Two new homoisoflavonoids from Caesalpinia pulcherrima

Two new homoisoflavonoids, (E)-7-methoxy-3-(4'-methoxybenzylidene)chroman-4-one (1) and (E)-7-hydroxy-3-(3',4',5'-trimethoxybenzylidene)chroman-4-one (5), along with three known homoisoflavonoids (Z)-7-hydroxy-3-(4'-methoxybenzylidene)chroman-4-one (isobon ducellin) (2), (E)-7-hydroxy-3-(4'-methoxybenzylidene)chroman-4-one (bonducellin) (3) and (E)-7-hydroxy-3-(2',4'-dimethoxybenzylidene)chroman-4-one (4) were isolated from the whole plant of Caesalpinia pulcherrima. The structures of these new compounds were elucidated by electron impact mass spectrometry (EI-MS) and 1D and 2D-NMR spectral studies. Antimicrobial activity of the new compounds was evaluated.     

Scillapersicene: a new homoisoflavonoid with cytotoxic activity from the bulbs of Scilla persica HAUSSKN

The phytochemical investigation of Scilla persica HAUSSKN bulbs led to the isolation of a novel homoisoflavonoid that named Scillapersicene (1) and identified as 3-(3′,4′-dihydroxybenzylidene)-8-hydroxy-5,7-dimethoxychroman-4-one along with five known homoisoflavonoids 2–6, whose structures were elucidated using HRFAB-MS, 1D and 2D NMR spectroscopic data. The known compounds were identified as 3-(3′,4′-dihydroxybenzyl)-5,8-dihydroxy-7-methoxychroman-4-one (2), 3,9-dihydro-autumnalin (3), autumnalin (4), 3-(3′,4′-dihydroxybenzylidene)-5,8-dihydroxy-7-methoxychroman-4-one (5) and scillapersicone (6). All compounds obtained, expect 2 and 4, showed strong cytotoxic activity against AGS cell line. The toxicity on AGS cell line was measured by 1, 3, 5 and 6 with IC₅₀ values of 8.4, 30.5, 10.7 and 24.2 μM, respectively. In addition, the physico-chemical properties of these natural compounds were optimised using density functional method (B3LYP) with standard 6-311+G* basis set. These natural products have low-energy gaps between the first ionisation potentials and highest occupied molecular orbital. In conclusion, the low-energy gap could cause reason for cytotoxic activity of homoisoflavonoids.     

Paeoniflorigenone,a new monoterpene from paeony roots

Paeoniflorigenone (1), a new monoterpene which produces a neuromuscular-blocking effect in mice, was isolated from paeony roots and its structure was elucidated.     

The new cassane-type diterpenes from Caesalpinia minax

Four new cassane-type diterpenes, Neocaesalpin S (1), Neocaesalpin T (2), Neocaesalpin U (3), and Neocaesalpin V (4) were isolated from Caesalpinia minax HANCE together with seven known compounds Neocaesalpin A (5), Neocaesalpin K (6), Neocaesalpin L (7), Neocaesalpin M (8), Neocaesalpin O (9), Neocaesalpin MP (10), and Magnicaesalpin (11). Their structures were elucidated on the basis of 1D- and 2D-NMR, MS, and circular dichroism (CD) analysis. Compounds 1-4 were tested against liver cancer (HepG-2) and breast cancer (MCF-7), and showed mild antiproliferative activity.     

A new furanoid diterpene from Caesalpinia pulcherrima

A new cassane-type diterpene isovouacapenol E (1) was isolated from the leaves of Caesalpinia pulcherrima, together with the known compounds caesaldekarin A (3), spathulenol (4), caryophyllene oxide (5), phytol, and sitosterol. The structure of 1 was elucidated by spectral data interpretation.     

Krametosan, a new trinorlignan from the roots of Krameria tomentosa

A new phenylcoumarone type trinorlignan, krametosan (1), along with the known norlignans, ratanhiaphenol I (2) and 2-(2'-hydroxy-4',6'-dimethoxyphenyl)-5-(E)-propenylbenzofuran (3), the lignan conocarpan (4) and dinorlignan decurrenal (5), were isolated from the CHCl3 extract of the roots of Krameria tomentosa. The structure of these compounds were elucidated by the spectroscopic methods.     

Floroselin,a new coumarin from the roots of Seseli sessiliflorum

Chemistry of Natural Compounds - A new coumarin has been isolated from the roots ofSeseli sessiliflorum for which the structure of...     

Floroselin, a new coumarin from the roots of Seseli sessiliflorum

Conclusions A new coumarin has been isolated from the roots ofSeseli sessiliflorum for which the structure of 3-angeloyloxy-2,2-dimethyl-4-(trans-3-methylthioacryloyloxy)-3, 4-dihydropyrano-5,6:8,7-coumarin has been proposed. This is the first time that esters of 3-methylthioacrylic acid have been found in the coumarin series.All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 517–521, September–October, 1970.     

