共查询到20条相似文献,搜索用时 15 毫秒
1.
Qing‐Xiong Yang Min Xu Ying‐Jun Zhang Hai‐Zhou Li Chong‐Ren Yang 《Helvetica chimica acta》2004,87(5):1248-1253
Four new steroidal saponins, named disporosides A–D ( 1 – 4 ), corresponding to (3β,25R)‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐glucopyranosyl)oxy]‐5β‐spirostan ( 1 ), (3β,25R)‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐[6‐O‐hexadecanoyl‐β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐glucopyranosyl)oxy]‐5β‐spirostan ( 2 ), (3β,22R,25R)‐26‐[(β‐D ‐glucopyranosyl)oxy]‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl)oxy]‐5β‐furostan ( 3 ), and (3β,22R,25R)‐26‐[(β‐D ‐glucopyranosyl)oxy]‐3‐[(β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→6)]‐β‐D ‐glucopyranosyl)oxy]‐5β‐furostan ( 4 ), have been isolated from the fresh rhizomes of Disporopsis pernyi, together with the three known compounds Ys‐I, agavoside B, and (3β,25R)‐3‐[(β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranosyl)oxy]‐5α‐spirostan‐12‐one. Their structures were elucidated by spectroscopic analyses, chemical transformations (acid hydrolysis), and comparison with literature data. 相似文献
2.
Debabrata Acharya Anne‐Claire Mitaine‐Offer Nutan Kaushik Tomofumi Miyamoto Thomas Paululat Marie‐Aleth Lacaille‐Dubois 《Helvetica chimica acta》2008,91(12):2262-2269
Four new furostanol steroid saponins, borivilianosides A–D ( 1 – 4 , resp.), corresponding to (3β,5α,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐hydroxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐galactopyranoside ( 1 ), (3β,5α,22R,25R)‐ 26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐galactopyranoside ( 2 ), (3β,5α,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 3 ), and (3β,5α,25R)‐26‐(β‐D ‐glucopyranosyloxy)furost‐20(22)‐en‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→3)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 4 ), together with the known tribuluside A and (3β,5α,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐22‐methoxyfurostan‐3‐yl O‐β‐D ‐xylopyranosyl‐(1→2)‐O‐[β‐D ‐xylopyranosyl‐(1→3)]‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[α‐L ‐rhamnopyranosyl‐(1→2)]‐β‐D ‐galactopyranoside were isolated from the dried roots of Chlorophytum borivilianum Sant and Fern . Their structures were elucidated by 2D ‐NMR analyses (COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectrometry. 相似文献
3.
Olivier Placide Noté Anne‐Claire Mitaine‐Offer Tomofumi Miyamoto Thomas Paululat Dieudonné Emmanuel Pegnyemb Marie‐Aleth Lacaille‐Dubois 《Magnetic resonance in chemistry : MRC》2009,47(3):277-282
From the stem bark of Tetrapleura tetraptera, two new oleanane‐type saponins, tetrapteroside A 3‐O‐{6‐O‐[(2E,6S)‐2,6‐dimethyl‐6‐hydroxyocta‐2,7‐dienoyl]‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐(1 → 4)‐[β‐D ‐glucopyranosyl‐(1 → 2)]‐β‐D ‐glucopyranosyl}‐3,27‐dihydroxyoleanolic acid (1), and tetrapteroside B 3‐O‐{ β‐D ‐glucopyranosyl‐(1 → 2)‐6‐O‐[(E)‐feruloyl]‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐(1 → 4)‐[β‐D ‐glucopyranosyl‐(1 → 2)]‐β‐D ‐glucopyranosyl}‐3,27‐dihydroxyoleanolic acid (2), were isolated. Further extractions from the roots led to the isolation of four known oleanane‐type saponins. Their structures were elucidated by the combination of mass spectrometry (MS), one and two‐dimensional NMR experiments. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
4.
