从根霉 30 78菌丝体的甲醇提取物中分离得到 9个化合物 ,通过波谱分析 ,鉴定为 5α,8α 表二氧 (2 0S ,2 2E ,2 4R) 麦角甾 6 ,2 2 二烯 3β 醇 (1)、甘油醇 1 单油酸酯 (2 )、4 羟基苯乙酮 (3)、4 羟基苯乙酸 (4 )、(2 0S ,2 2E ,2 4R) 麦角甾 7,2 2 二烯 3β ,5α ,6 β 三醇 (5 )、(S) 3 羟基 3 苯基丙酸 (6 )、胸腺嘧啶 (7)、尿嘧啶(8)和腺苷 (9

刘光晔

张国林

李伯刚

李国友

Institutional Repository of Chengdu Institute of Biology, CAS

© 1994-2010 China Academic Journal Electronic Publishing House. All rights reserved.    http://www.cnki.net
　　　　 天然产物研究与开发　 　　　　　
2004 　Vol. 16 　No. 4 NATURAL PRODUCT RESEARCH AND DEVELOPMEN T 　 　　　　　　　　　　
　
　
　
　
　　Received 23 February 2004 ;Accepted 18 March 2004
　 3 Corresponding author Tel/ Fax :86228285225401 ; E2mail :zhanggl
@cib. ac. cn
METABOL ITES OF R HI ZO PUS A R R HI ZUS 3078
L I Guo2you ,L I Bo2gang ,L IU Guang2ye ,ZHAN G Guo2lin 3
( Chengdu Institute of Biology , the Chinese Academy of Sciences ,Chengdu 　610041 ,China)
Abstract 　Nine compounds were isolated from the methanol extract of the mycelium of Rhizopus arrhiz us 3078. On
the basis of spectral data ,they were determined to be 5α, 8α2epidioxy2(20 S , 22 E , 24 R )2ergosta26 ,222dien23β2ol
(1) , (9 Z)2glycerin212monooleate (2) ,42hydroxyacetophenone (3) ,42hydroxyphenylacetic acid (4) , (20 S , 22 E ,
24 R)2ergosta27 ,222dien23β,5α,6β2triol (5) , ( S)232hydroxy232phenylpropionic acid (6) ,thymine (7) ,uracil (8)
and adenosine (9) .
Key words 　Rhizopus arrhiz us ; mycelium ; ergosterol ; 42hydroxyphenylacetic acid ; ( S )232hydroxy232phenylpropi2
onic acid
根霉 3078 的代谢产物的研究
李国友 　李伯刚 　刘光晔 　张国林 3
(中国科学院成都生物研究所 　成都 　610041)
摘　要 　从根霉 3078 菌丝体的甲醇提取物中分离得到 9 个化合物 ,通过波谱分析 ,鉴定为 5α, 8α2表二氧2
(20 S ,22 E ,24 R)2麦角甾26 ,222二烯23β2醇 (1) 、甘油醇212单油酸酯 (2) 、42羟基苯乙酮 (3) 、42羟基苯乙酸 (4) 、
(20 S ,22 E ,24 R)2麦角甾27 ,222二烯23β, 5α, 6β2三醇 (5) 、( S )232羟基232苯基丙酸 (6) 、胸腺嘧啶 (7) 、尿嘧啶
(8)和腺苷 (9) 。
关键词 　少根霉 ;菌丝体 ;麦角甾醇 ;42羟基苯乙酸 ; ( S )232羟基232苯基丙酸
Introduction
In the process of food fermentation ,the nutrition and fla2
vor were greatly changed due to two reasons. Firstly ,some
proteins were converted into small peptides and amino acid
by enzymes secreted by microorganism[1 ,2 ] . Secondly ,the
metabolites of microorganism may affect the nutrition and
flavor [3 ] . Fermented bean curd is a traditional Chinese
food produced by fermentation ,which has good flavor and
nutrition. In our study ,we examined the metabolites of the
Rhizopus arrhiz us 3078 ,which was used in the bean curd
fermentation. Based on spectral data and comparison with
known compounds , nine compounds isolated were deter2
mined as 5α, 8α2epidioxy2( 20 S , 22 E , 24 R )2ergosta26 ,
222dien23β2ol ( 1) , ( 9 Z)2glycerin212monooleate (2 ) , 42
