scholarly journals Two Novel Norwithasteroids with Unusual Six- and Seven-Membered Ether Rings in Side Chain from Flos Daturae

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Bing-You Yang ◽  
Yong-Gang Xia ◽  
Yan-Yan Wang ◽  
Qiu-Hong Wang ◽  
Hai-Xue Kuang
Keyword(s):  
Carboxylic Acid ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Side Chain ◽  
Macroporous Resin ◽  
Datura Metel ◽  
Naturally Occurring ◽  
The Family ◽  
Proliferation In Vitro

Chemical investigation of 50% ethanol eluate fraction of macroporous resin for the flower of Datura metel L. collected in Jiangsu province of China resulted in the isolation of two novel naturally occurring norwithasteroids, baimantuoluoline I (1) and baimantuoluoside J (2). Their structures were elucidated as 5α, 6β, 12β-trihydroxy-1-oxo-2-en-ergosta-21,24;22,29-diepoxy-26-carboxylic acid (1) and 5α, 6β, 12β, 25-tetrahydroxy-1-oxo-2-en-ergosta-21,24;22,29-diepoxy-26-carboxylic acid (2) on the basis of extensive spectroscopic analysis, including 1D, 2D-NMR, and HR-ESI-MS. According to the literatures, this study represents the first report of the norwithasteroids in the side chain with unusual six- and seven-membered ether rings instead of those with an unmodified skeleton (δ-lactone or δ-lactol side chain) and a modified skeleton (γ-lactone or γ-lactol side chain) in the family of withanolides. Meanwhile, compounds 1 and 2 were evaluated for their immunosuppressive activity against mice splenocyte proliferation in vitro.

scholarly journals Diterpenoid Alkaloids from Delphinium aemulans

2018 ◽  
Vol 13 (11) ◽  
pp. 1934578X1801301
Author(s):  
Nurfida Ablajan ◽  
Bo Zhao ◽  
Wenjuan Xue ◽  
Zukela Ruzi ◽  
Jiangyu Zhao ◽  
...  
Keyword(s):  
2D Nmr ◽  
Diterpenoid Alkaloids ◽  
Diterpenoid Alkaloid ◽  
Esi Ms ◽  
Mtt Method ◽  
Naturally Occurring ◽  
Spectroscopic Analyses ◽  
Type C ◽  
Mcf 7

A new naturally occurring lycoctonine-type C19-diterpenoid alkaloid aemulansine (1), together with ten known alkaloids (2–11), were isolated from the whole herb of Delphinium aemulans Navski. Their structures were elucidated by extensive spectroscopic analyses, including 1D, 2D NMR and HR-ESI-MS. Compounds 1–10 were also evaluated in vitro for cytotoxicity against A549, Hela and MCF-7 cells using the MTT method.

scholarly journals Oropheayunnol, an Unusual 22,23-Epoxy Apotirucallane Triterpenoid from Orophea Yunnanensis

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700
Author(s):  
Wen-Jian Lan ◽  
Jun Wang ◽  
Yan-Qiong Guo ◽  
Sheng Yin
Keyword(s):  
Nasopharyngeal Carcinoma ◽  
Cell Line ◽  
Carcinoma Cell ◽  
Epoxy Group ◽  
2D Nmr ◽  
Side Chain ◽  
Spectroscopic Methods ◽  
Phytochemical Study ◽  
Nasopharyngeal Carcinoma Cell

A new apotirucallane-type triterpenoid with an unusual 22,23-epoxy group in the side chain, 22,23-epoxy-apotirucalla-14-ene-3α,7α,24α,25-tetraol (1), was isolated from the leaves and twigs of Orophea yunnanensis. The structure of 1 was established on the basis of HRESIMS, 1D, and 2D NMR spectroscopic methods. This is the first phytochemical study of Orophea yunnanensis, and the biogenetic origin of 1 was postulated. Compound 1 exhibited weak cytotoxicity in vitro against the growth of CNE1 nasopharyngeal carcinoma cell line with an IC50 value of 9.7 μg/mL.

scholarly journals A New Monoterpenoid and a New Flavonoid Glycoside from the Peels of Clausena lansium

