488-15-3Relevant academic research and scientific papers
Cremastrine, a pyrrolizidine alkaloid from Cremastra appendiculata
Ikeda, Yoshitaka,Nonaka, Hikaru,Furumai, Tamotsu,Igarashi, Yasuhiro
, p. 572 - 573 (2005)
A new pyrrolizidine alkaloid, cremastrine (1), was isolated from the bulbs of Cremastra appendiculata. Its configuration was determined by spectroscopic and chemical analyses. Compound 1 inhibited the binding of tritium-labeled N-methylscopolamine to the muscarinic M3 receptor with a Ki value of 126 nM.
Structure of Majusculamide C, a Cyclic Depsipeptide from Lyngbya majuscula
Carter, Daniel C.,Moore, Richard E.,Mynderse, Jon S.,Niemczura, Walter P.,Todd, James S.
, p. 236 - 241 (1984)
Majusculamide C, a novel cyclic depsipeptide that inhibits the growth of a number of fungal plant pathogens, has been shown to consist of seven α-amino acid units, one β-amino acid unit, and one hydroxy acid unit.The structures of the units have been determined by acid hydrolysis of the fungicide to glycine, L-alanine, L-N-methylpivaline, L-N,O-dimethyltyrosine, racemic 2-amino-4-methylpentanone, 3-amino-2-methylpentanoic acid of undefined stereochemistry, and N-glycine.Sequencing of the units implied from the structures of the hydrolysis products has been achieved by mass spectral and proton NOE studies.
Keramamides E, G, H, and J, New Cyclic Peptides Containing an Oxazole or a Thiazole Ring from a Theonella Sponge
Kobayashi, Jun'ichi,Itagaki, Fumio,Shigemori, Ilideyuki,Takao, Toshifumi,Shimonishi, Yasutsugu
, p. 2525 - 2532 (1995)
Four new cyclic peptides, keramamides E (1), G (2), H (3), and J (4), containing an oxazole or a thiazole ring have been isolated from the Okinawan marine sponge Theonella sp. and the structures elucidated by 2D NMR data and degradation experiments.The sequence of amino acid residues in 1 - 4 was determined on the basis of FAB MS/MS data.
The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria
Choi, Hyukjae,Pereira, Alban R.,Cao, Zhengyu,Shuman, Cynthia F.,Engene, Niclas,Byrum, Tara,Matainaho, Teatulohi,Murray, Thomas F.,Mangoni, Alfonso,Gerwick, William H.
, p. 1411 - 1421 (2010)
Two related peptide metabolites, one a cyclic depsipeptide, hoiamide B (2), and the other a linear lipopeptide, hoiamide C (3), were isolated from two different collections of marine cyanobacteria obtained in Papua New Guinea. Their structures were elucidated by combining various techniques in spectroscopy, chromatography, and synthetic chemistry. Both metabolites belong to the unique hoiamide structural class, characterized by possessing an acetate extended and S-adenosyl methionine modified isoleucine unit, a central triheterocyclic system comprised of two α-methylated thiazolines and one thiazole, and a highly oxygenated and methylated C-15 polyketide unit. In neocortical neurons, the cyclic depsipeptide 2 stimulated sodium influx and suppressed spontaneous Ca2+ oscillations with EC50 values of 3.9 μM and 79.8 nM, respectively, while 3 had no significant effects in these assays.
Cytotoxic veraguamides, alkynyl bromide-containing cyclic depsipeptides from the marine cyanobacterium cf. Oscillatoria margaritifera
Mevers, Emily,Liu, Wei-Ting,Engene, Niclas,Mohimani, Hosein,Byrum, Tara,Pevzner, Pavel A.,Dorrestein, Pieter C.,Spadafora, Carmenza,Gerwick, William H.
, p. 928 - 936 (2011)
A family of cancer cell cytotoxic cyclodepsipeptides, veraguamides A-C (1-3) and H-L (4-8), were isolated from a collection of cf. Oscillatoria margaritifera obtained from the Coiba National Park, Panama, as part of the Panama International Cooperative Biodiversity Group program. The planar structure of veraguamide A (1) was deduced by 2D NMR spectroscopy and mass spectrometry, whereas the structures of 2-8 were mainly determined by a combination of 1H NMR and MS2/MS3 techniques. These new compounds are analogous to the mollusk-derived kulomo'opunalide natural products, with two of the veraguamides (C and H) containing the same terminal alkyne moiety. However, four veraguamides, A, B, K, and L, also feature an alkynyl bromide, a functionality that has been previously observed in only one other marine natural product, jamaicamide A. Veraguamide A showed potent cytotoxicity to the H-460 human lung cancer cell line (LD50 = 141 nM). (Chemical Equation Presented).
