Two Rare Hydroazulene-type Sesquiterpenes from the Roots of Aristolochia yunnanensis

2014 ◽  
Vol 69 (6) ◽  
pp. 742-746 ◽  
Author(s):  
Zhuo Du ◽  
Feng-Ni Wen ◽  
Ji-Ping Zhang ◽  
Jian-Feng Wua ◽  
Fang Liu ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Cell Lines ◽  
Spectroscopic Data ◽  
Cytotoxic Activities ◽  
Moderate Activity ◽  
Electronic Circular Dichroism ◽  
The Third ◽  
The Absolute ◽  
First Time ◽  
Circular Dichroïsm

Two new sesquiterpenes, named aristoyunnolin I (1) and J (2), together with eight known compounds (3 - 10) were isolated from the roots of Aristolochia yunnanensis. Compounds 1 and 2 feature a rare hydroazulene-type sesquiterpene skeleton and represent the third and fourth examples of this kind found in nature. The structures were determined from spectroscopic data, and the absolute configurations of 1 - 3 were assigned by comparing experimental with simulated electronic circular dichroism (ECD) spectra. Compounds 1, 2, 6 - 10 were isolated from this plant for the first time. The cytotoxic activities of 1 - 10 were evaluated against P-388 and A-549 cell lines. Only compounds 4 and 5 showed moderate activity with IC50 values ranging from 12.0 to 18.2 μM.

scholarly journals (±)-Perforison A, A Pair of New Chromone Enantiomers from Harrisonia perforata

2017 ◽  
Vol 12 (1) ◽  
pp. 1934578X1701200
Author(s):  
Wen-Juan Yuan ◽  
Wen-Fen Gao ◽  
Jia-Hui Zhang ◽  
Pei Cao ◽  
Yu Zhang ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Spectroscopic Data ◽  
Cytotoxic Activities ◽  
Significant Activity ◽  
Electronic Circular Dichroism ◽  
Extensive Analysis ◽  
Circular Dichroïsm

(+)-Perforison A and (-)-perforison A, a new pair of chromone enantiomers, along with four known compounds, were isolated from the leaves and stems of Harrisonia perforata. Their structures and absolute configurations were determined on the basis of extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. The cytotoxic activities in vitro of these compounds were evaluated, but none showed significant activity.

scholarly journals A New Diterpenoid with a Rearranged Skeleton from Salvia prattii

2017 ◽  
Vol 12 (8) ◽  
pp. 1934578X1701200
Author(s):  
Hiroshi Kawabe ◽  
Riyo Suzuki ◽  
Hiroshi Hirota ◽  
Keiichi Matsuzaki ◽  
Xun Gong ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Hela Cell ◽  
Cell Lines ◽  
Absolute Configuration ◽  
Electronic Circular Dichroism ◽  
Methyl Group ◽  
Spectroscopic Analyses ◽  
Hela Cell Lines ◽  
The Absolute ◽  
Circular Dichroïsm

A new diterpenoid with a rearranged skeleton, prattinin A (1), was isolated along with five known compounds (2–6) from the roots of Salvia prattii. The structure of 1 bearing a methyl group at the C-5 position was established by extensive spectroscopic analyses and the absolute configuration of 1 was elucidated by comparing the calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1, 3, 4, and 5 exhibited moderate or weak cytotoxicity against HL-60 and HeLa cell lines.

scholarly journals Absolute Configuration Sensing of Chiral Aryl- and Aryloxy-Propionic Acids by Biphenyl Chiroptical Probes

Chemosensors ◽  
2021 ◽  
Vol 9 (7) ◽  
pp. 154
Author(s):  
Stefania Vergura ◽  
Stefano Orlando ◽  
Patrizia Scafato ◽  
Sandra Belviso ◽  
Stefano Superchi
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Environmental Pollutants ◽  
Red Shift ◽  
Electronic Circular Dichroism ◽  
Configuration Assignment ◽  
Clear Sign ◽  
The Absolute ◽  
Circular Dichroïsm

The absolute configuration of chiral 2-aryl and 2-aryloxy propionic acids, which are among the most common chiral environmental pollutants, has been readily and reliably established by either electronic circular dichroism spectroscopy or optical rotation measurements employing suitably designed 4,4′-disubstituted biphenyl probes. In fact, the 4,4′-biphenyl substitution gives rise to a red shift of the diagnostic electronic circular dichroism signal of the biphenyl A band employed for the configuration assignment, removing its overlap with other interfering dichroic bands and allowing its clear sign identification. The largest A band red shift, and thus the most reliable results, are obtained by employing as a probe the 4,4′-dinitro substituted biphenylazepine 3c. The method was applied to the absolute configuration assignment of 2-arylpropionic acids ibuprofen (1a), naproxen (1b), ketoprofen (1c) and flurbiprofen (1d), as well as to the 2-aryloxypropionic acids 2-phenoxypropionic acid (2a) and 2-naphthoxypropionic acid (2b). This approach, allowing us to reveal the sample’s absolute configuration by simple optical rotation measurements, is potentially applicable to online analyses of both the enantiomeric composition and absolute configuration of these chiral pollutants.

scholarly journals Use of Circular Dichroism to Determine the Absolute Configuration of a Pimarane Diterpenoid from the Southern African Sclerocroton integerrimus (Euphorbiaceae)

