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21.
Lupane-type triterpenoids have shown a potential effect against neurodegenerative disorders. Alzheimer’s disease, one of the common neurodegenerative disease, is evident by the accumulation of amyloid-beta (Aβ) plaque in the extracellular regions of the brain. β-site amyloid precursor protein cleaving enzyme 1 (BACE1) is a key enzyme for the Aβ formation viathe cleavage of amyloid precursor protein (APP). Therefore, to find the potent BACE1 inhibitors and furthermore to explore the role of the functional group responsible for the strong BACE1 inhibitory activity, we synthesized a series of triterpenoids with lupane skeleton starting from the natural compounds calenduladiol and lupeol. Compound 1 revealed a potent competitive BACE1 inhibitory activity (IC50 = 16.77 ± 1.16 μM; Ki = 19.38). Furthermore, the molecular docking simulation revealed the importance of Tyr198 residue along with the other hydrophobic interactions for the strong affinity of 1‒BACE1 complex. To sum up, our results demonstrated the importance of carbonyl moiety at 3 and 16 position of lupane-type triterpenoid over the hydroxyl group at the same position. 相似文献
22.
Thao Quyen Cao Nguyen Viet Phong Jang Hoon Kim Dan Gao Hoang Le Tuan Anh Viet-Duc Ngo Le Ba Vinh Young Sang Koh Seo Young Yang 《Molecules (Basel, Switzerland)》2021,26(15)
The bitter melon, Momordica charantia L., was once an important food and medicinal herb. Various studies have focused on the potential treatment of stomach disease with M. charantia and on its anti-diabetic properties. However, very little is known about the specific compounds responsible for its anti-inflammatory activities. In addition, the in vitro inhibitory effect of M. charantia on pro-inflammatory cytokine production by lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs) has not been reported. Phytochemical investigation of M. charantia fruit led to the isolation of 15 compounds (1−15). Their chemical structures were elucidated spectroscopically (one- and two-dimensional nuclear magnetic resonance) and with electrospray ionization mass spectrometry. The anti-inflammatory effects of the isolated compounds were evaluated by measuring the production of the pro-inflammatory cytokines interleukin IL-6, IL-12 p40, and tumor necrosis factor α (TNF-α) in LPS-stimulated BMDCs. The cucurbitanes were potent inhibitors of the cytokines TNF-α, IL-6, and IL-12 p40, indicating promising anti-inflammatory effects. Based on these studies and in silico simulations, we determined that the ligand likely docked in the receptors. These results suggest that cucurbitanes from M. charantia are potential candidates for treating inflammatory diseases. 相似文献
23.
Hui-Ling Ma Jin-Yi Qin Lei Wang Sheng-Xiang Yang Ming-Hua Chiu Xian-Min Zhang Jin-Ming Gao 《Chemistry of Natural Compounds》2008,44(1):44-47
A new triterpene, taraxast-20(30)-en-3β,12β-diol (1), and eight known compounds were isolated from the leaves of Craibiodendron yunnanense. Their structures were established on the basis of spectral evidence.
Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 35–37, January–February, 2008. 相似文献
24.
Eighteen different triterpene saponins isolated from Polygala tenuifolia were investigated by electrospray ionization ion trap multiple-stage mass spectrometry (ESI-ITMS(n)) in positive and negative ion modes. MS(1)-MS(3)/MS(4) spectra of the both modes were analyzed, and they all gave fragments in line and shared common fragmentation patterns. Key fragments from MS(n) spectra of both the modes and their proposed fragmentation pathways were constructed with examples illustrated for the formation of characteristic fragments in the saponins. Two special fragmentation patterns were proposed: (1) the formation of fragments by cleavage of CH(2)O from Delta(12)-14alpha-CH(2)OH of the oleanene-type saponin aglycone in both positive and negative MS(n) (n > or = 2) modes; (2) the occurrence of fragments by cleavage of CO(2) and 3-glucose as the characteristic structure feature of 23-COOH at the oleanene-type saponin aglycones coupled with 3-Glc substitutes in the negative MS(n) (n > or = 2) modes. Peak intensities in MS(n) spectra were also correlated with structural features and fragmentation preferences of the investigated saponins, which are discussed in detail. In general, fragments formed predominantly by cleavages of glycosidic bonds in the positive mode, while selective cleavages of acyl bonds preceded that of glycosidic bonds in negative MS(n) (n > or = 2) mode, both of which could well be applied to the structural analysis of these saponins. Interpretation of MS(n) spectra presented here provided diagnostic key fragment ions important for the structural elucidation of saponins in P.tenuifolia. 相似文献
25.
