2011 International Conference on Agricultural and Biosystems Engineering

Advances in Biomedical Engineering Vols. 1-2

Persimmon tannin composition and function*
Tianying Zhang, Gang Li and Haizhen Mo

Chunxiang Zhi

Department of Food Science
Henan Institute of Science and Technology
Xinxiang City,Henan Province, China
Corrosponding author: Haizhen Mo, email: mohz@163.com,

Institute of Animal Health Inspection
Veterinary Bureau of Shangshui County
Zhoukou City, Henan Province, China

Abstract – In accordance to the chemical structure of
tannins, persimmon tannin were divided into hydrolysable tannin
and condensed tannin. Persimmon contains large amount of
condensed tannins. Persimmon tannins comprising a large
variety of structures, give persimmon many health function and
is the key factors that affect product quality in persimmon
processing. This article mainly introduced the research situation
of persimmon tannin, health function and prospect that the
research of persimmon tannin could go on, could promote the
development of the persimmon industry.

Persimmon accumulates condensed tannin in fruit and
leaf, which is responsible for astringency trait. As early as the
first time in 1920, it’s the first time that tannins were divided
into thehydrolysable tannins and condensed tannins by
Freudenberg et al.[9].In 1954, leucoanthocyanidins were
confirmed to be identical with condensed tannins by BateSmith. Tannin and anthocyanin linked together for the first
time is the great guiding significance for studying the
molecular structure of tannins.
Tannins have been defined by Bate-Smith as water
soluble phenolic compounds having molecular weights
between 500 and 3000, and they have ability to precipitate
alkaloids, gelatin and other proteins[10, 11]. In 1923,
persimmon tannins were carried out a preliminary study by
Japanese scholar Komatsu Matsunami, and were speculated
that the basic formula of tannin is C19H20O9. The tannins
molecule may contain the root bark phenolics and gallic acid
monomers[12]. In 1962, Ito and Oshima extracted of soluble
persimmon tannins which is the cause of astringency, had two
substances delphinidin and glucose with a strong acid
treatment, the main component is leucodelphindin, in its C-3
position on the base with a glucose[13]. Later, Ito and Joslyn
studies suggest that persimmon tannin is not only
leucodelphindin, may also contain other more complex
components. Persimmon tannins was generated not only a
large number of leucodelphindin, but also gallic
acid,gallocatechin and catechin galate with acid thermal
degradation. They believed that persimmon tannins was a
class of polymers linked several low molecular weight
compounds through the C-C bond. The theory Was first
proposed that persimmon tannin was condensed tannins main
with delphinidin[14]. In 1977, Matsuo and Ito summarized
previous studies and further evidenced the doctrine that
persimmon tannin is Proanthocyanidins.
Persimmon tannin was deposited with the K2HPO4 and
degradated with benzyl mercaptan. The degradation products
separated by silica gel TLC , Identified by H-NMR and the
results suggested that the proposed condensed tannins
structure consists of four monomer compounds,
catechin,gallocatechin,catechin-3-O-gallate and gallocatechin
-3-O-gallate, with a molar ratio of 1 : 2 : 1 : 2.These units are

Index Terms – persimmon, tannin; composition; health

As improving of living standards, people will not only
focus on health function of food, but also on the sensory
properties of food. Proanthocyanidins (condensed tannins)
have attract many attention for their beneficial effects in
nutrition and on health[1]. Persimmon Proanthocyanidins
(condensed tannins) have been associated with antioxidant
activity, anti-inflammatory activity, and atherosclerosis
prevention, and so on [2].
Persimmon fruit contains abundant condensed tannins
[3], so it was astringent. Astringency increases with the mean
degree of polymerization; Furthmore, small differences in
flavonoid configurations can produce significant differences
in sensory properties. Epicatechin is more astringent than its
chiral isomer catechin. Similarly, the bond location and the
identity of the monomeric units influenced the astringency of
synthesized dimers and trimers [4, 5]. Condensed tannin is a
phenolic oligomer resulting from the polymerization of
flavan-3-ol units, which consists of two types of subunits,
extension and terminal units[6, 7]. As a final product of the
flavonoid pathway, Condensed tannin is an important flavour
compound and key factor that affect product quality in
persimmon process. The biological activities of persimmon
tannin are probably its complex chemical structure and
contents, such as the monomeric flavan-3-ol units, the types of
interflavan bonds and the degree of polymerization
(DP)[8].The composition , molecular structure and health
function of persimmon tannin were summarized in the article.
This provides the oretical basis for further research of
persimmon tannin and certain significance for the deep
processing of persimmon wine, persimmon vinegar, and
persimmon leaf tea.