2014 ◽  
Vol 9 (8) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Vuyelwa J. Tembu ◽  
Moses K. Langat ◽  
Neil R. Crouch ◽  
Dulcie A. Mulholland
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Spectroscopic Analysis ◽  
Stem Bark ◽  
Electronic Circular Dichroism ◽  
The Absolute ◽  
Circular Dichroïsm

From the stem bark and leaves of Sclerocroton integerrimus, eight compounds, including 17-hydroxy- ent-pimara-8(14),15-dien-3-one (1), were isolated. The structures of the compounds were determined on the basis of spectroscopic analysis. The absolute configuration of 17-hydroxy- ent-pimara-8(14),15-dien-3-one was confirmed from electronic circular dichroism studies.

scholarly journals Cytotoxic Secondary Metabolites Isolated from the Marine Alga-Associated Fungus Penicillium chrysogenum LD-201810

Marine Drugs ◽  
2020 ◽  
Vol 18 (5) ◽  
pp. 276
Author(s):  
Lin-Lin Jiang ◽  
Jin-Xiu Tang ◽  
Yong-Heng Bo ◽  
You-Zhi Li ◽  
Tao Feng ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Cell Lines ◽  
Penicillium Chrysogenum ◽  
Marine Alga ◽  
2D Nmr ◽  
Ionization Mass ◽  
Human Carcinoma ◽  
Hydroxyphenylacetic Acid ◽  
The Absolute ◽  
Circular Dichroïsm

A new pentaketide derivative, penilactonol A (1), and two new hydroxyphenylacetic acid derivatives, (2’R)-stachyline B (2) and (2’R)-westerdijkin A (3), together with five known metabolites, bisabolane-type sesquiterpenoids 4–6 and meroterpenoids 7 and 8, were isolated from the solid culture of a marine alga-associated fungus Penicillium chrysogenum LD-201810. Their structures were elucidated based on extensive spectroscopic analyses, including 1D/2D NMR and high resolution electrospray ionization mass spectra (HRESIMS). The absolute configurations of the stereogenic carbons in 1 were determined by the (Mo2(OAc)4)-induced circular dichroism (CD) and comparison of the calculated and experimental electronic circular dichroism (ECD) spectra, while the absolute configuration of the stereogenic carbon in 2 was established using single-crystal X-ray diffraction analysis. Compounds 2 and 3 adapt the 2’R-configuration as compared to known hydroxyphenylacetic acid-derived and O-prenylated natural products. The cytotoxicity of 1–8 against human carcinoma cell lines (A549, BT-549, HeLa, HepG2, MCF-7, and THP-1) was evaluated. Compound 3 exhibited cytotoxicity to the HepG2 cell line with an IC50 value of 22.0 μM. Furthermore, 5 showed considerable activities against A549 and THP-1 cell lines with IC50 values of 21.2 and 18.2 μM, respectively.

scholarly journals Isolation and Absolute Configurations of Diversiform C17, C21 and C25 Terpenoids from the Marine Sponge Cacospongia sp.

Marine Drugs ◽  
2018 ◽  
Vol 17 (1) ◽  
pp. 14 ◽  
Author(s):  
Xingwang Zhang ◽  
Ping-Lin Li ◽  
Guo-Fei Qin ◽  
Shengying Li ◽  
Nicole de Voogd ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Cell Lines ◽  
Optical Rotation ◽  
Human Tumor ◽  
Chiral Hplc ◽  
Pure Compounds ◽  
New Compounds ◽  
First Time ◽  
Optically Pure ◽  
Circular Dichroïsm

Chemical investigation of MeOH extract of a South China Sea sponge Cacospongia sp. yielded 15 terpenoids belonging to three different skeleton-types, including the unusual C17 γ-lactone norditerpenoids (1–3), the rare C21 pyridine meroterpenoid (7), and the notable C25 manoalide-type sesterterpenoids (4–6, 8–10). Compounds 1–5 were initially obtained as enantiomers, and were further separated to be optically pure compounds (1a, 1b, 2a, 2b, 3a-r, 3b-r, 4a, 4b, 5a and 5b) by chiral HPLC, with a LiAlH4 reduction aid for 3. Compounds 3a/3b (a pair of inseparable enantiomers), 4a, 5a, 6, and 7 were identified as new compounds, while 1a/1b and 2a/2b were obtained from a natural source and were determined for their absolute configurations for the first time. This is also the first time to encounter enantiomers of the well-known manoalide-type sesterterpenoids from nature. The structures with absolute configurations of the new compounds were unambiguously determined by comprehensive methods including HR-ESI-MS and NMR data analysis, optical rotation comparison, experimental and calculated electronic circular dichroism (ECD), and Mo2(OAc)4 induced circular dichroism (ICD) methods. The cytotoxicity of the isolates against selected human tumor cell lines was evaluated, however, the tested compounds showed no activity against selected cell lines.

Photophysical properties of quinoxaline-fused [7]carbohelicene derivatives

RSC Advances ◽  
2015 ◽  
Vol 5 (89) ◽  
pp. 72907-72915 ◽  
Author(s):  
Chunyu Liu ◽  
Yanling Si ◽  
Xiumei Pan ◽  
Guochun Yang
Keyword(s):  
Circular Dichroism ◽  
Nonlinear Optics ◽  
Charge Transport ◽  
Transport Properties ◽  
Photophysical Properties ◽  
Electronic Circular Dichroism ◽  
First Time ◽  
Circular Dichroïsm

The electronic circular dichroism, UV-Vis absorption, nonlinear optics, and charge transport properties of novel quinoxaline-fused 7-carbohelicene derivatives have been investigated for the first time.

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