Lamellarins O and P: New Aromatic Metabolites From the Australian Marine Sponge Dendrilla cactos

1994 ◽  
Vol 47 (10) ◽  
pp. 1919 ◽  
Author(s):  
S Urban ◽  
MS Butler ◽  
RJ Capon
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Pyrrole Ring ◽  
Ring System ◽  
Aromatic Rings ◽  
Partial Synthesis ◽  
Structure Class

A specimen of Dendrilla cactos collected during trawling operations in Bass Strait, Australia, has yielded two new alkaloids, lamellarin-O (17) and lamellarin-P (18). Both these metabolites are examples of the lamellarin structure class, previously reported from tunicates and a mollusc; however, in these examples the pyrrole ring system is not fused to adjacent aromatic rings. The structures of (17) and (18) were secured by spectroscopic analysis and partial synthesis.

Alkyl and Alkenyl Resorcinols From an Australian Marine Sponge, Haliclona Sp (Haplosclerida : Haliclonidae)

1991 ◽  
Vol 44 (10) ◽  
pp. 1393 ◽  
Author(s):  
RA Barrow ◽  
RJ Capon
Keyword(s):  
Natural Products ◽  
Marine Sponge ◽  
Spectroscopic Analysis ◽  
Chemical Degradation ◽  
Plant Source ◽  
Marine Plant ◽  
Plant Sources ◽  
Structure Class

Eleven alkyl and alkenyl resorcinols have been isolated from the Australian marine sponge Haliclona sp. Three of these, (3), (5) and (10), have previously been described from Australian terrestrial and marine plant sources. The remaining eight, (13)-(20), are new natural products whose structures have been secured by a combination of spectroscopic analysis and chemical degradation. This report represents the first account of this structure class being isolated from a non-plant source.

The Bastadins Revisited: New Chemistry From the Australian Marine Sponge Ianthella basta

1991 ◽  
Vol 44 (2) ◽  
pp. 287 ◽  
Author(s):  
MS Butler ◽  
TK Lim ◽  
RJ Capon ◽  
LS Hammond
Keyword(s):  
Great Barrier Reef ◽  
Marine Sponge ◽  
Structure Elucidation ◽  
Spectroscopic Analysis ◽  
Oxidative Cyclization ◽  
Barrier Reef ◽  
Structure Class

A specimen of Ianthella basta, collected from the Great Barrier Reef, Australia, has been found to contain the recently reported tetramer of bromotyrosine , bastadin-9 (6a), along with a new example of this structure class, bastadin-12 (9a). The structure for bastadin-12 (9a) was confirmed by detailed spectroscopic analysis and derivatization, and represents the first reported example of this structure class derived from an alternative oxidative cyclization . As earlier biosynthetic arguments to the structure elucidation of some bastadins were based on the premise that only one cyclization pathway was possible (leading to 13,32-dioxa-4,22-diazabastarane), the discovery of (9a) introduces an added dimension to the identification of new and known bastadins. Also isolated and identified as their methyl ethers were two new dimers of bromotyrosine, hemibastadin-1 (10) and hemibastadin-2 (11).

scholarly journals New from Old: Thorectandrin Alkaloids in a Southern Australian Marine Sponge, Thorectandra choanoides (CMB-01889)

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 97
Author(s):  
Shamsunnahar Khushi ◽  
Angela A. Salim ◽  
Ahmed H. Elbanna ◽  
Laizuman Nahar ◽  
Robert J. Capon
Keyword(s):  
Marine Sponge ◽  
Tissue Specificity ◽  
Spectroscopic Analysis ◽  
Transformation Products ◽  
Chemical Fractionation ◽  
Cancer Tissue ◽  
Michael Acceptor ◽  
Michael Acceptors ◽  
Stable Ring

Thorectandra choanoides (CMB-01889) was prioritized as a source of promising new chemistry from a library of 960 southern Australian marine sponge extracts, using a global natural products social (GNPS) molecular networking approach. The sponge was collected at a depth of 45 m. Chemical fractionation followed by detailed spectroscopic analysis led to the discovery of a new tryptophan-derived alkaloid, thorectandrin A (1), with the GNPS cluster revealing a halo of related alkaloids 1a–1n. In considering biosynthetic origins, we propose that Thorectandrachoanoides (CMB-01889) produces four well-known alkaloids, 6-bromo-1′,8-dihydroaplysinopsin (2), 6-bromoaplysinopsin (3), aplysinopsin (4), and 1′,8-dihydroaplysinopsin (10), all of which are susceptible to processing by a putative indoleamine 2,3-dioxygenase-like (IDO) enzyme to 1a–1n. Where the 1′,8-dihydroalkaloids 2 and 10 are fully transformed to stable ring-opened thorectandrins 1 and 1a–1b, and 1h–1j, respectively, the conjugated precursors 3 and 4 are transformed to highly reactive Michael acceptors that during extraction and handling undergo complete transformation to artifacts 1c–1g, and 1k–1n, respectively. Knowledge of the susceptibility of aplysinopsins as substrates for IDOs, and the relative reactivity of Michael acceptor transformation products, informs our understanding of the pharmaceutical potential of this vintage marine pharmacophore. For example, the cancer tissue specificity of IDOs could be exploited for an immunotherapeutic response, with aplysinopsins transforming in situ to Michael acceptor thorectandrins, which covalently bind and inhibit the enzyme.

