Complete assignments of <sup>1</sup>H and <sup>13</sup>C NMR spectral data for benzylidenebenzyl butyrolactone lignans

Silva, Rosangela da; Pedersoli, Susimaire; Lacerda, Valdemar; Donate, Paulo Marcos; Albuquerque, Sérgio de; Bastos, Jairo Kenupp; Araújo, Ana Lúcia Santos de Matos; Silva, Márcio Luís Andrade e

doi:10.1002/mrc.1655

Cited by 16 publications

(9 citation statements)

References 15 publications

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“…The formation of additional unsaturated system in the aglycone is also well reflected in the 13 than those found in the spectrum of 1 (Table 2), in the range characteristic of the carbon atoms signals of α,β-unsaturated lactones. [34,35] The π -electron coupling between C(2) C(3) bond and the carbonyl C(1) O group within the structures of 2-5 is confirmed also by FT-IR spectra (Fig. 5a) in which the band of the ν[C(1) O] stretching vibrations, found by the second derivative function at 1749 cm −1 in the spectrum of 1, is shifted towards lower wavenumbers (to about 1716 cm −1 ) in the spectra of 2-5.…”

Section: Resultsmentioning

confidence: 98%

Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy‐aminoalkyl‐α,β‐unsaturated derivatives of the macrolide antibiotic josamycin

Przybylski

Pyta

Stefańska

et al. 2010

Magnetic Reson in Chemistry

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Four new hydroxy-aminoalkyl derivatives of alpha,beta-unsaturated macrolide-josamycin (2-5) have been synthesised and their structures have been studied by means of (1)H and (13)C NMR and FT-IR methods. Complete assignment of resonances in the (1)H and (13)C NMR spectra has been made on the basis of (1)H-(13)C HSQC, (1)H-(13)C HMBC, (1)H-(1)H COSY, (1)H-(1)H NOESY 2D experiments. Spectroscopic data indicated that for the derivatives 3 and 4 some equilibrium between two different structures exists in contrast to derivatives 2 and 5. The lowest-energy structures of the new derivatives of josamycin have been calculated and visualised by PM5 method at semi-empirical level of theory, taking into account the NMR and FT-IR data. The most significant differences between the structures of josamycin and its newly synthesised derivatives' were found in the conformation of the macrolide aglycone part and in the mutual orientation of the 4-O-isovalerylmycarosylmycaminose moiety relative to the aglycone part. PM5 semi-empirical calculations indicated that the structures of the new macrolide derivatives are stabilised by rather weak intramolecular hydrogen bonds in agreement with spectroscopic data. Antimicrobial properties of the new derivatives 2-5 as well as those having an acetate group at C-3 (6 and 7) were determined and compared to that of the parent macrolide antibiotic josamycin (1).

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Section: Resultsmentioning

confidence: 98%

Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy‐aminoalkyl‐α,β‐unsaturated derivatives of the macrolide antibiotic josamycin

Przybylski

Pyta

Stefańska

et al. 2010

Magnetic Reson in Chemistry

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“…1). Lignan derivatives (3-10) were identified as (Ϫ)-savinin (3), [6][7][8] (ϩ)-sesamine (4), [9][10][11] (Ϫ)-hinokinin (5), 12,13) (ϩ)-dihydrosesamin (6), 14,15) (Ϫ)-yatein (7), 16,17) (ϩ)-piperitol (8), 14) (ϩ)-xanthxylol (9), 18) and (ϩ)-7-oxohinokinin (10), 19) respectively. Compounds 11 and 12 were identified as (Ϫ)-hinokiic acid (11) 20) and (ϩ)-cryptomeridiol (12).…”

Section: Resultsmentioning

confidence: 99%

“…2 indicates that the structure of 1 is 9-acetoxy-3,4:3Ј,4Ј-bismethylenedioxy-7,9Ј-epoxylignan. Thus 1 should be an acetate of dihydrosesamin (6 (6) and criptomeridiol (12) ( Table 1). The 13 C-NMR spectral data (Table 1) of 2 showed a summation of carbon chemical shifts belonging to 6 and 12.…”

Section: Resultsmentioning

confidence: 99%

Neurite Outgrowth-Promoting Active Constituents of the Japanese Cypress (Chamaecyparis obtusa)

