全 文 ：应用与环境生物学报　 2006, 12(1):30 ～ 33 　 　
Chin J A pp lEnviron B io l=ISSN 1006-687X 　 2006-02-25
　
Chem ical Study onPoikilospermum naucleiforum
ZHANG A ilian
1, 2, 3＆ ZHANG Guo lin1*
(1Chengdu Institute of B io logy , 2Chengdu Institute o fOrgan icChem istry , Ch inese Academ y of Sciences, Chengdu 610041, Ch ina)
(3GraduateUn iversity of Ch inese Academy of Sciences, Bei jing 100039, C hina)
Abstract　F rom the stem s o fPoik ilospermum naucleiforum , ten com pounds, u rso lic acid(1), 2α, 3β, 19α-trihydroxy-u rs-12-
ene-28-oic ac id (2), lupeo l(3), β-sito stero l(4), β-daucostero l(5), emod in 8-O-β-D-g lucopy ranoside (6), 5α, 8α-ep id-
ioxy-(22E , 24R)-ergosta-6, 22-d iene-3β-ol(7), (2S , 3S , 4R , 8E)-2N-[ (2′R)-2′-hydroxy tetraco sanoy l] -1, 3, 4-trihydroxy-8-
octadecene (8), 1-O-β-D-glucopy rano sy l-(2S, 3S , 4R , 8Z)-2N-[ (2′R)-2′-hydroxy te traco sanoy l] -3, 4-dihydroxy-8-octadecene
(9) and 1-O-β-D-g lucopy rano sy l-(2S, 3S , 4R , 8E)-2N-[ (2′R)-2′-hyd roxy te tracosanoy l] -3, 4-dihydroxy-8-octadecene (10),
w ere isola ted. Theyw ere characterized by spec tra l ev idence or by comparing them w ith authentic sam ples. F ig 1, Tab 1, Ref 9
Keywords　Poikilosperm um naucleiforum;ceram ide;cerebroside
CLC　Q949. 737. 506
锥头麻的化学成分研究
张爱莲 1, 2, 3 　张国林 1*
(1中国科学院成都生物研究所;2中国科学院成都有机化学研究所　成都　610041)
(3中国科学院研究生院　北京　 100039)
摘　要　从锥头麻枝叶中分离到 10个化合物:熊果酸 (1)、 2α, 3β, 19α-三羟基-12-烯-28-乌苏酸 (2)、羽扇豆醇(3)、β-
谷甾醇(4)、β-胡萝卜苷 (5)、大黄素 8-O-β-D-吡喃葡萄糖苷 (6)、 5α, 8α-表二氧-(22E , 24R)-麦角甾-6, 22-二烯-3β-醇
(7)、(2S, 3S , 4R , 8E)-2-[ (2′R)-2′-羟基二十四烷酰氨基 ] -1, 3, 4-三羟基-8-十八烷烯 (8)、 1-O-β-D-吡喃葡萄糖-(2S ,
3S, 4R , 8Z)-2-[ (2′R)-2′-羟基二十四烷酰氨基 ] -3, 4-二羟基-8-十八烷烯(9)、 1-O-β-D-吡喃葡萄糖-(2S , 3S , 4R , 8E)-2-
[ (2′R)-2′-羟基二十四烷酰氨基 ] -3, 4-二羟基-8-十八烷烯(10), 其中化合物 9、10以混合物形式分离得到.应用波谱方
法及与已知品对照的手段鉴定了它们的结构. 图 1表 1参 9
关键词　锥头麻;神经酰胺;脑苷脂
CLC　Q949. 737. 506
　　Poik ilospermum (Ur ticaceae) consists of about 20 spec ie s in
the wo rld and its tw o species(P. naucleiflorum , P. lanceola tum)
are found in China. P. naucleiforum Roxb. ex L ind.l m ainly oc-
curs in China, Nepa l, India, Burm a, Tha iland, Kam puchea and
V ietnam [ 1, 2] . The chem ica l constituents o f this genus we re no t re-
ported befo re.