Soumeya Bencharif‐Betina Tomofumi Miyamoto Chiaki Tanaka Zahia Kabouche Anne‐Claire Mitaine‐Offer Marie Aleth Lacaille‐Dubois 《Helvetica chimica acta》2012,95(9):1573-1580
Two new oleanane‐type triterpene saponins, afrocyclamins A and B ( 1 and 2 , resp.), were isolated from a MeOH extract of the roots of Cyclamen africanum Boiss . & Reuter , together with three known triterpenoid saponins, lysikokianoside, deglucocyclamin I, and its dicrotalic acid derivative. The structures were elucidated, on the basis of 1D‐ and 2D‐NMR experiments and mass spectrometry as (3β,20β)‐13,28‐epoxy‐16‐oxo‐3‐{O‐β‐D ‐xylopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}oxy}oleanan‐29‐al ( 1 ) and (3β,16α,20β)‐16,28,29‐trihydroxy‐olean‐12‐en‐3‐yl O‐4‐O‐(4‐carboxy‐3‐hydroxy‐3‐methyl‐1‐oxobutyl)‐β‐D ‐xylopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranosyl‐(1→4)‐O‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranoside ( 2 ). 相似文献
5.
Mohamed Elbandy Tomofumi Miyamoto Clment Delaude Marie‐Aleth Lacaille‐Dubois 《Helvetica chimica acta》2002,85(9):2721-2728
Five new triterpene saponins 1 – 5 were isolated from the roots of Muraltia ononidifolia E. Mey along with the two known saponins 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid 28‐[O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester and 3‐O‐(β‐D ‐glucopyranosyl)medicagenic acid 28‐[O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester (medicagenic acid=(4α,2β,3β)‐2,3‐dihydroxyolean‐12‐ene‐23,28‐dioic acid). Their structures were elucidated mainly by spectroscopic experiments, including 2D‐NMR techniques, as 3‐O‐(β‐D ‐glucopyranosyl)medicagenic acid 28‐[O‐β‐ D ‐apiofuranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester ( 1 ), 3‐O‐(β‐D ‐glucopyranosyl)medicagenic acid 28‐{[O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl} ester ( 2 ), 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl} ester ( 3 ), 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid 28‐[O‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl] ester ( 4 ), and 3‐O‐[O‐β‐D ‐glucopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl]medicagenic acid ( 5 ). 相似文献
6.
He‐Shui Yu Peng Zou Xin‐Bo Song Li‐Ping Kang Yi‐Xun Liu Xu Pang Jie Zhang Jing Fu Yang Zhao Cheng‐Qi Xiong Da‐Wei Tan Li‐Juan Zhang Bai‐Ping Ma 《Helvetica chimica acta》2011,94(7):1351-1358
A new furostanol saponin, sisalasaponin C ( 1 ), and a new spirostanol saponin, sisalasaponin D ( 2 ), were isolated from the fresh leaves of Agave sisalana, along with three other known steroidal saponins and two stilbenes. Their structures were identified as (3β,5α,6α,22α,25R)‐3,26‐bis[(β‐D ‐glucopyrano‐ syl)oxy]‐22‐hydroxyfurostan‐6‐yl β‐D ‐glucopyranoside ( 1 ), (3β,5α,25R)‐12‐oxospirostan‐3‐yl 6‐deoxy‐α‐L ‐mannopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→3)‐[β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→2)]‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 2 ), (3β,5α,6α,22α,25R)‐22‐methoxyfurostane‐3,6,26‐triyl tris‐β‐D ‐glucopyranoside, cantalasaponin‐1, polianthoside D, (E)‐ and (Z)‐2,3,4′,5‐tetrahydroxystilbene 2‐O‐β‐D ‐glucopyranosides. The last three known compounds were isolated from the fresh leaves of Agavaceae for the first time. The structures of the new compounds were elucidated by detailed spectroscopic analysis, including 1D‐ and 2D‐NMR experiments, and chemical techniques. 相似文献
7.
