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
ztyztyzty2.ok@163.com

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.

II. TANNIN COMPOSITION AND MOLECULAR

STRUCTURE
Persimmon accumulates condensed tannin in fruit and
leaf, which is responsible for astringency trait. As early as the
first time in 1920, its 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

function

I. INTRODUCTION
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

ICABE2011
389

linked by the C-4 C-6 or C-8 to form a polymer [14, 15]

Fig.1.

Fig.1 Chemical structures of persimmon tannin and related catechin

In Ito and Oshimas study, the main component of

persimmon tannin was named diospyrin, which is
leucopetunidim -3-glucosides. The study by Yonemori et
al.[16] is that catechin was the main phenolic compounds in
persimmon. Small molecular weight components dominated in
non-astringent and high molecular weight components
dominated in astringent. Fei XQ et al. [17] thought that the
main ingredients of persimmon tannin have three kinds,
namely gallic acid, epigallocatechin and catechin. Diospyrin
Fig.2 in comparison with the catechinsFig.3 was
found by Chen XN et al. [18] that they are almost the same
basic unit, but the individual terminal units. In recent years,
with the separation of technology development, the use of
HPLC,MS,NMR and other cutting-edge technology, more and
more condensed tannins were isolated and identified.

At present, five different flavan -3- alcohol such as

catechin, epicatechin, epigallocatechin, epigallocatechin-3-Ogallate, epicatechin-3-O-gallate were isolated from the
persimmon fruit and leaves.Purification of persimmon tannin
with AB-8 macroporous resin, Gu HF et al.[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.The degradation products are
epicatechin, epigallocatechin - 3 - O-gallate, epicatechin - 3 O-gallate and an unknown Monomer, the products of three
known to exist in the ratio of 1:73:1. Akagi et al.[20]analyze
the condensed tannin fractions, epicatechin - phloroglucinol
adducts, epicatechin - 3 0 gallate - phloroglucinol
adducts, epigallocatechin - phloroglucinol adduct and an
unknown substance by acid catalytic degradation - HPLC
method in the case of excess pyrogallol. The unknown
component recognized as a form epigallocatechin-3-0 - gallate
- phloroglucinol adducts was separated by TLC method and
then charactered charactered by mass spectrometry, nuclear
magnetic resonance.
Epigallocatechin-3-0-gallate - phloroglucinol adduct is
the most important component of persimmon.In
phloroglucinol analyses of condensed tannins in persimmon
fruit,few hydrolyzed monomers for the terminal CT units were
also found. This indicates a high degree of CT polymerization
in persimmon fruit, which is consistent with a previous report
by Matsuo and Ito [14] .Condensed tannin, was analyzed by
HPLC-MS after extracted with 70% aqueous acetone and
thiolysis by Kawakami [21]. The main component is
procyanidins oligomer consist of one terminal units of

Fig.2 Molecular Structure of diospyrin

Fig.3 Molecular Structure of catechin

390

catechin and four heterogeneous extensions unit, including

epicatechin - 4 - BTE (benzylthioether), epigallocatechin - 3 0- gallate - 4BTE, epicatechin - 3 -0- gallate - 4- BTE,
epigallocatechin - 4- BTE. Proanthocyanidins (condensed
tannin) is a class of flavan-3-ol polymer formed different
compounds,
because
its
polymerization
degree,componentunit, connecting way, causing the analytic
determination more difficulty[22]. In the following two
decades, As a consequence tannins, except for lower
molecular weight oligomers which can be more easily
separated, have been mostly overlooked.

found that alcohol extracts of persimmon has a better total

antioxidant activity.

III. FUNCTION OF TANNIN AND ITS APPLICATION

D. Quench the fluorescence of Bovine serum albumin (BSA)

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, 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.
Quenching mechanism is static quenching.

C. Lower cholesterol,
cerebrovascular diseases

prevent

cardiovascular

and

Kawakami et al. [21] feeding rats with condensed tannins

of Persimmon, can lower cholesterol levels. It is considered
condensed tannin restrain pancreatic -amylase activity.
Tannins can reduce cholesterol absorption in intestinal to
lower lipid concentrations, and reduce the incidence of
cardiovascular disease [31].

