Supramolecular isomerism in the hydrogen-bonded network of (5R,10R)-3,8-dihydroxy-5,10-diethoxy-5,10-dihydrochromeno[5,4,3-cde]chromene monohydrate

Wu, Jian‐Zhong; Lin, Long; Yu, Ying; Wan, Xia; Yin, Xian‐Hong

doi:10.1007/s11224-007-9206-6

“…S48). This precursor is hypothesized to dimerize between the α-C atoms via the well-known radical coupling reaction for phenols (Jian-Zhong Wu et al, 2007;Liu et al, 2006). Subsequently, condensation between each OH group and each CHO group of the opposite monomer yields the two pyrone rings, such as seen for compound 6 ( Fig.…”

Section: Structural Elucidation Of Compounds 1-8mentioning

confidence: 99%

Monomeric and Dimeric Bromophenols from the Red Alga Ceramium Sp. with Antioxidant and Anti-Inflammatory Activities

Zhang¹,

Glukhov²,

Yu³

et al. 2020

Preprint

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LC-MS2-based molecular networking using the Global Natural Products Social (GNPS) tool revealed a rich assortment of brominated compounds present in the antioxidant fraction of a red algal extract (Ceramium sp.) Further chemical investigation led to discovery of one monomeric bromophenol (lanosol isopropyl ether, 1) and seven dimeric ones (bromourceolatols A-G, 2-8), all of which are previously undescribed. Their structures were elucidated by extensive analysis of their spectroscopic data. Compounds 2-8 were determined to be racemic trans-type isomers by NOESY, specific optical rotation, and ECD. Compounds 1 and 3 displayed antioxidant activity with their EC50 of 44.4 and 47.0 μM, respectively, for scavenging DPPH free radicals while compounds 2 and 4 had approximate EC50 values of ~ 64 μM. Furthermore, compounds 2, 3, and 7 exhibited relatively potent anti-inflammatory activity at 32 μM by quenching 97%, 47%, and 73% of nitric oxide induced by bacterial lipopolysaccharide in macrophage RAW264.7 cells, respectively.

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“…Wu et al [336] report on the supramolecular isomerism in the hydrogen-bonded network of (5R,10R)-3,8-dihydroxy-5,10-diethoxy-5,10-dihydrochromeno[5,4,3-cde]chromene monohydrate. When the newly synthesized compound was recrystallized from aqueous methanol the initially formed infinite supramolecular structure was changed from 3D to 2D.…”

Section: Issuementioning

confidence: 99%

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Ponikvar

¹

,

Liebman

²

2008

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In this study, we relate the contents of the journal Structural Chemistry for the calendar year 2007 and thermochemistry. The year's articles were briefly summarized and a thermochemical comment written to supplement them. Frequently questions were asked and future research was suggested.Keywords Structural Chemistry Á Thermochemistry Á Thermodynamics Á Enthalpy of formation Á Enthalpy of phase change Á Enthalpy of reaction As practiced disciplines, structural chemistry and thermochemistry are very often unrelated. In this study, these disciplines are linked as relations are explicitly made using the contents of the journal Structural Chemistry (Vol. 18) for the calendar year 2007 as a scaffold for our analysis, for our selected articles in the discipline of structural chemistry. These studies have been reviewed by us, where we give them a thermochemical flavor. While this commentary is most generally written in terms of brief summaries of literature papers involving enthalpies of formation and/or reaction, not uncommonly we raise questions and even suggest possible future research. We are not, however, going to give a thermochemical slant on book reviews, honorary dedications, and obituaries although these works will be cited in our text.As such, this article is a sequel to our earlier related reviews of Structural Chemistry for the calendar years 2000 through 2004 [1-5]. Reviews for 2005 and 2006 are currently being prepared. Issue 1In the first article in the first issue of Structural Chemistry for 2007, Hargittai [6] asserted that while research is currently usually carried out in big groups, the most important ideas, observations and discoveries still belong to individuals who have to bring down dogmas or open entirely new areas in science. This may bring solace to the thermochemical community in which research groups are generally small, and the number of new practitioners sadly few.In the past decade, the crystal engineering of multidimensional arrays and networks containing metal ions has achieved considerable progress because of the increased interest in the potential utility of these compounds as zeolite-like materials [7-11], catalysts [12], or magnetic materials [13][14][15]. The thermochemistry of these species is complicated by their inherent complexity: however, estimation approaches of their key thermochemical quantities are increasingly reliable [16]. In the second article of this issue, by Wang et al. [17], the versatility of malonate dianion as a ligand for the construction of extended networks with different topologies dependent on the coordination geometry of the metal ion was discussed. The synthesis and structure of a novel malonate-bridged copper(II) compound in which copper(II) ions have two different coordination environments in a novel three-dimensional (3D) network was described. Metal malonates have been studied from a

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Monomeric and Dimeric Bromophenols from the Red Alga Ceramium Sp. with Antioxidant and Anti-Inflammatory Activities

Zhang

¹

,

Glukhov²,

H³

et al. 2020

Preprint

View full text Add to dashboard Cite

LC-MS2-based molecular networking using the Global Natural Products Social (GNPS) tool revealed a rich assortment of brominated compounds present in the antioxidant fraction of a red algal extract (Ceramium sp.) Further chemical investigation led to discovery of one monomeric bromophenol (lanosol isopropyl ether, 1) and seven dimeric ones (bromourceolatols A-G, 2-8), all of which are previously undescribed. Their structures were elucidated by extensive analysis of their spectroscopic data. Compounds 2-8 were determined to be racemic trans-type isomers by NOESY, specific optical rotation, and ECD. Compounds 1 and 3 displayed antioxidant activity with their EC50 of 44.4 and 47.0 μM, respectively, for scavenging DPPH free radicals while compounds 2 and 4 had approximate EC50 values of ~ 64 μM. Furthermore, compounds 2, 3, and 7 exhibited relatively potent anti-inflammatory activity at 32 μM by quenching 97%, 47%, and 73% of nitric oxide induced by bacterial lipopolysaccharide in macrophage RAW264.7 cells, respectively.

show abstract

Supramolecular isomerism in the hydrogen-bonded network of (5R,10R)-3,8-dihydroxy-5,10-diethoxy-5,10-dihydrochromeno[5,4,3-cde]chromene monohydrate

Cited by 3 publications

References 37 publications

Monomeric and Dimeric Bromophenols from the Red Alga Ceramium Sp. with Antioxidant and Anti-Inflammatory Activities

Monomeric and Dimeric Bromophenols from the Red Alga Ceramium Sp. with Antioxidant and Anti-Inflammatory Activities

Interplay of thermochemistry and Structural Chemistry, the journal (volume 18, 2007) and the discipline

Monomeric and Dimeric Bromophenols from the Red Alga Ceramium Sp. with Antioxidant and Anti-Inflammatory Activities

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