Lipoxygenase inhibitory sphingolipids from Launaea nudicaulis

Four new sphingolipids: nudicaulin A [(2S,3S,4R,14E)-2-{[octadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 1], nudicaulin B [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol; 2], nudicaulin C [(2S,3S,4R,14E)-2-{[(2R)-2-hydroxyoctadecanoyl]amino}tetraeicos-14-ene-1,3,4-triol-1-O-β-D-glucopyranoside; 3], and nudicaulin D [(2S,3S,4R)-2-{[(2R,3S,12E)-2,3-dihydroxyeicos-12-enoyl]amino}octadecane-1,3,4-triol; 4] together with 1-hexatriacontanol, β-sitosterol, octadecyl 4-hydroxycinnamate, elaidic acid, cholesta-5,22-diene-3,7-diol, oleanolic acid, apigenin, and β-sitosterol 3-O-β-D-glucopyranoside were isolated from the methanolic extract of the whole plant of Launaea nudicaulis. Their structures were elucidated using 1H and 13C NMR spectra and 2D NMR analyses (HMQC, HMBC, and COSY) in combination with mass spectrometry (EI-MS, HR-EI-MS, FAB-MS, and HR-FAB-MS) experiments and comparison with literature data of related compounds. Compounds 1-4 displayed moderate inhibitory potential against enzyme lipoxygenase in concentration-dependent manner with IC?? value ranges 103-193 μM.     

A new thiophene and two new monoterpenoids from Xanthium sibiricum

Three new compounds (1–3), together with six known compounds (4–9), were isolated from the fruits of Xanthium sibiricum. The structures and the absolute configurations of sibiricumthionol (1), (+)-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [(+)-2], ( ? )-(5Z)-6-methyl-2-ethenyl-5-hepten-1,2,7-triol [( ? )-2], (2E,4E,1′S, 2′R, 4′S, 6′R)-dihydrophaseic acid (3), (+)-xanthienopyran [(+)-4] and ( ? )-xanthienopyran [( ? )-4] were established by extensive spectroscopic analyses, X-ray crystallographic analysis, ECCD analysis and ECD calculations. Caffeic acid (7) and caffeic acid ethyl ester (8) weekly inhibited α-glucosidase enzymatic activity by 44.5% and 40.2%, respectively, at 40 μM. Protocatechuic acid (9) selectively exhibited cytotoxicity against HepG2 cell lines, with an IC₅₀ value of 2.92 μM.     

Chemical Constituents of Typhonium Giganteum Engl

Abstract

A new cerebroside, named typhonoside (1), was isolated from the root tuber of Typhonium giganteum Engl. along with three known compounds dipalmitin (2), α-monopalmitin (3) and 2,6-diamino-9-β-D-ribofuranosylpurine (4). The structure of 1 was determined to be 1-O-β-D-glucopyranosyl-(2S,3S,4R,8Z)-2-[(2′-hydroxyl-docosanoyl)amino]-8-otadecene-1,3,4-triol on the basis of spectral data.     

Triterpenoid Saponins from Leaves and Stems of Panax Quinquefolium L

Abstract

In the chemical investigation on the saponin composition of leaves and stems of Panax quinquefolium L., two new minor dammarane saponins, quinquenoside L₁ (1) and L₂ (2) have been isolated. By means of physico-chemical evidences and spectral analysis their structures were established as 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranosy-dammara-23,25-diene-3β, 12β, 20(S)-triol (1) and 3-O-[β-D-glucopyranosyl-(1-2)-β-D-glucopyranosyl]-20-O-β-D-D-glucopyranosyl-(24Z)-dammar-24-ene-3β, 12β, 20(S), 26-tetraol (2).     