Beatriz Hernández‐Carlos Miriam Carmona‐Pineda Claudia Villanueva‐Cañongo Jesús F. López‐Olguín Agustín Aragón‐García Pedro Joseph‐Nathan 《Magnetic resonance in chemistry : MRC》2009,47(11):994-1003
The chemical study of Sechium mexicanum roots led to the isolation of the two new saponins {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (1) and {3‐O‐β‐D ‐glucopyranosyl (1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐[β‐D ‐apiosyl‐(1 → 3)]‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (2), together with the known compounds {3‐O‐β‐D ‐glucopyranosyl‐(1 → 3)‐β‐D ‐glucopyranosyl‐2β,3β,6β,16α,23‐pentahydroxyolean‐12‐en‐28‐oic acid 28‐O‐α‐L ‐rhamnopyranosyl‐(1 → 3)‐β‐D ‐xylopyranosyl‐(1 → 4)‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐α‐L ‐arabinopyranoside} (3), tacacosides A1 (4) and B3 (5). The structures of saponins 1 and 2 were elucidated using a combination of 1H and 13C 1D‐NMR, COSY, TOCSY, gHMBC and gHSQC 2D‐NMR, and FABMS of the natural compounds and their peracetylated derivates, as well as by chemical degradation. Compounds 1–3 are the first examples of saponins containing polygalacic and 16‐hydroxyprotobasic acids found in the genus Sechium, while 4 and 5, which had been characterized partially by NMR, are now characterized in detail. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
8.
Anne‐Claire Mitaine‐Offer Tomofumi Miyamoto Claire Jolly Clment Delaude Marie‐Aleth Lacaille‐Dubois 《Helvetica chimica acta》2005,88(11):2986-2995
Twelve triterpene saponins were isolated by successive MPLC over silica gel from four species of Polygalaceae: From Polygala ruwenzoriensis, five new saponins 1 – 5 of which 1 – 4 as two pairs of (E)/(Z)‐isomers, together with the four known compounds tenuifoline, (E)‐ and (Z)‐senegasaponin b, (E)‐ and (Z)‐senegin II, and polygalasaponin XXVIII, from the genus Carpolobia, one new saponin 6 from C. alba and the known arilloside ( 11 ) from C. lutea, and another new triterpene glycoside 7 from Polygala arenaria. Their structures were established mainly by 600‐MHz 2D‐NMR techniques (1H,1H‐COSY, TOCSY, NOESY, HSQC, HMBC) as 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐α‐L ‐arabinopyranosyl‐(1 → 4)‐O‐β‐D ‐xylopyranosyl‐(1 → 4)‐O‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐4‐O‐[(E)‐4‐methoxycinnamoyl]‐β‐D ‐fucopyranosyl} ester ( 1 ) and its (Z)‐isomer 2 , 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐α‐L ‐arabinopyranosyl‐(1 → 4)‐O‐β‐D ‐xylopyranosyl‐(1 → 4)‐O‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐4‐O‐[(E)‐3,4‐dimethoxycinnamoyl]‐β‐D ‐fucopyranosyl} ester ( 3 ) and its (Z)‐isomer 4 , 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐[O‐β‐D ‐galactopyranosyl‐(1 → 4)‐O‐β‐D ‐xylopyranosyl‐(1 → 4)‐O‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐β‐D ‐fucopyranosyl] ester ( 5 ), 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐α‐L ‐arabinopyranosyl‐(1 → 3)‐O‐[β‐D ‐galactopyranosyl‐(1 → 4)]‐O‐β‐D ‐xylopyranosyl‐(1 → 4)‐O‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐O‐[β‐D ‐apiofuranosyl‐(1 → 3)]‐4‐O‐acetyl‐β‐D ‐fucopyranosyl} ester ( 6 ), and 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐β‐D ‐galactopyranosyl‐(1 → 4)‐O‐[β‐D ‐glucopyranosyl‐(1 → 3)]‐O‐β‐D ‐xylopyranosyl‐(1 → 4)‐O‐α‐L ‐rhamnopyranosyl‐(1 → 2)‐β‐D ‐fucopyranosyl} ester ( 7 ) (presenegenin = (2β,3β,4α)‐2,3,27‐trihydroxyolean‐12‐ene‐23,28‐dioic acid). 相似文献
9.