In th is study, ten com pounds we re ob ta ined from the 95%
e thano lic ex trac t o fP. naucleiforum stem s. On the basis o f spectra l
ev idence o r comparison of them w ith authentic samp les, they w ere
identified as urso lic acid (1), 2α, 3β, 19α-trihydroxy-urs-12-ene-
28-o ic ac id (2), lupeo l (3), β-sitostero l (4), β-dauco ste ro l
(5), em od in 8-O-β-D-g lucopyranoside (6), 5α, 8α-epidioxy-
(22E , 24R)-ergosta-6, 22-diene-3β-o l(7), (2S , 3S , 4R , 8E)-2N-
[ (2′R)-2′-hyd roxy te tracosanoy l] -1, 3, 4-trihydroxy-8-octadecene
(8), 1-O-β-D-g lucopy rano sy l-(2S , 3S , 4R , 8Z )-2N-[ (2′R)-2′-
hyd roxy te tracosanoy l] -3, 4-dihydroxy-8-oc tadecene (9) and 1-O-
β-D-g lucopyranosy l-(2S , 3S , 4R , 8E)-2N-[ (2′R)-2′-hyd roxy te tra-
cosanoy l] -3, 4-d ihydroxy-8-oc tadecene (10). Am ong them , com-
pounds 9 and 10 we re obtained as m ix ture s. F ig. 1 show s the
Received:2005-03-24　　A ccepted:2005-05-25
*C orresponding au thor(E-m ail:zhanggl@ cib. ac. cn)
structure o f the above chem icals.
1　Experiment
1. 1　General expermi enta l procedures
M elting po ints w ere determ ined using an XRC-1 me lting po in t
appa ra tus(Sichuan University Sc ience Instruments Factory) and
unco rrected. IR spec traw ere obta ined on a Perk in E lm er spectrum
one FT-IR spec trom eter (KB r d isc). Op tical ro tations w ere de te r-
m ined w ith a Perkin E lm er 341 autom atic po la rim ete r. M ass spec-
tra we re obtained on F inngen-LCQDECA m ass spectrom e te r (ES IMS
o rAPC IM S). NM R spec tra we re recorded on Bruke rAdvance 600
(or Varianuni ty Inova 400) spec trome terw ith TM S as in te rnal stand-
a rd. Silica gel H (Qingdao H aiyang Chem ica l Co. , L td. , when
no tm en tioned, silica ge l w ith 160 ～ 200 m esh w as used. ), MC I
ge l(CHP 20P, 75 ～ 150 μ, M itsub ish i Chem ica lCo rpo ra tion, Ja-
pan) and RP-18 silica ge l (P repex 40 ～ 63 μm , Phenomenex)
w ere used for co lum n chrom atography. Silica ge l GF254 (0 ～ 40
μm , Qingdao Ha iy ang Chem ical Co. , L td. ) w as used for TLC
p la tes, w hich w e re activa ted at 110℃ fo r2 h. TLC w as visua lized
by spray ing an iline-phtha lic acid solution (0. 93 g aniline and
1. 66 g ph thalic acid in 100 m L n-bu tanol), 10% (w) ethanol so-
lu tion o f phosphom o lybdic ac id and 5% (w) FeC l3 aqueous so lu-
tion w ith sm a ll amount o fHC l(aq. ). A ll so lven ts inc luding pe tro-
leum ethe r(60 ～ 90 ℃) w ere d istilled prior to use.
1. 2　P lantm aterial
The stem s of P. naucleiforum w ere co llec ted in Novem be r
1999 from X ishuangbanna, Yunnan, Ch ina. The plan t m ateria l
w as identified by P ro .f Cui Jingyun o f the X ishangbanna T ropica l
Botanical Garden, the Ch inese Academ y o f Sc ience s (CAS). A
voucher specim en(No:GF-125) w as deposited a t X ishangbanna
T ropica l Botanical Garden, CAS.
Fig. 1　 S tru ctures of com pounds f rom P. naucleiforum
1. 3　Extraction and separation
The air-dried and pow de red stem s o fP. naucleiforum (5. 0
kg) w ere soaked w ith 25 L 95% e thano l for 3 tim es(eve ry tim e 7
day s) at room tem pe ra ture. The e thano l wa s evaporated under re-
duced pressu re to g ive 80 g residue, wh ich w as disso lved in H2O
(2 L) and ex tracted successive ly w ith E tOAc (2 L × 5) and n-
butano l(2 L × 5) to g ive correspond ing frac tions A (48 g) and
B (25 g).
