The Triterpenoid Saponins of Rhizomes of Panax laponicus C.A. Meyer var. angustifolius(Burk.) Cheng et Chu

From the rhizome of Panax japonicus C. A. Meyer var. angustifolius (Burk.) Cheng et Chu collected in Yunnan, 10 triterpenoid saponins were isolated with SiO2 chromatograph and reversed phase chromatograph. The saponins were identified as ginsenoside Ro (1), Rd (7), Rg1 (8), Rhl (9), notoginsenoside R1 (6), chikusetsusaponin Ⅳ(4), Ⅳa(2), zingibroside R1(3), oleanolic acid 28-β-D-glucoside (10) and oleanolic acid 3-β-D-glucuronoside (5) respectively, by means of 13C-NMR, MS of acetate, and chemical methods, as well as compared with authentic samples. Among the rest, (5), a prosaponin of ginsenoside Ro (1) was firstly isolation from species of genus Panax. The fact that saponin constituents of rhizome of var. angustifolius was similar to P. japonicus and var. major, further supported the view that three taxes belonged to a variational limit of one species.     

羽叶三七根茎的三萜皂甙成分及其化学分类学意义

羽叶三七(Panax japonicus C. A. Meyer var. bipinnalifidus (Scem.) Wu et Feng)又称疙瘩七,产我国西北部至西南部山区,是人参届植物中分布海拔和纬度均较高的一个种类。在陕西省秦岭地区主要产于南北坡海拔2100—2900米的针叶林下阴湿处。民间以其根茎入药,具有清热解毒、顺气健胃、活血祛瘀、滋补强壮之效。作为国产人参属植物皂甙成分系统研究的一个部分,本文报告秦岭产羽叶三七根茎的皂甙成分,并讨论其化学分类学意义。     

Acylated flavonoid glycosides from Bassia muricata.

From the arial parts of Bassia muricata, two acylated flavonoid glycosides quercetin-3-O-(6"-caffeoyl)-sophoroside and quercetin-3-O-(6"-feruloyl)-sophoroside have been isolated together with two known flavonoid glycosides quercetin-3-O-sophoroside and quercetin-3,7-O-beta-diglucopyranoside, as well as four known triterpenoidal saponins, oleanolic acid-3-O-beta-glucopyranoside, chikusetsusaponin IVa, chikusetsusaponin IVa methyl ester and oleanolic acid-3,28-beta-diglucopyranoside. The structures of the isolated compounds were verified by means of MS and NMR spectral analyses.     

New Triterpenoid Glycosides from Hemsleya penxianensis var. gulinensis

Two new triterpenoid saponins were isolated from the rools of Hemsleya penxianensis var. gulinensis together with seven known saponins oleanolic acid 28-O-β-D-glucopyranoside (1), oleanolic acid 3-O-β-D-glucuropyranoside(3), 3-O-β-D-glucuropyranosyl-oleanolic acid-28-O-α-L-arabinopyranoside(4).     

古蔺雪胆中的新三萜皂苷

从采自四川汉源县的古蔺雪胆(Hemsleya penxianensis var.gulinensiks)中分到9个三萜皂苷化合物,通过化学反应和光谱方法鉴定了它们的结构。其中7个为已知化合物,分别为齐墩果酸-28-O-β-D-比喃葡萄糖苷(1),3-O-β-D-吡喃葡萄糖醛基齐墩果酸苷(3),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-吡喃阿拉伯糖苷(4),3-O-β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(5),3-O-α-L-阿拉伯糖基—(1→3)—β—D-吡喃葡萄糖醛基—齐墩果酸—28—O—β—D—吡喃葡萄糖苷(6),3—O—(6′—丁酯)—β-D-吡喃葡萄糖醛基—齐墩果酸—28-O-α-L-阿拉伯糖苷(7),3-O-(6′-丁酯)—β—D吡喃葡萄糖醛基—齐墩果酸—28-O-β-D-吡喃葡萄糖苷(8)。两个新化合物,即雪胆皂苷A(2)和雪胆皂苷B(9)。     

