全 文 ：天然产物研究与开发 Nat Prod ResDev 2006 , 18:411-414
文章编号:1001-6880(2006)03-0411-04
Received July 13, 2005;Accepted August 30, 2005
＊Corresponding author Tel:86-28-85225401;E-mail:zhanggl@cib.ac.cn
钮子瓜化学成分研究
李洪娟1 , 2 ,罗应刚1 ,何志恒1 , 2 ,张国林1＊
(1 中国科学院成都生物研究所 ,成都 610041;2 中国科学院研究生院 ,北京 100039)
摘 要:从民间药物钮子瓜全草 95%乙醇提取物中首次分离得到 14 个化合物 , 应用波谱方法及与已知品对照
的手段鉴定它们为(2S , 3S , 4R , 10E)-2-[(2R)-2-羟基二十四烷酰氨基] -10-十八烷-1 , 3 , 4-三醇(1)、(2S , 3S , 4R)-
2-二十四烷酰胺基-十八烷-1 , 3 , 4-三醇(2)、胡萝卜苷(3)、swertish(4)、苯甲酸(5)、水杨酸(6)、loliolide(7)、胸腺嘧
啶(8)、尿嘧啶(9)、(23Z)-9 , 19-环阿尔廷-23-烯-3β , 25-二醇(10)、(20S , 22E , 24R)-5α, 8α-表二氧-麦角甾-6 , 22-二
烯-3β-醇(11)、十六烷酸-1-甘油酯(12)、大豆脑苷Ⅰ(13)、(22E , 24S)-24-甲基-5α-胆甾-7 , 22-二烯-3β , 5α, 6β-三醇
(14)。
关键词:钮子瓜;神经酰胺;甾体;swertish;loliolide
中图分类号:R284.2 文献标识码:A
Phytochemical Study on Zehneria maysorensis
LI Hong-juan1 ,2 ,LUO Ying-gang1 ,HE Zhi-heng1 ,2 ,ZHANG Guo-lin1＊
(1.Chengdu Institute of Biology , Chinese Academy of Sciences , Chengdu 610041 , China;
2.Graduate School of Chinese Academy of Sciences , Beijing 100039 , China)
Abstract:Fourteen compounds were isolated from the 95% ethanol extract of the whole plants of folk medicinal herb Zehneria
maysorensis for the first time.On the basis of spectral data or comparison with authentic samples , they were characterized to be
(2S , 3S , 4R , 10E)-2-[ (2R)-2-hydroxytetracosanoylamino] 10-octadecene-1 , 3 , 4-triol(1),(2S , 3S , 4R)-2-tetracosanoyla-
mino-1 , 3 , 4-octadecanetriol(2), daucosterol(3), swertish(4), benzoic acid(5), salicylic acid(6), loliolide(7), thymine(8),
uracil(9),(23Z)-9 , 19-cycloart-23-ene-3β , 25-diol(10),(20S , 22E , 24R)-5α, 8α-epidioxy-ergosta-6 , 22-diene-3β-ol(11),
2 , 3-dihydroxypropyl hexadecoate(12), soya-cerebroside(13)and (22E , 24S)-24-methyl-5α-cholesta-7 , 22-diene-3β , 5α, 6β-
triol(14).
Key words:Zehneria maysorensis;ceramides;steroids;swertish;loliolide
Zehneria maysorensis(Cucurbitaceae), a folk medicinal
herb , is mainly distributed in Africa and tropical and sub-
tropical area of Asia[ 1] .The whole plants were used for
the treatment of cystitis and headache[ 2] .The chemical
constituents of this genus were not reported.In this study ,
fourteen compounds were isolated from the aqueous
ethanolic extract of the whole plants.They were elucidated
to be (2S , 3S , 4R , 10E)-2-[(2R)-2-hydroxytetra-
cosanoylamino] -10-octadecene-1 ,3 ,4-triol(1),(2S , 3S ,
4R)-2-tetracosanoylamino-1 , 3 , 4-octadecanetriol (2),
daucosterol(3), swertish(4), benzoic acid(5), salicylic
acid(6), loliolide(7), thymine(8), uracil(9),(23Z)-9 ,
19-cycloart-23-ene-3β ,25-diol(10), (20S , 22E , 24R)-
5α,8α-epidioxy-ergosta-6 , 22-diene-3β-ol(11), 2 , 3-dihy-
droxy propyl hexadecoate(12), soya-cerebroside(13)and
(22E , 24S)-24-methyl-5α-cholesta-7 , 22-diene-3β , 5α,
6β-triol(14)on the basis of spectral data or comparison
with authentic samples.