F rac tion B (25 g) was first sub jec ted to m acropo rous resin
co lumn (D
101
, pore size 13 ～ 14 nm , 26 ～ 60 mesh, ф 9 ×L 50
cm) to rem ove suga r by CH3CH2OH-H2O (0 ∶ 1, 1 ∶ 0, each
5 000 m L) and fraction B′(2 g) was y ielded. B′(2 g) and A
(48 g) w ere com bined and separa ted on silica ge l co lum n(ф 9 ×
L 30 cm , 1 kg), and grad iently e luted w ith pe tro leum ethe r-ace-
tone (100∶ 1, 50 ∶ 1, 20 ∶ 1, 5 ∶ 1, CH3OH, each 5 000
mL) to y ie ld sub frac tionsAA (19 g), AB (10 g), AC (2 g) and
AD (16 g). AB (10 g) was separa ted by silica ge l co lumn (ф 7
×L 16 cm , 300 g) e luted w ith pe tro leum e ther-ace tone (10 ∶
1) to y ie ld subfrac tions ABA-ABE. ABA (0. 5 g) was separated
by silica ge l co lum n(ф 4 ×L 8 cm , 200 ～ 300 mesh, 50 g) u-
sing pe tro leum e ther-acetone (30 ∶ 1) as so lven ts to g ive com-
pounds 3 (10 m g) and 7 (2 mg). The recry sta llization o f ABB
(1. 8 g) from CHC l3 gave compound 4 (500 mg). C om pound 1
(7 mg)w as iso la ted from ABC (2 g) by silica ge l co lum n(ф 4. 8
×L 22 cm, 200 g) e luted w ith CHC l3-CH3OH (30 ∶ 1). Com-
pound 2 (10 m g)w as y ie lded from ABD (0. 3 g) by silica ge l co l-
um n(ф 2. 5 × L 8 cm , 200 ～ 300 m esh, 30 g) e luted w ith
CHC l3-CH3OH (20 ∶ 1). AD (16 g) w as separated by silica ge l
co lumn (ф 7 ×L 26 cm , 500 g) e luted w ith CHC l3-CH3OH (10
∶ 1) to y ie ld subfractions ADA-ADD. Compounds 5 (300 m g)
and 8(36 m g) we re ob tained from ADB(2. 8 g) by silica ge l co l-
um n(ф5 ×L 11 cm , 200 ～ 300 m esh, 100 g) e lu ted w ith ch lo r-
o form-acetone (3 ∶ 1). Com pound 6 (3 mg) and the m ix ture of
compounds 9 and 10(90 mg) w ere iso la ted from ADC (2. 1 g) by
silica ge l co lumn (ф 5 ×L 20 cm, 200 ～ 300 m esh, 200 g) e lu-
ted w ith CHC l3-CH3OH (10 ∶ 1).
31　 1期 ZHANG Ailian et a l. :C hem ical S tudy onPo iki losperm um naucleiforum 　　
1. 4　Identification of sugars in compounds 6, 9 and
10
The samp les(6, 3 mg;9 and 10, 10 mg) we re dissolved in
2 m L 95% e thano l and 2 mL 2 m o l /L HC l was then added to the
so lution. The m ix tu re w as re fluxed for 2 hours at 90 ℃, and the
e thano l wa s evapo ra ted under reduced pressure. The aqueous
phase w as ex tracted w ith EtOAc. Suga rs w ere left a t the aqueous
phase.
The sugars ob ta ined from hydro lysis we re iden tified by com pa-
ring their TLC behav iou r w ith those of standa rd sam ples (S1 ∶
CHC l3 /CH3OH /H2O =8 ∶ 4∶ 1, S2∶ n-BuOH /CH3COCH3 /
H2O =4∶ 1 ∶ 1, S3∶ CHC l3 /CH3OH /H2O /HOAc =8∶ 4
∶ 1 ∶ 1. 4) and by the ir optica l ro tations.
2　Identification
Ursolic ac id (1):C30H48O 3 , wh ite am o rphous pow de r;R f
0. 45 (CHC l3-CH3OH 15 :1);ESIM S (negative m ode) m /z:
455 [ M-H] -;[ α] 20D +61. 3°(c 0. 10, E tOH) [ lit3[ α] 20D +62°
(c 0. 095, E tOH)] ;IRυKB rm ax cm - 1:3 435, 2 927, 2 871, 1 693,
1 636, 1 456, 1 387, 1 030, 997;1H NM R (400MH z, C5D5
N):δ1. 08 (3H , s), 1. 14(3H , d, J =5. 2 H z), 1. 18 (3H ,
s), 1. 20(3H, s), 1. 21 (3H , s), 1. 24(3H, s), 1. 43 (3H ,
d, J =6. 8 H z), 5. 69 (1H , s, 12-H), 3. 64 (1H , m , 3-H);
13C NM R (100MH z, C5D5N):δ38. 9(C-1), 28. 1 (C-2), 78.