圆果雪胆中的皂甙成分

从圆果雪胆（Ｈｅｍｓｌｅｙａ ａｍａｂｉｌｉｓ）的块茎中分离到１０个化合物,其中３个雪胆皂甙是首次从该种植物中得到,它们的结构通过光谱和化学的方法鉴定为齐墩果酸－３－Ｏ－α－吡喃阿拉伯糖（１→３）－β－葡萄糖醛酸甙,２８－Ｏ－β－Ｄ－吡喃葡萄糖齐墩果酸３－Ｏ－α－吡喃阿拉伯糖（１→３）－β－Ｄ－葡萄糖醛酸,２８－Ｏ－β－Ｄ－吡喃葡萄糖齐墩果酸３－Ｏ－「β－Ｄ－吡喃葡萄糖（１→２）」－「α－吡喃阿     

马槟榔甜味蛋白的研究Ⅱ．甜蛋白Ⅱ和甜蛋白Ⅰ的比较

从马槟榔（Capparis masaikai Levl．）种子分离鉴定了二种甜蛋白：甜蛋白I（mabinlinⅠ或MaⅠ）分子量MWll600,等电点PⅠll.8;甜蛋白Ⅱ（mabinlinⅡ或MaⅡ）MW 10400,PⅠll.3。另一组分mabinlinⅡ MW10200,pl 11.8,可能是提取过程产物。MaⅡ有84个氨基酸残基,比MaⅠ少15个。它们有80个氨基酸残基是共同的,都是缺丝氨酸和蛋氨酸的单一多肽链。MaⅠ还缺赖氨酸和酪氨酸。测不出有自由SH基。在8 M尿素中用巯基乙醇还原处理,两种甜蛋白分子都可转变为二聚体而失去甜味。     

广东冬青中的三萜及三萜皂甙成分

从广东冬青（Ｉｌｅｘ ｋｗａｎｇｔｕｎｇｅｎｓｉｓ）的叶中分离得到四个三萜皂甙和三个三萜成分,通过光谱解析及化学方法,三个三萜成分分别鉴定为齐墩果酸（１）、熊果酸（２）和常春藤皂甙元（３）;四个三萜皂甙成分分别鉴定为齐墩果酸３－Ｏ－β－Ｄ－吡喃葡萄糖基－（１→３）－α－Ｌ－吡喃阿拉伯糖甙（４）、齐墩果酸３－Ｏ－β－Ｄ－吡喃葡萄糖基－（１→２）－α－Ｌ－吡喃阿拉伯糖甙（５）、齐墩果酸３－Ｏ－β－Ｄ－     

Studies on the Chemical Constituents from Root Bark of Aralia armata (Wall.) Seem.

Eleven constituents were isolated from root bark of Aralia armata (Wall.) Seem. Their structures were elucidated by spectra(IR, MS, 1H-NMR and 13C-NMR) and chemical analyses. They were deglucose chikusetsusaponin Ⅳ (AT–Ⅰ), chikusetsusaponin Na (AT–Ⅱ ), zingibroside R1 (AT–Ⅲ), ginsenin R0 (AT–IV), decaisneanaside (AT–Ⅴ), armatoside (AT-Ⅶ), araloside A (AT–Ⅶ), octacosanoic acid (AT–Ⅷ), β-sitosterol (ATIX ), mixture of β-sitosterol and stigmastterol (AT–×), oleanolic acid (AT–Xl ). They were for the first time found in this plant, AT–Ⅵ is a new saponin.     

Triterpenoid Saponins from Pulsatilla cernua (Thunb.)Bercht. et Opiz.

To investigate saponins from the roots of Pulsatilla cernua (Thunb.) Bercht. et Opiz., two new compounds together with five known triterpenoid saponins were isolated. The structures of the two new triterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 1) and 3-O-[α-L-arabinopyranosyl(1→3)]-[α-L-rhamnopyranosyl (1→2)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 2) by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

Further saponins from Meryta lanceolata

Five new oleanane-type saponins along with 11 known ones were isolated from the leaves and stems of Meryta lanceolata. The new saponins were characterised by spectroscopic analysis including FAMS, 1 and 2D NMR experiments and the results of hydrolysis as 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] hederagenin 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl] ester, 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] oleanolic acid 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl]ester, 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] oleanolic acid 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-6-O-acetyl glucopyranosyl-(1-->6)-beta-d-glucopyranosyl]ester, 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-d-glucopyranosyl-(1-->3)-alpha-l-arabinopyranosyl] oleanolic acid 28-O-[alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranosyl] ester and 3-O-[beta-d-glucopyranosyl-(1-->2)-beta-d-glucuronopyranosyl] hederagenin, respectively.     