2016 ◽  
Vol 11 (5) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Hui-Dong Deng ◽  
Cai-Hong Cai ◽  
Shuai Liu ◽  
Yan-Bo Zeng ◽  
Wen-Li Mei ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Carboxylic Acid ◽  
Inhibitory Activity ◽  
2D Nmr ◽  
Flavonoid Glycoside ◽  
Esi Ms ◽  
Inhibition Zones

One new monoterpenoid, nerol oxide-8-carboxylic acid (1), and one new flavonoid glycoside, claulansoside A (2), together with six known compounds, clausenamide (3), quercetin (4), isorhamnetin (5), dihydromyric (6), 2′',3′'-dihydroxyanisolactone (7) and ( E,E)-8-(7-hydroxy-3,7-dimethylocta-2,5-dienyloxy)psoralen (8), have been isolated from the peels of Clausena lansium (Lour.) Skeels. Their structures were determined using a combination of 1D, and 2D NMR (HMQC, HMBC, COSY and NOESY) techniques, and HR-ESI-MS analyses. Compounds 1 and 7 exhibited antibacterial activity against Staphylococcus aureus with the diameter of inhibition zones of 11.5 mm and 14.2 mm. Compounds 3 and 6 showed α-glucosidase inhibitory activity in vitro.

scholarly journals In Vitro Activities of Noveltrans-3,5-Disubstituted Pyrrolidinylthio-1β-Methylcarbapenems with Potent Activities against Methicillin-Resistant Staphylococcus aureus andPseudomonas aeruginosa

2000 ◽  
Vol 44 (3) ◽  
pp. 489-495 ◽  
Author(s):  
Rie Nagano ◽  
Kaneyoshi Shibata ◽  
Yuka Adachi ◽  
Hideaki Imamura ◽  
Terutaka Hashizume ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Side Chain ◽  
The Novel ◽  
Good Activity ◽  
Penicillin Binding Protein ◽  
Coagulase Negative Staphylococci ◽  
Methicillin Resistant ◽  
The Family

ABSTRACT The in vitro activities of the novel 1β-methylcarbapenems J-111,225, J-114,870, and J-114,871, which have a structurally unique side chain that consists of a trans-3,5-disubstituted 5-arylpyrrolidin-3-ylthio moiety at the C-2 position, were compared with those of reference antibiotics. Among isolates of both methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-resistant coagulase-negative staphylococci (MRCoNS), 90% were inhibited by J-111,347 (prototype), J-111,225, J-114,870, and J-114,871 at concentrations of 2, 4, 4, and 4 μg/ml (MICs at which 90% of isolates are inhibited [MIC90s]), respectively, indicating that these agents were 32- to 64-fold more potent than imipenem, which has an MIC90 of 128 μg/ml. Although these drugs were less active in vitro than vancomycin, which had MIC90s of 1 and 2 μg/ml for MRSA and MRCoNS, respectively, the new carbapenems displayed better killing kinetics than vancomycin. The potent anti-MRSA activity was ascribed to the excellent affinities of the new carbapenems for penicillin-binding protein 2a of MRSA. Since the new carbapenems also exhibited good activity against gram-positive and -negative bacteria including clinically important pathogens such as penicillin-resistantStreptococcus pneumoniae, Haemophilus influenzae, members of the family Enterobacteriaceae,Pseudomonas aeruginosa, and Clostridium difficile, as well as MRSA, the novel carbapenems are worthy of further evaluation.

scholarly journals Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 69 ◽  
Author(s):  
Kazuki Watanabe ◽  
Yoshihiro Mimaki ◽  
Haruhiko Fukaya ◽  
Yukiko Matsuo
Keyword(s):  
Spectroscopic Analysis ◽  
Apoptotic Cell ◽  
2D Nmr ◽  
Phytochemical Analysis ◽  
X Ray ◽  
C 23 ◽  
The Family ◽  
Ic50 Values ◽  
Cycloartane Glycosides ◽  
New Compounds

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

MWL fraction with a high concentration of lignin-carbohydrate linkages: Isolation and 2D NMR spectroscopic analysis

