- PF1163A and B, new antifungal antibiotics produced by Penicilium sp. II. Physico-chemical properties and structure elucidation
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The structures of new antifungal antibiotics, PF1163A and B, were elucidated by spectroscopic analyses of the degradation products and by X-ray crystallography of the de-2-hydroxyethyl derivative of PF1163B. Both antibiotics consist:of a 13-membered macrocyclic structure containing a derivative of N-methyl tyrosine and a hydroxy fatty acid. PF1163A differs from PF1163B by having an additional hydroxyl group on the side chain.
- Sasaki, Toru,Nose, Hiroshi,Hosoya, Ayako,Yoshida, Shigemi,Kawaguchi, Mami,Watanabe, Takashi,Usui, Takayuki,Ohtsuka, Yasuo,Shomura, Takashi,Takano, Satoko,Tatsuta, Kuniaki
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- Cyanopeptolin 954, a chlorine-containing chymotrypsin inhibitor of Microcystis aeruginosa NIVA Cya 43
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A new depsipeptide, cyanopeptolin 954 (1), was isolated from the freshwater cyanobacterium Microcystis aeruginosa NIVA Cya 43. The structure of the compound was elucidated by chemical and spectroscopic analyses, including 2D NMR and GC-MS of the hydrolysate. The major structural differences compared to previously characterized heptadepsipeptides of Microcystis are the replacement of the basic amino acid in position 4 by L-leucine, the presence of L-phenylalanine in position 6, and the uncommon residue 3′-chloro-N-Me-L- tyrosine in position 7. Cyanopeptolin 954 inhibited chymotrypsin with an IC 50 value of 45 nM. Nostopeptin BN920, formerly isolated from the cyanobacterium Nostoc, was isolated from the same strain of Microcystis, and a cis amide bond between Phe (6) and N-Me-Tyr (7) was shown. Nostopeptin BN920 inhibited chymotrypsin with an IC50 value of 31 nM.
- Von Elert, Eric,Oberer, Lukas,Merkel, Petra,Huhn, Thomas,Blom, Judith F.
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- Structural Diversity and Anticancer Activity of Marine-Derived Elastase Inhibitors: Key Features and Mechanisms Mediating the Antimetastatic Effects in Invasive Breast Cancer
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Three new 3-amino-6-hydroxy-2-piperidone (Ahp)-containing cyclic depsipeptides, named loggerpeptins A–C (1–3), along with molassamide (4), were discovered from a marine cyanobacterium, extending the structural diversity of this prevalent scaffold of cyanobacterial serine protease inhibitors. Molassamide, which contains a 2-amino-butenoic (Abu) unit in the cyclic core, was the most potent and selective analogue against human neutrophil elastase (HNE). Given the growing evidence supporting the role of HNE in breast cancer progression and metastasis, we assessed the cellular effects of compounds 3 and 4 in the context of targeting invasive breast cancer. Both compounds inhibited cleavage of the elastase substrate CD40 in biochemical assays; however, only 4 exhibited significant cellular activity. As CD40 and other receptor proteolytic processing culminates in NFκB activation, we assessed the effects of 4 on the expression of target genes, including ICAM-1. ICAM-1 is also a direct target of elastase and, in our studies, compound 4 attenuated both elastase-induced ICAM-1 gene expression and ICAM-1 proteolytic processing by elastase, revealing a potential dual effect on migration through modulation of gene expression and proteolytic processing. Molassamide also specifically inhibited the elastase-mediated migration of highly invasive triple-negative breast cancer cells.
- Al-Awadhi, Fatma H.,Paul, Valerie J.,Luesch, Hendrik
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p. 815 - 825
(2018/03/27)
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- Octaminomycins A and B, cyclic octadepsipeptides active against Plasmodium falciparum
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Two new cyclic octadepsipeptides, octaminomycins A (1) and B (2), were isolated from a microbial metabolite fraction library of Streptomyces sp. RK85-270 based on Natural Products Plot screening. Their structures were elucidated on the basis of HRESIMS, 1D and 2D NMR spectroscopic data, and MS/MS experiments for sequence analysis. The absolute configurations of the constituent amino acid residues were determined by a combination of single-crystal X-ray diffraction and Marfey's methodology. Notably, octaminomycins A (1) and B (2) showed good in vitro antiplasmodial activity against chloroquine-sensitive as well as chloroquine-resistant strains with no cytotoxicity up to 30 μM. (Chemical Equation Presented).
- Jang, Jun-Pil,Nogawa, Toshihiko,Futamura, Yushi,Shimizu, Takeshi,Hashizume, Daisuke,Takahashi, Shunji,Jang, Jae-Hyuk,Ahn, Jong Seog,Osada, Hiroyuki
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p. 134 - 140
(2017/02/05)
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- Kurahamide, a cyclic depsipeptide analog of dolastatin 13 from a marine cyanobacterial assemblage of Lyngbya sp.
