Studies on New Steroidal Saponins from Allii macrostemonis Bulbus and Their Antitumor Activities

Two new steroidal saponins(2, 3) and two known compounds(1, 4) were isolated from 75% ethanol extract of Allii macrostemonis bulbus by various spectral methods. The two new steroidal saponins were respectively elucidated as (25S)-26-O-β-D-glucopyranosyl-5α-furostanol-2α,3β,22,26-tetrol-3-O-β-D-glucopyranosyl(1→2)-[β-D- glucopyranosyl(1→3)]-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside(2) and 26-O-β-D-glucopyranosyl-5α- furostanol-25(27)-ene-3β,22,26-tetrol-3-O-β-D-glucopyranosyl(1→2)-[β-D-glucopyranosyl(1→3)]-β-D-glucopyranosyl- (1→4)-β-D-galactopyranoside(3). Compound 4 was obtained from this medical plant for the first time. The activity experiments of proliferation inhibition on tumor cells were performed by cell counting kit-8(CCK-8) method for compound 2(25S-configuration) and its isomer(compound 1, 25R-configuration). The results show that compounds 1 and 2 have weak inhibition on lung cancer A549 cells, melanoma A375 cells and breast cancer MCF-7 cells as well as certain inhibitory effect on liver cancer HepG2 cells, and the inhibitory effect of compound 1 is stronger than that of compound 2.     

Two new furostanol saponins from Tribulus terrestris L.

<正>Two new furostanol glycoside,26-O-β-D-glucopyranosyl-(25S)-5α-furost-3β,22α,26-triol-3-O-β-D-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside(1) and 26-O-β-D-glucopyranosyl-(25S)-5α-furost-20(22)-en-2α,3β,26-triol-3-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(2) were isolated fromthe fruits of Tribulus terrestris L.The structures of two new furostanol saponins were elucidated by spectroscopic methods.     

两个非对映异构三萜皂甙的结构鉴定

从合欢皮95%乙醇提取物中分得2个新三糖链九糖皂甙(1,2),经化学方法和光谱分析,将其结构分别鉴定为:3-O-[β-D-吡喃木糖基-(1→2)-β-D-吡喃阿拉伯糖基-(1→6)-β-D-葡萄糖基]-21-O-(6S)-2-反式-2,6-二甲基-6-O-[4-O-((6R)-2-反式-2,6-二甲基-6-O-β-D-吡喃鸡纳糖基-2,7-辛二烯酸基)-β-D-吡喃鸡纳糖基]-2,7-辛二烯酸基金合欢酸28-O-β-D-吡喃葡萄糖基-(1→3)-[α-L-呋喃阿拉伯糖基-(1→4)]-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖基酯(1)和3-O-[β-D-吡喃阿拉伯糖基-(1→2)-β-D-吡喃呋糖基-(1→6)-β-D-葡萄糖基]-21-O-(6S)-2-反式-2,6-二甲基-6-O-[4-O-((6S)-2-反式-2,6-二甲基-6-O-β-D-吡喃鸡纳糖基-2,7-辛二烯酸基)-β-D-吡喃鸡纳糖基]-2,7-辛二烯酸基金合欢酸28-O-β-D-吡喃葡萄糖基-(1→3)-[α-L-呋喃阿拉伯糖基-(1→4)]-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖基酯(2),分别命名为合欢皂甙J₁₄(JulibrosideJ₁₄)和合欢皂甙J₁₅(JulibrosideJ₁₅)     

两头尖的化学成分研究(Ⅱ)

两头尖系毛莨科银莲花属植物多被银莲花(Anemone raddeanaRegel)的干燥根茎,分布于我国东北及山东等地．其味辛性热,具有祛风湿、消痈肿之功效．其总皂苷具有显著的抗肿瘤、抗炎、镇痛、镇静及抗惊厥作用．近年来,国内学者对其化学成分进行了较深入研究,已分离出近20种三萜皂苷类成分以及多种挥发油和多糖类成分．我们从两头尖中分离并鉴定了3个双糖链三萜皂苷化合物,其中化合物1为新化合物．化合物2和3为首次从两头尖中获得的已知化合物．     

人参根中丙二酰基三七人参皂苷-R4的分离及其结构表征

从新鲜人参根中分离得到了1个新化合物, 根据理化性质和谱学方法并与文献报道的相关化合物的数据进行比较, 鉴定其结构为丙二酰基三七人参皂苷-R4(Malonyl-notoginsenoside-R4, 1).     

