白花刺参中两个新三萜皂甙

从著名藏药白花刺参（Morina nepalensis var.alba Hand.-Mazz)的水溶性部分分离到2个新三萜皂甙-刺参甙K（1）和刺参甙L（2）,以及一个已知三萜皂甙mazusaponinⅠ（3)。应用波谱和化学方法,刺参甙K和刺参甙L的结构分别鉴定为3-O-α-L-arabinopyranosyl-（1→）-β-D-xylopyranosyl siaresinolic acid(1)和3-O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl siaresinolic acid28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside(2)。     

中国特有药用植物铁破锣中的新皂甙类成分

从铁破锣（Beesia calthaefolia(Maxim.)Ulbr.根茎中分离得到5个化合物（1－5）,经化学和波谱学方法鉴定,其中2个为有机酸－铁破锣酸（beesic acid,9-phenyl-2E,4E,6E,8E-nontetraenoic acid,1)和香草酸（2）;3个为齐墩果酸型三萜皂甙：oleanolic acid-3-o－α-Larabinopyranosyl-－28－O-α-L-rhamnopyranosyl-(1→4）-β-D-glucopyranosyl-（1→6）-β-D-glucopyranosyl ester(3),hederasaponin B(oleanolic acid-3-O-α-L-rhamnopyranosyl-(1→2)-α－L-arabinopyranosly-28-Oα-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6）－β－D－glucopyranosyl ester,4)和铁破锣皂甙Q（beesioside Q,oleanolic acid-3-O-β-D-glucopyranosyl-(1→3）－α－L-rhamnopyranosyl-(1→2)-α-L-arabinopyranolsyl-28-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6）－β－D－glucopyranosyl ester,5)。化合物1系首次从自然界中分离得到,化合物5为新化合物。     

白首乌甙A,B和C的结构

从著名中药白首乌(Cynanchum auricutatum Royle ex Wight)根中分离得到7个C_2(?)体甙。其小4个已知物——wilfosidc C3N (Ⅰ), C1N (Ⅱ), C1G (Ⅲ), K1N (Ⅴ),和另外3个新C_(21)甾体甙,命名为白首乌甙A (Ⅵ),B (Ⅶ),C(Ⅳ) (cynauricusidc A, B,C)。经光谱数据分析和化学反应,证明其结构分别为:开德甙元 3-氧-β D-葡萄糖吡喃基-(1→4)-α-L-加拿大麻糖吡喃基-(1→4)-β-D-加拿大麻糖吡喃基-(1→4)-α-L-迪吉糖吡喃基-(1→4)-β-D-加拿大麻糖吡喃甙(kidjoranin 3-O-β-D-glucopyranosyl-(1→4)-α-L-cymaropyranosy-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside, Ⅵ);萝藦甙元 3-氧-α-L-加拿大麻糖吡喃基-(1→4)-β-D-加拿大麻糖吡喃基-α-L-迪吉糖吡喃基-(1→4)-β-D-加拿大麻糖吡喃甙(metaplexigenin -O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-(1→4)-β-cymaropyranoside,Ⅶ);告达庭 3-氧-β-D-葡萄糖吡喃基-(1→4)-β-L-葡萄糖吡喃基-(1→4)-α-L-加拿大麻糖吡喃基-(1→4)-β-D-加拿大麻糖吡喃基-(1→4-α-L-迪吉糖吡喃基-(1→4)-β-D-加拿大麻糖吡喃基(caudatin 3-O-β-D-glucopyranosy-(1→4)-β-D-glucopyr     

羽叶点地梅的化学成分

首次从中国特有的单属单种植物羽叶点地梅(Pomatosace filicula Maxim.)分离到13个化合物.应用波谱技术(尤其是2D-NMR:TOCSY,HMQC,HMBC)及化学方法鉴定了它们的结构.其中,化合物3为一新的三萜皂苷类化合物,其结构为13β,28-epoxy-16-oleananone-3-O-[α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→2)]-β-D-glucopyranoside,命名为羽叶点地梅甲苷(pomatoside A).     