Fig.1 Compounds isolated from Z.maysorensis
Results and Discussion
Compound 4 was isolated from the ethyl acetate-soluble
fraction of the 95%EtOH extract.The IR band at 1653
cm-1 and the 13C NMR signal atδ181.9 or 182.3 sug-
gested the presence of conjugated carbonyl group.The off-
yellow coloration of the solution of 4 , the yellowish orange
visualization when reacted with Mg-HCl(36.5%)and UV
absorption atλmax273 and 333 nm suggest that 4 may be a
flavone.The 1H and 13C NMR signals showed that 4 was a
mixture(Table 1).Unfortunately , we can not separate
them through column chromatography , thin layer chro-
matography , and even high performance liquid chromatog-
raphy.
The structure of 4 was established by 2-D NMR experi-
ments including 1H-1H COSY , HSQC , and HMBC(Fig.
1).It is a C-glycoside of flavone ,which gives two series of
NMR signals(Table 1)due to rotational isomers with a
molar ratio of 1:1 concluded from the integral in1H NMR
spectrum.It is reported that 6 or 8-C-glycoside of flavone ,
such as Spinosin , displayed the same NMR phenomenon
because of the rotational barrier between 7-OMe and the
glycosyl moiety[ 3-5] .
Experimental
General
Melting points were determined on an X-6 melting point
apparatus and are uncorrected.IR spectra and optical ro-
tations were obtained on a Perkin Elmer spectrum one FT-
IR spectrometer(KBr disc)and a Perkin Elmer 341 auto-
matic polarimeter , respectively.ESIMS and APCIMS spec-
tra were obtained on Finnigan-LCQDECA mass spectrome-
ter.NMR spectra(1H:600 MHz;13 C:150 MHz)were
recorded on a Bruker Avance spectrometer with TMS as
internal standard.Silica gel H(HA:160 ～ 200 mesh;HB:
200 ～ 300 mesh),MCI gel and RP-18 silica gel were used
for column chromatography(CC).The plates for thin layer
chromatography(TLC)were precoated with Silica gel GF254(0 ～ 40μm)and activated at 110°C for 2 hours.Spots on
TLC plates were visualized by spraying 10%ethanol solu-
tion of phosphomolybdic acid.
Plant material
The whole plants of Z .maysorensis were collected in
Xishuangbanna of Yunnan Province in December 2001
and identified by Prof.Fading Fu in Chengdu Institute of
Biology , the Chinese Academy of Sciences(CAS).A
voucher specimen(GF-106)was deposited at the Herbari-
um of Chengdu Institute of Biology ,CAS.
Extraction and isolation
The air-dried and powdered whole plants(5.0 kg)were
soaked with 95%EtOH(20 L×5 , each 7 days)at room
temperature.The combined extract was evaporated under
reduced pressure to give 330 g residue , which was sus-
pended in H2O(2 L)and portioned successively with
petroleum ether(2 L ×5), EtOAc(2 L×5)and n-BuOH
(2 L×5)to give corresponding fractions A(144 g),B(19
g)and C(20 g).
Fraction B was subjected to CC on silica gel(600 g ,HA)
eluted with petroleum ether-acetone(50:1 , 40:1 , 30:1 ,
20:1 ,10:1 ,5:1 ,2:1 , each 2000 mL)and CHCl3-CH3OH
(30:1 ,20:1 ,10:1 , 5:1 ,0:1 , each 2000 mL)to give 10
fractions B1-B10.1(20 mg), 2(4 mg), 3(20 mg)and 4
(15 mg)were precipitated successively from B2 , B6 , B9
and B10.B3 was separated by CC on silica gel(7 g ,HB)
eluted with petroleum ether-acetone(20:1)to yield 5(4
mg).B4 was separated by CC over silica gel(35 g ,HB)e-
luted with petroleum ether-acetone(20:1)to afford 6(62
mg).B5 was subjected to CC on silica gel(50 g ,HB)elut-
ed with petroleum ether-acetone(10:1)to give 7(15mg).