Two dammarane‐type saponins with a novel aglycone derived from the parent 16,22‐epoxy‐24‐methylidenedammarane and lotoside A, a new lotogenin derivative, were isolated from the MeOH extract of the stem bark of the Brazilian medicinal plant Zizyphus joazeiro, in addition to the known saponin 3β‐{{O‐[O‐[α‐L ‐arabinofuranosyl‐(1→2)]‐O‐[β‐D ‐glucopyranosyl‐(1→3)]]‐α‐L ‐arabinopyranosyl}oxy}jujubogenin ( 1 ). The structures of the new compounds were determined as 16,22‐epoxy‐3β‐[(β‐D ‐glucopyranosyl)oxy]‐24‐methylidenedammarane‐15α,16α,20β‐triol ( 2 ), 16,22‐epoxy‐3β‐{{O‐[O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐apiofuranosyl‐(1→3)]]‐β‐D ‐glucopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}‐24‐methylidenedammarane‐15α,16α,20β‐triol ( 3 ), and 3β‐{{O‐[O‐[β‐D ‐glucopyranosyl‐(1→2)]‐O‐[β‐D ‐apiofuranosyl‐(1→3)]]‐β‐D ‐glucopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl}oxy}lotogenin ( 4 ) by means of 1D‐ and 2D‐NMR spectroscopy, as well as FAB mass spectrometry. For the novel aglycone, we propose the name joazeirogenin and, for the new saponins, joazeiroside A ( 2 ) and B ( 3 ). Joazeirogenin was found to be 16,22‐epoxy‐24‐methylidenedammarane‐3β,15α,16α,20β‐tetrol. 相似文献
10.
Three new furostanol glycosides, named ciliatasides A, B, and C ( 1 – 3 , resp.), have been isolated from the roots of Digitalis ciliata, along with two known furostanol glycosides. The structures of the new compounds were identified as (2α,3β,5α,14β,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐2‐hydroxyfurost‐20(22)‐en‐3‐yl β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranoside ( 1 ), (2α,3β,5α,14β,22R)‐26‐(β‐D ‐glucopyranosyloxy)‐2‐hydroxy‐22‐methoxyfurost‐25(27)‐en‐3‐yl β‐D ‐galactopyranosyl‐(1→2)‐[β‐D ‐xylopyranosyl‐(1→3)]‐β‐D ‐glucopyranosyl‐(1→4)‐β‐D ‐galactopyranoside ( 2 ), and (2α,3β,5α,14β,22R,25R)‐26‐(β‐D ‐glucopyranosyloxy)‐2,22‐dihydroxyfurostan‐3‐yl β‐D ‐glucopyranosyl‐(1→2)‐[β‐D ‐glucopyranosyl‐(1→3)]‐β‐D ‐galactopyranoside ( 3 ). 相似文献
11.
Günter Michl Dawit Abebe Franz Bucar Asfaw Debella Olaf Kunert MartinG. Schmid Efrem Mulatu Ernst Haslinger 《Helvetica chimica acta》2000,83(2):359-363
Two new bisdesmosidic triterpenoid saponins, i.e. 1 and 2 , were isolated, besides the three known saponins 3 – 5 , from the MeOH extract of the aerial parts of Achyranthes aspera Linn. (Amaranthaceae). Their structures were elucidated as β‐D ‐glucopyranosyl 3β‐[O‐α‐L ‐rhamnopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranuronosyloxy]machaerinate ( 1 ) and β‐D ‐glucopyranosyl 3β‐[O‐β‐D ‐galactopyranosyl‐(1→2)‐O‐α‐D ‐glucopyranuronosyloxy]machaerinate ( 2 ) by NMR spectroscopy, including 2D‐NMR experiments (machaerinic acid=3β,21β‐dihydroxyolean‐12‐en‐28‐oic acid). The other saponins were identified as β‐D ‐glucopyranosyl 3β[O‐α‐L ‐rhamnopyranosyl‐(1→3)‐O‐β‐D ‐glucopyranuronosyloxy]oleanolate ( 3 ), β‐D ‐glucopyranosyl 3‐β‐[O‐β‐D ‐galactopyranosyl‐(1→2)‐O‐β‐D ‐glucopyranuronosyloxy]oleanolate ( 4 ), and β‐D ‐glucopyranosyl 3β‐[O‐β‐D ‐glucopyranuronosyloxy]oleanolate ( 5 ) (oleanolic acid=3β‐hydroxyolean‐12‐en‐28‐oic acid). 相似文献
12.
