- Kinase-Inhibitory Nucleoside Derivatives from the Pacific Bryozoan Nelliella nelliiformis
-
Marine organisms are a valuable source of bioactive natural products, yet bryozoan invertebrates have been relatively understudied. Herein, we report nelliellosides A and B, new secondary metabolites of the Pacific bryozoan Nelliella nelliiformis, found using NMR-guided isolation. Their structures, including absolute configurations, were elucidated using spectroscopic and chromatographic techniques. Total synthesis of the natural products and four analogues was also achieved, in addition to an assessment of their biological activity, especially kinase inhibition.
- Bracegirdle, Joe,Gordon, Dennis P.,Harvey, Joanne E.,Keyzers, Robert A.
-
-
Read Online
- A comparative study of the neutral and acidic polysaccharides from Allium macrostemon Bunge
-
Neutral and acidic polysaccharides, named AMP40N and AMP40S respectively, were isolated and purified from the dried bulbs of Allium macrostemon Bunge. Both of them showed a single and symmetrically sharp peak, indicating they were homogeneous polysaccharides. Molecular weights of AMP40N and AMP40S were determined to be 18.2 and 105.1 kDa, respectively. AMP40N was composed of arabinose and glucose, while AMP40S was composed of rhamnose, arabinose, glucose and galactose and a certain amount of uronic acid. FT-IR, periodic acid oxidation, Smith degradation, methylation and GC-MS analysis revealed that non-reducing terminal and →2,6)-Glc-(1→ existed in AMP40N and AMP40S. The glycosidic linkage of arabinose in AMP40N was →2)-Ara-(1→, whereas it was Ara-(1→ in AMP40S. AMP40S had (1→2)-linked l-rhamnose residue. Both AMP40N and AMP40S exhibited strong anti-tumor potential against human gastric carcinoma cells BGC-823, in particular, AMP40S presented significantly higher inhibitory rate of 85.94% than AMP40N of 52.63%.
- Zhang, Zhanjun,Wang, Fuhua,Wang, Mingchun,Ma, Liping,Ye, Hong,Zeng, Xiaoxiong
-
p. 980 - 987
(2015/01/09)
-
- Cyclopentadienyl-ruthenium(II) and iron(II) organometallic compounds with carbohydrate derivative ligands as good colorectal anticancer agents
-
New ruthenium(II) and iron(II) organometallic compounds of general formula [(η5-C5H5)M(PP)Lc][PF6], bearing carbohydrate derivative ligands (Lc), were prepared and fully characterized and the crystal structures of five of those compounds were determined by X-ray diffraction studies. Cell viability of colon cancer HCT116 cell line was determined for a total of 23 organometallic compounds and SAR's data analysis within this library showed an interesting dependency of the cytotoxic activity on the carbohydrate moiety, linker, phosphane coligands, and metal center. More importantly, two compounds, 14Ru and 18Ru, matched oxaliplatin IC50 (0.45 μM), the standard metallodrug used in CC chemotherapeutics, and our leading compound 14Ru was shown to be significantly more cytotoxic than oxaliplatin to HCT116 cells, triggering higher levels of caspase-3 and -7 activity and apoptosis in a dose-dependent manner.
- Florindo, Pedro R.,Pereira, Diane M.,Borralho, Pedro M.,Rodrigues, Cecília M. P.,Piedade,Fernandes, Ana C.
-
p. 4339 - 4347
(2015/06/08)
-
- New dammarane-type saponins from the roots of panax notoginseng
-
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. Copyright
- Qiu, Li,Jiao, Yang,Huang, Gui-Kun,Xie, Ji-Zhao,Miao, Jian-Hua,Yao, Xin-Sheng
-
p. 102 - 111
(2014/02/14)
-
- Two new compounds from the roots of Ilex pubescens
-
A new triterpenoid glycoside, heterobetulinic acid 3-O - D-glucopyranosyl(1→2) - D-xylopyranoside (1), together with a new phenylacrylic acid derivative, 3S,4-dihydroxyl-2-methylene-but-1-enyl caffeate (2), were isolated from the roots of Ilex pubescens. Their structures were elucidated by HR-ESI-MS, 1-D and 2-D NMR analyses and chemical methods. In addition, the absolute configuration of 2 was established by the application of a modified Mosher's method.
- Wu, Ting,Zhang, Qing-Wen,Zhang, Xiao-Qi,Liu, Ge,Wang, Lei,Jiang, Miao-Miao,Feng, Yi-Fan,Ye, Wen-Cai
-
experimental part
p. 1408 - 1412
(2012/10/18)
-
- New triterpenoid sapoin from Ardisia gigantifolia Stapf.