hydroxyacetophenone ( 3 ) , 42hydroxyphenylacetic acid
(4) , (20 S ,22 E ,24 R)2ergosta27 ,222dien23β,5α,6β2tri2
ol ( 5 ) , ( S )232hydroxy232phenylpropionic acid ( 6 ) , thymine (7) ,uracil (8) and adenosine (9) . Compound 1exhibited some cytotoxic effect [4 ] . Compound 5 possessedantinociceptive activity ( inhibition = 47. 6 % , 5 mg/kg) [5 ] . From the results , it could be estimated that themetabolites of Rhizopus arrhiz us 3078 used in the fer2mentation of bean curd may have some effect on humanbeings.ExperimentalGeneralMelting points were measured on XRC21 micromelting2point apparatus and uncorrected. IR spectra were recordedon a Perkin Elmer Spectrum One FT2IR spectrometer .Silica gel (200～300 mesh) for column chromatography(CC) and GF254 (30～40μm) for TLC were purchasedfrom Qingdao Marine Chemical Factory ,Qingdao ,China.NMR spectra were carried out on Bruker Advance 600spectrometer , TMS as internal standard. Optical rotations
were measured on Perkin Elmer Model 341 polarimeter .
Microorganism and culture media
Rhizopus arrhiz us 3078 was obtained from Chengdu
Institute of Biology , the Chinese Academy of Sci2
772
© 1994-2010 China Academic Journal Electronic Publishing House. All rights reserved.    http://www.cnki.net
ences. It was maintained on potato dextrose agar slant
( PDA) at 4 ℃.
Culture medium was comprised of dextrose ( 20 g/
L) ,yeast extract (1 g/ L) , KH2 PO4 (3 g/ L) ,MgSO4·
7H2O (1. 5 g/ L ) ,potato extract (200 g potato was
extracted with 1 Liter boiling water for 20 min) ,and
its p H was adjusted to 6. 0 with NaOH (aq) .
Fermentation
The fresh mycelium grown on PDA medium at 28 ℃
for 5 d was inoculated into 500 mL flasks containing
250 mL potato dextrose medium ,which were steril2
ized at 121 ℃and 15 psi for 30 min. Flasks with in2
oculated medium were placed in rotary shaker at 28
℃and incubated at 180 rpm for 7 d.
Extraction and isolation
The total mycelium was filtrated and dried at 55 ℃ in
oven. The dried mycelium (180 g) was extracted (1 L ×
5) exhaustively with methanol at 50 ℃ (2 h each) . Evap2
oration of the solvent from the extract in vacuo gave a
residue ( 28 g) . The residue was chromatographied on a
silica gel column (420 g ,5. 5 cm ×31. 0 cm) eluted gra2
diently by petroleum ether (bp . 60～90 ℃)2acetone (20∶
1 ,15∶1 ,10∶1 ,5∶1 ,2 L each) and CHCl32CH3OH (20∶1 ,
15∶1 ,10∶1 ,7∶1 ,5∶1 ,3∶1 ,2 L each) . Based on the TLC
monitoring , the collected fractions were combined into
nine fractions (A :0. 5 g ;B :8. 5 g ;C :1. 1 g ;DA :1. 75 g ;
DB :0. 75 g ; E :0. 17 g ; F :1. 36 g ; G:0. 3 g ; H :1. 6 g) .
