全 文 ：天然产物研究与开发 Nat Prod Res Dev 2013，25:624-627
文章编号:1001-6880(2013)5-0624-04
Received:August 10，2012 Accepted:November 13，2012
Foundation Item:The 973 Program，Ministry of Science and Technology
of China，(No． 2011Cb512010) ;National Natural Science Foundation
of China(Nos． 21166009;81160391)
* Corresponding author E-mail:sxp628@ 126． com
大果榕茎的化学成分
邵泰明，宋小平* ，韩长日，陈光英，陈文豪，戴春燕，宋鑫明
海南师范大学教育部热带药用植物化学省部共建重点实验室;海南师范大学化学化工学院，海口 571158
摘 要:运用硅胶柱色谱和 Sephadex LH-20 柱色谱，以及制备薄层色谱等方法从大果榕茎的 95%乙醇提取物中
分离得到 11 个化合物，通过理化性质和波谱数据鉴定为:染料木黄酮(1) ，wighteone(2) ，5 7，4，trihydroxy-6-(2-
hydroxy-3-methyl-3-butenyl)isoflavone(3) ，5 7，4-trihydroxy-3-(2-hydroxy-3-methyl-3-butenyl)isoflavone(4) ，alpin-
umisoflavone(5) ，derrone(6) ，(3R)-5-formylmellein(7) ，3β-(1-Hydroxyethyl)-7- hydroxy-1-isobenzofuranone(8) ，反
式对羟基肉桂酸乙酯(9) ，β-谷甾醇(10) ，β-胡萝卜苷(11)。化合物 4，7，8，9 为首次从该属植物中分离得到，化
合物 1-10 为首次从该植物中分离得到。
关键词:大果榕;榕属;化学成分;异黄酮
中图分类号:R284. 2 文献标识码:A
Chemical Constituents from the Stems of Ficus auriculata Lour
SHAO Tai-ming，SONG Xiao-ping* ，HAN Chang-ri，CHEN Guang-ying，
CHEN Wen-hao，DAI Chun-yan，SONG Xin-ming
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education，Hainan Normal University;College of
chemistry and chemical engineering，Hainan Normal University，Hainan 571158，China
Abstract:Eleven compounds were isolated from 95% ethanol extracts of the stems of Ficus auriculata Lour． The constit-
uents were isolated and purified by silica gel column chromatography，Sephadex LH-20 and preparative TLC． Their struc-
tures were identified on the physiochemical characteristics and basis of spectral data． Their structures were identified as
genistein(1) ，wighteone(2) ，5 7，4，trihydroxy-6-(2-hydroxy-3-methyl-3-butenyl)isoflavone(3) ，5 7，4-trihydroxy-3-
(2-hydroxy-3-methyl-3-butenyl)isoflavone(4) ，alpinumisoflavone(5) ，derrone(6) ，(3R)-5-formylmellein(7) ，3β-(1β-
hydroxyethyl)-7-hydroxy-1-isobenzofuranone(8) ，trans-p-hydroxycinnamic acid ethyl ester(9) ，β-sitosteral(10) ，and β-
daucosterol(11)． Compounds 4，7，8，9 were reported from the genus Ficus for the first time． Compounds 1-10 were isola-
ted from this plant material for the first time．
Key words:Ficus auricalata;Ficus;Chemical constituents;isoflavone
Introduction
The genus of Ficus comprises about 1000 species in the
world，among which about 120 are distributed in China
［1］． F． auriculata distributed in Ledong，Dongfang，
Baoting，Lingao of Hainan province China ［2］． It has
been used as Chinese folk medicine for the treatment of
hyperactivity cough，nocturnal emission［3］． The leaves
of F． auriculata have antioxidant，antiinflammatory，an-
tidiabetic and hepatoprotective activity，and fruit has a
strong antibacterial activity ［4-6］． In order to investigate
the constituents of this plant，eleven compounds were i-
solated from the 95% ethanol extracts and identified as
genistein(1) ，wighteone(2) ，5 7，4，-trihydroxy-6-(2-
hydroxy-3-methyl-3- butenyl)isoflavone(3) ，5，7，4-
trihydroxy-3-(2-hydroxy-3-methyl-3-butenyl ) isofla-
vone(4) ，alpinumisoflavone(5) ，derrone(6) ，(3R)-5-
formylmellein(7) ，3β-(1-Hydroxyethyl)-7-hydroxy-1-
isobenzofuranone(8) ，trans-p-phydroxycinnamic acid
ethyl ester(9) ，β-sitosteral(10) ，and β-daucosterin
(11)． Compounds 4，7，8，9 were reported from the ge-
nus Ficus for the first time． Compounds 1-10 were iso-
lated from this plant material for the first time．
Experimental
Apparatus and reagents
