scholarly journals New Diterpenes with a Fused 6-5-6-6 Ring System Isolated from the Marine Sponge-Derived Fungus Trichoderma harzianum

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 480 ◽  
Author(s):  
Takeshi Yamada ◽  
Ayano Fujii ◽  
Takashi Kikuchi
Keyword(s):  
Mass Spectrometry ◽  
Marine Sponge ◽  
Trichoderma Harzianum ◽  
Fast Atom Bombardment ◽  
2D Nmr ◽  
Cd Spectroscopy ◽  
Ring System ◽  
Chemical Structures ◽  
Modified Mosher’S Method ◽  
Halichondria Okadai

New diterpenes, namely, trichodermanins F–H, with a fused 6-5-6-6 ring system were isolated from the fungus Trichoderma harzianum OUPS-111D-4 separated from a marine sponge Halichondria okadai. These chemical structures were elucidated by 1D and 2D NMR as well as high-resolution fast atom bombardment mass spectrometry (HRFABMS) spectral analyses. We established their absolute stereostructures by application of the modified Mosher’s method or circular dichroism (CD) spectroscopy. In addition, their cytotoxicities were assessed using several cancer cell lines, with 1 and 2 exhibiting modest activities.

scholarly journals Guaianolide Sesquiterpene Lactones from Centaurothamnus maximus

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 2055
Author(s):  
Taha A. Hussien ◽  
Tarik A. Mohamed ◽  
Abdelsamed I. Elshamy ◽  
Mahmoud F. Moustafa ◽  
Hesham R. El-Seedi ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Biosynthetic Pathway ◽  
Fast Atom Bombardment ◽  
Arabian Peninsula ◽  
Sesquiterpene Lactones ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Chemical Structures ◽  
Aerial Parts

Centaurothamnus maximus (family Asteraceae), is a leafy shrub indigenous to the southwestern Arabian Peninsula. With a paucity of phytochemical data on this species, we set out to chemically characterize the plant. From the aerial parts, two newly identified guaianolides were isolated: 3β-hydroxy-4α(acetoxy)-4β(hydroxymethyl)-8α-(4-hydroxy methacrylate)-1αH,5αH, 6αH-gual-10(14),11(13)-dien-6,12-olide (1) and 15-descarboxy picrolide A (2). Seven previously reported compounds were also isolated: 3β, 4α, 8α-trihydroxy-4-(hydroxymethyl)-lαH, 5αH, 6βH, 7αH-guai-10(14),11(13)-dien-6,12-olide (3), chlorohyssopifolin B (4), cynaropikrin (5), hydroxyjanerin (6), chlorojanerin (7), isorhamnetin (8), and quercetagetin-3,6-dimethyl ether-4’-O-β-d-pyranoglucoside (9). Chemical structures were elucidated using spectroscopic techniques, including High Resolution Fast Atom Bombardment Mass Spectrometry (HR-FAB-MS), 1D NMR; 1H, 13C NMR, Distortionless Enhancement by Polarization Transfer (DEPT), and 2D NMR (1H-1H COSY, HMQC, HMBC) analyses. In addition, a biosynthetic pathway for compounds 1–9 is proposed. The chemotaxonomic significance of the reported sesquiterpenoids and flavonoids considering reports from other Centaurea species is examined.

scholarly journals A New Chlorinated Phenolic Compound From the Antarctic Lichen, Pertusaria dactylina

2020 ◽  
Vol 15 (3) ◽  
pp. 1934578X2090288
Author(s):  
Man H. Koo ◽  
Min J. Kim ◽  
Jae E. Seo ◽  
Ji H. Kim ◽  
Se J. Han ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Phenolic Compound ◽  
Fast Atom Bombardment ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Inhibitory Effect ◽  
Two Dimensional ◽  
One Dimensional ◽  
The Antarctic

A new chlorinated phenolic compound, methyl-3-chloro-2-hydroxy-4-methoxy-6-pentylbenzoate (1) and 4 known compounds (2-5) were isolated from the Antarctic lichen, Pertusaria dactylina ( Pertusariaceae). The structure of the new compound was determined by means of One-dimensional and two dimensional nuclear magnetic resonance (1D and 2D NMR) and high-resolution fast atom bombardment mass spectrometry (HRFABMS) experiments. The antimicrobial activities of compounds 1 to 5 against Staphylococcus aureus and Candida albicans were evaluated. The results showed that compound 1 exhibited a weak inhibitory effect against C. albicans with an IC50 value of 67 ± 7 μg/mL.

