Cycloabiesesquine A, a unique sesquiterpenoid from Abies delavayi

Yang, Xian‐Wen; Ding, Yuanqing; Li, Xing-Cong; Ferreira, Daneel; Shen, Yun‐Heng; Li, Sumei; Wang, Ning; Zhang, Wei‐Dong

doi:10.1039/b905710b

Cited by 31 publications

(6 citation statements)

References 15 publications

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“…4. 11 There is an overall agreement between experimental and TD-DFT calculated ECD spectra of 3S, 4R, 6S, 7S, 9S, 12S, 13S, 15S, 16S-1. Therefore, the absolute configuration of 1 was established as depicted in Fig.…”

supporting

confidence: 53%

Lycopalhine A, a novel sterically congested Lycopodium alkaloid with an unprecedented skeleton from Palhinhaea cernua

Dong

Yang

et al. 2012

Chem. Commun.

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supporting

confidence: 53%

Lycopalhine A, a novel sterically congested Lycopodium alkaloid with an unprecedented skeleton from Palhinhaea cernua

Dong

Yang

et al. 2012

Chem. Commun.

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“…The HMBC correlations from H-9 to C-8, and C-10, H-12 to C-10, and C-11, H-13 to C-10, and C-11 established the terminal diene unit ( Supplementary Figure S20 ). The key HMBC correlations of H 3 -16 to C-2, C-3, and C-4 and H-2 to C-1, C-3, C-4, and C-5 indicated the presence of a five-membered carbocycle containing a ketone carbonyl and a trisubstituted double bond ( Figure 2 ), as well as by comparison of the data with that of in agreement with the data of cycloabiesesquine A [ 25 ]. The two fragments may be connected via the correlations of H-15 to C-5, C-6, and C-7, H-14 to C-6 and H-7 to C-6, C-7, and C-8 in the HMBC spectrum.…”

Section: Resultsmentioning

confidence: 76%

“…The two fragments may be connected via the correlations of H-15 to C-5, C-6, and C-7, H-14 to C-6 and H-7 to C-6, C-7, and C-8 in the HMBC spectrum. Two double bonds in the molecule possessed 2 Z and 9 E configuration on the basis of the chemical shifts of C-16 and C-13 (δ 15.6 and 11.6, respectively) [ 24 , 25 ].…”

Section: Resultsmentioning

confidence: 99%

New Sinularianin Sesquiterpenes from Soft Coral Sinularia sp.

et al. 2013

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Four new sesquiterpenes, sinularianins C–F (3–6), together with known sinularianins A (1) and B (2) were identified from a South China Sea soft coral Sinularia sp. Compounds 1–6 were evaluated for inhibition of NF-κB activation using the cell-based HEK293 NF-κB luciferase reporter gene assay. Compounds 1 and 4 were exhibited a potent effect with inhibitory rates of 41.3% and 43.0% at the concentration of 10 µg/mL, respectively.

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“…Many good examples have been reported, for example, 110 and its epimers 111 to 113 [156], an isoflavone 114 [157], and new dinorditerpenoids, trigonostemons A-D (115 to 118) [158], 119 [159], 120 [160] and 121 [161] were assigned with the assistance from comparing the computed ECD with experimental ECD spectra. The specific ECD spectra are not summarized here.…”

Section: Electronic Circular Dichroism (Ecd)mentioning

confidence: 99%

Progression of Absolute Configuration Determination in Natural Product Chemistry Using Optical Rotation (Dispersion), Matrix Determinant and Electronic Circular Dichroism Methods

Sheng-Ding¹,

Shen²,

Luo³

et al. 2011

COC

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With the development of separation materials, more and more complex natural products with poly-stereogenic centers are obtained. However, due to small quantity of the isolated compounds, or no crystal formed, or complex 2D NMR correlation signals, absolute configuration identification for these compounds becomes difficult. Now, computational methods provide researchers many benefits in structural determinations for chiral natural products. Computational methods include (1) optical rotation (OR) and its dispersion (ORD) computations; (2) electronic circular dichroism (ECD or CD) calculations; (3) computations of determinant of matrix for stereogenic centers. In methods (1) to (2), the mostly used quantum theory contained density functional theory (DFT) with different basis sets, e.g. B3LYP/aug-cc-pVDZ//B3LYP/6-31G(d). Effects from solvents on OR value can be investigated using different corresponding software. In the cases, optimizations performed in the corresponding solution are helpful to obtain the correct predictions although it is not usual at present time. Matrix model as one of the mathematic methods is different from quantum methods, which is of easily being understood and effective in absolute configuration assignment for acyclic chiral compounds. In this review, necessary theory basis for the three methods are simply introduced for modern readers, the focus of which is the application of these methods in natural product chemistry by various examples reported in different journals from 1998 to the end of April of 2010 except for matrix method to the May of 2010 based on an experimental chemist's viewpoints.

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Cycloabiesesquine A, a unique sesquiterpenoid from Abies delavayi

Abstract: Cycloabiesesquine A, representing a unique carbon skeleton among the sesquiterpenoids, was isolated from Abies delavayi and by extensive spectroscopic and computational methods, its structure was elucidated as (7S,8R,12R)-4,8-dihydroxy-1,3,5,10-tetraen-8,12-cyclobisabolan-9-one.

Cited by 31 publications

References 15 publications

Lycopalhine A, a novel sterically congested Lycopodium alkaloid with an unprecedented skeleton from Palhinhaea cernua

Lycopalhine A, a novel sterically congested Lycopodium alkaloid with an unprecedented skeleton from Palhinhaea cernua

New Sinularianin Sesquiterpenes from Soft Coral Sinularia sp.

Progression of Absolute Configuration Determination in Natural Product Chemistry Using Optical Rotation (Dispersion), Matrix Determinant and Electronic Circular Dichroism Methods

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