B7 was subjected to CC on silica gel(150 g , HB)eluted
with CHCl3-CH3OH(40:1 ,30:1 , 15:1 , 10:1 , each 1000
mL)to give 8(2 mg).B8was subjected to CC on silica gel
(150 g ,HB)eluted with CHCl3-CH3OH(30:1 ,20:1 , 15:
1 ,10:1 , each 1000 mL)to give 9(10 mg).
Fraction A was subjected to CC on silica gel(1300 g ,HA)
eluted with petroleum ether-acetone(100:1 , 50:1 , 40:1 ,
30:1 ,20:1 , 10:1 , 5:1 , 2:1 , each 2000 mL)and CHCl3-
CH3OH(10:1 , 5:1 , 0:1 , each 2000 mL)to give 8 frac-
tions A1-A8.A5 was subjected to CC on MCI gel eluted
with CH3OH-H2O(80%, 85%, 90%, 100%, each 3000
mL)to give fractions A5A-C.A5Bwas subjected to CC on
silica gel(150 g ,HB)eluted with petroleum ether-acetone
(10:1)to give 10(5 mg).A6was subjected to CC on MCI
gel eluted with CH3OH-H2O(80%, 85%, 90%, 100%,
each 3000 mL)to give fractions A6A-C.11(4 mg)and 12
(70 mg)were obtained from A6B separated by CC on sili-
ca gel(25 g ,HB)eluted with petroleum ether acetone(10:
1 ,8:1 , 5:1 , each 300 mL).A8 was subjected to CC on
MCI gel eluted by CH3OH-H2O(80%, 85%, 90%,
100%, each 3000 ml)to give fractions A8A and B.13(20
mg)and 14(3 mg)were obtained from A8A separated by
CC on silica gel(100 g ,HB)eluted with CHCl3-CH3OH
(30:1 ,20:1 ,15:1 ,10:1 , each 300 mL).
Structure Identification
(2S , 3S , 4R , 10E)-2-[ (2R)-2-Hydroxytetracosanoy
lamino]-10-octadecene-1 , 3 , 4-triol(1) White amor-
phous power(acetone),mp.138 ～ 139 ℃,[α] 20D +9.2 ℃
(c 0.61 , pyridine);ESIMS(negative mode)m/z:680
[ M-H]-;IRυmax cm-1:3339 , 3221 , 2919 , 2850 , 1622 ,
1545 ,1476 ,1023;1H NMR(C5D5N):δ8.60(1H , d , J =
8.9Hz , NH), 5.54(1H , dt , J =15.3 , 6.3 Hz , H-10),
412 Nat Prod ResDev Vol.18
5.48(1H ,dt , J =15.3 ,6.3 Hz ,H-11),5.13(1H , dd , J
=8.5 , 4.3 Hz , H-2), 4.62(1H , m , H-2′), 4.52 and
4.43(each 1H , dd , J =10.7 , 4.9 Hz ,H-1), 4.36(1H ,
m ,H-3),4.29(1H ,m ,H-4), 2.12 ～ 2.30(3H ,m), 1.94
～ 2.05(4H , m), 1.67 ～ 1.80(3H , m), 1.31 ～ 1.45
(5H ,m), 1.24 ～ 1.29(53H , m), 0.85(6H , t , J =6.8
Hz , H-18 and H-24′);13C NMR(C5D5N):δ176.2(C-
1′),131.7(C-11), 131.5(C-10), 77.7(C-3), 73.7(C-
4),73.4(C-2′), 62.9(C-1), 53.8(C-2), 36.6(C-3′),
35.0(C-5),34.2(C-12), 33.8(C-9),30.4 ,30.5 ,30.7 ,
30.8 , 30.9 , 31.1 , 31.2(C-13-C-16 and C-5′-C-22′),
27.6(C-6), 26.7(C-4′), 23.8(C-23′and C-17), 15.1
(C-18 and C-24′).The mp., [ α] D , IR and NMR data
were in accordance with those reported[ 6] .