-
One new triterpenoid sapoin with two known triterpenoid sapoins: 3β-O-{α-l-rhamnopyranosyl-(1 → 3)-[β-d-xylopyranose-(1 → 2)]-β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranosyl}-3β-hydroxy-13β,28-epoxy-oleanan-16-oxo-30-al (1), 3β-O-{α-l-rhamnopyranosyl-(1 →
- Gong, Qiang Qiang,Mu, Li Hua,Liu, Ping,Yang, Shi Lin,Wang, Bo,Feng, Yu Lin
-
experimental part
p. 449 - 452
(2011/02/26)
-
- Two new cytotoxic disulfated holostane glycosides from the sea cucumber Pentacta quadrangularis
-
Two new disulfated triterpene glycosides, pentactasides B and C (1 and 2, resp.), were isolated from the sea cucumber Pentacta quadrangularis collected from the South China Sea. Their structures were elucidated by extensive spectral analysis (2D-NMR and M
- Han, Hua,Xu, Qiang-Zhi,Yi, Yang-Hua,Gong, Wei,Jiao, Bing-Hua
-
experimental part
p. 158 - 167
(2010/04/23)
-
- Five furostanol saponins from fruits of Tribulus terrestris and their cytotoxic activities
-
Two new furostanol saponins, terrestroside A, 3-O-{β-D-xylopyranosyl- (1 → 3)-[ β-D-xylopyranosyl(1 → 2)] β - D-glucopyranosyl(1 → 4)-[α-L-rhamnopyranosyl(1 → 2)] β- D-galactopyranosy}-26- O -β D-glucopyranosyl-L-5a-furost-20(22)-en-(25R)-3,26-diol (1) an
- Wang, Jue,Zu, Xuyu,Jiang, Yuyang
-
experimental part
p. 1436 - 1444
(2010/04/23)
-
- Antioxidant activity of a water-soluble polysaccharide purified from Pteridium aquilinum
-
A water-soluble crude polysaccharide, obtained from fern Pteridium aquilinum, was fractionated by DEAE-Sepharose Fast-Flow column chromatography, and purified by Sephacryl S-400 HR column chromatography. The average molecular weight (Mw) of the purified polysaccharide (PLP) is 458,000 Da. The monosaccharide components of PLP were characterized by gas chromatography (GC), and the majority of the monosaccharide components was glucose (relative mass 58.1%) with low levels of galactose, mannose, rhamnose, and arabinose (relative mass 18.7%, 6.8%, 10.2%, and 6.1%, respectively). The Fourier-transform infrared spectra (FTIR) of PLP revealed typical characteristics of polysaccharides. On the basis of the ferric-reducing antioxidant power assay (FRAP), DPPH radical-scavenging, the superoxide radical assay, and self-oxidation of 1,2,3-phentriol assay, the antioxidant activities of PLP were investigated. The purified polysaccharide was demonstrated to have strong reductive power (FRAP value: 827.6 μmol/L), moderate scavenging activities against DPPH radicals (83.1%) and superoxide radicals (60.5%), and moderate inhibiting power for self-oxidation of 1,2,3-phentriol (52.4%).
- Xu, Wentao,Zhang, Fangfang,Luo, YunBo,Ma, Liyan,Kou, Xiaohong,Huang, Kunlun
-
experimental part
p. 217 - 222
(2009/04/11)
-
- Two new cytotoxic nonsulfated pentasaccharide holostane (=20-hydroxylanostan-18-oic acid γ-lactone) glycosides from the sea cucumber Holothuria grisea
-
Two new lanostane-type nonsulfated pentasaccharide triterpene glycosides, 17-dehydroxyholothurinoside A (1) and griseaside A (2), were isolated from the sea cucumber Holothuria grisea. Their structures were elucidated by spectroscopic methods, including 2D-NMR and MS experiments, as well as chemical evidence. Compounds 1 and 2 possess the same pentasaccharide moieties but differ slightly in their side chains of the holostane-type triterpene aglycone. The structures of the two new glycosides were established as (3β,12α)-22, 25-epoxy-3-{(O-β-D-glucopyranosyl-(1 → 4)-O-[O-3-O-methyl-β-D- glucopyranosyl-(1 → 3)-O-β-D-glucopyranosyl-(1 → 4)-6-deoxy-β-D-glucopyranosyl-(1 → 2)]-β-D-xylopyranosyl)-oxy}- 12,20-dihydroxylanost-9(11)-en-18-oic acid γ-lactone (1) and (3β,12α)-3-{(O-β-D-glucopyranosyl-(1 → 4)-O-[O-3-O-methyl- β-D-glucopyranosyl-(1 → 3)-O-β-D-glucopyranosyl-(1 → 4)-6-deoxy-β-D-glucopyranosyl-(1 → 2)]-β-D-xylopyranosyl)oxy}-12, 20,22-trihydroxylanost-9(11)-en-18-oic acid γ-lactone (2). The 17-dehydroxyholothurinoside A (1) and griseaside A (2) exhibited significant cytotoxicity against HL-60, BEL-7402, Molt-4, and A-549 cancer cell lines.
- Sun, Guo-Quan,Li, Ling,Yi, Yang-Hua,Yuan, Wei-Hua,Liu, Bao-Shu,Weng, Yi-Yi,Zhang, Shi-Long,Sun, Peng,Wang, Zeng-Lei
-
experimental part
p. 1453 - 1460
(2009/02/07)
-
- Acylic sugar derivatives for GC/MS analysis of 13C-enrichment during carbohydrate metabolism
-
Metabolic profiling with stable-isotope tracers in combination with gas chromatography/mass spectrometry (GC/ MS) is a well-established technique for measuring substrate redistribution within metabolic pathways. This analysis relies on the ability to localize and quantify the fractional incorporation of 13C isotope into each carbon atom of precursor-derived metabolites. In this paper, several carbohydrate derivatization procedures (peracetylation, deuterioalditol acetates, and aldononitrile acetates) are evaluated for the positional isotopic information obtained by gas chromatography/electron impact mass spectrometry (GC/EI-MS). These derivatives have been compared for the quantitative evaluation of 13C distribution into isotopomers of 13C-labeled aldoses and ketoses, and the fragmentation pathways for 15 hexoses, pentoses, and amino sugars of biological origin have been assessed. In addition, a new type of carbohydrate derivative (dialkyldithioacetal acetates) has been developed for GC/MS that retains the charge on the anomeric carbon of the original monosaccharide. Electron impact ionization of these derivatives generates well-resolved base peaks arising from C1-C2 bond cleavage with charge retention at the C1 thiol groups. The dialkyldithioacetal acetates are uniquely well suited for measuring isotopic enrichment into the characteristic anomeric carbon of aldose sugars and will facilitate the global analysis of metabolic flux in carbohydrate pathways.
- Price, Neil P. J.
-
p. 6566 - 6574
(2007/10/03)
-