Holzforschung ◽  
2007 ◽  
Vol 61 (1) ◽  
pp. 1-7 ◽  
Author(s):  
Mikhail Yu. Balakshin ◽  
Ewellyn A. Capanema ◽  
Hou-min Chang
Keyword(s):  
Loblolly Pine ◽  
Spectroscopic Analysis ◽  
Direct Detection ◽  
2D Nmr ◽  
Side Chain ◽  
High Concentration ◽  
Hmbc Correlation ◽  
Nmr Techniques ◽  
C Nmr ◽  
Hmbc Technique

Abstract A preparation enriched in lignin-carbohydrate fragments (LCC-AcOH) was isolated in the course of purification of loblolly pine crude milled wood lignin (MWL). The preparation contained approximately equal amounts of lignin and carbohydrates, with high amounts of arabinose and galactose compared to their levels in wood. LCC-AcOH was investigated by 2D 1H-13C (HMQC and HMBC) correlation NMR techniques and quantitative 13C NMR. The HMQC spectra allowed direct detection of phenyl glycoside, ester and benzyl ether lignin-carbohydrates linkages in high amounts. The assignment of these structures was supported by the HMBC technique. It is noteworthy that in the ester lignin-carbohydrate linkages, a uronic acid residue was attached not to the benzylic position of lignin, as commonly believed, but to the γ-position of the side chain.

scholarly journals Antimicrobial and DNA Gyrase-Inhibitory Activities of Novel Clorobiocin Derivatives Produced by Mutasynthesis

2004 ◽  
Vol 48 (4) ◽  
pp. 1307-1312 ◽  
Author(s):  
Ute Galm ◽  
Stefanie Heller ◽  
Stuart Shapiro ◽  
Malcolm Page ◽  
Shu-Ming Li ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Alkyl Substituent ◽  
Dna Gyrase ◽  
Antibacterial Activities ◽  
Side Chain ◽  
Acid Moiety ◽  
E Coli ◽  
Polar Groups ◽  
Reduced Activity

ABSTRACT Twenty-eight novel clorobiocin derivatives obtained from mutasynthesis experiments were investigated for their inhibitory activity towards Escherichia coli DNA gyrase and for their antibacterial activities towards clinically relevant gram-positive and gram-negative bacteria in comparison to novobiocin and clorobiocin. Clorobiocin was the most active compound both against E. coli DNA gyrase in vitro and against bacterial growth. All tested modifications of the 3-dimethylallyl-4-hydroxybenzoyl moiety reduced biological activity. The highest activities were shown by compounds containing a hydrophobic alkyl substituent at position 3 of the 4-hydroxybenzoyl moiety. Polar groups in this side chain, especially amide functions, strongly reduced antibacterial activity. Replacement of the alkyl side chain with a halogen atom or a methoxy group at the same position markedly reduced activity. Transfer of the pyrrole carboxylic acid moiety from O-3" to O-2" of l-noviose moderately reduced activity, whereas the complete absence of the pyrrole carboxylic acid moiety led to a loss of activity. Desclorobiocin derivatives lacking the chlorine atom at C-8 of the 3-amino-4,7-dihydroxycoumarin moiety also showed low activity. Lack of a methyl group at O-4" of l-noviose resulted in an inactive compound. From these findings it appears that clorobiocin represents a “highly evolved” structure optimized for bacterial transport and DNA gyrase inhibition.

scholarly journals Semisynthesis of Selenoauraptene

Molecules ◽  
2021 ◽  
Vol 26 (9) ◽  
pp. 2798
Author(s):  
Serena Fiorito ◽  
Francesco Epifano ◽  
Lorenzo Marchetti ◽  
Salvatore Genovese
Keyword(s):  
Short Communication ◽  
Biologically Active ◽  
Side Chain ◽  
Radical Scavenger ◽  
In Vitro Activity ◽  
Naturally Occurring ◽  
Antioxidant Agents ◽  
Approved Drugs ◽  
First Time