This work is supported by Henan Science and Technology Office to HZ. Mo.

978-0-9831693-9-0/10/$25.00 ©2011 IERI


gallate .The degradation products are epicatechin.Purification of persimmon tannin with AB-8 macroporous resin. The study by Yonemori et al.3 Molecular Structure of catechin 390 .phloroglucinol adduct is the most important component of persimmon. The main component is procyanidins oligomer consist of one terminal units of Fig. In recent years. epicatechin . The unknown component recognized as a form epigallocatechin-3-0 . was analyzed by HPLC-MS after extracted with 70% aqueous acetone and thiolysis by Kawakami [21].2 Molecular Structure of diospyrin Fig. 15] (Fig.phloroglucinol adducts was separated by TLC method and then charactered charactered by mass spectrometry. epicatechin .Condensed tannin. Akagi et al.alcohol such as catechin. the main component of persimmon tannin was named diospyrin.1 Chemical structures of persimmon tannin and related catechin In Ito and Oshima’s study. which is consistent with a previous report by Matsuo and Ito [14] .phloroglucinol adduct and an unknown substance by acid catalytic degradation . namely gallic acid. but the individual terminal units.few hydrolyzed monomers for the terminal CT units were also found.MS. which is leucopetunidim -3-glucosides. At present. Small molecular weight components dominated in non-astringent and high molecular weight components dominated in astringent. Diospyrin (Fig. Epigallocatechin-3-0-gallate .NMR and other cutting-edge technology. This indicates a high degree of CT polymerization in persimmon fruit. Fei XQ et al.HPLC method in the case of excess pyrogallol. Gu HF et al. with the separation of technology development. epigallocatechin and catechin. epigallocatechin . epicatechin .3 O-gallate and an unknown Monomer.[16] is that catechin was the main phenolic compounds in persimmon. epigallocatechin.O-gallate.phloroglucinol adducts.1).2) in comparison with the catechins(Fig. epicatechin-3-O-gallate were isolated from the persimmon fruit and leaves. epigallocatechin .3 . the products of three known to exist in the ratio of 1:73:1.3) was found by Chen XN et al. [17] thought that the main ingredients of persimmon tannin have three kinds. epicatechin.linked by the C-4 C-6 or C-8 to form a polymer [14.[20]analyze the condensed tannin fractions. epigallocatechin-3-Ogallate. nuclear magnetic resonance.[19] divided it into small molecular weight tannins tannins and high molecular weight tannins with 10000Da of polysulfone ultrafiltration membrane and used thiolysis-HPLC to evaluate high molecular weight tannin. [18] that they are almost the same basic unit.In phloroglucinol analyses of condensed tannins in persimmon fruit.phloroglucinol adducts.3 – 0 – gallate . more and more condensed tannins were isolated and identified. Fig. the use of HPLC. five different flavan -3.

