Chlorosphaerolactylates A-D: The Natural Chlorinated Lactylates Isolated from the Portuguese Cyanobacterium Sphaerospermopsis Sp. LEGE 00249

The unprecedented natural chlorinated lactylates, chlorosphaerolactylates A-D (1-4), were isolated from the methanolic extract of the cyanobacterium Sphaerospermopsis sp. LEGE 00249 through a combination of bioassay-guided and MS-guided approaches. Compounds 1-4 are esters of (mono-, di- or tri-)chlorinated lauric acid and lactic acid, whose structures were assigned on the basis of spectrometric and spectroscopic methods inclusive of 1D and 2D NMR experiments. High-resolution mass-spectrometry datasets also demonstrated the existence of other minor components that were identified as chlorosphaero(bis)lactylate analogues. The chlorosphaerolactylates were tested for potential antibacterial, antifungal and antibiofilm properties using bacterial and fungal clinical isolates. Compounds 1-4 inhibited the growth of Staphylococcus aureus S54F9 and Candida parapsilosis SMI416, as well as, affected the biofilm formation of coagulase-negative Staphylococcus hominis FI31.

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A New Sesquiterpene Lactone Sulfate from Reichardia gaditana (Asteraceae)

Zeitschrift für Naturforschung B ◽

10.1515/znb-2007-0121 ◽

2007 ◽

Vol 62 (1) ◽

pp. 132-134 ◽

Cited By ~ 8

Author(s):

Christian Zidorn ◽

Ernst-Peter Ellmerer ◽

Werner Heller ◽

Richard Greil ◽

Manuela Guggenberger ◽

...

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

High Resolution ◽

Structure Elucidation ◽

Methanolic Extract ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

2D Nmr Spectroscopy ◽

Asteraceae Family ◽

Resolution Mass

The new sesquiterpenoid 8-deoxy-15-(3′-hydroxy-2′-methyl-propanoyl)-lactucin 3′-sulfate (1) was isolated from the methanolic extract of roots of Reichardia gaditana L. The compound was isolated by silica gel column chromatography (CC) and repeated Sephadex LH-20 CC. Structure elucidation was accomplished by high-resolution mass spectrometry and by 1D- and 2D-NMR spectroscopy. The chemosystematic significance of the new compound is discussed in the context of sesquiterpenoids from other members of the Lactuceae tribe of the Asteraceae family.

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New Constituents from Gymnocarpos decander

Planta Medica ◽

10.1055/s-0043-111599 ◽

2017 ◽

Vol 83 (14/15) ◽

pp. 1200-1206 ◽

Cited By ~ 1

Author(s):

Houria Bechlem ◽

Teresa Mencherini ◽

Mohamed Bouheroum ◽

Samir Benayache ◽

Roberta Cotugno ◽

...

Keyword(s):

Mass Spectrometry ◽

High Resolution ◽

Antiproliferative Activity ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Spectroscopic Methods ◽

Nmr Analysis ◽

Aerial Parts ◽

Phytochemical Investigation ◽

Resolution Mass

AbstractThe phytochemical investigation of Gymnocarpos decander aerial parts extract afforded two new saponins, 3-O-β-D-glucuronopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-O-β-D-apiofuranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester (1), 3-O-β-D-glucuronopyranosyl-2β,3β,16α-trihydroxyolean-12-en-28-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester (2), and three new flavonol glycosides, isorhamnetin 3-O-2′′′′-O-acetyl−β-D-xylopyranosyl-(1 → 6)-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (3), isorhamnetin 3-O-2‴-O-acetyl−β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside (4), and quercetin 3-O-2‴-O-acetyl−β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside (5), together with three known compounds. Their structures were determined by spectroscopic methods including 1D and 2D NMR analysis and high-resolution mass spectrometry. The new isolates were investigated for their potential cytotoxic activity on three cancer cell lines. Compounds 1 and 2 showed moderate antiproliferative activity.

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A New Glucuronolactone Glycoside Phoenixoside B from the Seeds of Phoenix Dactylifera

Natural Product Communications ◽

10.1177/1934578x1300800926 ◽

2013 ◽

Vol 8 (9) ◽

pp. 1934578X1300800

Author(s):

Sumbul Azmat ◽

Rehana Ifzal ◽

Faryal Vali Mohammad ◽

Viqar Uddin Ahmad ◽

Aqib Zahoor

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

Soluble Fraction ◽

2D Nmr ◽

Phoenix Dactylifera ◽

2D Nmr Spectroscopy ◽

High Resolution Mass ◽

Resolution Mass

A new glucuronolactone glycoside, phoenixoside B (1), has been isolated from the n-butanol soluble fraction of seeds of Phoenix dactylifera. The structure was characterized as 1-(1-ethyl-β-D-glucosyl)-4,5-diethyl-[α-D-glucofuranourono-6,3-lactone] on the basis of 1D and 2D-NMR spectroscopy and high-resolution mass spectrometry.