Melting points were determined on a WRX-4 mi-
cromelting-point apparatus(uncorrected)． NMR spectra
were measured on a Bruker AV-400 instrument with
TMS as the internal standard． Silica gel used for col-
umn chromatography(CC)was supplied by Qingdao
Marine Chemical Factory(Qingdao，China)． Sephadex
LH-20 was used(Pharmacia，Sweden)． TLC and pre-
parative TLC were purchased from Yantai Chemical In-
dustry Institute(Yantai，China)． All solvents were pur-
chased from XiLong Chemical Reagent Factory(Shan-
Tou，China)． The optical density was measured by an
enzyme-labeled detector(Elx800，BioTek Instruments，
Inc)．
Plant materials
The sterm of F． auriculata were collected in Jian feng
ling National Forest Park，Hainan Province China，in
2010，and authenticated by associate Prof． Zhong
Qiong-Xin，College of Life Science，Hainan Normal U-
niversity． A voucher specimen was deposited in the Key
Laboratory of Tropical Medicinal Plant Chemistry of
Ministry of Education，Hainan Normal University．
Extraction and isolation
The dried sterm of F． auriculata(13． 5 kg)were pow-
dered and extracted with 95% aqueous ethanol(v /v)
three times at room temperature(3 × 5 d)． The extract
was suspended in 2． 0 L of water and then partitioned
with petroleum ether，CHCl3，EtOAc successively． The
petroleum ether soluble fraction(240 g)was chromato-
graphed on a silica gel column eluted with petroleum e-
ther /EtOAc(100∶ 1 to 1∶ 100，v /v)to afford major frac-
tions 1-20． Fraction 4(3． 45g)purified by recrystalliza-
tion to yield compounds 10(750． 3mg) ;Fraction 6
(5. 40 g)was subjected to CC(silica gel，petroleum e-
ther /EtOAc，10 ∶ 1 to 0 ∶ 1)and purified by CC(Sepha-
dex LH-20，CHCl3 /MeOH，2 ∶ 3)to provide compounds
5(45． 4mg) ，6(23． 5mg) ，and 7(13． 0 mg) ;Fraction 7
(2． 40 g)was further chromatographed over Sephadex
LH-20(CHCl3 /MeOH，2 ∶ 3) ，followed by PTLC to
give compounds 8(13． 3 mg) ，9(8． 7 mg) ;Fraction 10
(4． 70 g)was further chromatographed over Sephadex
LH-20(CHCl3 /MeOH，2 ∶ 3) ，followed by PTLC to
give compounds 1(20． 1 mg) ，2(13． 5 mg) ，3(24． 4
mg)and 4(13． 2 mg)． The ethyl acetate fraction(23g)
was subjected to silica gel CC(CHCl3 /MeOH 100∶ 1→
2∶ 1)to yield 11(14． 4 mg)．
Identification
Fig. 1 Structures of compounds 1-9
Compound 1 White powder，C15 H10 O5，
1H NMR
(Acetone，400 MHz) ，δ:13. 04(1H，s，OH-5) ，8. 18
(1H，s，H-2) ，7. 46(2H，d，J = 7. 6 Hz，H-2，6) ，
6. 91(2H，d，J = 7. 6 Hz，H-3，5) ，6. 42(1H，s，H-
8) ，6. 29 (1H，s，H-6) ;13 C NMR (Acetone，100
MHz) ，δ:182. 6(C-4) ，166. 1(C-7) ，164. 9(C-5) ，
160. 0(C-8a) ，159. 5(C-4) ，155. 3(C-2) ，132. 2(C-
2，6) ，125. 0(C-3) ，124. 0(C-1) ，117. 0(C-3，5) ，
107. 1(C-4a) ，100. 8(C-6) ，95. 5(C-8). It was identi-
fied as genistein by comparison of the physical and
spectral data with the reported data ［7］.
Compound 2 Yellow powder，C20 H18 O5，
1H NMR
(MeOD，400 MHz) ;δ:13. 01(1H，s，OH-5) ，8. 01
(1H，s，H-2) ，7. 36(2H，d，J = 8. 0 Hz，H-2，6) ，
6. 84(2H，d，J = 8. 0 Hz，H-3，5) ，6. 37(1H，s，H-
8) ，5. 23(1H，t，J = 7. 2 Hz，H-2″) ，3. 31(2H，d，over-
lapped，H-2″) ，1. 78(3H，s，H-4″) ，1. 66(3H，s，H-
5″) ;13 C NMR(MeOD，100 MHz)δ:182. 3(C-4) ，
163. 7(C-7) ，160. 5(C-5) ，158. 8(C-4) ，157. 6(C-
8a) ，154. 6(C-2) ，132. 1(C-3″) ，131. 5(C-2，6) ，
124. 6(C-3) ，123. 5(C-1) ，123. 4(C-2″) ，116. 3(C-
3，5) ，113. 1(C-6) ，106. 1(C-4a) ，93. 9(C-8) ，26. 0
(C-5″) ，22. 3(C-1″) ，18. 0(C-4″). It was identified as
wighteone by comparison of the physical and spectral
data with the reported data［8］.