黄花倒水莲皂甙Reinioside C在大鼠体内代谢产物的鉴定

为了探讨五环三萜皂甙ReiniosideC在大鼠体内代谢产物的结构,单剂量口服ReiniosideC,5h后放血处死,用制备型高效液相色谱方法对血液和各脏器进行提取分离,从大肠内容物和粪中,分离得到了7种代谢产物.用FAB-MS,¹H NMR和¹³C NMR方法鉴定了它们的结构.     

宽叶秦岭藤根部的化学成分

通过正相和反相硅胶柱层析从宽叶秦岭藤根部乙醇提取物中分离纯化得到19个化合物,经波谱分析并结合化学方法鉴定了其结构,其中4个为新化合物,它们分别是3,5-二羟基二十烷酸羽扇豆醇酯(3),2-羟甲基-5-甲氧基苯基-O-β-D-吡喃葡萄糖甙(11),Δ5-孕甾烯-3β,20(S)-二醇-20-O-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖甙(18,秦岭藤甙C)和Δ5-孕甾烯-3β,20(S)-二醇-3-O-β-D-吡喃葡萄糖基-20-O-β-D-吡喃葡萄糖基(1→6)-β-D-吡喃葡萄糖甙(19,秦岭藤甙D).     

Two New Steroidal Saponins from Diuranthera inarticulata

There are only three species in the genus Diuranthera (Liliaceae), which is endemic in the southwest of China1. Four steroidal saponins, diuranthosides A-C and chloromalo-side A were isolated from the fresh roots of D. major. This paper deals with the structure elucidation of two new steroidal saponins, diuranthosides D and E, which were isolated from the methanolic extract of whole plant of D. inarticulata Wang et K. Y. Lang.Diuranthoside D (1), [(]-38 (c 0.08, pyridine), afforded galac…     

Terpenoid Glucosides from Aster Smithianus

A diterpenoid trisaccharide, smithoside A, and a saponin, smithoside B, as well as six known compounds, apigenin, apigenin-7-O-glucoside, daucosterol, shanzhiside methyl ester, 8-acetylshanzhiside methyl ester and acteoside, were isolated from Aster smithianus. On the basis of spectral evidence and chemical analytical results, smithosides A and B were identified as pimar-15(16)-β-ene-8β,11α-diol-3β-O-β-D-glucopyranosyl(1→3)-[β-glucopyranosyl(1→2)]-β-D-glucopyranoside and 2β,3β,16β,21β,23-pentahydroxy-12-ene-28 oleanoic acid lactone-3-O-β-D-glucopyranosyl(1→3)-β-D-glucopyranoside, respectively.     

A new dammarane-type triterpene saponin from Gynostemma pentaphyllum

<正>One new dammarane-type triterpene saponin,named(20S)-3β,20,21-trihydroxydammar-24-ene 3-O-[α-L-rhamnopyranosyl- (1→2)][β-D-xylopyranosyl(1→3)]-β-D-glucopyranoside(1),was isolated from the aerial parts of Gynostemma pentaphyllum (Thunb.) Makino.Its structural elucidation was accomplished mainly on the basis of the interrelation of spectroscopic methods, such as IR,HR-TOF-MS,NMR.     