Li Fan Jincai Lu Beibei Xu Song Gao Hongfen Zhang Runxiang Liu 《Helvetica chimica acta》2010,93(1):58-64
Two new oleanolic acid‐type triterpenoid saponins, raddeanosides R22 and R23 ( 1 and 2 , resp.), together with four known saponins were isolated from the rhizome of Anemone raddeana Regel. The structures of the new compounds were elucidated as oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 1 ) and oleanolic acid 3‐O‐α‐L ‐arabinopyranosyl(1→3)‐α‐L ‐rhamnopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 2 ). The four known compounds were identified as oleanolic acid 3‐O‐α‐L ‐arabinopyranoside ( 3 ), oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→4)‐α‐L ‐arabinopyranoside ( 4 ), hederasaponin B ( 5 ), and hederacholchiside E ( 6 ) on the basis of chemical and spectral evidences. Compound 4 is reported for the first time from the Anemone genus, while the other three known compounds have been already found in this plant. 相似文献
13.
Christian Wegner Matthias Hamburger Olaf Kunert Ernst Haslinger 《Helvetica chimica acta》2000,83(7):1454-1464
In the search for the cause for the formation of persistent foam in the Rhine River below the Rhine Fall at Schaffhausen, an investigation of the tensioactive principles from the aquatic plant Ranunculus fluitans L. (Ranunculaceae) was carried out. Two new (see 1 and 2 ) and four known bisdesmosidic triterpene saponins (see 4 – 6 ) were isolated along with the two known diacylglycerol galactosides 7 and 8 . The saponin structures were established by the identification of the aglycon and sugar moieties by HPLC and chiral capillary zone electrophoresis (CZE), ion‐spray LC/MS and extensive 1‐ and 2D homo‐ and heteronuclear NMR spectroscopy. The structures of the new oleanane‐type saponins were identified as 3‐O‐[β‐D ‐glucopyranosyl‐(1→3)‐α‐L ‐arabinopyranosyl]‐28‐O‐[α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl]hederagenin ( 1 ) and 3‐O‐[β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl]oleanolic acid [α‐L ‐rhamnopyranosyl‐(1→4)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl] ester ( 2 ). LC/MS Studies of tensioactive fractions revealed the presence of additional glycoglycerolipids. 相似文献
14.
Three new triterpenoid saponins, ardisicrenoside I ( 1 ), ardisicrenoside J ( 2 ), and ardisicrenoside M ( 3 ), along with eight known compounds, were isolated from the roots of Ardisia crenata Sims . Their structures were elucidated as 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 1 ), 16α‐hydroxy‐30,30‐dimethoxy‐3β‐O‐{α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 2 ), 30,30‐dimethoxy‐16‐oxo‐3β‐O‐{β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐[β‐D ‐glucopyranosyl‐(1→2)]‐α‐L ‐arabinopyranosyl}‐13β,28‐epoxyoleanane ( 3 ), ardisiacrispin A ( 4 ), ardisiacrispin B ( 5 ), ardisicrenoside B ( 6 ), ardisicrenoside A ( 7 ), ardisicrenoside H ( 8 ), ardisicrenoside G ( 9 ), cyclamiretin A‐3β‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 10 ), and cyclamiretin A‐3β‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐glucopyranosyl‐(1→4)‐α‐L ‐arabinopyranoside ( 11 ) by means of chemical and spectral analysis, and their cytotoxicities were evaluated in vitro. 相似文献
15.