Monoterpenes from the fruits of Amomum kravanh

Two new monoterpenes, (7S)-p-cymene-2,7,8-triol (1) and (3R,4R,6S)-p-menth-1-ene-3,6,10-triol (2), were isolated from the fruits of Amomum kravanh. Their structures were established by spectroscopic data. The absolute configuration of the 7,8-diol moiety in 1 was assigned by CD data after addition of Mo₂(OAc)₄ in dimethyl sulfoxide (DMSO) solution. Compounds 1 and 2 exhibited weak activity of anti-platelet aggregation in vitro.     

Elaeocarpionoside,a megastigmane glucoside from the leaves of <Emphasis Type="Italic">Elaeocarpus japonicus</Emphasis> Sieb. et Zucc.

From a 1-BuOH-soluble fraction of an extract of the leaves of Elaeocarpus japonicus, six megastigmane glucosides (1–6) were isolated. Five were known compounds (2–6), i.e. amelopsisionoside, citroside A, roseoside, alangionoside A and turpinionoside A, respectively. The structure of the new compound, named elaeocarpionoside, was elucidated to be (3R,4R,5S,6S,7E,9R)-megastigman-7-ene-3,4,9-triol 9-O-β-d-glucopyranoside by spectroscopic analyses and the modified Mosher’s method.     

A new cerebroside from Uvaria tonkinensis var. subglabra

A new cerebroside, subglain A (1), together with five known compounds (2–6) have been isolated from the stems of Uvaria tonkinensis var. subglabra. The structure of 1 has been determined to be 1-O-β-D-glucopyranosyl-(2S,3S,4R,8Z,2′R)-2-[N-(2′-hydroxytetracosanyl)-N-(1″,2″-dihydroxyethyl)-amide]-8-tetradecene-1,3,4-triol by spectroscopic evidence. The known compounds were identified as schisandriside (2), erythritol (3), β-D-glucopyranose (4), kaempferol-3,7-O-α-L-dirhamnoside (5), and (+)-lyoniresinol (6).     

New Bioactive Pregnadiene-derived Glycosides from the Gulf of California Gorgonian Muricea cf. austera

Abstract

Two new steroidal glycosides, pregna-5,20-diene-3-O-β-glucopyranoside (1), and pregna-5,20-diene-3-O-β-(6′-O-acetyl) glucopyranoside (2), and the known trihydroxy sterol, pregna-5-ene-3β,20α,21-triol (3) have been isolated from the Gulf of California gorgonian Muricea cf austera. The structures of the new compounds were established on the basis of chemical and spectral studies. Compound 2, and its per-acetylated derivative, 4, displayed moderate in vitro cytotoxicity (IC₅₀ = 17.3 and 14.3 μg/mL) toward HCT-116 human colon carcinoma. Compound 3 showed growth inhibition of Staphylococcus aureus and Bacillus subtilis at 250 μg/disk, in the agar disk-diffusion assay.     

Two new triterpenoid saponins from Glochidion puberum

Two new triterpenoid saponins, puberosides A and B, were isolated from the aerial parts of Glochidion puberum. Their structures were elucidated as 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-22α-benzoyloxy-olean-12-ene-16α,28-diol (1) and 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-28-benzoyloxy-olean-12-ene-16α,22α-diol (2) by analysis of their spectroscopic data.     

New acylated triterpene saponins from Polygala tenuifolia willd

Two new acylated presenegenin glycosides E-onjisaponin H (5) and Z-onjisaponin (6) together with seven known saponins were isolated from the roots of Polygala tenuifolia Willd. Compounds 5 and 6 were obtained as a pair of isomers due to trans and cis-p-methoxycinnamoyl. Their structures were elucidated mainly by 2D-NMR techniques including ¹H–¹HCOSY, TOCSY, HSQC, HMBC as 3-O-(β-d-glucopyranosyl) presenegenin 28-{O-β-d-apiofuranosyl-(1 → 3)-O-[β-d-xylopyranosyl-(1 → 4)]-O-α-l-rhamnopyranosyl-(1 → 2)-O-[α-l-rhamnopyranosyl-(1 → 3)]-4-O-[(E)-p-methoxycinnamoyl]-β-d-fucopyranosyl} ester (5) and its (Z)-isomer (6).     