526Vol. 25 SHAO Tai-ming，et al:Chemical Constituents from the Stems of Ficus auriculata Lour
Compound 3 Yellow powder，C20 H18 O6，
1H NMR
(MeOD，400 MHz) ，δ:13. 16(1H，s，OH-5) ，8. 03
(1H，s，H-2) ，7. 36(2H，d，J = 8. 0 Hz，H-2，6) ，
6. 84(2H，d，J = 8. 0 Hz，H-3，5) ，6. 38(1H，s，H-
8) ，4. 76，4. 70(1H each，s，= CH2) ，4. 41(1H，t，J =
6. 4 Hz，H-2″) ，3. 01(1H，dd，J = 6. 4 Hz，J = 13. 6
Hz，Ha-1″) ，2. 90(1H，dd，J = 7. 2 Hz，J = 13. 6 Hz，
Hb-1″) ，1. 83(3H，s，H-4″) ;
13 C NMR(MeOD，100
MHz) ，δ:182. 3(C-4) ，164. 6(C-7) ，161. 3(C-5) ，
158. 8(C-4) ，158. 0(C-8a) ，154. 7(C-2) ，148. 7(C-
3″) ，131. 5(C-2，6) ，124. 7(C-3) ，123. 5(C-1) ，
116. 3(C-3，5) ，111. 1 (= CH2) ，110. 5 (C-6) ，
106. 1(C-4a) ，94. 4(C-8) ，76. 3(C-2″)29. 8(C-1″) ，
17. 8(C-4″). It was identified as 5，7，4，2-hydroxy-3-
methyl-3-butenyl isoflavone by comparison of the phys-
ical and spectral data with the reported data［9］.
Compound 4 White powder，C20 H18 O6，
1H NMR
(Acetone，400 MHz) ，δ:13. 06(1H，s，OH-5) ，8. 15
(1H，s，H-2) ，7. 37(1H，s，H-2) ，7. 34(1H，d，J =
8. 0 Hz，H-6) ，6. 87(1H，d，J = 8. 0 Hz，H-5) ，6. 41
(1H，s，H-8) ，6. 28(1H，s，H-6) ，4. 98，4. 78(1H
each，s，= CH2) ，4. 42(1H，t，J = 6. 0 Hz，H-2″) ，2. 91
(2H，m，overlapped，H-1″) ，1. 81(3H，s，H-4″) ;13 C
NMR(Acetone，100 MHz) ，δ:182. 6(C-4) ，166. 2(C-
7) ，164. 9(C-5) ，160. 0(C-8a) ，158. 1(C-4) ，155. 3
(C-2) ，149. 5(C-3″) ，134. 0(C-2) ，130. 4(C-6) ，
127. 8(C-3) ，125. 1(C-3) ，124. 1(C-1) ，117. 7(C-
5) ，111. 6(= CH2) ，107. 1(C-4a) ，100. 8(C-6) ，
95. 5(C-8) ，78. 0(C-2″) ，39. 8(C-1″) ，19. 3(C-4″). It
was identified as 5，7，4-trihydroxy-3-(2-hydroxy-3-
methyl-3-butenyl)isoflavone by comparison of the
physical and spectral data with the reported data［10］.
Compound 5 Yellow crystal，C20 H16 O5，
1H NMR
(CDCl3，400 MHz)δ:13. 08(1H，s，OH-5) ，7. 81
(1H，s，H-2) ，7. 33(2H，d，J = 8. 4 Hz，H-2，6) ，
6. 83(2H，d，J = 8. 4 Hz，H-3，5) ，6. 72(1H，d，J =
10. 4 Hz，H-4″) ，6. 34(1H，s，H-8) ，5. 62(1H，d，J =
10. 4 Hz，H-3″) ，1. 47(6H，s，CH3-5″，6″) ;
13 C NMR
(CDCl3，100 MHz)δ:181. 1(C-4) ，159. 7(C-7) ，
157. 4(C-5) ，156. 9(C-8a) ，156. 1(C-4) ，152. 7(C-
2) ，130. 4(C-2，6) ，128. 3(C-3″) ，123. 7(C-3) ，
122. 9(C-1) ，115. 7(C-3，5) ，115. 5(C-4″) ，106. 1
(C-4a) ，105. 7(C-6) ，95. 0(C-8) ，78. 2(C-2″) ，28. 4
(C-5″，6″). It was identified as alpinumisoflavone by
comparison of the physical and spectral data with the
reported data［11］.