ChemInform Abstract: Reactivity of the 1H-Pyrrole Ring System. Nitration, Sulfonation, and Halogenation

ChemInform ◽  
2010 ◽  
Vol 22 (6) ◽  
pp. no-no
Author(s):  
M. ARTICO
Keyword(s):  
Pyrrole Ring ◽  
Ring System

scholarly journals NEW ANTIBIOTICS CONTAINING THE 1, 2-DITHIOLO[4, 3-b]PYRROLE RING SYSTEM

1969 ◽  
Vol 22 (5) ◽  
pp. 233-236 ◽  
Author(s):  
W. VON DAEHNE ◽  
W. O. GODTFREDSEN ◽  
L. TYBRING ◽  
KJELD SCHAUMBURG
Keyword(s):  
Pyrrole Ring ◽  
Ring System ◽  
New Antibiotics

Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety

2017 ◽  
Vol 15 (48) ◽  
pp. 10172-10183 ◽  
Author(s):  
Carl Jacky Saint-Louis ◽  
Renée N. Shavnore ◽  
Caleb D. C. McClinton ◽  
Julie A. Wilson ◽  
Lacey L. Magill ◽  
...  
Keyword(s):  
Electron Donor ◽  
Spectroscopic Analysis ◽  
Ring System ◽  
Quantum Yields ◽  
System P ◽  
Donor And Acceptor ◽  
Electron Donor And Acceptor

Methods to tune the luminescence wavelength and the quantum yields by controlling the power and location of electron-donor and acceptor substituents on the ring system.

scholarly journals Crystal structure of 2,3-bis(4-methylphenyl)benzo[g]quinoxaline

2018 ◽  
Vol 74 (4) ◽  
pp. 548-550
Author(s):  
Young-Inn Kim ◽  
Seong-Jae Yun ◽  
Sung Kwon Kang
Keyword(s):  
Crystal Structure ◽  
Rotation Axis ◽  
Ring System ◽  
Dihedral Angles ◽  
Aromatic Rings ◽  
Light Emitting ◽  
Light Emitting Devices ◽  
Compound C ◽  
Organic Light ◽  
Phenyl Rings

The title compound, C26H20N2, was obtained during a search for new π-extended ligands with the potential to generate efficient phosphors with iridium(III) for organic light-emitting devices (OLEDs). The benzoquinoxaline ring system is almost planar (r.m.s. deviation = 0.076 Å). A pseudo-twofold rotation axis runs through the midpoints of the C2—C3 and C9—C10 bonds. The two phenyl rings are twisted relative to the benzoquinoxaline ring system, making dihedral angles of 53.91 (4) and 36.86 (6)°. In the crystal, C—H...π (arene) interactions link the molecules, but no π–π interactions between aromatic rings are observed.

scholarly journals Two New Thyminenol Derivatives from the Marine Sponge Haliclona sp

2014 ◽  
Vol 9 (4) ◽  
pp. 1934578X1400900
Author(s):  
Bin Wang ◽  
Yaocai Lin ◽  
Yinning Chen ◽  
Riming Huang
Keyword(s):  
Marine Sponge ◽  
Spectroscopic Analysis

Investigation of the marine sponge Haliclona sp. led to the isolation of two new thyminenol derivatives, named cis-thyminenol (1) and trans-thyminenol (2). The structures of the new isolates were elucidated on the basis of extensive spectroscopic analysis.

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.

Lamellarin-S: a New Aromatic Metabolite From an Australian Tunicate, Didemnum sp.

1996 ◽  
Vol 49 (6) ◽  
pp. 711 ◽  
Author(s):  
S Urban ◽  
RJ Capon
Keyword(s):  
Spectroscopic Analysis ◽  
K 12 ◽  
Structure Class

An Australian tunicate Didemnum sp. has yielded a new alkaloid lamellarin-S (1) along with the known compound lamellarin-K (12). Of this structure class, lamellarin-S (1) is the first example that demonstrates atropisomerism , and its structure was secured by spectroscopic analysis.

Sign in / Sign up

Export Citation Format

Share Document