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Mycology: An International Journal on Fungal Biology
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Hericenones and erinacines: stimulators of nerve
growth factor (NGF) biosynthesis in Hericium erinaceus
Bing-Ji Ma
a
, Jin-Wen Shen
a
, Hai-You Yu
a
, Yuan Ruan
a
, Ting-Ting Wu
a
& Xu Zhao
a
a
Department of Traditional Chinese Medicine , Agronomy College of Henan Agricultural
University , Zhengzhou, 450002, Henan Province, China
Published online: 29 Apr 2010.
To cite this article: Bing-Ji Ma , Jin-Wen Shen , Hai-You Yu , Yuan Ruan , Ting-Ting Wu & Xu Zhao (2010) Hericenones and
erinacines: stimulators of nerve growth factor (NGF) biosynthesis in Hericium erinaceus , Mycology: An International Journal
on Fungal Biology, 1:2, 92-98, DOI: 10.1080/21501201003735556
To link to this article: http://dx.doi.org/10.1080/21501201003735556
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Mycology
Vol. 1, No. 2, June 2010, 92–98
ISSN 2150-1203 print/ISSN 2150-1211 online
© 2010 Mycological Society of China
DOI: 10.1080/21501201003735556
http://www.informaworld.com
TMYC
Hericenones and erinacines: stimulators of nerve growth factor (NGF)
biosynthesis in Hericium erinaceus
Mycology
Bing-Ji Ma*, Jin-Wen Shen, Hai-You Yu, Yuan Ruan, Ting-Ting Wu and Xu Zhao
Department of Traditional Chinese Medicine, Agronomy College of Henan Agricultural University, Zhengzhou 450002,
Henan Province, China
(Received 20 December 2009; final version received 24 February 2010)
This review surveys the chemical and biological literature dealing with the isolation, structural elucidation and bioactivity
of hericenones and erinacines from the fruiting body and mycelium of Hericium erinaceus, concentrating on work that has
appeared in the literature up to December 2009.
Keywords: Hericium erinaceus; hericenones; erinacines; structures; bioactivities
1. Introduction
Nerve growth factor (NGF) has potent biological activities,
such as preventing neuronal death and promoting neurite
outgrowth, and is essential to maintain and organize neu-
rons functionally (Obara and Nakahata 2002). It is
assumed that functional deficiency of NGF is related to
Alzheimer’s disease and plays a part in the etiology of the
disease process (Allen and Dawbarn 2006). NGF is
expected to be applied to the treatment of Alzheimer’s dis-
ease (Takei et al. 1989). However, NGFs are proteins and
so are unable to cross the blood–brain barrier; it is also eas-
ily metabolized by peptidases. Therefore, its application as
a medicine for treatment of neurodegenerative disorders
will be difficult. Alternatively, research has been carried
out on low-molecular weight compounds that promote NGF
biosynthesis, such as catecholamines (Furukawa et al. 1986),
scabronions (Obara et al. 1999), cyrneines (Marcotullio et al.
2007), hericenones and erinacines.
Hericium erinaceus is a mushroom belonging to the
family Hericiaceae and has been known as Chinese med-
icine or food in China and Japan without harmful effects.
H. erinaceus grows on old or dead broadleaf trees and
has been used as a medicine for treatment of gastricism
in traditional Chinese medicine for more than 1000 years
(Mizuno et al. 1999). Recently, the chemical constituents
of H. erinaceus have been investigated for its interesting
and significant bioactivities. Hericenones and erinacines
were isolated from the fruiting body and mycelium of
H. erinaceus, respectively, and most of the compounds
promote NGF biosynthesis in rodent cultured astrocytes
(Table 1). These results suggest the value of H. erinaceus
for the treatment and prevention of dementia. However,
there has been no review article on bioactive compounds
isolated from H. erinaceus to date. This report covers the
isolation and structural elucidation of hericenones and
erinacines from the fruiting body and mycelium, and
their biological activity of stimulating NGF biosynthesis.