Binding of an important cause of persimmon Tannin and protein led to enzyme inactivation. As a consequence tannins. Quenching mechanism is static quenching. causing the analytic determination more difficulty[22].4β. Agkistrodon acutus. phospholipase A2. L-amino acid oxidase activity from Agkistrodon halys Pallas. connecting way.4 . epicatechin epigallo-catechin gallate. Hara and Kudo et al.4β. It’s a broad problem exist in persimmon fruit products. epigallocatechin . and then can solve related problem in persimmon process industry. A. C. Due to complex structure and properties of persimmon tannins. In the following two decades. the tannin caused secretion of intestinal fluid decreased. the results showed that the combination of persimmon tannin and BSA by the hydrophobic forces and electrostatic forces electrostatic forces causes occurred regularly of the BSA fluorescence quenching. thus depleting the environment of oxygen. Gu HF et al. and cobra venom could be significantly inhibited by persimmon tannin in vitro. Gorinstein et al. Only more comprehensive understanding of persimmon tannin. Philippines cobra. it easily causes tannin reversion after irritation and turbidity processing. It is considered condensed tannin restrain pancreatic α-amylase activity.gallate . Using a variety of system to evaluat the antioxidant capacity of persimmon tannin. As the convergence of persimmon tannin. the results showed the high molecular weight tannins in different antioxidant systems have shown superior results on the hydroxyl radical. including epicatechin . distribution and processing. so it can be recommended as the anti-atherosclerosis food. and catechol and pyrogallol in the orthophenolic hydroxyl groups are easily oxidized. have been mostly overlooked. The study by Han et al.6% percentage of total tannins. so further theories study need to do to learn the persimmon metabolic path and chemical structure change during processing. FUNCTION OF TANNIN AND ITS APPLICATION D. [28] studies have shown that persimmon peel and pulp has significant antioxidant effect on antiatheroscloresis and lowering cholesteroling on the laboratory mouse. and epicatechin can inhibit Staphylococcus aureus. ellagic acid.gallate . epicatechin . Japanese medicine in research of tannins to a variety of toxins inhibitory effect. and reduce the incidence of cardiovascular disease [31]. Lower cholesterol.[37] have shown that condensed tannin of persimmon leaf may prevent high-fat obesity. Listeria monocytogenes and Vibrio parahaemolyticus at low content. cerebrovascular diseases prevent cardiovascular and Kawakami et al. In Ito and Oshima [32] study. except for lower molecular weight oligomers which can be more easily separated. Proanthocyanidins (condensed tannin) is a class of flavan-3-ol polymer formed different compounds. Nakayama et al. and reacted with dietary protein.3 -0. E Other function Some polymer tannin has obvious anti-allergic effects. found that alcohol extracts of persimmon has a better total antioxidant activity. The production and acreage of China kept the highest in the world. calcium in the digestive tract. Xu SL [34] IV.nitro and C . FORECAST The cultivation of persimmon has a long history in China and Japan. [24] reported that Japanese persimmon leaves extracts can quickly have an effect on L.componentunit. Katsube et al [33] have found 70% ethanol extract of astringent persimmon has a strong anti-LDL (low density lipoprotein) oxidation. We should try to understand the pros and cons of tannin. and its activity is related with the degree of polymerization [31]. [30] indicated that methanol extracts of persimmon leaves have free radical scavenging ability and can inhibit lipid peroxidation in cells. Quench the fluorescence of Bovine serum albumin (BSA) Gu HF et al. the persimmon tannin has a catechol and a pyrogallol. Gu HF et al.[35]studied persimmon tannin have effect on quenching the fluorescence of bovine serum albumin (BSA) in the physiological pH by fluorescence spectroscopy and UV absorption spectroscopy. [21] feeding rats with condensed tannins of Persimmon. [26] reported that several enzymes activity such as proteolytic enzymes. India cobra[25].4βBTE. Because most persimmon tree planted in China are astringent persimmon variety. can lower cholesterol levels. [31] found that high molecular weight tannins is 83. superoxide anion radical scavenging. found that persimmon tannins can inhibit the activity of the snake venom protein and have a strong toxin detoxication of Taiwan's cobra. Action of antibacterial and antiviral Studies by Akiyama et al.BTE. [23] showed several tannins such as tannic acid. B.BTE.3 0. epigallocatechin . can use it widely. Thus the research can bring about greater social and economic benefits. gallic acid. After into the intestines. and the fruit contains a lot of persimmon tannin which seriously affect the storage.catechin and four heterogeneous extensions unit. III. Achiwa [36] suggest that persimmon tannin can inhibit C. carbohydrates to form complexes which affect gastric enzymes and absorption of the iron.nitroso compounds in the mutagenicity effect. Ahn [29] found that extracts of persimmon nuclear has free radical scavenging capacity in vivo. a large number of studies have shown that lipid peroxidation induced by oxygen free radicals is closely related with many diseases [27]. because its polymerization degree. Tannins can reduce cholesterol absorption in intestinal to lower lipid concentrations. The antioxidant activity of tannin Plant tannin has antioxidant and free radical scavenging activity. 391 .BTE (benzylthioether). it will be contribute to more comprehensive understanding and studying it in depth. it is mouth feel astringent after eating.