1 (C-3), 39. 1 (C-4), 55. 8 (C-5), 18. 8(C-6), 33. 5(C-7),
39. 5 (C-8), 48. 0(C-9), 37. 4 (C-10), 17. 4 (C-11), 125. 6
(C-12), 139. 2(C-13), 42. 5(C-14), 28. 3(C-15), 24. 9(C-
16), 48. 1(C-17), 53. 5(C-18), 39. 9(C-19), 39. 4(C-21),
37. 3 (C-22), 28. 8(C-23), 15. 6(C-24), 16. 8 (C-25), 17. 5
(C-26), 23. 6(C-27), 179. 8(C-28), 23. 9(C-29), 21. 4(C-
30). The optica l rota tion and NMR da ta resemb le close ly to those
o f ursolic acid[ 3 , 4] .
2α, 3β , 19α-Tr ihydroxy urs-12-ene-28-oic ac id ( 2):
C30H48O 5 , white am orphous powder, R f 0. 25 (CHC l3-CH3OH 15
:1);ESIM S (nega tive mode) m /z:487 [ M-H] -;[ α] 20D +
18. 6°(c 1. 00, CH3OH) [ lit5[ α] 20D +20. 4°(c 1. 59, CH3OH)] ;
IRυKB rm ax cm - 1:3 436, 2 925, 2 868, 1 688, 1 640, 1 458,
1 378, 1 095, 970;1H NM R (400MH z, C5D5N):δ0. 92 (3H ,
s), 1. 00(3H , s), 1. 12(3H , s), 1. 13(3H , d, J =6. 8 H z,
30-H), 1. 28 (3H , s), 1. 40 (3H , s), 1. 66 (3H , s);13C
NMR (100MH z, C
5
D
5
N):δ42. 9 (C-1), 66. 1 (C-2), 79. 3
(C-3), 38. 8 (C-4), 48. 8 (C-5), 18. 6 (C-6), 33. 5 (C-7),
40. 6 (C-8), 47. 6(C-9), 38. 7 (C-10), 24. 1 (C-11), 128. 0
(C-12), 139. 9(C-13), 42. 2(C-14), 29. 4(C-15), 26. 4(C-
16), 48. 3(C-17), 54. 6(C-18), 72. 7(C-19), 42. 4(C-20),
27. 1 (C-21), 28. 5(C-22), 29. 2(C-23), 22. 3 (C-24), 16. 7
(C-25), 17. 3(C-26), 24. 6(C-27), 180. 6(C-28), 26. 9(C-
29), 16. 6(C-30). The optica l ro ta tion and 13C NMR data w ere
in ag reement w ith tho se of 2α, 3β, 19α-trihyd roxy u rs-12-ene-28-
o ic acid[ 5] .
Lupeol(3):C30H50O, white needles (CHC l3), m p 214 ～
216℃;The m ixed m e lting point o f 3 and au then tic samp le in the
sam e as that of authen tic sam ple w ere the same; Its TLC behav io r
w as the sam e as tha t of authentic sam ple(pe tro leum e the r-ace tone
10 ∶ 1, R f 0. 40;petro leum e ther-E tOAc 8∶ 1, R f 0. 40).
β-S itosterol(4):white needles (CHC l3), m p 139 ～ 142
℃;Them ixed m e lting po in t o f 4 and au thentic sam ple in the same
as that o f au thentic sam ple;The TLC behav ior o f 4 w as the same
as that o f authentic sam p le (pe troleum e ther-acetone 10 ∶ 1, R f
0. 30;pe tro leum e ther-E tOAc 8 ∶ 1, R
f
0. 20).
β-Daucosterol(5):w hite pow de r (CH3 OH);The m ixed
m e lting point o f 5 and au then tic samp le in the same as tha t of au-
thentic sam plew e re the same;The TLC behav io r o f 5 w as in con-
sistentw ith that o f au then tic sam ple(CHC l3-CH3OH 6∶ 1, R f 0.
45;CHC l3-CH3COCH3 1∶ 1, R f0. 10).