珠子参化学成分分析

从珠子参根茎中分离得到7个化合物. 利用核磁共振、 质谱和红外等手段, 并结合其理化性质, 鉴定了其结构, 它们分别是24(R)-珠子参苷R1, 6-O-[β-D-吡喃葡萄糖基(1→2)-β-D-吡喃葡萄糖基]-20-O-[β-D-吡喃葡萄糖基(1→4)-β-D-吡喃葡萄糖基]-20(S)-原人参三醇、 6″-乙酰基-人参皂苷Rd、 人参皂苷Rf、 竹节参皂苷Ⅳa、 人参皂苷Rd和竹节参皂苷Ⅴ. 其中, 24(R)-珠子参苷R1和6-O-[β-D-吡喃葡萄糖基(1→2)-β-D-吡喃葡萄糖基]-20-O-[β-D-吡喃葡萄糖基(1→4)-β-D-吡喃葡萄糖基]-20(S)-原人参三醇为2个新化合物, 6″-乙酰基-人参皂苷Rd 和人参皂苷Rf为首次从珠子参根茎中得到.     

New C21 steroidal glycosides from the roots of Cynanchum stauntonii and their protective effects on hypoxia/reoxygenation induced cardiomyocyte injury

Phytochemical investigations from the roots of Cynanchum stauntonii led to obtain four new C_(21) steroidal glycosides(1–4) and one known compound stauntoside F(5). Their chemical structures were characterized by sophisticated analyses of IR, HRESI-TOF-MS, 1D, and 2D-NMR data, together with chemical methods, which showed interesting 13,14:14,15-disecopregnane-type skeleton or 14,15-secopregnane-type skeleton C_(21) steroidal glycosides. Among them, compound 1 was determined to be glaucogenin C 3-O-b-D-glucopyranosyl-(1 → 4)-b-D-cymaropyranosyl-(1 → 4)-b-D-digitoxopyranosyl-(1 → 4)-b-D-thevetopyranoside. Compound 2 was characterized to be hirundigenin 3-O-a-L-diginopyranosyl-(1 → 4)-b-D-cymaropyranosyl-(1 → 4)-b-D-digitoxopyranosyl-(1 → 4)-b-D-30-demethyl-thevetopyranoside. Compound 3 was identified to be(14S,16 S,20R)-14,16-14,20-15,20-triepoxy-14,15-secopregn-5-en-3-ol-3-O-a-L-cymaropyranosyl-(1 → 4)-b-D-digitoxopyranosyl-(1 → 4)-b-D-oleandropyranoside.Compound 4 was identified to be(14S,16 S,20R)-14,16-14,20-15,20-triepoxy-14,15-secopregn-5-en-3-ol-3-O-a-L-cymaropyranosyl-(1 → 4)-b-D-cymaropyranosyl-(1 → 4)-b-D-digitoxopyranosyl-(1 → 4)-b-Dthevetopyranoside. Among them, compound 2 was hirundigenin type C21 steroidal glycoside that existed in nature as epimers due to the presence of 14-hemiketal hydroxyl group in its structure. In addition, the anti-inflammatory and cardiomyocyte protective effects of compounds 1–4 were evaluated. We found that they exhibited significant protective effects on hypoxia/reoxygenation induced cardiomyocyte injury, but did not showed obvious anti-inflammatory function.     

A new glycoside from Polygala tenuifolia Willd

A new tdterpenoid glycoside, 3-β-O-β-D-glucopyranosyl presenegenin 28-O-α-L-arabipyranosyl（1 → 3）-6-β- xylopyranosyl（1 → 4）-[β-D-apiofuranosyl（1 → 3）]-Ct-L-rhamnopyranosyl（1 → 2）-[α-L-rhamnopyranosyl（1 → 3）]-β-D-fucopyranosyl ester （1） was isolated from the Polygala tenuifolia Willd., together with two known saponins, including polygalasaponinXXIV （2） and polygalasaponinXXVIII （3）. The structure of new compound was elucidated by spectroscopic methods.     

蒺藜果化学成分的分离和鉴定

分离鉴定了2个六糖呋甾皂苷, 其中化合物1为新化合物.     

