488-15-3Relevant articles and documents
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.
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.
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).
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.
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.
ANTIMICROBIAL PEPTIDES AND METHODS OF USE
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Paragraph 0009; 0139, (2020/02/14)
Cyclic depsipeptide-class molecules, referred to herein as persephacins (including analogs thereof), having similarities to aureobasidin A, are described. The persephacins have antimicrobial activity, such as antifungal activity against a diverse range of clinically -relevant fungal pathogens, antiprotozoan parasite activity, and antibacterial activity, and can be used for example in treatments of difficult-to-treat ocular fungal infections at lower concentrations than natamycin. The active compounds may be combined with a secondary compound in a composition.
Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore
Brumley, David A.,Chen, Qi-Yin,Gunasekera, Sarath P.,Luesch, Hendrik,Paul, Valerie J.
supporting information, p. 4235 - 4239 (2020/06/27)
New modified depsipeptides and geometric isomers, termed anaenamides A (1a) and B (1b), along with the presumptive biosynthetic intermediate, anaenoic acid (2), were discovered from a marine cyanobacterium from Guam. Structures were confirmed by total synthesis. The alkylsalicylic acid fragment and the C-terminal α-chlorinated α,β-unsaturated ester are novelties in cyanobacterial natural products. Cancer cell viability assays indicated that the C-terminal unit serves as the pharmacophore and that the double-bond geometry impacts the cytotoxicity.