[10] DW.Sci. ) Part isolation of leucoanthocyanin from kaki fruit Agricultural and Biological Chemistry. 131-134. L.. Die Chemie der Naturliche Gerbstoffe. Trombley.et al.supplemented with either whole persimmon or phenol-free persimmon. Sugiura A. 23(5): p. [11] I.. 2008. 435-442.) Proanthocyanidin: A Highly Galloylated. 493-501.S. . 1-6.Iwatsuki K. Carrillo.A. W. 1979. [14] Matsuo T . P. 63-66.A. . Plant polyphenols. . The effects of diets. Nutritional Biochemistry 1998: p. Mazauric ..J. Food Research International.. Biosci. 1996.Y. R. M. [25] Okonogi T. 58: p. Detoxification by persimmon tannin of snake venoms and bacterial toxins. B. K.. [37] Nakayama K.Y. Agricultural and Biological Chemistry..a. 70(3): p. Zemser M. Proanthocyanidins-a final frontier in flavonoid research? New Phytol.Biochem. 124-133. A.J. 41(2): p. Study on inhibitory effects of persimmon tannins on activities of major enzymes from several snake venoms and its mechanism.. Sci. 25-37. Scientia Agricultura Sinica 2008. B.T.J.. Clifford MN. N. 1962. . Analysis of condensed tannins: a review. 2001. J. 29(4): p. Mol. [29] Ahn HS. [2] Gorinstein S , Kulasek GW , Bartnikowska E.. J Sci Food Agric. 26: p. [20] Akagi T.. et al. 91: p. Toxicon. I. High Molecular Weight Persimmon (Diospyros kaki L.K.Park DK. 135-144. 2005. L. 9-28. 1990: p..M. [30] J Han. M... [33] Katsube T. [6] Aron.. Agric Food Chem. 208-217. Evaluation of bitterness and astringency of (+)-catechin and (–)-epicatechin in red wine and in model solution.L. 14(3): p. A. [16] Yonemori K. Berlin. 267(2): p. Ogiso A. J. Difference in tannin of non-astringent and astringent type fruits of Japanese persimmon (Diospyros Kaki Thunb) Japanese Society for Horticultural Science.K. Springer. Studies on the tannin of Japanese persimmon ( diospyros kaki L. MajorWater-Soluble Polyphenols , Proanthocyanidins , in Leaves of Persimmon (Diospyros Kaki) and Their α-Amylase Inhibitory Acitivity. The chemical structure of kaki-tannin from immature fruit of the persimmon (Diospyros kaki L. J Sensory Stud 1997. 79-104.Lim Y. 5: p. Free radical scavenging effect of Diospyros kaki.M. Chemical Plant tannins..phenol solution Food Science and Technology. R. Archives of Biochemistry and Biophysics. 6(Food Science): p. Li CM.. Bartnikowska E. 22: p. Canon..H. [27] Shi B. [34] Xu SL. Laminaria japonica and Undaria pinnatifida .. S. 80(7): p..2007.. 52(8): p.C. 223-227.H. J Yang.Zhang J.. Sharma. Mitsui S. 2002. [12] Hillis. Journal of Antimicrob Chemother. 67(12): p.S. Pell AN. Qi JH.G.. J. 21-40... and Y Tian. 2000: p.Oono T. Journal of Agricultural and Food Chemistry. H. N A T U R E. 1992: p. Tarascou . 2008. Antibacterial activity of plants used in cooking for aroma and taste.. 2000. 1983. 2000. 12: p. D-Y. R Choue. 2010.. Yamasaki O.A.. Condensed tannin from persimmon leaves prevented high-fat diet-induced obesity in mice. D. 2010. [26] Gut HF. Y. S. L. and Billot..H. 79(3): p.M. 43(5): p.a... H.[24] Hara-Kudo Y. O. Flavan-3-ols.J.. Gong BC.Shiwaku K. 2008..Z. Formation of Condensed Tannins in Plants.Chen MH.. 11: p. [5] Thorngate JH. Studies on the tannin of Japanese persimmon ( diospyros kaki L. Nakanami M. 17(5): p. nature. Ikegami A.).D. Japan. [7] Dixon. 241-245. Ohta e. 524-527. 1380-1385. K.. The hidden face of food phenolic composition. 