A. Action of antibacterial and antiviral

Studies by Akiyama et al. [23] showed several tannins
such as tannic acid, gallic acid, ellagic acid, epicatechin
epigallo-catechin gallate, and epicatechin can inhibit
Staphylococcus aureus. Hara and Kudo et al. [24] reported
that Japanese persimmon leaves extracts can quickly have an
effect on L. Listeria monocytogenes and Vibrio
parahaemolyticus at low content. Japanese medicine in
research of tannins to a variety of toxins inhibitory effect,
found that persimmon tannins can inhibit the activity of the
snake venom protein and have a strong toxin detoxication of
Taiwan's cobra, Philippines cobra, India cobra[25]. Gu HF et
al. [26] reported that several enzymes activity such as
proteolytic enzymes, phospholipase A2, L-amino acid oxidase
activity from Agkistrodon halys Pallas, Agkistrodon acutus,
and cobra venom could be significantly inhibited by
persimmon tannin in vitro. Binding of an important cause of
persimmon Tannin and protein led to enzyme inactivation.

Other function
Some polymer tannin has obvious anti-allergic effects,
and its activity is related with the degree of polymerization
[31]. Achiwa [36] suggest that persimmon tannin can inhibit
C- nitro and C - nitroso compounds in the mutagenicity effect.
Nakayama et al.[37] have shown that condensed tannin of
persimmon leaf may prevent high-fat obesity.
As the convergence of persimmon tannin, it is mouth feel
astringent after eating, and reacted with dietary protein,
carbohydrates to form complexes which affect gastric
enzymes and absorption of the iron, calcium in the digestive
tract. After into the intestines, the tannin caused secretion of
intestinal fluid decreased. We should try to understand the
pros and cons of tannin, it will be contribute to more
comprehensive understanding and studying it in depth.

B. The antioxidant activity of tannin

Plant tannin has antioxidant and free radical scavenging
activity, a large number of studies have shown that lipid
peroxidation induced by oxygen free radicals is closely related
with many diseases [27]. Gorinstein et al. [28] studies have
shown that persimmon peel and pulp has significant
antioxidant effect on antiatheroscloresis and lowering
cholesteroling on the laboratory mouse, so it can be
recommended as the anti-atherosclerosis food. Ahn [29] found
that extracts of persimmon nuclear has free radical scavenging
capacity in vivo. The study by Han et al. [30] indicated that
methanol extracts of persimmon leaves have free radical
scavenging ability and can inhibit lipid peroxidation in cells.
Gu HF et al. [31] found that high molecular weight tannins is
83.6% percentage of total tannins. Using a variety of system
to evaluat the antioxidant capacity of persimmon tannin, the
results showed the high molecular weight tannins in different
antioxidant systems have shown superior results on the
hydroxyl radical, superoxide anion radical scavenging. In Ito
and Oshima [32] study, the persimmon tannin has a catechol
and a pyrogallol, and catechol and pyrogallol in the orthophenolic hydroxyl groups are easily oxidized, thus depleting
the environment of oxygen. Katsube et al [33] have found
70% ethanol extract of astringent persimmon has a strong
anti-LDL (low density lipoprotein) oxidation. Xu SL [34]

IV. FORECAST
The cultivation of persimmon has a long history in China
and Japan. The production and acreage of China kept the
highest in the world. Because most persimmon tree planted in
China are astringent persimmon variety, and the fruit contains
a lot of persimmon tannin which seriously affect the storage,
distribution and processing. Its a broad problem exist in
persimmon fruit products, so further theories study need to do
to learn the persimmon metabolic path and chemical structure
change during processing. Due to complex structure and
properties of persimmon tannins, it easily causes tannin
reversion after irritation and turbidity processing. Only more
comprehensive understanding of persimmon tannin, can use it
widely, and then can solve related problem in persimmon
process industry. Thus the research can bring about greater
social and economic benefits.

391

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