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Le Hoang Vien Le Thi Hanh Tran Thi Hong Thanh Nguyen Van Nam Nguyen Hoai 《Natural product research》2020,34(8):1061-1067
AbstractFrom the MeOH extract of the Vietnamese sea cucumber Holothuria edulis, eight triterpene glycosides (1–8), including one new compound namely holothurin A5 (1), were isolated by using various chromatographic separations. Their structures were established by spectroscopic experiments including 1D, 2D NMR and HR-ESI-MS. Holothurin A5 (1) has a hydroperoxy group at C-25. To the best of our knowledge, this is the first report of this group in triterpene saponins obtained from sea cucumbers to date. In addition, the in vitro cytotoxicity against five human cancer cell lines (HepG2, KB, LNCaP, MCF7 and SK-Mel2) of all isolated compounds was also evaluated using SRB assays. 相似文献
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Hua Han Yang Hua Yi Ling Li Xiao Hua Wang Bao Shu Liu Peng Sun Min Xiang Pan Research Center for Marine Drugs School of Pharmacy Second Military Medical University Shanghai China 《中国化学快报》2007,18(2):161-164
A new triterpene glycoside, leucospilotaside A, along with a known saponin, isolated from sea cucumber Holothuria leucospilota, and its structure was elucidated as 3β-O-[4-O-sodiumsulfate-β-D-quinovopyranosyl-(1→2)-β-D-xylopyranosyl]-holosta-22-ketone-9-en-17α,25α-diol (1) by extensive spectroscopic analysis and chemical methods. Leucospilotaside A (1) has a ketone carbonyl group (22) in the aglycon side chain. 相似文献
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Guo‐Quan Sun Ling Li Yang‐Hua Yi Wei‐Hua Yuan Bao‐Shu Liu Yi‐Yi Weng Shi‐Long Zhang Peng Sun Zeng‐Lei Wang 《Helvetica chimica acta》2008,91(8):1453-1460
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. 相似文献
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Shunliang Zheng Yi Wang Jiashuo Wu Siyao Wang Huaifu Wei Yongchun Zhang Jianbo Zhou Yue Shi 《Molecules (Basel, Switzerland)》2022,27(14)
A low molecular weight fucosylated glycosaminoglycan sodium (LFG-Na) is a novel anticoagulant candidate from the sea cucumber Holothuria fuscopunctata that selectively inhibits intrinsic tenase (iXase). The molecular weight, molecular weight distribution and bioactivities are the critical quality attributes of LFG-Na. The determination of these quality attributes of such an oligosaccharides mixture drug is challenging but critical for the quality control process to ensure its safety and efficacy in clinical use. Herein, the molecular weight and molecular weight distribution of LFG-Na were successfully determined using high performance size exclusion chromatography coupled with multi angle laser light scattering and refractive index detector (HPSEC-MALLS-RID). Comparing to the conventional method, HPSEC-MALLS-RID based on the refractive index increment (dn/dc) did not require the reference substances to establish the calibration curve. The acceptance criteria of LFG-Na were established, the weight-average molecular weight () should be 4000 to 6000 Da, the polydispersity (/) < 1.40, and the fraction with molecular weights of 1500 to 8000 Da should be no less than 80% of the total. HPSEC-MALLS-RID was also utilized for the determination of the starting material native fucosylated glycosaminoglycan (NFG) to choose a better manufacturing process. Furthermore, APTT assay was selected and the potency of anti-iXase, referring to the parallel line assay (PLA) method, was established to clarify the consistency of its biological activities. The results suggest that HPSEC-MALLS-RID and bioactivity assays are critical quality control methods for multi-component glycosaminoglycan LFG-Na. The methods also provide a feasible strategy to control the quality of other polysaccharide medicines. 相似文献
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A new triterpene glycoside, leucospilotaside C, along with two known saponin, was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea, and its structure was elucidated as 3-0-{4′-O-sodiumsulfate-β′-D-xylopyranosyl}- holosta-22,25-epoxy-9-ene-3β,12α,17α-triol (1) by extensive spectroscopic analysis and chemical methods. The glycosides have the same triterpene aglycone, but differ in the oligosaccharide moieties. 相似文献
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A new triterpene glycoside, leueospilotaside C, along with two known saponin, was isolated from sea cucumber Holothuria leucospilota collected from the South China Sea, and its structure was elucidated as 3-O-{4'-O-sodiumsulfate-β-D-xylopyranosyl }-holosta-22,25-epoxy-9-ene-3β, 12a, 17a-triol (1) by extensive spectroscopic analysis and chemical methods. The glycosides have the same triterpene aglycone, but differ in the oligosaccharide moieties. 相似文献
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AbstractA new 12-membered macrolide, aspergillolide (1), along with nine known compounds (2–10), were isolated from the fungus Aspergillus sp. S-3-75 associated with the sea cucumber Holothuria nobilis Selenka. The structure and absolute stereochemistry of 1 were elucidated on the basis of extensive spectroscopic methods and single crystal X-ray diffraction analysis. 相似文献
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《中国化学快报》2006,(11)
A new sulfated triterpene glycoside named as 17-dehydroxyholothurin A 1 was isolated from the sea cucumber Holothuria impatiens. Its structure was elucidated on the basis of spectroscopic data (2D NMR and MS) and chemical evidence. Compound 1 showed cytotoxic activity against cancer cell lines MKN-28, MFC-7, KB, HL-60 and Hep G2 with IC50 values of 1.98, 4.53, 2.01, 4.69 and 2.80×10-6 mol/L, respectively. 相似文献
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Enas E. Eltamany Usama Ramadan Abdelmohsen Dina M. Hal Amany K. Ibrahim Hashim A. Hassanean Reda F. A. Abdelhameed Tarek A. Temraz Dina Hajjar Arwa A. Makki Omnia Magdy Hendawy Asmaa M. AboulMagd Khayrya A. Youssif Gerhard Bringmann Safwat A. Ahmed 《Molecules (Basel, Switzerland)》2021,26(6)
Chemical investigation of the methanolic extract of the Red Sea cucumber Holothuria spinifera led to the isolation of a new cerebroside, holospiniferoside (1), together with thymidine (2), methyl-α-d-glucopyranoside (3), a new triacylglycerol (4), and cholesterol (5). Their chemical structures were established by NMR and mass spectrometric analysis, including gas chromatography–mass spectrometry (GC–MS) and high-resolution mass spectrometry (HRMS). All the isolated compounds are reported in this species for the first time. Moreover, compound 1 exhibited promising in vitro antiproliferative effect on the human breast cancer cell line (MCF-7) with IC50 of 20.6 µM compared to the IC50 of 15.3 µM for the drug cisplatin. To predict the possible mechanism underlying the cytotoxicity of compound 1, a docking study was performed to elucidate its binding interactions with the active site of the protein Mdm2–p53. Compound 1 displayed an apoptotic activity via strong interaction with the active site of the target protein. This study highlights the importance of marine natural products in the design of new anticancer agents. 相似文献
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