A new homoflavonoid from the seed of Caesalpinia minax Hance

<正>A new homoflavonoid was isolated from the seed of Caesalpinia minax Hance.On the basis of spectral evidences,its structure was established and named as minaxin.     

Catomentosaponin,a new triterpene saponin from the roots of Catunaregam tomentosa

A new triterpene saponin, catomentosaponin (1) and 11 known analogues (2–12) were isolated from the roots of Catunaregam tomentosa. The structures of 1–12 were determined on the basis of extensive NMR and MS data analysis. The sugar residues were identified by co-TLC and HPLC analysis after hydrolysis. All isolated compounds were evaluated for their cytotoxicity against KB and HeLa cell lines. Compound 2 showed moderate cytotoxicity against KB cell with IC₅₀ value of 24.84 μM.     

Three new cassane diterpenes from the seeds of Caesalpinia minax Hance

Four fractions were prepared from the crude extract of Caesalpinia minax Hance and the inhibitory activity of nitric oxide (NO) production release of RAW 264.7 cells stimulated by lipopolysaccharide (LPS) was evaluated. The ethyl acetate (EtOAc) fraction showed obvious inhibitory effect. Bioassay-guided fractionation led to the isolation of three new cassane diterpenes, caesalmin X (1), caesalmin Y (2) and caesalmin Z (3), together with 19 known cassane diterpenoids (4–22). Their structures were mainly characterised on the basis of extensive spectroscopic analyses and comparison with reported data. Moreover, three compounds (20–22) which possessed furanditerpenoid 7,17-lactone structures, displayed moderate activities, with IC₅₀ value of 29.85, 27.38 and 25.40 μM, respectively.     

Caesaldecan, a cassane diterpenoid from the leaves of Caesalpinia decapetala

A new cassane diterpenoid, caesaldecan, was isolated from Caesalpinia decapetala with eight known compounds, spathulenol, 4,5-epoxy-8(14)-caryophyllene, squalene, lupeol, trans-resveratrol, quercetin, astragalin, and stigmasterol. The (1)H- and (13)C-NMR spectra of the new compound were completely assigned by using a combination of 2D NMR techniques, namely, (1)H-(1)H COSY, HMQC, HMBC, and ROESY.     

A new cassane diterpenoid lactone from the seed of Caesalpinia minax

A new cassane diterpenoid lactone was isolated from the seed of Caesalpinia minax.On the basis of spectral evidences,its structure was established as 12α-methoxyl,5α,14β-dihydroxy- 1α,6α,7β-triacetoxycass- 13(15)-en- 16,12-olide.     

Platycoside O, a new triterpenoid saponin from the roots of Platycodon grandiflorum

A new unusual minor triterpenoid saponin, platycoside O (1), was isolated from the 75% EtOH extract obtained from the roots of Platycodon grandiflorum, together with four known saponins: platycoside M-3 (2), platycoside J (3), platycoside F (4) and platycoside B (5). The structure of 1 was determined as 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-24-methoxyl, 24-oxo-28-oic acid 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside on the basis of spectral analysis and chemical evidence.     

Kansuinine J,a new macrocyclic diterpenoid from the roots of Euphorbia kansui

<正>A new macrocyclic diterpenoid,named kansuinine J(1),was isolated from the roots of Euphorbia kansui.Its structure was characterized on the basis of spectroscopic analysis.     

Coumarin-pi,a new antioxidant coumarin derivative from Paxillus involutus

Abstract

Chemical investigation of Paxillus involutus lead to the isolation of a new coumarin derivative coumarin-pi (1), and three known compounds (2-4). The structure of the new compound was elucidated by interpretation of 1D and 2D NMR data. Compound 1 possesses a rare benzofuranylcoumarin skeleton. The isolated compounds were evaluated for antioxidant activities and coumarin-pi (1) exhibited significant activity with IC₅₀ value of 16.3?μg/mL.     

Two new cassane diterpene lactams from the fruits of Caesalpinia mimosoides Lam

Two new cassane ditepenoid lactams, caesmimotam A (1) and B (2), along with eight known compounds (3–10) were isolated from the fruits of Caesalpinia mimosoides Lam. Their structures were identified by 1D and 2D NMR spectral data. Compounds 1 and 2 were evaluated for their cytotoxicity on HL-60, SMMC-7721, A-549, MCF-7 and SW-480 human cancer cell lines, but they were inactive.     

The structure of chuin,a new coumarin from the roots of Seseli tschuense

Conclusions 1. The polarographic behavior of galanthamine, lycorine, pancratine, hordenine, and dl-narwedine on a support of 0.01 N (C₂H₅)₄NOH has been studied.2. A chromatopolarographic method for determining the amount of galanthamine in a chloroform extract from plant raw material has been developed.Khimiya Prirodnykh Soedinenii, Vol. 6, No. 4, pp. 450–453, 1970