(2S , 3S , 4R)-2-Tetracosanoylamino-1 , 3 , 4-octade-
canetriol(2) White powder(acetone),mp.111 ～ 112
℃, [α] 20D +18.2 ℃(c 0.10 ,pyridine);ESI-MS(positive
mode)m/z:690 [M +Na] +;IRυmax cm-1:3434 , 2919 ,
2851 ,1735 ,1641 ,1546;1H NMR(C5D5N):8.56(1H , d ,
J =8.2 Hz , NH), 5.11(1H , m ,H-2), 4.50(2H , m , H-
1), 4.41(1H ,m ,H-3), 4.30(1H , m ,H-4), 2.46(2H , t ,
J =7.3 ,H-2′), 2.24(1H ,m ,H-5a),1.68 ～ 1.98(5H ,
m ,H-5b , H-6 and H-3′), 1.24-1.29(about 62H), 0.84
(6H , t , J =5.8 Hz ,H-18 ,H-24′);13C NMR(C5D5N):δ
173.1(C-1′),76.5(C-3),72.8(C-4),61.9(C-1), 53.5
(C-2), 36.6(C-2′), 33.7(C-5), 31.8(C-16 and C-
22′),29.4 ,29.5 ,29.6 ,29.7 ,29.8.29.9 ,30.0 ,30.1(C-
7-C-15 and C-4′-C-21′), 26.4(C-6), 26.2(C-3′), 22.7
(C-17 and C-23′), 14.0(C-18 and C-24′).The mp.,
[α] D , IR and NMR data were in accordance with those re-
ported[ 7] .
Swertish(4) Yellow powder(CH3OH), ESIMS(positive
mode)m/z:469 [ M+Na] + ,913 [ 2M +Na] +;IRυmax
cm-1:3430 , 2925 , 1653 , 1607 , 1567 , 1491 , 1450 , 1352;
UVλMeOH+NaOMemax :273 and 333 nm ,UVλMeoHmax :273 and 393
nm;1H NMR and 13C NMR data see Table 1.The IR ,UV
and NMR data were in agreement with those of swer-
tish[ 3] .
Table 1 NMR data of compound 4 in DMSO-d6
No. δC δH δC δH
2 163.7 163.8 - -
3 103.0 6.84(s) 103.0 6.85(s)
4 181.9 - 182.3 -
5 159.5 13.48(-OH) 160.2 13.50(-OH)
6 109.6 - 109.7 -
7 164.9 - 164.9 -
8 90.1 6.86(s) 91.0 6.88(s)
9 156.7 - 156.8 -
10 104.1 104.5 - -
1′ 121.0 - 121.0 -
2′, 6′ 128.5 7.98(2H , d ,
J =8.6 Hz) 128.5
7.98(2H , d ,
J=8.6Hz)
3′, 5′ 115.9 6.94(2H , d ,
J =8.6 Hz) 115.9
6.94(2H , d ,
J=8.6Hz)
4′ 161.3 10.40(-OH) 161.3 10.40(-OH)
1″ 72.5 4.57(1H , d ,
J =10.1 Hz) 72.8
4.59
(1H , d ,
J=9.8Hz)
2″ 69.6 3.99(m) 70.2 4.18(m)
3″ 79.0 3.17(m) 79.0 3.17(m)
4″ 70.8 3.07(m) 70.9 3.07(m)
5″ 81.7 3.17(m) 81.9 3.17(m)
6″ 61.7 3.68(m), 3.34(m) 61.7
3.68(m)
, 3.34(m)
7-OCH3 56.2 3.88(s) 56.5 3.90(s)
Loliolide(7) Colourless crystal(acetone), mp.146 ～
148 ℃,[α] 20D-99.2 ℃(c 0.66 , CHCl3);ESI-MS(posi-
tive mode)m/z:219 [ M +Na] + , ESI-MS(negative
mode)m/z:231 [ M +Cl ]-;IRυmax cm-1:3435 , 1733 ,
2977 ,2947 , 2924 , 2884 , 1621.1H NMR(CDCl3):δ5.70(1H , s ,H-7), 4.34(1H ,m ,H-3), 2.46 and 1.97(each
1H ,d , J =14.6 Hz , H-4), 1.78(3H , s , H-11), 1.78
(1H , dd , J =13.0 , 4.2 Hz , H-2a), 1.54(1H , dd , J =
14.6 ,3.8 Hz ,H-2b),1.47(3H , s ,H-9),1.27(3H , s ,H-
10);13C NMR(CDCl3):δ182.3(C-8), 171.8(C-6),
112.9(C-7),86.6(C-5), 66.9(C-3), 47.3(C-2), 45.6
(C-4), 35.9(C-1), 30.6(C-9), 27.0(C-11), 26.5(C-
10).Its mp., [α] D , IR and NMR data were in agreement
with those of loliolide[ 8] .
