Schisantherins LO and acetylschisantherin L from Kadsura coccinea

Liu, Jia-Sen; Li, Liang

doi:10.1016/s0031-9422(00)95108-2

Cited by 55 publications

(41 citation statements)

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“…The structure of the cyclooctadiene ring was also confirmed by the COSY connectivities HÀC(6)/ HÀC(7)/HÀC(8)/HÀC(9), HÀC(7)/Me (17), and HÀC(8)/Me (18). The CD curve of 1 showed a negative Cotton effect around 252 nm and a positive one around 224 nm favoring the (S)-biphenyl configuration [10] [11]. The relative configuration of 1 was determined by the NOESY data (Fig.…”

Section: (S)mentioning

confidence: 68%

Seven New Lignan Esters from Kadsura philippinensis

Cheng

Lin

Khalil

et al. 2011

Helvetica Chimica Acta

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Five new oxygenated lignans with a dibenzocyclooctadiene skeleton, kadsuphilols P -T (1 -5), and two new C 19 homolignans, kadsuphilols U and V (6 and 7), were isolated by chromatographic fractionation of an AcOEt extract of the stems of Kadsura philippinensis. The structures of the isolated metabolites were elucidated through extensive spectroscopic analysis including HR-ESI-MS and 2D-NMR (HMQC, COSY, and HMBC). The configuration at the chiral centers and at the biphenyl moiety were determined by interpretation of NOESY and CD data, respectively.

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Section: (S)mentioning

confidence: 68%

Seven New Lignan Esters from Kadsura philippinensis

Cheng

Lin

Khalil

et al. 2011

Helvetica Chimica Acta

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“…Kadoblongifolin A (1) was obtained as white powder, the molecular formula was established as C 22 [9,10] The NMR spectra (Table 1) of 1 were similar with those of 7 except for signals of cyclooctene moiety. Namely, the 13 C NMR and HMQC spectra showed carbon signals at δ C 134.1 (C-1), 100.5 (C-2), 147.6 (C-3), 137.4 (C-4), 142.0 (C-5), 118.0 (C-6), 131.5 (C-1 ), 107.9 (C-2 ), 150.9 (C-3 ), 134.8 (C-4 ), 148.7 (C-5 ), 115.3(C-6 ); one methylenedioxy group at δ C 101.5; and three methoxyl groups at δ C 59.9 (OMe-5), 55.8 (OMe-3 ), and 61.0 (OMe-4 ).…”

Section: Resultsmentioning

confidence: 96%

Complete assignments of ¹H and ¹³C NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia

Liu¹,

Xu²,

Peng³

et al. 2009

Magnetic Reson in Chemistry

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Two new dibenzocyclooctadiene lignans, named kadoblongifolins A (1) and B (2), and one new natural product dibenzocyclooctadiene lignan, named kadoblongifolin C (3), were isolated from the stems of Kadsura oblongifolia (K. oblongifolia), together with five known ones, schizanrin F (4), propinquanin C (5), schisantherin G (6), heteroclitin Q (7), kadsurarin (8). The structures of these new lignans were elucidated by a combination of high-resolution electron ionization mass spectrometry (HR-EI-MS), (1)H NMR, (13)C NMR, HMQC, HMBC, and NOESY spectra.

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“…The IR spectrum suggested the presence of hydroxyl (n max 3564, 3450 cm Ϫ1 ) and ester (1744, 1721 cm Ϫ1 ) functionalities in the molecule. The UV spectrum showed l max (MeOH) at 219, 257, and 280 nm while its CD spectrum exhibit strong negative cotton effect at l max 251 nm, designating 1 as a dibenzocyclooctadiene lignan [1][2][3][4][5] with an S-biphenyl configuration. Four new nona-oxygenated C 18 dibenzocyclooctadiene lignans, kadsuphilins C-F (1-4), were isolated from the EtOAc soluble portion of the alcoholic extract of the aerial parts of Kadsura philippinensis.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5] This type of lignans have been shown significant anti-HIV, 5) antioxidant, 6) antihepatotoxic, 7,8) antihepatitis, 9) cytotoxic, 10) antitumor-promotion, 11) and anti-lipid peroxidative activities. …”

