans from the leaves of D. kaki has also been reported by (Yasumasa et al., 1999) .

PHYTOCHEMISTRY:

Leaves : Leaves are reported to contain following compounds, 40-dihydroxy-a-truxillic acid tatarine C, myricetin, annulatin, trifolin, astragalin, hyperin, isoquercetin, rutin, quercetin, kampferol and kakispyrone and kaki saponin (Chen et al., 2007) .

Fruits: Commercially, there are generally two types of persimmon fruit: astringent and non-astringent. The heart-shaped hachiya is the most common variety of astringent persimmon. Astringent persimmons contain very high levels of soluble tannins and are unpalatable if eaten before softening. The non-astringent persimmon is squat like a tomato and is most commonly sold as fuyu. Non-astringent persimmons are not actually free of tannins as the term suggests, but rather are far less astringent before ripening, and lose more of their tannic quality sooner. Non-astringent persimmons may be consumed when still very firm to very soft (Wikipedia). Persimmon contains the following (g/100 g of fresh fruit)- water,80.3 g; protein, 0.58 g; total lipids, 0.19 g; total carbohydrates, 18.6 g; total dietary fiber, 1.48 g; and some minerals i.e., magnesium, iron, zinc, copper and manganese. A high concentration of antioxidants such as ascorbic acid (up to 7.5 mg), carotenoids (particularly cryptoxanthin, zeaxanthin and carotene), polyphenols and a specific group of polyphenols (tannins), catechin and gallocatechin, as well as the anti-tumor compounds betulinic acid and shibuol were found in persimmon. The dry residue of persimmon includes the following (g/100 g): polyphenols, 0.16-0.25; carotenoids, 0.002; and soluble and nonsoluble proteins, 0.64-1.3. Lipid soluble compounds in the rind and flesh of persimmon fruit includes mono-galactosyldiglycerides carotenoids, diacylglycerols,ceramideoligosides, digalactosyldiglycerides, phosphatidylglycerols, phosphatidylcholines and free and glycosylated sterols. In the fatty acid composition of the lipids unsaturated fatty acids linolenic, oleic, linoleic and palmitoleic predominated (>70 %). Some components of persimmon show special activities (Uchida et al., 1989). Persimmon tannins prolonged life and reduced the incidence of stroke in hypertensive rats. This effect was attributed to the fact that persimmon tannins are 20 times more potent than antioxidant vitamin E.  However, the effect of a persimmon-supplemented diet on lipid metabolism has not been examined (Gorinstein et al., 1998).

Roots: Dicoumarol derivatives gerberinol (C₂₁H₁₆0₆) and methylgerberinol (C₂₂H₁₈0₆) have been isolated from the roots of D. kaki Thunb. and D. kaki Thunb var. sylvestris Makino. Other napthaquinone derivates isolated from the roots of D. kaki were 7-methyljuglone, isodiospyrin, mamegakinone, plumbagin, diospyrin and a new 7-methyljuglone dimer named neodiospyrin. Also from the roots and woods of D. kaki var. sylvestris shinanolone, the binapthyl-1,1- quinone, lupeol, betulin and betulinic acid were identified (Tezuka et al., 1972).

Stems: Three compounds were isolated from the stem of D. kaki sylvestris and were identified as 7-methyljuglone, isodiospyrin, and taraxerol (Zhong and Feng, 1987) .

Seeds: The seeds of persimmon (3 varieties) contained 0.43-0.67 % lipids and complex lipids constituted 11.4 -18.3 % of this fraction. The complex lipids consisted of 18.5-22.3 % cerebrosides, 14.1-17.9% acylsterylglycosides, 8.3-10.3% phosphatidylinositols, 7.4-7.5% sterylglycosides, 5.2-7.2% monogalactosyldiglycerides, 3.7-5.3% sulfoquinovosyldiglycerides, 3.8-4.7% phosphatidyl-N,N-dimethylethanolamines, 2.5-4.2% phosphatidyl-N-methylethanolamines, and 27.4-30.7% unidentified constituents. The main fatty acids of these complex lipids were C18:1 (23.2-37.7), C18 (20.3-52.3) and C18:2 (9.9-33.8 %) (Suzuki et al., 1982).

Calyx: Twenty-three compounds were isolated from the calyx of D. kaki. Stearic acid, palmitic acid, succinic acid, syringic acid, vanillic acid, gallic acid, kaempferol, quercetin, trifolin, hyperin, β-sitosterol, β-sitosteryl-β-D-glucoside, friedelin, oleanolic acid, ursolic acid, and 19 β -hydroxyursolic acid (Zhong and Feng, 1987) .

CONCLUSION:

Extensive literature survey revealed that the plant D. kaki has a long history of traditional uses for the wide range of diseases. Various parts of the plant are widely used in folk medicine. In recent years, emphasis of research has been on utilizing traditional medicines that have long and proven history of treating various diseases. So, further studies need to be carried out to explore D. Kaki potantial in curing and treating various diseases.

REFRENCES:

1. Gilman E.G. and Watson D.G. Diospyros kaki Japenese Persimmon. Fact Sheet ST-229, a series of the environmental horticulture department, Florida cooperative extension service, Institute of food and agricultural sciences, University of Florida. 1993.

2. Sastry B.N. The wealth of India, Raw materials, vol III. CSIR, New Delhi, 1952. p136.

3. Creveld M. Diospyros kaki, de Wereldboom;droomproving. Dynamis : 25; 2001: (in English in LINKS 3/02).

4. Houghton P.J. In vitro testing of some West African and Indian plants used to treat snakebites. Médicament Et Nutrition : L’Approche Ethnopharmacologique. 1 ; 1993: 263-274.