Thymine(8) Yellow powder(CH3OH),mp.>300 ℃;
IRυmaxcm-1:3213 ,3063 ,1731 ,1675 , 1213;1H NMR(DM-
SO-d6):δ11.03(1H , s ,H-1),10.61(1H , s ,H-3),7.26
(1H , s , H-6), 1.73(3H , s ,-CH3);13C NMR(DMSO-
d6):δ165.4(C-4), 151.9(C-2), 138.2(C-6), 108.1
(C-5),12.3(-CH3).The mp., IR and NMR data were i-
dentical to those of thymine[ 9] .
Uracil(9) Yellow powder(CH3OH), mp.>300 ℃;
ESI-MS(negative mode)m/z:111 [ M-H]-;IRυmax cm-1:
3435 ,3114 , 1733 , 1714 , 1670 , 1643 , 1452 , 1418 , 1234;
1H NMR(DMSO-d6):δ11.04(1H , s ,H-1), 10.84(1H ,
s ,H-3),7.40(1H , d , J =7.6 Hz ,H-6),5.45(1H , d , J
=7.9 Hz ,H-5);13C NMR(DMSO-d6):δ164.8(C-4),
152.0(C-2), 142.6(C-6), 100.7(C-5).The m.p., IR
and NMR data were equal to those of uracil[ 9] .
(23Z)-9 , 19-Cycloart-23-ene-3β , 25-diol (10)
Colourless needles(acetone), mp.202 ～ 204 ℃, [α] 20D
+42.1 ℃(c 0.1 , CHCl3);1H NMR(CDCl3):δ5.60(2H ,m ,H-23 and H-24),3.28(1H ,m ,H-3),1.30(3H ,
s ,H-26), 1.30(3H , s ,H-27), 0.97(3H , s , H-18), 0.97
413Vol.18 LI Hong-juan et al:Phytochemical Study on Zehneria maysoensis
(3H , s ,H-29),0.88(3H , s ,H-28), 0.86(3H ,d , J =6.6
Hz ,H-21),0.81(3H , s ,H-30), 0.55 , 0.34(each 1H , d ,
J =3.8 Hz ,H-19);13C NMR(CDCl3):δ139.4(C-23),
125.6(C-24), 78.8(C-3), 70.7(C-25), 52.0(C-17),
48.8(C-14),48.0(C-8),47.1(C-5), 45.3(C-13), 40.5
(C-4),39.0(C-22),36.4(C-20), 35.6(C-12),32.8(C-
15), 32.0(C-1), 30.4(C-2), 30.0(C-26 and C-27),
29.9(C-19), 28.1(C-7), 26.4(C-16), 26.1(C-11),
26.0(C-10),25.4(C-30),21.1(C-6), 20.0(C-9), 19.3
(C-28), 18.3(C-21), 18.1(C-18), 14.0(C-29).The
mp.,[α] D and NMR data were equal to those of report-
ed
[ 10] .
2 ,3-Dihydroxypropyl hexadecoate(12) White powder
(acetone), EI-MS m/z(%):330 [ M+] (0.12), 299
(11.4),270(6.4),239(36.2),134(44.3), 112(26.4),
98(79.4), 43(100.0);IRυmax cm-1:3436 , 2931 , 2870 ,
1635 ,1100;1H NMR(CDCl3):δ4.21(1H ,dd , J =11.9 ,
4.6 Hz ,H-1′a), 4.15(1H , dd , J =11.6 ,6.1 Hz ,H-1′
b), 3.94(1H ,m , H-2′), 3.70(1H , dd , J = 11.8 , 4.6
Hz ,H-3″), 3.60(1H , dd , J =11.4 , 5.5 Hz , H-3′b),
2.50(1H , s , 2′-OH), 2.35(2H , t , J =7.5 Hz , H-2),
2.06(1H , s , 3′-OH), 1.64(2H , m , H-3), 1.29(24H ,
m),0.88(3H , t , J = 6.9 Hz , H-16).The EI-MS and
NMR data were equal to those reported[ 11] .