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Struthiolanone: A Flavanone-Resveratrol Adduct from Struthiola Argentea

Natural Product Communications ◽

10.1177/1934578x0800300216 ◽

2008 ◽

Vol 3 (2) ◽

pp. 1934578X0800300

Author(s):

Sloan Ayers ◽

Deborah L. Zink ◽

Robert Brand ◽

Seef Pretorius ◽

Dennis Stevenson ◽

...

Keyword(s):

Mass Spectrometry ◽

High Resolution ◽

Absolute Configuration ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Spectroscopic Techniques ◽

Cd Spectrum ◽

High Resolution Mass ◽

The Absolute ◽

Resolution Mass

Struthiolanone (1), a flavanone-resveratrol adduct, was isolated from Struthiola argentea. Its structure was determined by high-resolution mass spectrometry and 1D- and 2D-NMR spectroscopic techniques. The absolute configuration was determined by comparison of the CD spectrum of biflavonoids. This compound appears to be the first example of a flavanoid-stilbene adduct.

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A New Megastigmane Glycoside, Phoenixoside A, from Phoenix Dactylifera

Natural Product Communications ◽

10.1177/1934578x1200700103 ◽

2012 ◽

Vol 7 (1) ◽

pp. 1934578X1200700

Author(s):

Sumbul Azmat ◽

Aqib Zahoor ◽

Rehana Ifzal ◽

Viqar Uddin Ahmad ◽

Faryal Vali Mohammed

Keyword(s):

Mass Spectrometry ◽

Nmr Spectroscopy ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

Soluble Fraction ◽

2D Nmr ◽

Phoenix Dactylifera ◽

Cd Spectroscopy ◽

2D Nmr Spectroscopy ◽

Resolution Mass

A new megastigmane glycoside, phoenixoside A (1), has been isolated from the n-butanol - soluble fraction of seeds of Phoenix dactylifera. The structure was characterized as (6S,7Z,9R)-hydroxy-3-oxo-ionol-9- O-β-D-glucopyranosyl-(1″→6′)-β-D–glucopyranoside on the basis of 1D and 2D NMR spectroscopy, high-resolution mass spectrometry, and CD spectroscopy.

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Precursor-Directed Biosynthesis of Aminofulvenes: New Chalanilines from Endophytic Fungus Chalara sp.

Molecules ◽

10.3390/molecules26154418 ◽

2021 ◽

Vol 26 (15) ◽

pp. 4418

Author(s):

Mahsa Khoshbakht ◽

Jason Srey ◽

Donovon A. Adpressa ◽

Annika Jagels ◽

Sandra Loesgen

Keyword(s):

Mass Spectrometry ◽

Structure Elucidation ◽

Large Scale ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Chemical Diversity ◽

Epigenetic Modifier ◽

Nmr Techniques ◽

Directed Biosynthesis ◽

Resolution Mass

The plant endophyte Chalara sp. is able to biotransform the epigenetic modifier vorinostat to form unique, aniline-containing polyketides named chalanilines. Here, we sought to expand the chemical diversity of chalaniline A-type molecules by changing the aniline moiety in the precursor vorinostat. In total, twenty-three different vorinostat analogs were prepared via two-step synthesis, and nineteen were incorporated by the fungus into polyketides. The highest yielding substrates were selected for large-scale precursor-directed biosynthesis and five novel compounds, including two fluorinated chalanilines, were isolated, purified, and structurally characterized. Structure elucidation relied on 1D and 2D NMR techniques and was supported by low- and high-resolution mass spectrometry. All compounds were tested for their bioactivity but were not active in antimicrobial or cell viability assays. Aminofulvene-containing natural products are rare, and this high-yielding, precursor-directed process allows for the diversification of this class of compounds.

