Crocetin Esters, Picrocrocin and Its Related Compounds Present inCrocus sativusStigmas andGardenia jasminoidesFruits. Tentative Identification of Seven New Compounds by LC-ESI-MS

Abstract Various (metallo)porphyrins and related compounds have been intensively investigated by different research groups due to their extremely important role in living organisms along with their versatile applications in technology. The design of novel porphyrinoids by core-modification, or substitution of pyrrole nitrogens, with the elements of other groups of the Periodic Table has been considered as a highly promising methodology for tuning structures and properties of porphyrinoids and thus opening new possible applications for them. Much effort has been given to the modifications of the porphyrin core with elements of the main groups, namely O, S, Se (chalcogens), and the heavier congener of nitrogen, phosphorus. In general, the porphyrin core modification by replacing nitrogens with heteroatoms is a promising and effective strategy for obtaining new compounds with unusual structures and properties (optical, electrochemical, coordinating, etc.) as well as reactivity. These novel molecules can also be employed as promising building or construction blocks in various applications in the nanotechnology area.

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New Histamine-Related Five-Membered N-Heterocycle Derivatives as Carbonic Anhydrase I Activators

Molecules ◽

10.3390/molecules27020545 ◽

2022 ◽

Vol 27 (2) ◽

pp. 545

Author(s):

Niccolò Chiaramonte ◽

Alessio Gabellini ◽

Andrea Angeli ◽

Gianluca Bartolucci ◽

Laura Braconi ◽

...

Keyword(s):

Carbonic Anhydrase ◽

Imidazole Ring ◽

Aliphatic Chain ◽

Amino Group ◽

Carbonic Anhydrase I ◽

Terminal Amino ◽

Human Carbonic Anhydrase ◽

New Compounds ◽

Related Compounds ◽

Micromolar Range

A series of histamine (HST)-related compounds were synthesized and tested for their activating properties on five physiologically relevant human Carbonic Anhydrase (hCA) isoforms (I, II, Va, VII and XIII). The imidazole ring of HST was replaced with different 5-membered heterocycles and the length of the aliphatic chain was varied. For the most interesting compounds some modifications on the terminal amino group were also performed. The most sensitive isoform to activation was hCA I (KA values in the low micromolar range), but surprisingly none of the new compounds displayed activity on hCA II. Some derivatives (1, 3a and 22) displayed an interesting selectivity for activating hCA I over hCA II, Va, VII and XIII.

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Quantitation of capsiate and dihydrocapsiate and tentative identification of minor capsinoids in pepper fruits (Capsicum spp.) by HPLC-ESI-MS/MS(QTOF)

Food Chemistry ◽

10.1016/j.foodchem.2018.07.112 ◽

2019 ◽

Vol 270 ◽

pp. 264-272 ◽

Cited By ~ 7

Author(s):

Oreto Fayos ◽

María Savirón ◽

Jesús Orduna ◽

Gerardo F. Barbero ◽

Cristina Mallor ◽

...

Keyword(s):

Tentative Identification ◽

Esi Ms ◽

Capsicum Spp

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Cyclic Peroxides from a Two-Sponge Association of Plakortis communis-Agelas mauritiana

Natural Product Communications ◽

10.1177/1934578x1300800611 ◽

2013 ◽

Vol 8 (6) ◽

pp. 1934578X1300800

Author(s):

Pinus Jumaryatno ◽

Lynette K. Lambert ◽

John N. A. Hooper ◽

Joanne T. Blanchfield ◽

Mary J. Garson

Keyword(s):

2D Nmr ◽

Side Chain ◽

Relative Configuration ◽

Carboxylic Acid Groups ◽

Rp Hplc ◽

Chemical Shift Data ◽

New Compounds ◽

Cyclic Peroxide ◽

Related Compounds ◽

Shift Data

A cyclic peroxide 1 with an unusual phenethenyl side chain, together with the known peroxide 2 with a C4-sidechain have been isolated from a two-sponge association of Plakortis communis – Agelas mauritiana (Carter, 1883) collected near Mooloolaba, South-East Queensland, Australia. Metabolite purification was complicated by the presence of the free carboxylic acid groups in 1 and 2; therefore, diazomethane treatment was undertaken to afford methyl ester 3. Following RP-HPLC purification, the ring-opened analogues 4 and 5 were also obtained. The structures of the new compounds were elucidated on the basis of their 1D and 2D NMR and MS data, and by comparison with literature data. The relative configuration of the isolated peroxides was determined by the interpretation of JH-H values and comparison of the 13C chemical shift data with literature data for related compounds. The bromopyrrole alkaloid longamide (6) was also isolated.