Fr . C was chromatographied over silica gel column (50 g ,
2. 6 cm ×19. 0 cm) eluted with chloroform2acetone (100
∶1 ,500 mL) to give 1 (25 mg) . CC (column chromato2
graphy) of DB with petroleum ether ( bp . 60～90 ℃)2
acetone (5∶1 ,300 mL ;3∶1 ,300 mL) gave 2 (35 mg) .
Compound 3 (7 mg) was obtained from DA by CC over
silica gel column eluted with petroleum ether ( bp . 60～90
℃)2acetone (10∶1 ,200 mL) . CC of E over silica gel col2
umn ( 30 g , 2. 5 cm ×14. 0 cm) eluted with CHCl32
CH3OH ( 15 : 1 , 800 mL ) gave EA , EB and EC. Subse2
quent purification of EA by CC (8 g ,0. 8 cm ×20. 0 cm)
eluted with CHCl32CH3OH ( 15∶1 ,150 mL) afforded 4
(10 mg) . EB was subjected to CC over silica gel (8 g ,0. 8
cm ×20. 0 cm) with CHCl32CH3OH (10∶1 ,220 mL) to
afford 5 (5 mg) and 6 (5 mg) . Further CC of EC over sil2
ica gel ( 15 g , 1. 8 cm ×12. 0 cm) eluted with CHCl32
CH3OH (12∶1 ,250 mL) yield 7 (15 mg) . Compound 8
(10 mg) was isolated from F by CC over silica gel C218
(3. 6 cm ×20. 0 cm) with H2O2CH3OH ( 10∶1 , 1100
mL) . Compound 9 (25 mg) was obtained from H by CC
over silica gel column (50 g ,2. 4 cm ×27. 0 cm) eluted
with CHCl32CH3OH (5∶1 ,1000 mL) .
Identif ication
5α, 8α2Epidioxy2( 20 S , 22 E , 24 R )2ergosta26 , 222dien2
3β2ol ( 1) 　Colorless needles (petroleum ether ,bp . 60～
90 ℃) ,C28 H44O3 ,[α]20D240. 5°(c = 0. 1 ,CHCl3) ,mp. 175
～177 ℃; ESI2MS m/ z :429[ M + H] + (positive mode) ;
IRυKBrmax cm - 1 : 3380 (2OH) , 2955 , 2871 , 1631 (2CH =
CH2) ,1457 ,1378 ,1074 ,967 ;1 H NMR(CDCl3 ,600 MHz) : δ6. 53 (1H ,d , J = 8. 4 Hz , H26) ,6 . 27 (1H ,d , J = 8. 4Hz ,H27) ,5 . 23 (1H ,dd , J = 13. 5 ,7. 6 Hz , H223) ,5 . 17(1H ,dd ,J = 13. 5 ,7. 6 Hz , H222) ,3 . 97 (1H ,m , H23) ,1 . 01 (3H ,d , J = 6. 6 Hz , H221) ,0 . 94 (3H ,d , J = 4. 3Hz ,H228) ,0 . 92 (3H , s , H219) ,0 . 86 ( 3H , d , J = 4. 2Hz ,H226) ,0 . 85 (3H , s , H218) ,0 . 83 ( 3H , d , J = 4. 2Hz ,H227) ;13 C NMR ( CDCl3 ,150 MHz) :δ135. 6 ( C26) ,135. 4 ( C222) ,132. 5 ( C223) , 131. 0 ( C27) , 82. 4(C25) ,79. 7 (C28) ,66. 7 (C23) ,56. 4 (C217) ,51. 9 ( C2
872　　　　　　　　　 天然产物研究与开发 2004 　Vol. 16 　No. 4
© 1994-2010 China Academic Journal Electronic Publishing House. All rights reserved.    http://www.cnki.net
14) ,51. 2 (C29) ,44. 8 ( C213) ,43. 0 ( C224) ,40. 0 ( C2
20) ,39. 5 (C212) ,37. 2 ( C24) ,37. 1 ( C210) ,34. 9 ( C2
1) ,33. 3 ( C225) ,30. 3 ( C22) ,28. 9 ( C216) ,23. 6 ( C2
11) ,21. 1 (C221) ,20. 8 (C215) ,20. 2 (C226) ,19. 9 ( C2
27) , 18. 4 ( C219) , 17. 8 ( C228) , 13. 1 ( C218 ) . The
NMR data and optical rotation were in agreement with
those reported for 5α,8α2epidioxy2(20 S ,22 E ,24 R)2er2
gosta26 ,222dien23β2ol[6 ] .