Soya-cerebroside(13) White powder(CH3OH), mp.
194 ～ 195 ℃, [α] 20D +8.7 ℃(c 0.72 , CH3OH );ESIMS
(positive mode)m/z:736 [ M +Na ] + , 752 [ M +
K] +;1H NMR(CD3OD):δ5.73(1H ,brd , J =15.4 Hz ,
H-5), 5.48(1H , dd , J =15.4 Hz , 7.5 Hz , H-4), 5.43
(2H ,m ,H-8 and H-9),4.27(1H ,d , J =7.7 Hz ,H-1a),
4.12(2H , m , H-1b and H-3), 3.99(1H , m , H-2), 3.86
(1H ,d , J =11.4 Hz ,H-2′),2.07(4H , brs ,H-6 and H-
7),1.98(2H ,m ,H-10),1.70 and 1.56(each 1H ,m ,H-
3′),1.40(2H ,m ,H-4′), 0.90(6H , t , J =7.0 Hz ,H-16′
andH-18);13C NMR(CD3OD):δ175.8(C-1′), 133.0(C-5),130.6(C-9),129.8(C-4),129.2(C-8),103.3 ,
76.6 , 76.6 , 73.6 , 70.2 and 61.3(glc), 71.7(C-2′),
71.5(C-3), 68.3(C-1), 53.3(C-2), 34.4(C-3′), 32.3
(C-6),32.2(C-10), 31.7(C-7), 28.9-29.4(C-11-C-16
and C-5′-C-14′), 24.8(C-4′), 22.3(C-17), 22.3(C-
15′), 13.0(C-18), 13.0(C-16′).The mp., [ α] D and
NMR data were in accordance with those of soya-cerebro-
side[ 12] .
(22E , 24S )-24-Methyl-5α-cholesta-7 ,22-diene-3β ,
5α,6β-triol(14) Colourless needles(acetone),mp.246
248 ℃, [α] 20D-29.8 ℃(c 0.1 ,CHCl3);ESIMS(positive
mode)m/z:453 [ M+Na] +;1H NMR(CDCl3):δ5.36(1H ,m ,H-7),5.23(1H ,dd , J =15.1 , 7.2 Hz ,H-23),
5.17(1H ,dd , J =15.2 ,8.4 Hz ,H-22),4.08(1H ,m ,H-
3),3.62(1H , m ,H-6), 2.14(1H , d , J =11.6 Hz , H-
4a),1.78(1H ,dd , J =13.1 ,2.8 Hz ,H-4b),1.09(3H ,
s ,H-19),1.02(3H ,d , J =6.7 Hz ,H-21), 0.92(3H ,d ,
J =6.8 Hz ,H-28),0.84 and 0.82(each 3H , d , J =6.8
Hz ,H-26 and H-27), 0.59(3H , s ,H-18);13C NMR(CD-
Cl3):δ144.0(C-8),135.4(C-22),132.2(C-23), 117.5
(C-7), 75.9(C-5), 73.7(C-6), 67.7(C-3), 56.0(C-
17), 54.7(C-14), 43.8(C-13), 43.5(C-9), 42.8(C-
24), 40.4(C-20), 39.5(C-4), 39.2(C-12), 37.1(C-
10),33.0(C-25),32.9(C-1),30.9(C-2),27.9(C-16),
22.9(C-11), 22.0(C-15), 21.1(C-21), 19.9(C-26),
19.6(C-27), 18.8(C-19), 17.5(C-28), 12.3(C-18).
The mp.,[ α] D andNMR data were equal to those report-
ed[ 13] .
Compounds 3 ,5 ,6 ,11were identified as daucosterol ,ben-
zoic acid , salicylic acid ,(20S , 22E , 24R)-5α, 8α-epid-
ioxy-ergosta-6 ,22-diene-3β-ol by comparing them with au-
thentic samples on TLC and by co-mp..
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