Em od in 8-O-β-D-g lucopyranoside(6):C
21
H
20
O
10
, ye llow
need le s(CH3OH);R f 0. 50 (CHC l3-CH3OH 5∶ 1);m p 186 ～
187℃;[ α] 20D -14. 6°(c 0. 14, CH3OH);IR υKB rm ax cm - 1:3 426,
1 676, 1 626, 1 596, 1 071;UV λMeOHm ax nm ( logε):222 (4. 59),
249sh(4. 19), 271sh (4. 38), 283 (4. 40), 420 (3. 94), 438
(3. 91);ES IMS (negative mode) m /z:431 [ M-H] - , ES IMS
(positivem ode) m /z:455 [ M +N a] +, 269 [ M-g lc-H] +;D-
g lucose w as obta ined by hydro ly sing 6 and identified by its TLC be-
haviour(S1:R f = 0. 21, S2:R f = 0. 53;S3:R f = 0. 30) and
op tical ro ta tion([ α] 20D +55. 2°, c 0. 12, H2O);1H NM R (600
MH z, DMSO-d6):δ13. 20(1H , s, 1-OH), 11. 33 (1H , s, 6-
OH), 7. 46(1H, s, 4-H), 7. 27(1H , s, 5-H), 7. 16 (1H , s,
2-H), 6. 99(1H, s, 7-H), 5. 04(1H, d, J =7. 2H z, 1′-H),
2. 40 (3H , s, CH
3
);13C NM R (150MH z, DMSO-d
6
):δ161. 8
(C-1), 115. 2 (C-1a), 124. 8(C-2), 147. 5(C-3), 119. 9(C-
4), 132. 8(C-4a), 109. 1 (C-5), 137. 2 (C-5a), 165. 0 (C-
6), 109. 2(C-7), 162. 4(C-8), 115. 2(C-8a), 187. 0(C-9),
182. 9(C-10), 101. 5 (C-1′), 73. 9 (C-2′), 77. 1(C-3′), 70.
1 (C-4′), 78. 0(C-5′), 61. 2(C-6′), 22. 1 (3-CH3). The UV
and NMR da taw ere in acco rdance w ith those of em odin 8-O-β-D-
g lucopy rano side[ 6] .
5α, 8α-Epid ioxy-( 22E , 24R )-ergosta-6, 22-d iene-3β-ol
(7):C28H44O3 , co lour less needles(ace tone);R f 0. 37 (petro le-
um e ther-acetone 3 :1);m p 177 ～ 179 ℃ ( lit7 182 ～ 184 ℃);
APC IM S (positive m ode) m /z:429 [ M +H ] +, 879 [ 2M +
Na] +;[ α] 20D -32. 6°(c 0. 10, CH3OH) [ lit7 [ α] 20D -34°(c 0. 6,
CHC l
3
)] ;IR υKB r
max
cm -1:3 429, 2 957, 2 927, 1 631, 1 457, 1
383, 1 076;1H NMR (600MH z, CDC l3):δ6. 51(1H , d, J =
8. 6 H z, 7-H), 6. 25 (1H, d, J = 8. 6 H z, 6-H), 5. 23 (1H ,
dd, J =15. 1, 7. 7 H z, 23-H), 5. 15(1H , dd, J =15. 1, 8. 4
H z, 22-H), 3. 98(1H , m , 3-H), 1. 00(3H , d, J =6. 5 H z),
0. 91 (3 H , d, J =6. 8 H z), 0. 89 (3H, s), 0. 83 (3H, d, J
=6. 8 H z), 0. 82 (3H , s), 0. 81(3H , d, J = 6. 6 H z);13C
NM R (150MH z, CDC l
3
):δ34. 9 (C-1), 30. 3 (C-2), 66. 7
(C-3), 37. 3 (C-4), 82. 3 (C-5), 135. 6 (C-6), 131. 0 (C-
7), 79. 6 (C-8), 51. 3 (C-9), 37. 2 (C-10), 23. 6 (C-11),
39. 6 (C-12), 44. 8(C-13), 51. 9 (C-14), 20. 8 (C-15), 28. 8
32 　　　　　　　　应 用与 环 境生 物学 报　　Chin J App lEnviron B io l　　　　　　　　　　　　　　 　　　12卷
(C-16), 56. 4(C-17), 13. 1(C-18), 18. 4(C-19), 39. 9 (C-
20), 21. 1 (C-21), 135. 4 (C-22), 132. 5 (C-23), 43. 0 (C-
24), 33. 3(C-25), 20. 1(C-26), 19. 8(C-27), 17. 8(C-28).