In addition, this report examines the research on eri-
nacines produced by H. erinaceus grown in mycelial
culture and the cultural conditions for the fermentation of
H. erinaceus.
2. Hericenones in the fruiting body of H. erinaceum
Hericenones are aromatic compounds isolated from the
fruiting body of H. erinaceus. Fresh fruiting bodies of the
fungus were extracted with acetone. Repeated chromatog-
raphy of the chloroform-soluble fraction obtained by solvent
partitions (chloroform and then ethyl acetate) of the extract
with silica gel followed by HPLC with ODS column gave
hericenones. Hericenones A (1), B (2) (Kawagishi et al.
1990), C (3), D (4), E (5) (Kawagishi et al. 1991), F (6), G
(7), H (8) (Kawagishi et al. 1993), hericenes A–C (9–11)
(Alberto et al. 1995) and hericerin (12) (Kimura et al.
1991) were isolated from the mushroom H. erinaceus.
Hericenones C, D and E exhibited stimulating activity for
the biosynthesis of NGF in vitro. In the presence of
hericenones C, D, E and H at 33 μg/ml, mouse astroglial
cells secreted 23.5 ± 1.0, 10.8 ± 0.8, 13.9 ± 2.1 and 45.1 ±
1.1 pg/ml NGF into the culture medium, respectively. The
degree of activity for hericenones D was almost at the
same level as the potent stimulator, epinephrine. It is of
interest that the difference of the activity among those
compounds was dependent on the nature of the fatty acid
(Scheme 1).
*Corresponding author. Email: mbj123@sina.com
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Mycology 93
Erinacerin A (13) and B (14) were also isolated
from the fruiting bodies of H. erinaceus. It was found
that erinacerin A occurred as a racemate (Yaoita et al.
2005). 3-Hydroxyhericenone F (15), hericenone I (16)
and hericenone J (17) were isolated from the same
mushroom. 3-Hydroxyhericenone F showed the protective
activity against endoplasmic reticulum stress-dependent
Neuro2a cell death (Ueda et al. 2008) (Scheme 2).
3. Erinacines in the mycelium of H. erinaceum
A number of cyathane-type diterpenoids with potent
inductive activity for NGF synthesis were isolated from
the mushroom, for example scabronines A (Ohta et al.
1998), B–F (Kita et al. 1998) isolated from the fruiting
bodies of Sarcodon scabrosus, and the cyrneines A, B
(Marcotullio et al. 2006; Obara et al. 2007), C, D (Marcotullio
et al. 2007) isolated from the fruiting bodies of Sarcodon
cyrneus. All erinacines possess a cyathane skeleton con-
sisting of angularly condensed five-, six-, and seven-
membered rings. Erinacines A (18), B (19), C (20)
(Kawagishi et al. 1994), D (21) (Kawagishi et al. 1996a),
E (22), F (23), G (24) (Kawagishi et al. 1996b), H (25), I
(26) (Lee et al. 2000), P (27) (Kenmoku et al. 2000), Q
(28) (Kenmoku et al. 2002), J (29), K (30) (Kawagishi et al.
2006), R (31) (Ma et al. 2008) and erinacol (32) (Kenmoku
et al. 2004), isolated from the mycelia of H. erinaceus,
show stimulating activity for NGF biosynthesis. The fun-
gus was cultivated by shaking at 30°C for 4 weeks; then
the culture was centrifuged and the mycelia were
extracted with ethanol. The extract, after concentrating
the solvent, was fractionated by solvent partition
between ethyl acetate and water. Repeated silica gel
chromatography and HPLC of the ethyl acetate extract
gave erinacines. Erinacine F was a diastereomer of erina-
cine E in the sugar part. However, the stereochemistry of
the sugar part in erinacine F remained undetermined
since NOSY experiments did not give any valuable
information. In the bioassay using mouse astroglial cell,
the amounts of NGF secreted into the medium in the
presence of erinacines A, B, and C at 1.0 mM were 250.1
± 36.2, 129.7 ± 6.5 and 299.1 ± 59.6 pg/ml, respectively.