Pleosporin A, an antimalarial cyclodepsipeptide from an elephant dung fungus (BCC 7069)
Isaka, Masahiko,Palasarn, Somporn,Komwijit, Somjit,Somrithipol, Sayanh,Sommai, Sujinda
, p. 469 - 471 (2014)
Cyclodepsipeptides SCH 217048 (1), SCH 218157 (2), and a new analog, pleosporin A (3), were isolated from cultures of an unidentified elephant dung fungus of the family Pleosporaceae. The structure of 3 was elucidated on the basis of detailed spectroscopic interpretation. The absolute configurations of 1-3 were determined by chiral column HPLC analysis and Marfey's method. Cyclodepsipeptides 1-3 exhibited antimalarial activity against Plasmodium falciparum K1 with respective IC50 values of 1.6, 6.4, and 1.6 μg/mL, while they did not show cytotoxicity against KB, MCF-7 and NCI-H187 cell-lines or non-cancerous Vero cells at 50 μg/mL.
Pitipeptolides A and B, new cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula
Luesch,Pangilinan,Yoshida,Moore,Paul
, p. 304 - 307 (2001)
Two new cyclodepsipeptides have been isolated from a population of the marine cyanobacterium Lyngbya majuscula collected at Piti Bomb Holes, Guam. They appear to be unique to this particular Guamanian collection and have been named pitipeptolides A (1) and B (2). Their structures have been elucidated by spectroscopic techniques and by characterization of degradation products. Distinctive features include the presence of a 2,2-dimethyl-3-hydroxy-7-octynoic acid residue in 1 and a 2,2-dimethyl-3-hydroxy-7-octenoic acid residue in 2, previously shown to be biosynthetic signatures of cyanobacterial metabolites. Pitipeptolides A (1) and B (2) exhibit weak cytotoxicity against LoVo cancer cells, but possess moderate antimycobacterial activity and stimulate elastase activity.
New steroidal constituents of the underground parts of Ruscus aculeatus and their cytostatic activity on HL-60 cells
Mimaki, Yoshihiro,Kuroda, Minpei,Kameyama, Aiko,Yokosuka, Akihito,Sashida, Yutaka
, p. 298 - 303 (1998)
Phytochemical examination of the underground parts of Ruscus aculeatus has led to the isolation of a total of twelve steroidal saponins, including seven new ones. The structures of the new saponins were determined by spectroscopic analysis and chemical evidence. The furostanol saponin, having a diglycoside moiety modified with a (2S,3S)-2-hydroxy-3-methylpentanoic acid group and an acetic acid group, and its corresponding spirostanol saponin exhibited cytostatic activity on leukemia HL-60 cells.
Further insight into the asymmetric vinylogous Mukaiyama aldol reaction (VMAR); Application to the synthesis of the C27-C45 segment of lagunamide A
Banasik, Brent A.,Wang, Lee,Kanner, Arielle,Mikael Bergdahl
, p. 2481 - 2490 (2016)
Two iterative vinylogous Mukaiyama aldol reactions (VMAR) have been applied in order to selectively install three contiguous stereocenters at C37, C38 and C39, of the southern hemisphere of lagunamide A. The VMAR methodology allows straightforward access of enantiomerically pure material of the essential segment via seven steps, and in an overall yield of 34%. The synthesis has an orthogonal protecting group strategy, essential for upcoming synthesis for completion of lagunamide A. We also demonstrate that steric bulk of the chiral oxazolidinone pose certain challenges when employing stereochemically crowded α-substituted aldehydes in various VMAR's. A simple synthesis of the essential (2R,3S)-2-hydroxy-3-methylpentanoic acid fragment via Mitsunobu chemistry was also accomplished and incorporated into the C27-C45 fragment of lagunamide A.
Structure revision of isocereulide A, an isoform of the food poisoning emetic Bacillus cereus toxin cereulide
Ehling-Schulz, Monika,Hofmann, Thomas F.,Kranzler, Markus,Stark, Timo D.,Walser, Veronika
supporting information, (2021/05/31)
The emetic Bacillus cereus toxin cereulide presents an enormous safety hazard in the food industry, inducing emesis and nausea after the consumption of contaminated foods. Additional to cereulide itself, seven structurally related isoforms, namely the isocereulides A-G, have already been elucidated in their chemical structure and could further be identified in B. cereus contaminated food samples. The newly performed isolation of isocereulide A allowed, for the first time, 1D- and 2D-NMR spectroscopy of a biosynthetically produced isocereulide, revealing results that contradict previous assumptions of an L-O-Leu moiety within its chemical structure. By furthermore applying posthydrolytical dipeptide analysis, amino acid and α-hydroxy acid analysis by means of UPLC-ESITOF- MS, as well as MSn sequencing, the structure of previously reported isocereulide A could be corrected. Instead of the L-O-Leu as assumed to date, one L-O-Ile unit could be verified in the cyclic dodecadepsipeptide, revising the structure of isocereulide A to [(D-O-Leu-D-Ala-L-O-Val-L-Val)2(DO- Leu-D-Ala-L-O-Ile-L-Val)].