2391-2396. S. F. The study of the method of determination of persimmon tannin content with sodium carbonate . 2001.. [21] Kawakami K.et al. 501(1): p.M.. K. 16-22. 52(2): p. Coq . Katsuzaki H,et al. Differences in the composition of sweet. Journal of Radio Analytical and Nuclear Chemistry 2006. L. 2004. 67:p. F. 42: p. 392 . [35] Gu HF. occurrence. J. 2004. S.H. 1920. 1094-1117. Myricetin. IIZUKA S. [4] Kallithraka S. [13] Ito S . li CM. [18] Chen XN.J. A. [17] Fei XQ.. Z. [15] Inoue K. Dou HL. Xu YJ. L.Dou HL. Kondo K. Shufen XU. [8] Chunmei LI. Food Res.Biotechnol.HIRAYAMA M.. [28] Gorinstein S.A. Sugita-Konishi Y.L. T. Lee JY. 156. Animal Feed Scienee and Teehnolog. Florida:CRC PressBoca Raton. 4. 710-712 [31] Gu HF. 303-308. lei CM..Y. 1962. 104-107. 2009.Hu WF.. ) Part isolation of leucoanthocyanin from kaki fruit Agricultural and Biological Chemistry. [23] Akiyama H. Morawiec M,et al.occurrence and biological activity. Structural features and antioxidant activity of tannin from persimmon pulp. 156. [19] Gu HF..Y. Forest Research. Fitoterapia. 52: p..S. 2010. 1999. Food Chem. Nutrition Research. DPPH radical scavenging assay.Hwang SG. Inhibitory effects of persimmon (Diiospyros kaki) and constituents on the mutagenicity of C-nitro and Cnitroso compounds formed by reaction of sorbic acid with sodium nitrite.H. Beijing:China Forestry Publishing House..P. 2002. and FolinCiocalteu assay..et al. 55:p. Soc. Fluorescence Quench to Bovine Serum Albumin by Persimmon Tannin. J. 9033–9042. Preparation and antioxidan tactivity of tannin from persimm on pulp. 48(4): p. 275-281. 1978. 2820-2824. .. 487-491. 1958. 29. Condensed Tannin Composition Analysis in Persimmon (Diospyros kaki Thunb. Proanthocyanidins and tannin-like compounds – nature...A.Chen MH.. 1995.. Food Science. 73: p.531535. In vitro Antioxidant Properties of Extract of Non-astringent Persimmons. 74(7): p. [9] K. O. Hu WF. 12(4): p. Journal of Food Protection.Food Agric. dietary intake and effects on nutrition and health.Anuurad E.Zhang J.23(5):241-245.. The influence of persimmon peel and persimmon pulp on the lipid metabolism and antioxidant activity of rats fed cholesterol. [3] Macheix.on rats fed cholesterol. Freudenberg.) Fruit by Acid Catalysis in the Presence of Excess Phloroglucinol J. 26: p. S... H. REFERENCES [1] Santos-Buelga C. Transactions of the CSA E...S. astringent type persimmon tannin and characteristics of Luotian persimmon tannin.. Adsorptive removal of uranium and thorium with a cross linked persimmon peel gel. [22] Schofield P. Sensory evaluation of bitterness and astringency of 3R(–)-epicatechin and 3S(+)-catechin. 1637-1643. 165: p.397.K. S. J. Screening for antioxidant activity in edible plant products Comparison of low-density lipoprote in oxidation assay. John D. A-Linked Tannin with an Unusual Flavonol Terminal Unit.et al. Hort. [32] Ito S . Journal of the Japanese Society for Food Science and Technolog.. 2008. Fruit phenolics. 369-373.E. 1265-1273. Fluriet. 1371. 910-917. Annals of Nutrition and Metabolism. Y.Wan QH . 2007. Antibacterial action of several tannins against staphylococcus aureus. 2010. [36] Achiwa T. Antioxidative activity of persimmon and grape seed extract: in vitro and in vivo. Beijing: Science Press. Xie and S.Xu YJ. 2004.