Glycosides from Roots of Cyathula officinalis Kuan

To search for new and bioactive compounds from traditional Chinese medicines, a new glycoside,3-O-[α-L-rhamnopyranosyl-(l-→3)-(n-butyl-β-D-glucopyranosiduronate)]-28-O-β-D-glucopyranosyl oleanolic acid (1), was isolated from the roots of Cyathula officinalis Kuan, along with 3-O-(methyl-β-D-glucopyranosiduronate)-28-O-β-D-glucopyranosyl oleanolic acid (2), 3-O-β-D-glucopyranosyl oleanolic acid (3), 3-O-β-D-glucuronopyranosyl oleanolic acid (4), 3-O-[α-L-rhamnopyranosyl-(l→3)-(β-D-glucuronopyranosyl)] oleanolic acid (5), 3-O-(β-D-glucuronopyranosyl)-28-O-β-D-glucopyranosyl oleanolic acid (6), 28-O-β-D-glucuronopyranosyl-(1→4)-β-D-glucopyranosyl hederagenin (7), 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl oleanolic acid (8), and 3-O-[β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl]-28-O-β-D-glucopyranosyl oleanolic acid (9). The structures of these compounds were determined based on spectral and chemical evidence. The 50 per cent growth-inhibiting (GI50) of compounds 1 and 5 against MDA-MB-231(a human breast cancer cell line) was 3.44 × 10-4 and 4.66 × 10-4 mol/L, respectively.     

滇重楼地上部分的甾体皂甙

从滇重楼Paris polyphylla Sm. var. yunnanensis (Fr.) H-M.地上部分分离得到3个甾体皂甙,经光谱测定和化学降解证明其化学结构分别为:偏诺皂甙元3O-α-L-鼠李吡喃糖基(1→2)〔α-L-鼠李吡喃糖基(1→4))-β-D-葡萄吡喃糖甙(A);孕甾-5,16-二烯-3β-醇-20-酮,3β-O-α-L-鼠李吡喃糖基(1→2)〔α-L-鼠李吡喃糖基(1→4)〕-β-D-葡萄吡喃糖甙(B);孕甾-5,16-二烯-3β-醇-20-酮,3β-O-α-L-鼠李吡喃糖基(1→2)〔α-L-鼠李吡喃糖基(1→4)-α-L-鼠李吡喃糖基(1→4)〕-β-D-葡萄吡喃糖甙(C)。甙A、B和C在滇重楼根中尚未发现,甙C系首次从重楼属植物中获得,而甙A具有止血的活性。     

滇产植物皂素成分的研究——Ⅵ.滇重楼皂甙(2)

从滇重楼干根粉中分离出三个甾体皂甙,鉴定为薯芋皂甙元-3-O-α-L-鼠李吡喃糖(1→2)-β-D-葡萄吡喃糖甙V,偏诺皂甙元-3-O-α-L-鼠李吡喃糖(1→2)-β-D-葡萄吡喃糖甙Ⅵ,偏诺皂甙元-3-O-α-L-鼠李吡哺糖(1→4)-α-L-鼠李吡喃糖(1→4)-〔α-L-鼠李吡喃糖(1→2)〕-β-D-葡萄吡喃糖甙Ⅶ.皂甙Ⅵ和Ⅶ已显示出有趣的生理活性。     

盾叶薯蓣地上部分的三个新甾体皂甙

从盾叶薯蓣Dioscorea zingiberensis Wright地上部分分离鉴定了四个甾体皂甙,经鉴定甙A为约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖甙;甙B为24α-羟基约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)]β-D-葡萄吡喃糖甙;甙C为约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)][β-D-葡萄吡喃糖基(1→4)]-β-D-葡萄吡喃糖基;甙D为约莫皂甙元-3-O-[α-L-鼠李吡喃糖基(1→2)][β-D-葡萄吡喃糖基(1→3)]-β-D-葡萄吡喃糖甙。前三者为新化合物,分别命名为盾叶皂甙A_1、A_2、A_3(zingiberoside A_1、A_2、A_3),其中盾叶皂甙A_2的甙元为一新甾体皂甙元,命名为盾叶皂甙元(zingiberogenin)。     

屏边三七根茎中的两个新的齐墩果酸皂甙

从屏边三七(Panax stipuleanatus Tsai et Feng)根茎中分离到二个齐墩果烷型新皂甙,命名为屏边三七甙(stipuleanoside)R_1和R_2,其化学结构经光谱分析和化学降解反应,分别确定为齐墩果酸-3-O-β-D-葡萄吡喃糖基(1→3)[α-L-阿拉伯呋喃糖基(1→4)]-β-D-葡萄吡喃糖醛酸甙(1)和齐墩果酸[28-O-β-D-葡萄吡喃糖基]-3-O-β-D-葡萄吡喃糖基(1→3)[α-L-阿拉伯呋喃糖基(1→4)]-β-D-葡萄吡喃糖醛酸甙(3)。     

滇产植物皂素成分的研究——Ⅹ.五指莲的两个新甾体皂甙(1)