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2-(2-(4-Methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic Acid

Molbank ◽

10.3390/m1315 ◽

2022 ◽

Vol 2022 (1) ◽

pp. M1315

Author(s):

Boris V. Lichitsky ◽

Andrey N. Komogortsev ◽

Valeriya G. Melekhina

Keyword(s):

Mass Spectrometry ◽

Acetic Acid ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Target Product ◽

Atom Economy ◽

Initial Interaction ◽

Work Up ◽

Resolution Mass

A simple and efficient protocol for the synthesis of the previously unknown 2-(2-(4-methoxyphenyl)furo[3,2-h]quinolin-3-yl)acetic acid was elaborated. The suggested method is based on the telescoped multicomponent reaction of 8-hydroxyquinoline, 4-methylglyoxal, and Meldrum’s acid. The studied process includes the initial interaction of the starting compounds in MeCN followed by intramolecular cyclization to the target product in refluxing acetic acid. The advantage of this approach is the application of readily available starting materials, atom economy, and a simple work-up procedure. The structure of the synthesized furylacetic acid derivative was proven by 1H, 13C, 2D-NMR, IR spectroscopy, and high-resolution mass spectrometry.

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Two New Hygroline and Tropane Alkaloids Isolated from Schizanthus Hookeri and S. Tricolor (Solanaceae)

Natural Product Communications ◽

10.1177/1934578x1701200311 ◽

2017 ◽

Vol 12 (3) ◽

pp. 1934578X1701200

Author(s):

Sylvian Cretton ◽

Orlando Muñoz ◽

Jorge Tapia ◽

Laurence Marcourt ◽

Louis Maes ◽

...

Keyword(s):

Mass Spectrometry ◽

High Resolution ◽

High Resolution Mass Spectrometry ◽

Tropane Alkaloids ◽

Spectroscopic Methods ◽

Antiparasitic Activity ◽

Aerial Parts ◽

High Resolution Mass ◽

Resolution Mass

Two new hygroline and tropane alkaloids, 4-hydroxybenzenepropanoylhygroline (1) and 3α,4β-dihydroxy-6β-angeloyoxytropane (2) have been isolated from the aerial parts of Schizanthus hookeri and S. tricolor, respectively, two plants indigenous from Chile. Their structures were elucidated by spectroscopic methods and high resolution mass spectrometry. Their antiparasitic activity and cytotoxicity were measured.

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Comprehensive Overview on the Chemistry and Biological Activities of Selected Alkaloid Producing Marine-Derived Fungi as a Valuable Reservoir of Drug Entities

Biomedicines ◽

10.3390/biomedicines9050485 ◽

2021 ◽

Vol 9 (5) ◽

pp. 485

Author(s):

Fadia S. Youssef ◽

Jesus Simal-Gandara

Keyword(s):

Mass Spectrometry ◽

Nuclear Magnetic Resonance ◽

High Resolution Mass Spectrometry ◽

Biological Activities ◽

2D Nmr ◽

Considerable Effect ◽

Spectroscopic Techniques ◽

Two Dimensional ◽

Comprehensive Overview ◽

Resolution Mass

Marine-associated fungal strains act as a valuable reservoir of bioactive diverse secondary metabolites including alkaloids which are highly popular by their biological activities. This review highlighted the chemistry and biology of alkaloids isolated from twenty-six fungal genera associated with marine organisms and marine sea sediments. The selected fungi are from different marine sources without focusing on mangroves. The studied fungal genera comprises Acrostalagmus, Arthrinium, Chaetomium, Cladosporium, Coniothyrium, Curvularia, Dichotomomyces, Eurotium, Eutypella, Exophiala, Fusarium, Hypocrea, Microsphaeropsis, Microsporum, Neosartorya, Nigrospora, Paecilomyces, Penicillium, Pleosporales, Pseudallescheria, Scedosporium, Scopulariopsis, Stagonosporopsis, Thielavia, Westerdykella, and Xylariaceae. Around 347 alkaloid metabolites were isolated and identified via chromatographic and spectroscopic techniques comprising 1D and 2D NMR (one and two dimensional nuclear magnetic resonance) which were further confirmed using HR-MS (high resolution mass spectrometry) and Mosher reactions for additional ascertaining of the stereochemistry. About 150 alkaloids showed considerable effect with respect to the tested activities. Most of the reported bioactive alkaloids showed considerable biological activities mainly cytotoxic followed by antibacterial, antifungal, antiviral, antioxidant; however, a few showed anti-inflammatory and antifouling activities. However, the rest of the compounds showed weak or no activity toward the tested biological activities and required further investigations for additional biological activities. Thus, alkaloids isolated from marine-associated fungi can afford an endless source of new drug entities that could serve as leads for drug discovery combating many human ailments.

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