S. Lakshmi K. Subramanian T. Steiner B. Varghese 《Journal of chemical crystallography》1999,29(10):1141-1143
The X-ray crystal structure of the triterpenoid piscidinol-C from the leaves of Walsura piscidia is determined. The compound, which is an apotirucallane derivative, crystallizes in the orthorhombic space group C2221 with a = 18.985(4), b = 13.092(5), c = 24.690(7) Å, and D
calc = 1.209 g cm–1 for Z = 8. 相似文献
26.
Lu-Lu Yang Qi-Qi Zhou Song Fan Chun-Lu Liu Hui-Jun Li 《Biomedical chromatography : BMC》2024,38(5):e5835
The saponin-enriched extract from Celosiae Semen is a promising resource owing to its lipid-lowering activity. However, triterpenoid saponins are difficult to extract owing to their high molecular weight and strong water solubility. The aim of this paper was to explore an eco-friendly and effective technology of extraction and enrichment of total triterpenoid saponins to obtain high lipid-lowering fractions. Initially, Box–Behnken design experiments were employed to optimize the heat reflux extraction process on the basic of mono-factor experiments. Afterwards, the crude extract was further purified using D-101 resin, and the purification parameters were investigated based on adsorption/desorption experiments and biological activity assay. Under optimal conditions, the purity of the finally obtained total triterpenoid saponins was increased by 7.28-fold. The lipid-lowering activities of the six main triterpenoid saponins were evaluated in HepG2 cells induced by palmitic acid. The results of Oil Red O staining showed that the compounds all exhibited potential lipid-lowering activity. The structure–activity relationship analysis suggested that the oligosaccharide chain at C-28 played an essential role in their lipid-lowering activity and the substituent group at C-23 site also showed important effects. The optimal extraction and purification methods may facilitate the utilization of Celosiae Semen for the industrial production as a functional food and drug. 相似文献
27.
Two unprecedented tricyclic-iridal triterpenoids, belamcandanes A–B (1–2), have been isolated from the rhizomes of Belamcanda chinensis. The structures of 1 and 2 were assigned by interpretation of spectroscopic data including NMR and MS, and their absolute configurations were assigned by ECD calculation. Compounds 1–2 possess a spiro[4,5]decane core structure and a α-terpineol moiety, representing the first example of tricyclic-iridal triterpenoids. The plausible biogenetic pathway for 1 and 2 is also proposed. 相似文献
28.
Two New Lanostane-type Triterpenoids from Mulgedium tataricum 总被引:1,自引:0,他引:1
Xiao Xiong WANG Zhong Jian JIA 《中国化学快报》2006,17(2):204-206
Mulgedium tataricum L. has long been used for treatment of appendicitis, erysipelas andextravasated blood1. From the methanol extract of the whole plants, two newtriterpenoids 1 and 2 were isolated. In this paper, we report the structural elucidation ofth… 相似文献
29.
Hong Wei LIU Xin Sheng YAO Nai Li WANG Guo Ping CAI 《中国化学快报》2006,17(2):211-214
The Aesculus genus consists of about thirty species distributed in Asia, Europe andAmerica. There are sixteen species distributed in China, and most of them are used asherbal medicines for the treatment of distention and pain in the chest and abdomen. Anu… 相似文献
30.
A new compound 1 was isolated from the methanolic extract of the stems of the Caesalpinia pulcherrima Linn. along with a reported compound (2) 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester. The new compound 1 has m.p. 272–274°C, m.f. C46H74O17, [M]+ m/z 898. It was characterised as 3-O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl hederagenin 28-O-β-D- xylopyranosyl ester by various colour reactions, chemical degradations and spectral analyses. Antibacterial activity of compound 1 was screened against various Gram-positive and Gram-negative bacteria and showed significant results. 相似文献