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Four New Nonaoxygenated C18 Dibenzocylcooctadiene Lignans from Kadsura philippinensis

Shen

Lin

Ahmed

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Plants belonging to genus Kadsura (Schizandraceae) have been used for long time in traditional Chinese medicine to treat several diseases and have been well known as a rich source of C 18 dibenzocyclooctadiene lignans. [1][2][3][4][5] This type of lignans have been shown significant anti-HIV, 5) antioxidant, 6) antihepatotoxic, 7,8) antihepatitis, 9) cytotoxic, 10) antitumor-promotion, 11) and anti-lipid peroxidative activities. 12)Our previous investigation on the chemical constituents of Kadsura philippinensis ELMER, growing in the Southern islet of Taiwan, led to the isolation of twelve dibenzocyclooctadiene lignans including new kadsuphilins A and B, 6-epigomisin and 1-demethylkadsuphilin A from the EtOAc soluble portion of the alcoholic extact. 13) Further chromatographic separation and purification of the more polar fractions afforded additional four new polyoxygenated dibenzocylcooctadiene lignans, kadsuphilins C-F (1-4) and schizanrin G (5).14) Their structures were elucidated on the bases of spectroscopic analyses, including 2D NMR experiments, comparison of the spectral data with those of the related metabolites. Their stereochemistries were assigned by CD and NOESY spectra. The in vitro antiplatelet aggregation activity of metabolites 1-5 also have been evaluated. Results and DiscussionThe EtOAc-soluble portion from the alcoholic extract of Kadsura philippinensis was subjected to flash column chromatography over silica gel. Eluted polar fractions were further isolated or purified using normal or reversed phase HPLC to afford the new kadsuphilins C-F (1-4) and schizanrin G (5).Kadsuraphilin C (1) had a molecular formula C 31 H 32 O 11 , as deduced from its HR-ESI-MS (m/z 581.2020, [MϩH] ϩ ) and NMR spectral data (Tables 1, 2). The IR spectrum suggested the presence of hydroxyl (n max 3564, 3450 cm Ϫ1 ) and ester (1744, 1721 cm Ϫ1 ) functionalities in the molecule. The UV spectrum showed l max (MeOH) at 219, 257, and 280 nm while its CD spectrum exhibit strong negative cotton effect at l max 251 nm, designating 1 as a dibenzocyclooctadiene lignan [1][2][3][4][5] with an S-biphenyl configuration. Four new nona-oxygenated C 18 dibenzocyclooctadiene lignans, kadsuphilins C-F (1-4), were isolated from the EtOAc soluble portion of the alcoholic extract of the aerial parts of Kadsura philippinensis. The structures of 1-4 were elucidated on the basis of extensive spectroscopic analyses, including 2D NMR (HMQC, HMBC, and NOESY) experiments, comparison of the spectral data with those of the related metabolites. The stereochemistries of the biphenyl and octadiene moieties were deduced from circular dichorism (CD) and the NOESY spectra, respectively. The in vitro antiplatelet aggregation activity of metabolites 1-4 also have been evaluated.

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Schisantherins LO and acetylschisantherin L from Kadsura coccinea

Cited by 55 publications

References 3 publications

Seven New Lignan Esters from Kadsura philippinensis

Seven New Lignan Esters from Kadsura philippinensis

Complete assignments of ¹H and ¹³C NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia

Four New Nonaoxygenated C18 Dibenzocylcooctadiene Lignans from Kadsura philippinensis

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Schisantherins LO and acetylschisantherin L from Kadsura coccinea

Cited by 55 publications

References 3 publications

Seven New Lignan Esters from Kadsura philippinensis

Seven New Lignan Esters from Kadsura philippinensis

Complete assignments of 1H and 13C NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia

Four New Nonaoxygenated C18 Dibenzocylcooctadiene Lignans from Kadsura philippinensis

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Complete assignments of ¹H and ¹³C NMR data for new dibenzocyclooctadiene lignans from Kadsura oblongifolia