从重楼属植物五指莲Paris axialis H.Li.根茎中分离到三个甾体皂甙,经化学降解,质谱,核磁共振谱分析,证明其中两个甙为新的化合物,即偏诺皂甙元-3-O-β-D-葡萄吡喃糖基(1→3)[α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖甙(Ⅰ)和24α-羟基偏诺皂甙元-3-O-β-D-葡萄吡喃糖基(1→3)][α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖(Ⅲ);另一个鉴定为薯芋皂甙元-3-O-β-D-葡萄吡喃糖基(1→3)[α-L-鼠李吡喃糖基(1→2)]-β-D-葡萄吡喃糖甙(Ⅱ)。     

Discovery and characterization of a fructosylated capsule polysaccharide and sialylated lipopolysaccharide in a virulent strain of Actinobacillus suis

We are developing a serotyping system for Actinobacillus suis based on its capsule (K) and lipopolysaccharide O-chain (O) structures. Previously, we have shown that less virulent strains of this swine pathogen express a (1→6)-β-D-glucan as both K- and O-chain polysaccharides and were serologically classified as K:1/O:1. Here, we show that representative A. suis strains with a high (H91-0380; serotype K:2/O:2) and intermediate (C84; serotype K:2/O:1) degree of virulence possess a capsule polysaccharide (K:2) composed of an O-acetylated diglycosyl phosphate repeat decorated with fructose: [→4)-3-O-Ac-β-D-GlcpNAc-(1→3)-[β-D-Fruf-(2→2)]-α-D-Galp-(1→PO(4)(-)→]. In addition, the serotype O:2 lipopolysaccharide was shown to express a sialylated O-chain [→3)-β-D-Galp-(1→4)-[Neu5Ac-(2→3)-α-D-Galp-(1→6)]-β-D-Glcp-(1→6)-β-D-GlcpNAc-(1→]. As (1→6)-β-D-glucan is ubiquitous in the environment, low levels of antibodies in the animals are predicted to prevent disease by K:1/O:1 strains. The greater potential associated with K:2/O:2 and K:2/O:1 strains is most likely due to the absence of (1→6)-β-D-glucan as the K antigen and, in the case of K:2/O:2, the presence of sialic acid in the lipopolysaccharide, a nonulosonic acid known to promote evasion of host recognition.     

Oleanane-type glycosides from Weigela x Styriaca and two cultivars of W. florida: “Minor black” and “Brigela”

Sixteen oleanane-type glycosides were extracted from three Weigela hybrids and cultivars: W. x Styriaca, W. florida “Minor black” and W. florida “Brigela”, and four of them were previously undescribed ones: 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyloleanolic acid, 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid, 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid, and 3-O-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyloleanolic acid. Their full structural elucidation required extensive 1D and 2D NMR experiments, as well as mass spectrometry analysis. Six compounds among the known ones were in sufficient amount to be tested for their antifungal activity against Candida albicans, and their antibacterial activity against Staphylococcus aureus and Pseudomonas aeruginosa.     

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－     

Triterpene saponins from Cyclamen hederifolium

Five triterpene saponins never reported before, hederifoliosides A-E, and four known triterpene saponins were isolated from the tubers of Cyclamen hederifolium. The structures of hederifoliosides A-E were determined as 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-oic acid 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 3β,16α-dihydroxy-13β,28-epoxyolean-30-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-[β-D-glucopyranosyl-(1 → 6)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,30-trihydroxyolean-12-en-28-al 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, 30-O-β-D-glucopyranosyl-(1 → 2)-O-β-D-glucopyranosyl-3β,16α,28,30-tetrahydroxyolean-12-en 3-O-{[β-D-glucopyranosyl-(1 → 2)-O]-β-D-xylopyranosyl-(1 → 2)-O-[β-D-glucopyranosyl-(1 → 3)]-O-β-D-glucopyranosyl-(1 → 4)-O-α-L-arabinopyranoside}, by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including Hela, H-446, HT-29, and U937. None of the tested compounds, in a range of concentrations between 1 and 50 μM, caused a significant reduction of the cell number.     

Anti-diabetic effects of a kaempferol glycoside-rich fraction from unripe soybean (Edamame, Glycine max L. Merrill. 'Jindai') leaves on KK-A(y) mice

The anti-diabetic effects of a kaempferol glycoside-rich fraction (KG) prepared from leaves of unripe Jindai soybean (Edamame) and kaempferol, an aglycone of kaempferol glycoside, were determined in genetically type 2 diabetic KK-A(y) mice. The hemoglobin A(?c) level was decreased and tended to be decreased by respectively feeding KG and kaempferol (K). The area under the curve (AUC) in the oral glucose tolerance test (OGTT) tended to be decreased by feeding K and KG. The liver triglyceride level and fatty acid synthase activity were both decreased in the mice fed with KG and K when compared to those parameters in the control mice. These results suggest that KG and K would be useful to improve the diabetes condition. The major flavonoids in KG were identified as kaempferol 3-O-β-D-glucopyranosyl(1→2)-O-[α-L-rhamnopyranosyl(1→6)]-β-D-galactopyranoside, kaempferol 3-O-β-D-glucopyranosyl(1→2)-O-[α-L-rhamnopyranosyl(1→6)]-β-D-glucopyranoside, kaempferol 3-O-β-D-(2-O-β-D-glucopyranosyl) galactopyranoside and kaempferol 3-O-β-D-(2,6-di-O-α-L-rhamnopyranosyl) galactopyronoside, suggesting that these compounds or some of them may be concerned with mitigation of diabetes.     