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Kurahamide, a new dolastatin 13 analog, was isolated from a marine cyanobacterial assemblage, consisting mostly of Lyngbya sp. Its gross structure was elucidated by spectroscopic analysis, and the stereochemistries were assigned based on a chiral HPLC analysis of hydrolysis products. Kurahamide strongly inhibited elastase and chymotrypsin in vitro. In addition, kurahamide moderately inhibited the growth of human cancer cells, including HeLa and HL60 cells.
- Iwasaki, Arihiro,Sumimoto, Shinpei,Ohno, Osamu,Suda, Shoichiro,Suenaga, Kiyotake
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p. 609 - 613
(2014/06/09)
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- Thalassospiramide G, a new γ-amino-acid-bearing peptide from the marine bacterium Thalassospira sp
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In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2-3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy- penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl) ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of thalassospiramide D (3), including 4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA), was rigorously determined by 1H-1H coupling constant analysis and chemical derivatization. Thalassospiramides A and D (2-3) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC50 values of 16.4 and 4.8 μM, respectively.
- Um, Soohyun,Pyee, Yuna,Kim, Eun-Hee,Lee, Sang Kook,Shin, Jongheon,Oh, Dong-Chan
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p. 611 - 622
(2013/05/23)
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- Stigonemapeptin, an Ahp-containing depsipeptide with elastase inhibitory activity from the bloom-forming freshwater cyanobacterium Stigonema sp.
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Stigonemapeptin (1), a depsipeptide containing an Ahp (3-amino-6-hydroxy-2- piperidone) residue, was isolated from a bloom sample of the freshwater cyanobacterium Stigonema sp. collected from North Nokomis Lake in the Highland Lake District of northern Wisconsin. The planar structure was determined by 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of the amino acids were determined using the advanced Marfey's method after acid hydrolysis. Stigonemapeptin (1), characterized by the presence of the Ahp residue, also contained the modified amino acids Abu (2-amino-2-butenoic acid) and N-formylated Pro. Stigonemapeptin (1) showed in vitro elastase and chymotrypsin inhibitory activity, with IC50 values of 0.26 and 2.93 μM, respectively.
- Kang, Hahk-Soo,Krunic, Aleksej,Orjala, Jimmy
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experimental part
p. 807 - 811
(2012/06/29)
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- The facile production of N-methyl amino acids via oxazolidinones
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A range of oxazolidinones derived from N-carbamoyl α-amino acids were prepared by an efficient method as key intermediates in the synthesis of N-methyl amino acids and peptides. The method was readily applied to most α-amino acids except those with basic side chains. The oxazolidinones were converted by reductive cleavage into N-methyl α-amino acids. CSIRO 2000.
- Aurelio, Luigi,Brownlee, Robert T. C.,Hughes, Andrew B.,Sleebs, Brad E.
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p. 425 - 433
(2007/10/03)
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- Micropeptin T-20, a novel phosphate-containing cyclic depsipeptide from the cyanobacterium Microcystis aeruginosa
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Micropeptin T-20, a novel glyceric acid 3-O-phosphate and 3-amino-6- hydrooxy-2-piperidone-containing cyclic depsipeptide, was isolated from a cyanobacterium Microcystis aeruginosa. The structure was identified as 1 by 2D NMR and chemical degradation analyses. Micropeptin T-20 inhibited chymotrypsin.
- Okano, Tomoki,Sano, Tomoharu,Kaya, Kunimitsu
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p. 2379 - 2382
(2007/10/03)
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- A practical approach for the optically pure N-Methyl-α- amino acids
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A new practical synthesis of N-Methyl-α-amino acids by racemization free methodology has been developed. The method involves the reductive cleavage of N-protected oxazotidinones using hydrogen in the presence of Pd/C to give the title compounds in quantitative yields.
- Reddy, G. Vidyasagar,Rao, G. Venkat,Iyengar
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p. 1985 - 1986
(2007/10/03)
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- Total syntheses of naturally occurring bis(methylthio)silvatin and its three stereoisomers
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Total syntheses of naturally occurring bis(methylthio)silvatin and its three stereoisomers were achieved from l,4-dimethyl-3-(p-hydroxy)benzyl-2,5-piperazinedione. The configurational structures of the four stereoisomers, thus obtained, were definitely determined by the comparisons of their mps, specific rotations and NMR spectra.
- Yonezawa, Yasuchika
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p. 1151 - 1159
(2007/10/03)
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- Studies on the antitumor cyclic hexapeptides obtained from Rubiae radix
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Antitumor cyclic hexapeptides named RA-VII, V, IV and III were isolated from the MeOH extracts of Rubia cordifolia and R. akane.
- Itokawa,Takeya,Mihara,Mori,Hamanaka,Sonobe,Iitaka
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p. 1424 - 1427
(2007/10/02)
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