Compound 6 Yellow crystal，C20 H16 O5，
1H NMR
(CDCl3，400 MHz)δ:12. 92(1H，s，OH-5) ，7. 89
(1H，s，H-2) ，7. 40(2H，d，J = 7. 6 Hz，H-2，6) ，
6. 91(2H，d，J = 7. 6 Hz，H-3，5) ，6. 68(1H，d，J =
10. 0 Hz，H-4″) ，6. 29(1H，s，H-6) ，5. 59(1H，d，J =
10. 0 Hz，H-3″) ，1. 47(6H，s，CH3-5″，6″) ;
13 C NMR
(CDCl3，100 MHz)δ:180. 9(C-4) ，162. 3(C-5) ，
159. 6(C-7) ，155. 8(C-4) ，152. 3(C-2) ，152. 2(C-
8a) ，130. 4(C-2，6) ，127. 5(C-3″) ，123. 6(C-3) ，
123. 1(C-1) ，115. 5(C-3，5) ，114. 6(C-4″) ，106. 0
(C-4a) ，101. 1(C-8) ，100. 4(C-6) ，78. 1(C-2″) ，
28. 2(C-5″，6″). It was identified as derrone by com-
parison of the physical and spectral data with the repor-
ted data［12］.
Compound 7 Pale yellow oil C11 H10 O4，
1H NMR
(DMSO，400 MHz) ，δ:11. 81(1H，br s，OH-8) ，10. 07
(1H，s，-CHO) ，8. 05(1H，d，J = 8. 8 Hz，H-6) ，7. 07
(1H，d，J = 8. 8 Hz，H-7) ，4. 82(1H，m，H-3) ，3. 87
(1H，dd，J = 17. 6 Hz，2. 8 Hz，Ha-4) ，3. 06 (1H，
dd，J = 15. 2 Hz，12. 0 Hz，Hb-4) ，1. 46(3H，d，J = 6. 4
Hz，-CH3) ;
13C NMR(DMSO，100 MHz) ，δ:190. 7(-
CHO) ，168. 8(C-1) ，165. 1(C-8) ，144. 2(C-4a) ，
138. 6(C-6) ，124. 3(C-5) ，116. 1(C-7) ，108. 9(C-
8a) ，75. 2(C-3) ，29. 7(C-4) ，20. 2(-CH3). It was i-
dentified as(3R)-5-formylmellein by comparison of the
physical and spectral data with the reported data［13］.
Compound 8 Yellow oil C10 H10 O4，
1H NMR
(CDCl3，400 MHz) ，δ:11. 0(1H，s，OH-7) ，7. 55
(1H，t，J = 8. 0 Hz，H-5) ，7. 02(2H，t，J = 8. 0 Hz，H-
4，H-6) ，4. 62(1H，m，H-3) ，4. 61(1H，m，H-1) ，
1. 53(3H，d，J = 5. 6 Hz，H-2) ;13C NMR(CDCl3，100
MHz) ，δ:168. 4(C-1) ，162. 0(C-7) ，141. 1(C-9) ，
136. 9(C-5) ，117. 9(C-6) ，116. 1(C-4) ，106. 6(C-
8) ，79. 9(C-1) ，69. 2(C-3) ，17. 9(C-2). It was i-
dentified as 3β-(1β-hydroxyethyl)-7-hydroxy-1-iso-
benzofuranone by comparison of the physical and spec-
tral data with the reported data［14］.
Compound 9 White crystal C11 H12 O3，
1H NMR
(CDCl3，400 MHz) ，δ:7. 63(1H，d，J = 16. 0 Hz，H-
7) ，7. 42(2H，d，J = 8. 0 Hz，H-2，H-6) ，6. 84(2H，d，
626 Nat Prod Res Dev Vol. 25
J = 8. 0 Hz，H-3，H-5) ，6. 30(1H，d，J = 16. 0 Hz，H-
8) ，5. 50(1H，br s，OH-3) ，4. 25(2H，q，J = 7. 2 Hz，
H-1) ，1. 33(3H，t，J = 7. 2 Hz，H-2) ;13 C NMR
(CDCl3，100 MHz) ，δ:167. 5(C-9) ，157. 6(C-4) ，
144. 3(C-7) ，129. 9(C-2，C-6) ，127. 3(C-1) ，115. 8
(C-3，C-5) ，115. 7(C-8) ，60. 4(C-1) ，14. 3(C-2)
. It was identified as trans-p-hydroxycinnamic acid eth-
yl ester by comparison of the physical and spectral data
with the reported data［15］.
Compound 10 White needles crystal;It was charac-
terized by comparing it with authentic sample on
TLC. It was identified as β-sitosterol［16］.
Compound 11 White amorphous powder;It was
characterized by comparing it with authentic sample on
TLC. It was identified as β-daucosterol［17］.
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