Synthesis and biological activity studies of new hybrid molecules containing tryptamine moiety

The synthesis of N′-(4-substitutedphenylsulfonyl)-2-{4-[2-(1H-indol-yl)ethyl]-3-(4-chlorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetohydrazides (3a–c), 2-{4-[2-(1H-indol-3-yl)ethyl]-3-(4-chlorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N′-aryl methylidene acetohydrazides (4a–f) and 4-[2-(1H-indol-3-yl)ethyl]-5-(4-substitutedbenzyl)-2-[(5-sulfanyl-1,3,4-oxadiazol-2-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones (5a, b) was performed starting from the corresponding acid hydrazides (2a, b) which was reported earlier. The treatment of 1,3,4-oxadiazole derivatives (5a, b) with hydrazine hydrate produced 4-amino-5-sulfanyl-4H-1,2,4-triazol-3-yl derivatives (6a, b). Then, compound 6b was converted to the corresponding Schiff base (7) by the treatment with anisaldehyde. The synthesis of 5-(4-chlorobenzyl)-4-[2-(1H-indol-3-yl)ethyl]-2-[(4-benzyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (8) and 5-(4-methylbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-2-[(4-benzyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (10) was carried out by the reaction of acid hydrazides (2a, b) with aryl iso(thio)cyanates either via the formation of the intermediates (9a, b) (for 10) or direct cyclization (for 8). 1,3-Oxa(thia)zol-2(3H)-ylidene]acetohydrazide derivatives (11a, b) were obtained by the reaction of 9a, b with 4-chlorophenacyl bromide. All newly synthesized compounds were screened for their antimicrobial activities and some of which was found to be active against the test microorganisms.     

Three new dammarane-type triterpene saponins from the leaves of Panax ginseng C.A. Meyer

Three new dammarane-type triterpene ginsenosides, together with six known ginsenosides, were isolated from the leaves of Panax ginseng C.A. Meyer. The new saponins were named as ginsenoside Rh₁₁, ginsenoside Rh₁₂, and ginsenoside Rh₁₃. Their structures were elucidated as (20S)-3β,6α,12β,20-tetrahydroxydammara-25-ene-24-one 20-O-β-d-glucopyranoside (1), (20S)-3β,12β,20,24,25-pentahydroxydammarane 20-O-β-d-glucopyranoside (2), and (20S,23E)-3β,12β,20,25-tetrahydroxydammara-23-ene 20-O-β-d-glucopyranoside (3) on the basis of 1D and 2D NMR experiments and mass spectra. The known ginsenosides were identified as ginsenoside M_7cd, ginsenoside Rg₆, ginsenoside Rb₃, gypenoside XVII, gypenoside IX, and 20-(E)-ginsenoside F₄.     

Chemical Constituents of Pseudopterogorgia Species of the Indian Ocean

Abstract

A new ceramide, (2S,3R,4E)-1,3-dihydroxy-2-[(hexadecanoyl)amino]-nonadeca-4-ene (1), cholest-5-en-3β,7β,19-triol (2), identified as its, peracetyl derivative (3), and batyl alcohol (4) were isolated from Pseudopterogorgia species. 1 exhibited antibacterial activity against Gram-positive and Gram-negative bacteria.     