5. Okonogi T. Hattori Z. Ogiso A. and Mitsui S. Detoxification by persimmon tannin of snake venoms and bacterial toxins. Toxicon. 75(5); 1979: 524-7.

6. Mallavadhani U.V. Panda A.K. Rao Y.R. Pharmacology and chemotaxonomy of Diospyros. Phytochemistry. 49(4); 1998: 901-905.

7. Sa Y.S., Kim S.J. Choi H.S. The anticoagulant fraction from the leaves of Diospyros kaki L. has an antithrombotic activity. Arch. Pharm. Res. 28(6); 2005: 667-74.

8. Chen G.X.J. Xu S.X. Zhang R.Q. Chemical constituents of the leaves of Diospyros kaki and their cytotoxic effects. J. Asian. Nat. Prod. Res. 9(4): 2007: 347–353.

9. Kawase M. Motohashi N. Satoh K. Sakagami H. Nakashima H. Tani S. Shirataki Y. Kurihara T. Spengler G. Wolfard K. Molnár J. Biological activity of persimmon (Diospyros kaki) peel extracts. Phytother. Res. 17(5): 2003; 495-500.

10. Funayama S. Hikino H. Hypotensive principles of Diospyros kaki leaves. Chem. Pharm. Bull. 27(11): 1979; 2865-2867.

11. Lee H.C. and Lee H.S. Acaricidal activity and fuction of mite indicator using Plumbagin and its derivates isolated from Diospyros Kaki Thunb.roots (ebenaceae). J. Microbiol. Biotechnol. 18 (2): 2008; 189- 193.

12. Li C. Bei W. Li Y. Lou J. Ethylacetate extract of Diospyros kaki leaf for preventing and treating hyperglycemic, diabetes and metabolic syndromes. Faming zhuanli. Shenqing. Gongkai. shuomingshu. 32: 2007; 21 -23.

13. An B.J. Kwak J.H. Park J.M. Lee J.Y. Park T.S. Lee J.T. Son J.H. Jo C. Byun M.W. Inhibition of enzyme activities and the antiwrinkle effect of polyphenol isolated from the persimmon leaf (Diospyros kaki folium) on human skin. Dermatol. Surg. 31: 2005; 848-54 .

14. Kyung K.O Kyoon Young. Pharmaceutical composition for protecting liver containing triterpenoid compound separated from Diospyros kaki folium. No pp. given. CODEN: KRXXA7 KR 2005043130 A 20050511 Patent Kongbo. 2005.

15. Achiwa Y. Hibasami H. Katasuzaki H. Imai K. Komia T. Inhibitory effects of persimmon (Diospyros kaki) extract and related polyphenol compounds on growth of human lymphoid leukemia cells. Biosc. Biotechnol. Biochem. 61(7): 1997; 1099-101.

16. Uchida S. Ohta H. Niwa M. Mori A. Nonaka G. Ozaki M. Prolongation of life span of stroke prone spontaneously hypersensitive rats (SHRSP) ingesting persimmon tannin. Chem. Pharm. Bull. 38(4): 1990; 1049-1052.

17. Lee H.C. Lee H.S. Acaricidal activity and fuction of mite indicator using Plumbagin and its derivates isolated from Diospyros Kaki Thunb.roots (ebenaceae). J. Microbiol. Biotechnol. 18 (2): 2008; 189- 193.

18. Lilian J. Qianghua Z. Guiyou C. Study on antimicrobial activities of leaves and isolation and elucidation of the active compounds. Shipin. Kexue. 24(3): 2003; 129-131.

19. Kato H. Sakagami R. Harada M. Sakurai J.U.T. Yamanaka S. Kaki tannins and oligosaacharides as intraoral pathogenic bacterial agents. Jpn.Kokai. Tokkyo Koho. 2006. 7pp.coden jkxxxaf jp 2006298827 a 20061102. patent written in Japanese.Application JP 2005-123412 20050421.Priority: can 145 : 432248 AN2006: 1147642 caplus.

20. Yasumasa Y. Aya Y. Yoneda A. Noriko Y. Nobuji N. Identification of kaempferol from the leaves of Diospyros kaki and its antimicrobial activity against streptococcus mutans. Biocontrol. Sci. 4(2): 1999; 97-100.

21. Gorinstein S. Bartnikowska E. Kulasek G. Marina Z.M. Soo S.K. Samkeun L. Byeongjin C. Antifungal activity of Plumbagin purified from the leaves of Nepenthes Ventricosa X maxima against phytopathogenic fungi. Plant. Pathol. J. 23(2): 2007; 113-115.

22. Tezuka M. Kuroyanagi M. Yoshihira K. Natori S. Napthaquinone derivatives from Diospyros kaki THUNB and D. kaki THUNB. var. sylvestris MAKINO. Chem. Pharm. Bull. 20(9): 1972; 2029-2035.

23. Zhong S. Feng S. Napthoquinones and a triterpene from stem of Diospyros kaki var sylvestris. Zhongguo. Yaoke. xuebao. 18(4): 1987; 279-80.

24. Suzuk I.K. Itoh S. Tsuyuki H. Lipids in persimmon.II. Complex lipids of the seeds of persimmon. Nippon. Shokuhin. Kongo. Gakkaishi. 29(5): 1982; 310-15.

Received on 11.08.2011 Accepted on 18.08.2011

© Asian Pharma Press All Right Reserved

Asian J. Res. Pharm. Sci. 1(3): July-Sept. 2011; Page 55-58