The amounts of NGF secreted into the medium in the
presence of erinacines E and F at 5.0 mM were 105 ± 5.2
and 175 ± 5.2 pg/ml, respectively. These activities were
much stronger than that (69.2 ± 17.2 mM) of a known
potent stimulator, epinephrine, used as a positive control
in the bioassay.
Two erinacine derivatives (33
, 34) isolated from the
mycelia of H. erinaceus were claimed to induce the bio-
synthesis of NGF, which were expected to be applicable
for the treatment of dementia (Shimada et al. 1996).
Another two erinacine diterpenoids (35, 36) (Kawagishi
et al. 1995), isolated from the mycelia of H. erinaceus,
were also claimed to induce the production of NGF
(Scheme 3).
Cyatha-3, 12-diene (37), together with its isomer (38),
was isolated from the mycelia of H. erinaceus as a biosyn-
thetic intermediate of cyathane diterpenoids (Kenmoku
et al. 2001). Biotransformation of erinacine E was exam-
ined using 81 microorganisms. One of them, Caladario-
myces fumago ATCC 16373, was found to transform
erinacine E to a new analog CP-412,065 (39) at a conver-
sion rate of 29% (Saito et al. 1998) (Scheme 4).
4. Discussion
Hericenones and erinacines are two natural products
isolated from the fruiting body and mycelium of H. eri-
naceus, respectively, and most compounds exhibit the
Table 1. List of hericenones and erinacines in Hericium erinaceus.
No. Name Occurrence* References
1 Hericenone A a Kawagishi et al. 1990
2 Hericenone B a Kawagishi et al. 1990
3 Hericenone C a Kawagishi et al. 1991
4 Hericenone D a Kawagishi et al. 1991
5 Hericenone E a Kawagishi et al. 1991
6 Hericenone F a Kawagishi et al. 1993
7 Hericenone G a Kawagishi et al. 1993
8 Hericenone H a Kawagishi et al. 1993
9 Hericene A a Alberto et al. 1995
10 Hericene B a Alberto et al. 1995
11 Hericene C a Alberto et al. 1995
12 Hericerin a Kimura et al. 1991
13 Erinacerin A a Yaoita et al. 2005
14 Erinacerin B a Yaoita et al. 2005
15 3-Hydroxyhericenone F a Ueda et al. 2008
16 Hericenone I a Ueda et al. 2008
17 Hericenone J a Ueda et al. 2008
18 Erinacine A b Kawagishi et al. 1994
19 Erinacine B b Kawagishi et al. 1994
20 Erinacine C b Kawagishi et al. 1994
21 Erinacine D b Kawagishi et al. 1996
22 Erinacine E b Kawagishi et al. 1996
23 Erinacine F b Kawagishi et al. 1996
24 Erinacine G b Kawagishi et al. 1996
25 Erinacine H b Lee et al. 2000
26 Erinacine I b Lee et al. 2000
27 Erinacine P b Kenmoku et al. 2000
28 Erinacine Q b Lee et al. 2002
29 Erinacine J b Kawagishi et al. 2006
30 Erinacine K b Kawagishi et al. 2006
31 Erinacine R b Ma et al. 2008
32 Erinacol b Kenmoku et al. 2004
33 b Shimada et al. 1996
34 b Shimada et al. 1996
35 b Kawagishi et al. 1995
36 b Kawagishi et al. 1995
37 Cyatha-3,12-diene b Kenmoku et al. 2001
38 Cyatha-3,12-diene b Kenmoku et al. 2001
39 CP-412,065 b Saito et al. 1998
*Occurrence: a = fruiting body; b = mycelium.
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94 B.-J. Ma et al.
activity of promoting NGF synthesis. Hericenones and
erinacines are low-molecular weight compounds that
easily cross the blood–brain barrier. In a bioassay using
mouse astroglial cell, the amounts of NGF secreted into
the medium in the presence of erinacines were greater
than for hericenones. There is debate as to whether
hericenones are active components stimulating biosyn-
thesis of NGF and the recent result have shown that
hericenone C, D and E did not increase NGF mRNA
expression at 10–100 μg/ml in 1321 N1 cells (Mori et
al. 2008). Therefore, erinacines have potential as medi-
cines for degenerative neuronal disorders such as
Alzheimer’s disease and peripheral nerve regeneration.