Tan Pei Jean Khozirah Shaari Christian Paetz Intan Safinar Ismail Faridah Abas Nordin H. Lajis Viqar Uddin Ahmad 《Helvetica chimica acta》2009,92(10):1973-1982
Three new oleanane‐type triterpenoid saponins, 3‐O‐(α‐L ‐rhamnopyranosyl(1→2)‐β‐D ‐fucopyranosyl)‐28‐O‐{[α‐L ‐rhamnopyranosyl(1→2)] [β‐D ‐fucopyranosyl(1→6)]‐β‐D ‐glucopyranosyl} oleanolic acid ( 1 ), 3‐O‐[α‐L ‐rhamnopyranosyl(1→3)‐β‐D ‐fucopyranosyl]‐28‐O‐[α‐L ‐rhamnopyranosyl(1→4)‐β‐D ‐glucopyranosyl] oleanolic acid ( 2 ), and 3‐O‐{α‐L ‐rhamnopyranosyl(1→2)‐[3′,4′‐diacetoxy‐β‐D ‐fucopyranosyl]}‐28‐O‐[α‐L ‐rhamnopyranosyl(1→2)‐β‐D ‐glucopyranosyl] oleanolic acid ( 3 ) have been isolated from the stems of Xerospermum noronhianum. The structures of the saponins were determined as a series of bidesmosidic oleanane saponins based on spectral evidence. The anticholinesterase activity of the saponins 1 – 3 was also evaluated. 相似文献
16.
Mohamed Elbandy Tomofumi Miyamoto Clment Delaude Marie‐Aleth Lacaille‐Dubois 《Helvetica chimica acta》2003,86(2):522-531
Eight new acylated preatroxigenin saponins 1 – 8 were isolated as four inseparable mixtures of the trans‐ and cis‐4‐methoxycinnamoyl derivatives, atroximasaponins A1/A2 ( 1 / 2 ), B1/B2 ( 3 / 4 ), C1/C2 ( 5 / 6 ) and D1/D2 ( 7 / 8 ) from the roots of Atroxima congolana. These compounds are the first examples of triterpene saponins containing preatroxigenin (=(2β,3β,4α,22β)‐2,3,22,27‐tetrahydroxyolean‐12‐ene‐23,28‐dioic acid as aglycone. Their structures were elucidated on the basis of extensive 1D‐ and 2D‐NMR studies and FAB‐MS as 3‐O(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[O‐β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranoyl} ester ( 1 ) and its cis‐isomer 2 , 3‐O‐(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→ 2)‐O‐[O‐6‐O‐acetyl‐β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐ 4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl} ester ( 3 ) and its cis‐isomer 4 , 3‐O‐(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[O‐6‐ O‐acetyl‐β‐D ‐glucopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranoyl} ester ( 5 ) and its cis‐isomer 6 , 3‐O‐(β‐D ‐glucopyranosyl)preatroxigenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐[β‐D ‐apiofuranosyl‐(1→3)]‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐(trans‐4‐methoxycinnamoyl)‐β‐D ‐fucopyranosyl ester ( 7 ) and its cis‐isomer 8 . 相似文献
17.
Four new triterpenoid glycosides named asiaticoside C ( 1 ), D ( 2 ), E ( 3 ), and F ( 4 ) were isolated from the BuOH fraction of the EtOH extract of whole plants of Centella asiatica, together with three known compounds, asiaticoside ( 5 ), madecassoside ( 6 ), and scheffuroside B ( 7 ). Based on FAB‐MS, IR, 1H‐ and 13C‐NMR, and 2D‐NMR data (HMQC, HMBC, COSY), the structures of the new compounds were determined as (2α,3β,4α)‐23‐(acetyloxy)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 1 ), (2α,3β)‐2,3‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 2 ), asiatic acid 6‐O‐β‐D ‐glycopyranosyl‐β‐D ‐glucopyranosyl ester ( 3 ), (3β,4α)‐3,23‐dihydroxyurs‐12‐en‐28‐oic acid O‐α‐L ‐rhamnopyranosyl‐(1→4)‐O‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl ester ( 4 ). 相似文献
18.