Oleanane-type triterpenoids from Panax stipuleanatus and their anticancer activities

One newly (1) and 10 known oleanane-type triterpenoids (2-11) were isolated from the methanol extract of Panax stipuleanatus rhizomes. Based on their spectroscopic data, these compounds were identified as spinasaponin A methyl ester (1), pesudoginsenoside RP(1) methyl ester (2), spinasaponin A 28-O-glucoside (3), pseudoginsenoside RT(1) methyl ester (4), pseudoginsenoside RT(1) (5), stipuleanoside R(2) methyl ester (6), stipuleanoside R(2) (7), araloside A methyl ester (8), 3-O-β-D-glucopyranosyl (1→3)-β-D-glucuronopyranoside-28-O-β-D-glucopyranosyl oleanolic acid methyl ester (9), 3-O-β-D-xylopyranosyl (1→2)-β-D-glucopyranosyl-28-O-β-D-glucopyranosyl oleanolic acid (10), and chikusetsusaponin IVa (11). When the cytotoxic activities of the isolated compounds were evaluated, compound 1 exhibited significant cytotoxic activity with IC(50) values of 4.44 and 0.63 μM against HL-60 (leukemia) and HCT-116 (colon cancer) cell lines, respectively. Compound 2 showed potent cytotoxicity with an IC(50) of 6.50 μM against HCT-116, whereas it was less cytotoxic against HL-60 (IC(50)=41.45 μM). After HL-60 and HCT-116 were treated with compounds 1 and 2, increased production of apoptotic bodies was observed. Furthermore, compounds 1 and 2 in HCT-116 cells activated intrinsic and extrinsic apoptosis pathways by upregulating DR-5 and Bax, downregulating Bcl-2, activating caspase-9, and cleaving poly-ADP-ribose polymerase (PARP). We also observed the activation of ERK1/2 MAPK by both compounds in the HCT-116 cells. Together, compounds 1 and 2 might induce intrinsic and extrinsic apoptosis pathways through the activation of the ERK1/2 MAPK pathway in HCT-116 colon cancer cells. Structure-activity relationship analysis indicated that a carboxyl group at position-28 is potentially responsible for the cytotoxic effects.     

Triterpenoid saponins from Schefflera arboricola

Nine triterpenoid saponins were isolated from the leaves and stems of Schefflera arboricola. The saponins were characterised, on the basis of chemical and spectral evidence, as 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucuronopyranosyl] oleanolic acid, 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucuronopyranosyl] echinocystic acid, 3-O-[beta-D-apiofuranosyl-(1-->4)-beta-D-glucuronopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-ramnopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-[beta-D-galactopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-[beta-D-galactopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-beta-D-apiofuranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid and 3-O-beta-D-apiofuranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl ester.     

四川溲疏的化学成分研究(英文)

运用多种色谱技术从四川溲疏(Deutzia setchuenensis Franch)全草的95%乙醇提取物中首次分离到9个化合物。通过波谱方法和与已知品对照的手段将它们鉴定为:β-谷甾醇(1)、白桦酯醇(2)、hydrangetin(3)、齐墩果酸(4)、肉桂酸(5)、齐墩果酸-3-O-β-D-吡喃葡萄糖醛酸苷(6)、β-胡萝卜苷(7)、齐墩果酸-3-O-(β-D-吡喃葡萄糖醛酸-6-正丁酯)(8)和齐墩果酸-3-O-β-D-吡喃葡萄糖醛酸-28-O-β-D-吡喃葡萄糖苷(9)。     

Isolation and Identification of Steroidal Saponins and Sapogenins from Aspidistra zongbayi K. Y. Lang et Z. Y. Zhu

Two steroidal saponins were isolated from the n-BuOH extract of the rhizome of Aspidistra zongbayi K. Y. Lang et Z. Y. Zhu. Their structures were elucidated as 3-O-{β-D-glucopyr-anosyl (l→2)-[β-D-xylopyranosyl (1→3)]-β-D-glucopyranosyl (l→4)-β-D-glactopyranosyl}-diosgenin (aspidistrin) and proto-aspidistrin by physical and chemical methods. Three steroidal sapogenins were isolated from the acid-treated n-BuOH extract. They were identified as△3.5 deoxyfigogenin, diosgenin and gentrogenin, β-sitosterol was isolated from the rhizome of this plant also.     