scholarly journals Multi-Omic Profiling of Melophlus Sponges Reveals Diverse Metabolomic and Microbiome Architectures that Are Non-overlapping with Ecological Neighbors

Marine Drugs ◽  
2020 ◽  
Vol 18 (2) ◽  
pp. 124 ◽  
Author(s):  
Ipsita Mohanty ◽  
Sheila Podell ◽  
Jason S. Biggs ◽  
Neha Garg ◽  
Eric E. Allen ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Natural Products ◽  
Candidate Gene ◽  
Marine Sponge ◽  
Gene Clusters ◽  
Marine Sponges ◽  
Quantitative Comparison ◽  
Filter Feeding ◽  
Chemical Structures ◽  
Ecological Relevance

Marine sponge holobionts, defined as filter-feeding sponge hosts together with their associated microbiomes, are prolific sources of natural products. The inventory of natural products that have been isolated from marine sponges is extensive. Here, using untargeted mass spectrometry, we demonstrate that sponges harbor a far greater diversity of low-abundance natural products that have evaded discovery. While these low-abundance natural products may not be feasible to isolate, insights into their chemical structures can be gleaned by careful curation of mass fragmentation spectra. Sponges are also some of the most complex, multi-organismal holobiont communities in the oceans. We overlay sponge metabolomes with their microbiome structures and detailed metagenomic characterization to discover candidate gene clusters that encode production of sponge-derived natural products. The multi-omic profiling strategy for sponges that we describe here enables quantitative comparison of sponge metabolomes and microbiomes to address, among other questions, the ecological relevance of sponge natural products and for the phylochemical assignment of previously undescribed sponge identities.

scholarly journals Orphan Flavonoids and Dihydrochalcones from Primula Exudates

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Tshering Doma Bhutia ◽  
Karin M. Valant-Vetschera ◽  
Lothar Brecker
Keyword(s):  
Mass Spectrometry ◽  
2D Nmr ◽  
Chemical Structures ◽  
Novel Structures

Two orphan flavonoids containing an oxepin structure in ring A and named as Primcortusin (1) and 3’-OH-Primcortusin (2) were isolated from leaf exudates of Primula cortusoides, while P. glutinosa exudates yielded two dihydrochalcone derivatives (3,4). These novel structures have not been detected in other species of Primula so far. Chemical structures were elucidated by 2D NMR and mass spectrometry. The nature of compounds 1 and 2 is discussed, and ideas about their possible origin and that of unsubstituted flavone and other irregular substituted Primula flavones are presented.

scholarly journals New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 100
Author(s):  
Sherif Ebada ◽  
Werner Müller ◽  
Wenhan Lin ◽  
Peter Proksch
Keyword(s):  
Spectral Analysis ◽  
Marine Sponge ◽  
Parent Compound ◽  
2D Nmr ◽  
Chemical Structures ◽  
Nmr Data ◽  
Ic50 Values ◽  
Nanomolar Range ◽  
Mouse Lymphoma

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

scholarly journals Two New Cyclopeptides and One New Nonenolide from Xylaria sp. 101

2011 ◽  
Vol 6 (12) ◽  
pp. 1934578X1100601
Author(s):  
Yao-Yao Li ◽  
Zhi-Yu Hu ◽  
Yue-Mao Shen
Keyword(s):  
Mass Spectrometry ◽  
Fruiting Body ◽  
Yunnan Province ◽  
2D Nmr ◽  
Fungal Strain ◽  
Chemical Structures ◽  
Spectroscopic Analyses

Two novel cyclopeptides, xylarotides A (1), and B (2), and one novel nonenolide, xylarolide (3), along with two known compounds, coriloxin (4), and 2-hydroxy-3-methoxy-5-methyl- p-benzoquinone (5) were isolated from the fungal strain Xylaria sp. 101. This strain was isolated from the fruiting body of Xylaria sp. collected in Gaoligong Mountain, Yunnan Province. The chemical structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR spectroscopic experiments, and on the basis of HR-Q-TOF mass spectrometry. Antibacterial assays of 1 - 3 were carried out; no effects on the growth of the tested bacteria and yeast were observed.

scholarly journals A New Megastigmane Glycoside, Phoenixoside A, from Phoenix Dactylifera

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.

Sign in / Sign up

Export Citation Format

Share Document