Jiang‐Tao Chen Hai‐Zhou Li Dong Wang Ying‐Jun Zhang Chong‐Ren Yang 《Helvetica chimica acta》2006,89(7):1442-1448
Three new dammarane monodesmosides, named notoginsenosides Ft1 ( 1 ), Ft2 ( 2 ), and Ft3 ( 3 ), together with three known ginsenosides, were obtained from a mild acidic hydrolysis of the saponins from notoginseng (Panax notoginseng (Burk .) F. H. Chen ) leaves. Their structures were elucidated to be (3β,12β,20R)‐12,20‐dihydroxydammar‐24‐en‐3‐yl O‐β‐D ‐xylopyranosyl‐(1 → 2)‐O‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranoside ( 1 ), (3β,12β)‐12,20,25‐trihydroxydammaran‐3‐yl O‐β‐D ‐xylopyranosyl‐(1 → 2)‐O‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranoside ( 2 ), and (3β,12β,24ξ)‐12,20,24‐trihydroxydammar‐25‐en‐3‐yl O‐β‐D ‐xylopyranosyl‐(1 → 2)‐O‐β‐D ‐glucopyranosyl‐(1 → 2)‐β‐D ‐glucopyranoside ( 3 ), by means of spectroscopic evidences. The known ginsenosides Rh2 and Rg3 4 – 6 were obtained as the major products from this acidic deglycosylation. 相似文献
19.
Gaoussou Timit Anne‐Claire Mitaine‐Offer Tomofumi Miyamoto Chiaki Tanaka Thomas Paululat Clment Delaude Marie‐Aleth Lacaille‐Dubois 《Helvetica chimica acta》2010,93(11):2237-2244
The five new presenegenin glycosides 1 – 5 were isolated from Securidaca welwitschii, together with one known sucrose diester. Compounds 1 – 4 were obtained as pairs of inseparable (E)/(Z)‐isomers of a 3,4‐dimethoxycinnamoyl derivative, i.e., 1 / 2 and 3 / 4 . Their structures were elucidated mainly by 2D‐NMR techniques and mass spectrometry as 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐[(E)‐3,4‐dimethoxycinnamoyl]‐β‐D ‐fucopyranosyl} ester ( 1 ) and its (Z)‐isomer 2 , 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐{O‐β‐D ‐galactopyranosyl‐(1→4)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐3‐O‐acetyl‐α‐L ‐rhamnopyranosyl‐(1→2)‐O‐[β‐D ‐glucopyranosyl‐(1→3)]‐4‐O‐[(E)‐3,4‐dimethoxycinnamoyl]‐β‐D ‐fucopyranosyl} ester ( 3 ) and its (Z)‐isomer 4 , and 3‐O‐(β‐D ‐glucopyranosyl)presenegenin 28‐[O‐β‐D ‐galactopyranosyl‐(1→3)‐O‐β‐D ‐xylopyranosyl‐(1→4)‐O‐α‐L ‐rhamnopyranosyl‐(1→2)‐β‐D ‐fucopyranosyl] ester ( 5 ) (presenegenin=(2β,3β,4α)‐2,3,27‐trihydroxyolean‐12‐ene‐23,28‐dioic acid). 相似文献
20.
Li Qiu Yang Jiao Gui‐Kun Huang Ji‐Zhao Xie Jian‐Hua Miao Xin‐Sheng Yao 《Helvetica chimica acta》2014,97(1):102-111
Three new dammarane‐type triterpenoid saponins, 1 – 3 , were isolated and identified as (20S)‐20‐O‐[β‐D ‐xylopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl‐(1→6)‐β‐D ‐glucopyranosyl]dammar‐24‐ene‐3β,6α,12β, 20‐tetrol ( 1 ), (20S)‐6‐O‐[(E)‐but‐2‐enoyl‐(1→6)‐β‐D ‐glucopyranosyl]dammar‐24‐ene‐3β,6α,12β,20‐tetrol ( 2 ), and (20S)‐6‐O‐[β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐xylopyranosyl]dammar‐24‐ene‐3β,6α,12β,20‐tetrol ( 3 ) from the roots of Panax notoginseng (Burkill ) F.H.Chen (Araliaceae). Their structures were elucidated on the basis of spectroscopic analyses, including 1D‐ and 2D‐NMR techniques and HR‐ESI‐MS, as well as by acidic hydrolysis. 相似文献