( 9 Z)2Glycerin212monooleate ( 2) 　Colorless oil , C21 H40
O4 ,ESI2MS m/ z :357 [ M + H] + ,379[ M + Na ] + (posi2
tive mode) ;1 H NMR ( CDCl3 ,600 MHz) :δ5. 36 (1H ,
dt ,J = 12. 0 ,6. 1 Hz , H29) ,5 . 33 (1H ,dt , J = 12. 0 ,6. 1
Hz ,H210) ,4 . 19 (1H ,dd ,J = 11. 9 ,4. 2 Hz , H21′) ,4 . 15
(1H ,dd ,J = 11. 9 ,4. 2 Hz , H21′) ,3 . 93 (1H ,m , H22′) ,
3 . 70 (1H ,dd ,J = 11. 4 ,3. 6 Hz , H23′) ,3 . 60 (1H ,dd , J
= 11. 4 ,5. 9 Hz , H23′) ,2 . 32 (2H ,t , J = 6. 7 Hz , H22) ,
1 . 98 (4H ,m ,H28 ,11) ,1 . 28 (24H) ,0. 86 (3H ,t , J = 6.
8 Hz ,H218) ;13C NMR (CDCl3 ,150 MHz) :δ174. 6 (C2
1) ,130. 2 (C29) ,129. 9 ( C210) ,70. 5 ( C22) ,65. 4 ( C2
1) ,63. 6 (C23) ,34. 4 ,32. 1 ,29. 9 ,29. 7 ,29. 5 ,29. 4 ,29.
3 ,27. 4 ,25. 1 ,22. 9 ,14. 3. The 1 H and 13 C NMR data
were identical with those reported for ( 9 Z)2glycerin212
monooleate[7 ] .
42Hydroxyacetophenone ( 3) 　Colorless needles (petrol2
eum ether ,bp . 60～90 ℃) , C8 H8O2 , mp. 107～108 ℃,
ESI2MS m/ z : 135 [ M2H ]2( negative mode) ; 1 H NMR
(CDCl3 ,600 MHz) :δ7. 90 (2H ,brd , J = 6. 6 Hz , H23 ,
5) ,6 . 91 (2H ,brd ,J = 6. 6 Hz , H22 ,6) ,2 . 56 (3H ,s , H2
8) ;13C NMR (CDCl3 ,150 MHz) :δ198. 2 (C27) ,161. 1
(C24) ,131. 3 ( C22 ,6) ,130. 1 ( C21) ,115. 6 ( C23 ,5) ,
26. 5 ( C28) . The 1 H and 13 C NMR data were identical
with those reported for 42hydroxyacetophenone[8 ] .
42Hydroxyphenylacetic acid ( 4 ) 　 Colorless needles
(CH3OH) , C8 H8O3 , mp. 148 ～150 ℃, ESI2MS m/ z :
153[ M + H] + (positive mode) ; 1 H NMR ( CD3OD ,600
MHz) :δ7. 08 (2H ,brd ,J = 8. 4 Hz ,H22 ,6) ,6 . 72 (2H ,
brd ,J = 8. 4 Hz , H23 ,5) ,3 . 48 (2H ,s , H27) ; 13 C NMR
(CD3OD ,150 MHz) :δ175. 1 (C28) ,156. 2 (C24) ,130.
1 (C22 ,6) ,125. 6 ( C21) ,115. 0 ( C23 ,5) ,39. 9 ( C27) .
The 1 H and 13C NMR data were in agreement with those
reported for 42hydroxyphenylacetic acid[8 ] .