Selenium-containing compounds are gaining more and more interest due to their valuable and promising pharmacological properties, mainly as anticancer and antioxidant agents. Ebselen, the up to now only approved drugs, is well known to possess very good glutathione peroxidase mimicking effects. To date, the most of efforts have been directed to build pure synthetic Se containing molecules, while less attention have been devoted to Se-based semisynthetic products resembling natural compounds like terpenes, polyphenols, and alkaloids. The aim of this short communication is to report the synthesis of the first example of a Se-phenylpropanoids, namely selenoauraptene, containing a selenogeranyl side chain in position 7 of the umbelliferone core. The key step was the Newman-Kwart rearrangement to obtain a selenocarbamate in which the Se atom was directly attached to umbelliferone (replacing its 7-OH function) followed by hydrolysis to get diumbelliferyl diselenide, which was finally easily converted to the desired Se-geranyl derivative in quite a good overall yield (28.5%). The synthesized adduct displayed a greater antioxidant and a radical scavenger in vitro activity than parent auraptene. The procedure we describe herein, to the best of our knowledge for the first time in the literature, represents an easy-to-handle method for the synthesis of a wide array of seleno analogues of naturally occurring biologically active oxyprenylated secondary metabolites.

scholarly journals Isolation of Sesquiterpenoids and Steroids from the Soft Coral Sinularia brassica and Determination of Their Absolute Configuration

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 523
Author(s):  
Giang Nam Pham ◽  
Da Yeun Kang ◽  
Min Ju Kim ◽  
Se Jong Han ◽  
Jun Hyuck Lee ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Leishmania Donovani ◽  
Spectroscopic Analysis ◽  
Soft Coral ◽  
Antimicrobial Effect ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Polyhydroxylated Steroids

Two undescribed rearranged cadinane-type sesquiterpenoids (1–2), named sinulaketol A-B, together with one new chlorinated steroid (3), one new gorgosterol (4), one known sesquiterpene (5), one known dibromoditerpene (6) and two known polyhydroxylated steroids (7–8) were isolated from the soft coral Sinularia brassica. The structures of these compounds were established by extensive spectroscopic analysis, including HRESIMS, 1D, and 2D NMR spectroscopy. Their absolute configurations were also determined by the ECD calculations and DP4+ probability analysis. Antileishmanial activity of compounds 1–8 was evaluated in vitro against the amastigote forms of Leishmania donovani, in which compounds 3, 6, and 7 inhibited the growth of L. donovani by 58.7, 74.3, 54.7%, respectively, at a concentration of 50 μM. Antimicrobial effect of the isolated compounds were also evaluated against Candida albicans, Staphylococcus aureus, and Escherichia coli. Compound 6, a brominated diterpene, exhibited antimicrobial effect against S. aureus.

scholarly journals Chemical rescue of mutant proteins in living cells by naturally occurring small molecules

2021 ◽  
Author(s):  
Daniel S. Hassell ◽  
Marc G. Steingesser ◽  
Ashley S. Denney ◽  
Courtney R. Johnson ◽  
Michael A. McMurray
Keyword(s):  
Protein Folding ◽  
Small Molecules ◽  
Protein Function ◽  
Therapeutic Interventions ◽  
Side Chain ◽  
Enzymatic Reactions ◽  
Chemical Rescue ◽  
Naturally Occurring

AbstractIntracellular proteins function in a complex milieu wherein small molecules influence protein folding and act as essential cofactors for enzymatic reactions. Thus protein function depends not only on amino acid sequence but also on the concentrations of such molecules, which are subject to wide variation between organisms, metabolic states, and environmental conditions. We previously found evidence that exogenous guanidine reverses the phenotypes of specific budding yeast septin mutants by binding to a WT septin at the former site of an Arg side chain that was lost during fungal evolution. Here we used a combination of targeted and unbiased approaches to look for other cases of “chemical rescue” by naturally occurring small molecules. We reportin vivorescue of hundreds of yeast mutants representing a variety of genes, including likely examples of Arg or Lys side chain replacement by the guanidinium ion. Failed rescue of targeted mutants highlight features required for rescue, as well as key differences between thein vitroandin vivoenvironments. Some non-Arg mutants rescued by guanidine likely result from “off-target” effects on specific cellular processes in WT cells. Molecules isosteric to guanidine and known to influence protein folding had a range of effects, from essentially none for urea, to rescue of a few mutants by DMSO. Strikingly, the osmolyte trimethylamine-N-oxide rescued ∼20% of the mutants we tested, likely reflecting combinations of direct and indirect effects on mutant protein function. Our findings illustrate the potential of natural small molecules as therapeutic interventions and drivers of evolution.

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