New cycloartanes and new iridoids from Dolichandrone spathacea collected in the mangrove forest of Soc Trang province,Vietnam

Abstract

Two new cycloartanes, named dolichandrone A (1) and dolichandrone B (2), as well as two new iridoids, named [6-O-[(E)-4-methoxycinnamoyl]-1β-hydroxy-dihydrocatalpolgenin (3) and 6-O-[(E)-4-methoxycinnamoyl]-1α-hydroxy-dihydrocatalpolgenin (4), together with four known iridoids (5–8), were isolated from the leaves and barks of Dolichandrone spathacea. Their structures were elucidated by means of extensive analysis of their HRESIMS, 1D and 2D NMR spectroscopic data. All of these compounds have been isolated for the first time from this plant. Compounds 1, 2, 5, and 7 were evaluated for their cytotoxic activity in vitro against four human cancer cell lines KB, Lu, HepG2, and MCF7. The results showed that only compound 2 exhibited a good cytotoxicity against KB cell line with IC₅₀ of 18.77 μM.     

Four new long-chain aliphatics from the feces of Trogopterus xanthipes

Chemical investigation of Trogopterus feces has led to the isolation of four new long-chain aliphatics, including two new fatty alcohols, 8,15-nonacosanediol (1) and 6,13-nonacosanediol (2), one new fatty acid ester, dihexyl 7,7′-oxydiheptanoate (3), and one new ceramide, (2R)-2-hydroxy-N-[(2S,3S,4R,11E)-1,3,4-trihydroxydocos-11-en-2-yl]heneicosanamide (4). Their structures were elucidated by means of chemical and extensive spectroscopic analysis. Compound 3 exhibited moderate activity of antithrombin in vitro.     

Puberosides C–E,triterpenoid saponins from Glochidion puberum

Three new triterpenoid glycosides, named puberosides C–E (1–3), were isolated from the water-soluble fraction of Glochidion puberum (Linn.) Hutch. Their structures were determined as 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-22α-trans-cinnamoyl-olean-12-ene-16α,28-diol, 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-α-l-arabinopyranosyl)oxy]-22α-cis-cinnamoyl-olean-12-ene-16α,28-diol, and 3α-[(O-β-d-glucopyranosyl-(1 → 3)-O-β-d-glucopyranosyl)oxy]-22α-benzoyloxy-olean-12-ene-16α,28-diol by the combination of 1D, 2D NMR, and MS spectral analyses.     

Two novel furostanol saponins from Ophiopogon japonicus

Two novel furostanol saponins were isolated from the fresh tubers of Ophiopogon japonicus. Comprehensive spectroscopic analysis allowed the chemical structures of the compounds to be assigned as (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-β-d-xylopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1, ophiopogonin F) and (25R)-26-[(O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-β-d-xylopyranosyl-(1 → 4)-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (2, ophiopogonin G). The rare furostanol saponins with two glucosyl residues at C-26 position were isolated from the natural source for the first time.     

Two new furostanol glycosides from the fibrous root of Ophiopogon japonicus (Thunb.) Ker-Gawl

Two new furostanol glycosides, ophiopogonins H (1) and I (2), were isolated from the fibrous root of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside and (25R)-26-[(O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-20α-hydroxyfurost-5,22-diene-3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside on the basis of spectroscopic means including HR-ESI-MS, 1D and 2D NMR experiments.     

Minor dammarane saponins from the hongshen extract of Shenmai injection

A new dammarane-type triterpenoid saponin, (20R)-ginsenoside ST₂ (1), along with five known saponins was isolated from the hongshen extract of Shenmai injection. The structure of 1 was elucidated to be (20R)-dammar-23(E)-ene-3β,6α,12β,20,25-pentol 6-O-β-d-glucopyranoside by means of spectroscopic methods.     

Two new triterpenoid saponins from Symplocos Chinensis

Two new triterpenoid saponins, symplocososides X (1) and Y (2) have been isolated from the roots of Symplocos chinensis, and their structures elucidated as 21β-O- cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (1) and 21β-O-cinnamoyl-22α-O-(2-methylbutanoyl)-15α, 16α, 28-trihydroxyolean-12-ene-3β-O-(3-O-acetyl)-[β-d-glucopyranosyl (1 → 2)]-α-l-arabinofuranosyl (1 → 4)-β-d-glucuronopyranoside (2) by spectral and chemical methods. Their antitumor activities have also been tested.