Triterpenoid Saponins from Pulsatilla cernua (Thunb.)

To investigate saponins from the roots of Pulsatilla cernua (Thunb.) Bercht. et Opiz., two new compounds together with five known triterpenoid saponins were isolated. The structures of the two new triterpenoid saponins, named cernuasides A and B, were elucidated as 3-O-[β-D-xylopyranosyl(1→2)]-[α-L-rhamnopyranosyl(1→4)]-α-Larabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 1) and 3-O-[α-L-arabinopyranosyl(1→3)]-[α-L-rhamnopyranosyl (1→2)]-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester (compound 2) by 1D, 2D-NMR techniques, ESIMS analysis, as well as chemical methods.     

Two new triterpene saponins from the anti-inflammatory saponin fraction of Ilex pubescens root

The saponin fraction from the ethanolic extracts of the root of Ilex pubescens Hook. et Arn. (Ilexaceae) was found to exhibit potent anti-inflammatory effects on carrageenan-induced paw edema in rats. Two novel triterpene saponins, pubescenosides C and D (1 and 2, resp.), together with five known saponins were isolated from this saponin fraction. The structures of 1 and 2 were elucidated as (20beta)-3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa-12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, and (20beta)-3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-beta-D-xylopyranosyl]ursa- 12,18-dien-28-oic acid 28-O-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectroscopic data. Five known saponins isolated from the saponin fraction were identified as ilexsaponin B(1), B(2), B(3), A(1), and chikusetsusaponin IV(a).     

Evaluation of novel antioxidant triterpenoid saponins from the halophyte Salicornia herbacea

As a part of an ongoing search for novel antioxidants from the salt marsh plants, bioactivity-isolation and structure determination of constituents from Salicornia herbacea were performed. One new triterpenoid saponin (4), along with three known saponins (1-3), has been isolated from n-BuOH fraction of S. herbacea. On the basis of the spectroscopic methods, the structure of the new saponin 4 was elucidated as 3β-hydroxy-23-oxo-30-noroleana-12, 20(29)-diene-28-oic acid 3-O-β-D-glucuronopyranosyl-28-O-β-d-glucopyranoside. Scavenging effects of saponins 1-4 were examined on 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical and peroxynitrite. Particularly, saponin 3 exerted significant antioxidant activity on both authentic peroxynitrite and peroxynitrite generated from morpholinosydnonimine (SIN-1).     

Triterpenoid saponins from Fagonia cretica

Four new triterpenoid saponins were isolated and identified from the aerial parts of Fagonia cretica. They were characterized as 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-beta-D-glucopyranosyl ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] 27-hydroxy oleanolic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester and 3beta-O-[beta-D-glucopyranosyl (1-->2)-alpha-L-arabinopyranosyl] olean-12-en-27-al-28-oic acid 28-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] ester. The structures of the saponins were assigned by spectral analyses (FABMS, 1H, 13C NMR, 1H-1H COSY, TOCSY, HMQC and HMBC spectra) and NOE experiments. To the best of our knowledge the genin 3beta hydroxy olean-12-en-27-al-28-oic acid is new.     

Study on Chemical Constituents of Gentianopsis barbata var. Stennocalyx H. W. Li ex T.N. Ho

Nine compounds were isolated from Gentianopsis barbata var. stennocalyx H. W. Li ex. T.N.Ho. Their structures are identified as 1-hydroxy4, 7, 8-trimethoxyxanthone (Ⅰ), 1, 7-dihydroxy-3, 8-dimethoxyxanthone (Ⅱ), 1, 7, 8-trihydroxy-3-methoxyxanthone (Ⅲ), 1-O-(β-D- xylopyranosyl-(1→6)-β-D-glucopyranosyl)-3, 7, 8-trimethoxyxanthone (Ⅳ), 1-O-(β-D-xylopy- ranosyl- (1→6)-β-D-glucopyranosyl)-7-hydroxy-3, 8-dimethoxyxanthone (Ⅴ), 1-O-(β-D-xylo- pyranosyl-(1→6)-β-D-glucopyranosyl)-7, 8-dihydroxy-3-methoxyxanthone (Ⅵ), luteolin-7-O- β-D-glucoside (Ⅶ), oleanolic acid (Ⅷ) and ursolic acid (Ⅸ) by means of chemical methods and UV, IR and NMR determinations respectively.