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)。     

中华青荚叶的一个新果糖酯

从山茱萸科中华青荚叶( Helwingia chinensis )的乙醇提取物中分离得到一个新果糖酯和十个已知化合物.通过现代波谱技术分别鉴定为:2- O -(E)-咖啡酰-3- O -(3, 5-二甲氧基香豆酰)-α-D-呋喃果糖甙(1),2- O -β-D-呋喃果糖基α-D-异吡喃糖酯(2),甘草甜素(3),4′-羟基-7- O -葡萄糖-2, 3-二羟黄酮甙(4),黄豆甙(5),5-葡萄糖芹菜甙(6),7- O -葡萄糖芹菜甙(7),4- O -葡萄糖香豆酸(8), 葡萄糖咖啡酸(9), 3β-赤杨醇(10), 薯蓣皂甙3- O -{α-L-鼠李糖吡喃糖基(1→2)-[α-L-阿拉伯呋喃糖基(1→3)]-β-D-葡萄糖吡喃糖} (11).     

Inhibition of NO Production by Grindelia argentina and Isolation of Three New Cytotoxic Saponins

A bioassay‐guided phytochemical analysis of the ethanolic extract of Grindelia argentina Deble & Oliveira ‐Deble (Asteraceae) allowed the isolation of a known flavone, hispidulin, and three new oleanane‐type saponins, 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,16α,23‐tetrahydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 2 ), 3‐O‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester, ( 3 ) and 3‐O‐β‐D ‐xylopyranosyl‐(1→3)‐β‐D ‐glucopyranosyl‐2β,3β,23‐trihydroxyolean‐12‐en‐28‐oic acid 28‐O‐β‐D ‐xylopyranosyl‐(1→2)‐β‐D ‐apiofuranosyl‐(1→3)‐β‐D ‐xylopyranosyl‐(1→3)‐α‐L ‐rhamnopyranosyl‐(1→2)‐α‐L ‐arabinopyranosyl ester ( 4 ), named grindeliosides A–C, respectively. Their structures were determined by extensive 1D‐ and 2D‐NMR experiments along with mass spectrometry and chemical evidence. The isolated compounds were evaluated for their inhibitory activities against LPS/IFN‐γ‐induced NO production in RAW 264.7 macrophages and for their cytotoxic activities against the human leukemic cell line CCRF‐CEM and MRC‐5 lung fibroblasts. Hispidulin markedly reduced LPS/IFN‐γ‐induced NO production (IC₅₀ 51.4 μM ), while grindeliosides A–C were found to be cytotoxic, with grindelioside C being the most active against both CCRF‐CEM (IC₅₀ 4.2±0.1 μM ) and MRC‐5 (IC₅₀ 4.5±0.1 μM ) cell lines.     

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     

Structural studies of the carbohydrate moiety of human antithrombin III

Human antithrombin III contains four asparagine-linked sugar chains in one molecule. The sugar chains were quantitatively released as radioactive oligosaccharides from the polypeptide portion by hydrazinolysis followed by N-acetylation and NaB³H₄ reduction. All of the oligosaccharides, thus obtained, contain N-acetylneuraminic acid. A same neutral nonaitol was released from all acidic oligosaccharides by sialidase treatment. By combination of the sequential exoglycosidase digestion and methylation analysis, their structures were elucidated as NeuAcα2 → 6Galβ1 → 4GlcNAcβ1 → 2Manα1 → 6-(NeuAcα2 → 6Galβ1 → 4GlcNAcβ1 → 2Manα1 → 3)Manβ1 → 4GlcNAcβ1 → 4GlcNAc, Galβ1 → 4GlcNAcβ1 → 2Manα1 → 6(NeuAcα2 → 6Galβ1 → 4GlcNAcβ1 → 2Manαl → 3)Manβ1 → 4GlcNAcβ1 → 4GlcNAc, and NeuAcα2 → 6Galβ1 → 4GlcNAcβ1 → 2Manα1 → 6(Galβ1 → 4GlcNAcβ1 → 2Manα1 → 3)Manβ1 → 4GlcNAcβ1 → 4GlcNAc.