( 20 S , 22 E , 24 R )2Ergosta27 , 222dien23β, 5α, 6β2triol
( 5) 　Colorless needles ( CHCl3) ,C28 H46 O3 , [α]20D260. 2°
(c = 0. 1 ,C5 H5N) ,mp. 250～252 ℃; ESI2MS m/ z :431
[ M + H] + (positive mode) ; IRυKBrmax cm - 1 :3380 (2OH) ,
2955 ,2871 , 1631 (2CH = CH2) , 1457 , 1378 , 1074 , 967 ;
1 H NMR (C5D5N ,600 MHz) :δ5. 72 (1H ,brs ,H27) ,5 .
24 (1H ,dd ,J = 15. 2 ,7. 2 Hz ,H222) ,5 . 17 (1H ,dd , J =
15. 2 ,7. 2 Hz , H223) ,4 . 83 (1H , m , H23) ,4 . 30 ( 1H ,
brs ,H26) ,1 . 50 (3H ,s ,H219) ,1 . 03 (3H ,d , J = 6. 7 Hz ,
H221) ,0 . 92 (3H ,d , J = 6. 7 Hz , H228) ,0 . 83 (6H ,d , J
= 4. 9 Hz , H226 , H227) ,0 . 63 (3H ,s , H218) ; 13 C NMR
(C5D5N , 150 MHz) :δ 141. 5 ( C28) , 136. 1 ( C222) ,
132. 0 (C223) ,120. 4 ( C27) ,76. 1 ( C25) ,74. 2 ( C26) ,
67. 5 ( C23) ,56. 1 ( C217) ,55. 2 ( C214) ,43. 7 ( C29 ,C2
13) ,43. 1 (C224) ,41. 9 ( C24) ,40. 8 ( C220) ,39. 8 ( C2
12) ,38. 0 (C210) ,33. 8 ( C22) ,33. 3 ( C225) ,32. 6 ( C2
1) ,28. 4 (C216) ,23. 4 ( C215) ,22. 4 ( C211) ,21. 3 ( C2
27) ,20. 1 (C226) ,19. 8 (C221) ,18. 8 (C219) ,17. 8 ( C2
28) , 12. 5 ( C218) . The NMR data and optical ratation
were identical with those reported for (20 S ,22 E ,24 R)2
ergosta27 ,222dien23β,5α,6β2triol[9 ] .
( S )232Hydroxy232phenylpropionic acid ( 6 ) 　Colorless
needles ( CH3OH) , C9 H10 O3 , [α]230. 5°( c = 0. 1 ,
CH3OH) , mp. 1172119 ℃, ESI2MS m/ z : 189 ( M +
Na) + (positive mode) ,165 ( M2H) 2 ( negative mode) ; IR
υKBrmax cm - 1 : 3295 (2OH) , 2965 , 2654 , 1698 (2C = O) ,
1496 ,1456 ,765 ,703 ; 1 H NMR ( CD3OD ,600 MHz) :δ
7. 38 (2H ,t , J = 7. 4 Hz , H23′,5′) ,7 . 33 (2H ,d , J = 7.
4 Hz ,H22′,6′) ,7 . 26 (1H ,t , J = 7. 4 Hz , H24′) ,δ5. 08
(1H ,dd ,J = 8. 8 ,5. 0 Hz ,H23) ,2 . 69 (1H ,dd ,J = 15. 2 ,
8. 8 Hz ,H22a) ,2 . 63 (1H ,dd , J = 15. 2 ,5. 0 Hz , H22b) ;
13C NMR (CD3OD ,150 MHz) :173. 7 ( C21) ,144. 0 ( C2
1′) ,128. 2 ( C22′,6′) ,127. 4 ( C24′) ,125. 7 ( C23′,5′) ,
70. 5 (C23) ,43. 8 (C22) . The NMR data and optical rota2
tion were identical with those reported for ( S)232hydrox2
yl232phenylpropionic acid[10 ] .