It has been reported that oral administration of erina-
cine A significantly increases the level of NGF in the
rat locus coeruleus and hippocampus, but not in the cer-
ebral cortex (Shimbo et al. 2005). However, the
detailed mechanism by which erinacines induces NGF
synthesis remains unknown. It is interesting that
hericenones have been only reported in the fruiting
bodies of H. erinaceus and erinacines only in the
mycelia.
Biosynthesis of natural products is complex and the
expression of many of the key synthase genes is affected
by a number of factors. Biosynthetic studies on the cyat-
hane skeleton, which does not follow the isoprene rule,
was carried out by Ayer and co-workers in the late 1970s
(Ayer et al., 1978; Kenmoku et al. 2001). However, the
search for fungal cyathadiene cyclases is still in progress.
The structural novelty and significant biological activi-
ties displayed by the erinacines have also made members
of this family attractive targets for total synthesis. Testi-
mony to this is found in the number and diversity of
approaches that have been developed to construct these
fascinating natural products (Wright and Whitehead 2000;
Takano et al. 2004; Trost et al. 2005), and construction of
Scheme 1. Structures of compounds 1–12.
O
O
OH
H
3
CO
O
NCH
2
CH
2
Ph
O
OH
H
3
CO
O
21
CHO
OH
H
3
CO
O
3 R= palmytoyl
OR
4 R= stearoyl
5 R= linoleoyl
CHO
H
3
CO
OR
O
O
6 R= palmytoyl
7 R= stearoyl
8 R= linoleoyl
CHO
OH
H
3
CO
9 R= palmytoyl
OR
11 R= stearo
y
l
10 R= oleoyl
OH
H
3
CO
NCH
2
CH
2
Ph
O
12
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Mycology 95
Scheme 2. Structures of compounds 13–17.
OH
H
3
CO
OH
H
3
CO
O
O
NCH
2
CH
2
Ph
O
13
O
O
14
OH
H
3
CO
OH
H
3
CO
O
O
O
O
16
O
17
O
H
3
CO
O
O
CHO
15
HO
O
O
Scheme 3. Structures of compounds 18–36.
18
O
CHO
O
OH
HO
OH
19
CHO
H
O
O
O
OH
OH
20
CH
2
OH
H
O
O
O
OH
OH
22
H
O
HO
OH
OH
OH
H
O
23
H
O
HO
OH
OH
OH
O
H
H
H
H
21
O
CHO
H
C
2
H
5
O
O
OH
OH
HO
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96 B.-J. Ma et al.
Scheme 3. (Continued)
33
O
CHO
H
C
2
H
5
O
O
OH
OH
HO
O
30
O
H
O
OH
OH
HO
HO
OAc
32
OH
H
H
O
AcO
CHO
O
HO
OH
H
OH
O
31
34
O
H
O
H
H
OH
HO
OH
HO
35
H
O
36
H
CHO
C
2
H
5
O
O
O
HO
OH
OH
O
24
H
O
HO
OH
OH
OH
O
H
H
O
25
O
COONa
O
HO
OH
OH
26
O
H
H
O
CH
2
OH
27
O
CHO
H
AcO
O
OH
OH
HO
28
O
CH
2
OH
H
AcO
O
OH
OH
HO
29
H
O
O
O
O
H
HO
O
O
H
H
H
OH
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Mycology 97
the 5-6-7 tricyclic core of the erinacines is the key step.
However, the low yield, multi-step synthetic methods
restrict their commercial application. Currently, fermen-
tation is perhaps the best way to provide erinacines for
further exploitation.
Acknowledgements
This project was supported by the National Natural Science
Foundation of China (30901957) and Program for Excellent
Young Teachers of He’nan Province, China.
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