Kuroyanagi

Ikeda

Gao³

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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There are many severe social problems associated with aging and reduced brain function worldwide and especially in Japan due to lengthning of the average life span. There is currently no definitive treatment for such diseases. In the course of our biological test-guided screening of Japanese woody plant extracts, we condacted several tests of biological activity on isolated biologically active constituents from woody plants. We reported the isolation of antibacterial constituents, 1,2) antioxidative constituents, 3) and antitumor-promoting constituents 4) from woody plants. Neuronal PC12 cell 5) neurite outgrowth testing of methanol extracts of woody plants collected in the northern part of Hiroshima prefecture identified the methanol extract of leaves of the Japanese cypress (Chamaecyparis obtusa) as an active sample. Japanese cypress is a popular architectural wood in Japan and is cultivated all nationwide. We isolated neurite outgrowth-promoting active constituents from the leaves of the plant using biological tests to give two new compounds along with known lignan derivatives. The structures of the new compounds were determined using chemical and spectral methods including two-dimensional NMR spectrum. Some of these compounds showed potent neurite outgrowth activity. This report describes the isolation of the constituents of C. obtusa and determination of their structures. We also report their neurite outgrowth-promoting activity. Results and DiscussionThe methanol extract of the leaves of C. obtusa was fractionated to an ethyl acetate layer (AcOEt lay.), an n-butanol layer (n-BuOH lay.) and, aqueous lay. Of these, the AcOEt lay. showed the most potent neurite outgrowth-promoting activity in PC12 cells in the presence of an inactive amount of NGF, so the fraction was successively separated by means of silica gel column chromatography (SiO 2 c.c.), preparative thin layer chromatography (PLC), and HPLC using a reversephase column to give two new compounds 1 and 2 along with eleven known compounds 3-13. Structures of the known compounds were determined by means of (4) (d C 147.8, 147.7, 146.9, 145.9, 136.4, 133.6, 121.4, 119.1, 108.8, 108.2, 108.0, 106.1), three carbinyl carbons (d C 83.0, 72.6, 62.5), three alkane carbons (d C 49.1, 42.3, 33.1), and methylenedioxy groups (d C 100.9). These data show that 1 is lignan monoacetate. The HMBC spectrum shown in Fig. 2 indicates that the structure of 1 is 9-acetoxy-3,4:3Ј,4Ј-bismethylenedioxy-7,9Ј-epoxylignan. Thus 1 should be an acetate of dihydrosesamin (6). Compound 1 ([a] D ϩ20.2°) was identified as an acetate of 6 in all respects including optical rotation ([a] D ϩ17.2°). These findings indicated that the configuration of 1 is identical to that Life and Environmental Sciences, Prefectural University of Hiroshima; 562 Nanatsuka, Shobara, Hiroshima 727-0023, Japan: b School of Traditional Chinese Medicines, Shenyang Pharaceutical University; 103 Wenhua Road, Shenyang 110016, P. R. China: c Hiroshima Prefectural Forestry Research Center; 168-1 Tokaichi, Miy...

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“…The lignans 1-3 were prepared from the respective benzylidenebenzyl butyrolactone lignans by reaction with NBS in CCl 4 …”

Section: Methodsmentioning

confidence: 99%

“…These compounds have numerous structure types and are widely distributed in various plant species. 1 We have recently performed biological studies on natural and synthetic lignans, and the structural elucidation of the compounds obtained by us has furnished important NMR data for dibenzylbutyrolactone, 2 aryltetralin, 3 and benzylidenebenzylbutyrolactone 4 skeletons, which contributed to completing the spectroscopic data found in the literature. 5 In this work, we synthesized the arylnaphthalene lignan lactones taiwanin C (1), 4-methyl dehydroretrodendrin (2) and justicidin B (3) (Fig.…”

Section: Introductionmentioning

confidence: 97%

Complete assignments of ¹H and ¹³C NMR spectral data for arylnaphthalene lignan lactones

Silva

Ruas

Donate

2007

Magnetic Reson in Chemistry

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Complete assignments of ¹H and ¹³C NMR spectral data for benzylidenebenzyl butyrolactone lignans

Cited by 16 publications

References 15 publications

Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy‐aminoalkyl‐α,β‐unsaturated derivatives of the macrolide antibiotic josamycin

Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy‐aminoalkyl‐α,β‐unsaturated derivatives of the macrolide antibiotic josamycin

Neurite Outgrowth-Promoting Active Constituents of the Japanese Cypress (Chamaecyparis obtusa)

Complete assignments of ¹H and ¹³C NMR spectral data for arylnaphthalene lignan lactones

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Complete assignments of 1H and 13C NMR spectral data for benzylidenebenzyl butyrolactone lignans

Cited by 16 publications

References 15 publications

Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy‐aminoalkyl‐α,β‐unsaturated derivatives of the macrolide antibiotic josamycin

Structure elucidation, complete NMR assignment and PM5 theoretical studies of new hydroxy‐aminoalkyl‐α,β‐unsaturated derivatives of the macrolide antibiotic josamycin

Neurite Outgrowth-Promoting Active Constituents of the Japanese Cypress (Chamaecyparis obtusa)

Complete assignments of 1H and 13C NMR spectral data for arylnaphthalene lignan lactones

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Complete assignments of ¹H and ¹³C NMR spectral data for benzylidenebenzyl butyrolactone lignans

Complete assignments of ¹H and ¹³C NMR spectral data for arylnaphthalene lignan lactones