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New Unusual Alkaloids from the Ascidian Eudistoma vannamei

Natural Product Communications ◽

10.1177/1934578x1400901212 ◽

2014 ◽

Vol 9 (12) ◽

pp. 1934578X1400901 ◽

Cited By ~ 1

Author(s):

Antônia Torres Ávila Pimenta ◽

Paula Christine Jimenez ◽

Letícia Veras Costa-Lotufo ◽

Raimundo Braz-Filho ◽

Mary Anne Sousa Lima

Keyword(s):

Mass Spectrometry ◽

Meoh Extract ◽

Peptide Derivative ◽

New Compounds ◽

Related Compounds

The MeOH extract of the ascidian Eudistoma vannamei was found to contain three novel compounds, the adenine alkaloid derivatives 9-[ N-(leucyl)-isoleucyl]-adenine (1) and 8-hydroxy-8-isopentyl-7,8-dihydroadenine (2), and the phenylalanine peptide derivative N-[ N-(leucyl)-isoleucyl]phenethylamine (3). Other previously related compounds isolated from this extract include thymidine, 2′-deoxyuridine and phenylalanine. The structures of the new compounds were elucidated through the use of NMR and mass spectrometry.

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Two New Compounds from Artemisia sacrorum

Natural Product Communications ◽

10.1177/1934578x1601100417 ◽

2016 ◽

Vol 11 (4) ◽

pp. 1934578X1601100

Author(s):

Qinghu Wang ◽

Rongjun Wu ◽

Narenchaoketu Han ◽

Nayintai Dai ◽

Jiesi Wu

Keyword(s):

Structure Elucidation ◽

2D Nmr ◽

Etoac Extract ◽

First Report ◽

Esi Ms ◽

New Compounds

Two new compounds, named as sacric acid A (1) and sacric acid B (2), were isolated from the EtOAc extract of Artemisia sacrorum Ledeb. This is the first report on the structure elucidation of these compounds based on UV, IR, and extensive 1D and 2D NMR spectroscopic, and ESI-MS techniques.

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Comparative Study of Naphthoquinone Contents of Selected Greek Endemic Boraginaceae Plants - Antimicrobial Activities

Natural Product Communications ◽

10.1177/1934578x1701200209 ◽

2017 ◽

Vol 12 (2) ◽

pp. 1934578X1701200

Author(s):

Teisa Tufa ◽

Harilaos Damianakos ◽

Konstantia Graikou ◽

Ioanna Chinou

Keyword(s):

Antimicrobial Activity ◽

Nmr Spectroscopy ◽

Comparative Study ◽

Pathogenic Fungi ◽

2D Nmr ◽

Antimicrobial Activities ◽

2D Nmr Spectroscopy ◽

Chromatographic Separations ◽

Esi Ms ◽

Related Compounds

The cyclohexane (Ch) extracts of the roots of five Greek endemic Boraginaceae plants, Onosma kaheirei Teppner, O. graeca Boiss., O. erecta Sibth. & Sm., Alkanna sfikasiana Kit Tan, Vold and Strid and Cynoglossum columnae Ten, were investigated for the presence of alkannin/shikonin-related compounds. All species, s except C. columnae and O. erecta, were found to contain this type of compounds. Seven compounds were obtained after several chromatographic separations from the Ch extracts of the investigated plants: deoxyalkannin (1), 2″-( S)- α-methylbutyrylalkannin (2), isobutyrylalkannin (3), propionylalkannin (4), acetylalkannin (5), β-hydroxyisovalerylalkannin (6), and β,β-dimethylacrylalkannin (7). All structures were identified by 1D 1H-/13C- and 2D NMR spectroscopy, assisted also by ESI-MS. The extracts and the isolated compounds exhibiting an interesting antimicrobial profile when evaluated for their antimicrobial activity against six Gram-positive and -negative bacteria and three human pathogenic fungi.

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Secondary metabolites of Phlebopus species from Northern Thailand

Mycological Progress ◽

10.1007/s11557-020-01643-y ◽

2020 ◽

Vol 19 (12) ◽

pp. 1525-1536

Author(s):

Boontiya Chuankid ◽

Hedda Schrey ◽

Benjarong Thongbai ◽

Olivier Raspé ◽

Norbert Arnold ◽

...

Keyword(s):

Secondary Metabolites ◽

2D Nmr ◽

Cytotoxic Activities ◽

Tumor Cell Lines ◽

Submerged Cultures ◽

Esi Ms ◽

Spectroscopic Analyses ◽

New Compounds ◽

Comprehensive Characterization

AbstractSubmerged cultures of the edible mushrooms Phlebopus portentosus and Phlebopus spongiosus were screened for their secondary metabolites by HPLC-UV/Vis and HR-LC-ESI-MS. Two new compounds, 9′-hydroxyphenyl pulvinone (1), containing an unusual pulvinone structure, and phlebopyron (2), together with the seven known pigments, atromentic acid (3), xerocomic acid (4), variegatic acid (5), methyl atromentate (6), methyl isoxerocomate (7), methyl variegatate (8), and variegatorubin (9) were isolated from the cultures. Their structures were assigned on the basis of extensive 1D/2D NMR spectroscopic analyses, as well as HR-ESI-MS, and HR-ESI-MS/MS measurements. Furthermore, the isolated compounds were evaluated for their antimicrobial and cytotoxic properties. 9′-hydroxyphenyl pulvinone (1), xerocomic acid (4), and methyl variegatate (8) exhibited weak to moderate cytotoxic activities against several tumor cell lines. The present paper provides a comprehensive characterization of pigments from the class of pulvinic acids that are present in the basidiomes of many edible bolete species.

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