Them p, op tical ro tation and 13C NMR da ta we re in ag reem entw ith
those o f 5α, 8α-ep id ioxy-(22E , 24R)-ergo sta-6, 22-diene-3β-o l[ 7] .
(2S, 3S, 4R, 8E)-2N-[ (2′R)-2′-Hydroxytetracosanoyl] -
1, 3, 4-tr ihydroxy-8-oc tadecene (8):C42H83NO5 , w hite pow de r
(M eOH), R f 0. 50(CHC l3-CH3OH 10 ∶ 1);[ α] 20D +10. 5°(c
0. 20, CHC l3-CH3 OH 1 ∶ 1);ES IMS (negative mode) m /z:
680 [ M-H ] -; IR υKB rm ax cm -1:3 335, 2 918, 2 850, 1 623,
1 544, 1 467, 1 067, 1 022, 722;1H NMR (600MH z, C5D5
N):δ8. 60 (1H , d, J =8. 3 H z, NHCO), 5. 52 (1H , dd, J
=14. 8, 6. 0 H z, 9-H), 5. 48(1H , dd, J =14. 8, 6. 0 H z, 8-
H), 5. 12 (1H , m , 2-H), 4. 62 (1H, m , 2′-H), 4. 51 (1H ,
m , 1a-H), 4. 43 (1H , m , 1b-H), 4. 34 (1H , m , 3-H), 4. 28
(1H , m , 4-H), 2. 19 ～ 2. 21 (3H , m), 1. 94 ～ 2. 03 (5H , m),
1. 70 ～ 1. 71 (3H , m), 1. 30 (br. s), 1. 24 (b r. s), 0. 85
(6H , br s, H-18 and 24);13C NMR (150 MH z, C
5
D
5
N):δ
63. 1 (C-1), 54. 0(C-2), 77. 9(C-3), 74. 0(C-4), 34. 9(C-
5), 34. 1 (C-7), 131. 8 (C-8), 131. 9 (C-9), 34. 4 (C-10),
24. 1 (C-17), 15. 4 (C-18), 176. 3 (C-1′), 73. 5 (C-2′),
36. 8 (C-3′), 26. 9(C-4′), 27-35 (n CH2), 15. 4 (C-24′). 　
　
Tab le 1　NMR data of com pounds 9 and 10 in pyrid ine-d5
No. 1H (J in H z) 13C 1H-1H COSY
1
4. 68 (dd , 10. 8, 6. 8),
4. 49 (dd, 10. 8, 4. 4) 70. 8 H-2, H-3
2 5. 27 (m) 52. 2 H-1, H-3, NH
3 4. 26 (dd, 7. 2, 4. 8) 76. 3 H-2, H-4
4 4. 18 (m) 72. 9 H-3, H-5
5
1. 96～ 2. 06 (m),
2. 18～ 2. 27 (m) 34. 3 H-4, H-6
6 1. 65～ 1. 73 (m) 27. 2 H-5, H-8
7 1. 95～ 2. 06 (m) 28. 4a 33. 7b H-6, H-8
8, 9 5. 39～ 5. 54 (m)
131. 3a ,
131. 1b ,
130. 9a , 130. 6b
H-7, H-10
10 1. 83～ 1. 91(m) 28. 0a, 33. 4b H-9
11～ 17 1. 25 (br. s) 23. 4 ～ 34. 4
18 0. 83 ( t, 6. 0) 14. 7
1′ 176. 1
2′ 4. 56 (dd, 7. 6, 3. 6) 72. 9 H-3′
3′ 1. 96～ 2. 06 (m),
2. 13～ 2. 22 (m) 36. 0 H-2′
4′～ 23′ 1. 25 (br. s) 23. 4 ～ 34. 4
24′ 0. 83 ( t, 6. 0) 14. 7
1″ 4. 92 (d, 7. 2) 105. 9 H-2″
2″ 3. 97 (m) 75. 5 H-1″, H-3″
3″ 4. 15 (m) 78. 9 H-2″, H-4″
4″ 4. 18 (m) 72. 0 H-3″, H-5″
5″ 3. 84 (m) 78. 8 H-4″, H-6″
6″ 4. 30 (dd, 12. 0, 5. 2),
4. 45 (dd, 12. 0, 2. 0) 63. 1 H-5″
NH 8. 56 (d, 8. 4) H-2
　 a from com pound 9, b from com pound 10
The IR and NM R data we re equa l to those of(2S , 3S , 4R , 8E)-1,
3, 4-trihydroxy-2N-[ ( 2′R )-2′-hydroxyte tracosanoy l] -8-octade-
cene[ 8] .