黑叶菝葜中呋甾烷甙

百合科菝葜属(SmilaxL.)植物在我国品种较多,且许多为民间药用,继前文我们又对黑叶菝葜(S.NigrescensWangetTang)的化学成分进行了研究,从其根部的乙醇提取物中得到4种呋甾烷甙,其中一种为新化合物,本文报道它们的结构鉴定。     

A new triterpenoid saponin from the roots of Ardisia crenata

A new triterpenoid saponin.3 β-O-{ β-D-glucopyranosyl-(1—4)-[ β-D-glucopyranosyl-[1-2)]- α-L-arabinopyranosyl}-16α, 28-dihydroxyolean-12-en-30-oic acid 30-O- β-D-glucopyranosyl ester(ardisicrenoside N.1),together with two known saponins, ardisicrenoside C(2) and D(3),were isolated from the roots of Ardisia crenata Sim.Their structures were elucidated by extensive spectral analysis and chemical evidences.Saponins 1 showed cytotoxicity against MCI-7 and NCI-H460 cancer cell lines at 11.0μmol/L and 22.1μmol/L in vitro.     

Two new steroidal glucosides from Ophiopogon.japonicus （L.f.） Ker-Gawl

Two new steroidal glucosides, 26-O-β-D-glucopyranosyl （25S）-furost-5-ene-1β,3β,22α,26-tetraol l-O-β-D-xylopyranosyl- （1 → 3）-[α-h-rhamnopyranosyl-（1 → 2）]-[β-D-fueopyranoside and （25R） spirost-5-ene-3β,14α-diol-3-β-O-β-L-rhanmopyranosyl- （1 → 2）-[β-D-xylopyranosyl（1 → 4）]-[-β-D-glucopyranoside, were isolated from the Ophiopogon japonicus （L.f.） Ker-Gaw. Their structures were elucidated by spectroscopic methods.     

Synthesis of Long Chain Fatty Acids Acylated Coumarin Glycoside Esters with Lipase as Catalyst

A series of novel coumarin glycoside esters(1―9) was synthesized through the acylation reaction of 4-methylcoumarin-7-O-β-D-glucoside(11) with different long chain fatty acids catalyzed by lipase in organic medium. The acylation occurred regioselectively at the 6'-OH of glycosyl moiety. The enzymatic synthesis was optimized to achieve 54%―70% yield using immobilized lipase(Novozym 435, 10 mg/mL) as catalyst and acetone and pyridine(9:1, volume ratio, water content<1%) as solvent with an acyl donor/coumarin glycoside molar ratio of 10:1 at a temperature of 40―50 ℃ for 96 h. All the synthesized compounds were confirmed.     

Flavonoid oligosides from georgian <Emphasis Type="Italic">Astragalus falcatus</Emphasis>

New flavonoid oligosides were isolated from leaves and flowers of Astragalus falcatus Lam. It was found on the basis of chemical transformations, UV, IR, PMR, ¹³ C NMR, HMBC, HSQC, 1D-TOCSY, and mass spectral properties that falcoside C had the structure quercetin 3-O-[β-D-glucopyranosyl(1 → 3)-α-Lrhamnopyranosyl(1 → 6)]-β-D-galactopyranoside 7-O-β-D-glucopyranoside; falcoside D, isorhamnetin 3-O-[β-D-xylopyranosyl(1 → 3)-α-L-rhamnopyranosyl(1 → 6)]-β-D-galactopyranoside 7-O-α-Lrhamnopyranoside.     

Studies on Triterpenoid Glycosides from Rhizomes of Panacis majoris and Their Antiplatelet Aggregation Activity

A new triterpenoid glycoside(1) and seven known triterpenoid glycosides, pseudoginsenoside RT2(2), yesanchinoside R2(3), vinaginsenoside R13(4), vinaginsenoside R8(5), notoginsenoside E(6), 6'-O-acetylginsenoside Re(7), 6"-O-acetylginsenoside Rb₁(8), were isolated from the rhizomes of Panacis majoris. The new triterpenoid glycoside was elucidated as 3-O-[β-D-glucopyranosyl-(1→2)-β-D-(6'-O-ethyl)-glucuronopyranosyl]-oleanolic acid-28-O-β-D-glucopyranoside by extensive spectroscopic and phytochemical methods. Compounds 2-8 were obtained from the plant for the first time. Compounds 3 and 4 displayed good activities against adenosine diphosphate (ADP)-induced platelet aggregation, and compounds 1, 5, 6 and 8 showed moderate activities. Compound 6 exhibited moderate antiplatelet aggregation activity induced by arachidonic acid(AA).