Thymine ( 7 ) 　White crystals ( CH3OH) , C5 H6O2N2 ,
mp. > 300 ℃, ESI2MS m/ z : 149 [ M + Na ] + ,275 [ 2M
+ Na ] + ( postitive mode) ; IR υKBrmax cm - 1 : 3260 , 3062 ,
1730 ,1679 , 1212 ; 1 H NMR ( DMSO2 d6 , 600 MHz) :δ
10. 97 (1H ,d , J = 5. 5 Hz , H21) ,10. 56 (1H ,s , H23) ,7.
22 (1H , d , J = 5. 5 Hz , H26) ,1 . 71 (3H , s ,2CH3) ; 13 C
NMR (DMSO2d6 ,150 MHz) :δ165. 6 (C24) ,152. 2 (C2
2) ,138. 4 (C26) ,108. 3 (C25) ,12. 5 (CH3) . The 1 H and
13 C NMR data were identical with those reported for
thymine[11 ] .
Uracil ( 8 ) 　 White powder ( H2O + CH3OH ) ,
C4 H4N2O2 , mp. > 300 ℃, ESI2MS m/ z : 135 [ M +
Na ] + ; IR υKBrmax cm - 1 : 3410 , 3110 , 1768 , 1738 , 1676 ,
1650 , 1450 , 1420 , 1235 ; 1 H NMR ( DMSO2 d6 , 600
MHz) :δ11. 12 (1H ,s , H21) ,10. 85 (1H ,s , H23) ,7 . 48
(1H ,d ,J = 7. 7 Hz , H26) ,5 . 75 (1H ,d , J = 7. 7 Hz , H2
5) ;13C NMR ( DMSO2 d6 ,150 MHz) :δ 165. 0 ( C24) ,
152. 2 (C22) ,142. 8 (C26) ,100. 9 (C25) . The 1 H and 13
C NMR data were identical with those reported for u2
racil[12 ] .
Adenosine( 9) 　White powder ( CHCl3 + CH3OH) , C10
H13N5O4 ,[α]20D250. 6°(c = 0. 1 , H2O) , mp. 2352236 ℃,
IR υKBrmax cm - 121 : 3330 , 2935 , 2850 , 1684 , 1608 , 1595 ,
9722004 　Vol. 16 　No. 4 李国友等 :根霉 3078 的代谢产物的研究 　　　　　　　　　
© 1994-2010 China Academic Journal Electronic Publishing House. All rights reserved.    http://www.cnki.net
1455 ,1422 ,1382 ,1338 ,1130 ; ESI2MS m/ z : 268 [ M +
H] + , 557 ( 2M + Na ) + ( positive mode ) ; 1 H NMR
(C5D5N ,600 MHz) :δ8. 71 (1H ,s , H28) ,8 . 60 (1H ,s ,
H22) ,8 . 32 (2H ,s ,NH2) ,6 . 70 (1H ,d , J = 6. 0 Hz , H2
1′) ,5 . 49 (1H ,t , J = 4. 8 Hz , H22′) ,5 . 05 (1H ,dd , J =
4. 8 ,3. 0 Hz ,H23′) ,4 . 74 (1H ,m , H24′) ,4 . 30 (1H ,dd ,
J = 12. 3 ,2. 4 Hz , H25′a) ,4 . 13 (1H ,dd , J = 12. 3 ,2. 4
Hz ,H25′b) ;13C NMR ( C5D5N ,150 MHz) :δ157. 7 ( C2
6) ,153. 3 (C22) ,149. 9 (C24) ,140. 5 (C28) ,121. 5 ( C2
5) ,90. 8 ( C21′) ,87. 8 ( C24′) ,75. 5 ( C23′) ,72. 4 ( C2
2′) ,63. 0 ( C25′) The NMR data and optical rotation
were identical with those reported for adenosine[13 ] .
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根霉3078的代谢产物的研究

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