　　1-O-β-D-G lucopyranosyl-(2S, 3S, 4R, 8Z /E)-2N-[ (2′R)-
2′-hydroxytetracosanoyl] -3, 4-d ihydroxy-8-octadecene ( 9,
10):C
48
H
93
NO
10
, white pow de r(M eOH), R
f
0. 30(CHC l
3
-CH
3
OH 6 ∶ 1);ES IMS (negative m ode) m /z:842 [ M-H] -;ES-
IM S (po sitive mode) m /z:866 [ M +H] +, 1709 [ 2M +H] +;
IRυKB rm ax cm - 1:1 636, 1 535 (NHCO), 3 382 (OH), 2 921,
2 851(C-H), 718 (n CH2), 1 078, 1 043 (C-O);EIMS (20
eV):646 [ M-C6H13O7 ] +(12. 1), 632 [ M-C7H15O7 ] +(5),
225 [ C14H27 CHOH] +(16. 7), 618 [ M-C14H27 CHOH] +(7),
338 [ CH3(CH2)21CHOH] +(34. 8), 281 (18. 3), 262 [ sphin-
go id-(H2O)2] +(39), 225 (16. 7), 112 (18. 1), 98 (17. 9);
D-g lucose w as obta ined by hydro ly sing the m ix tures of 9 and 10
and iden tified by its TLC (S1:R f=0. 21, S2:R f =0. 53;S3:R f
=0. 30) behaviour and optica l ro tation ([ α] 20 +D 51. 2°, c
0. 18, H
2
O);1H NMR, 13C NM R data and 1H-1HCOSY co rre la-
tions see Tab le 1. The IR and NMR da taw ere equa l to those of 1-
O-β-D-g lucopyranosy l-(2S , 3S , 4R , 8Z /E) -2N-[ ( 2′R )-2′-
hydroxy te tracosanoy l] -3, 4-d ihyd roxy-8-oc tadecene[ 9] .
R eferences
1　 Institutum B otan icum Agendae Academ iae S in icae (中国科学院植物研
究所). C laves Fam iliarum Generum qu e Corm ophytorum S inicorum (中
国高等植物科属检索表). B eijing (北京):S cience Press(科学出版
社), 1994. 139
2　 In stitutum Botanicum Kunm ingen se A cadem iae S inicae (中国科学院昆
明植物研究所). Flora Yunn anica (云南植物志). B eijing (北京 ):
Science Press(科学出版社), 1997, 7. 172
3　Guo H L (郭红丽), Zhou JY (周金云). S tudy on th e chem ical con-
s tituents of Periploca ca lophy lla. Ch in Pharm J (中国药学杂志 ),
2003, 38 (7):497～ 499
4　Du rh am DG , Liu X J, R ich ard sRME. A triterpene from R ubu spinfaen-
sis. Phytochem istry , 1994, 36 (6):1469～ 1472
5　 Seto T, Tanak a T, Tanaka O , N aruhash i N. β-G lucosy l esters of 19α-
hyd roxyurso lic acid derivatives in leaves ofR ubu s species. P hytoch em is-
try, 1984, 23 (12):2829～ 2834
6　C oskunM , Satake T, H oriK , Saiki Y, TankerM. An th raqu inone g ly-
cosides from Rhamnu s libano ticus. P hytoch em istry , 1990, 29 (6):
2018 ～ 2020
7　Gao JM , Hu L, L iu JK. A novel stero l from Ch inese tru fflesTuber Ind i-
cum. S teroid s, 2001, 66:771 ～ 775
8　Hua HM (华会明), ChengM S (程卯生), L iX (李铣). S tud ies on
the ceram ides ofLinaria vu lgarisM il.l Ch in J Med Chem (中国药物化
学杂志), 2000, 35 (1):57 ～ 59
9　 Ryu J, K im JS, Kang SS. C ereb rosides from Longan A rillu s. Arch
Pharm R es, 2003, 26 (2):138 ～ 142
33　 1期 ZHANG Ailian et a l. :C hem ical S tudy onPo iki losperm um naucleiforum