Structure elucidation and complete NMR spectral assignments of new furostanol glycosides from Solanum torvum

Two new furostanol glycosides, torvosides O (1) and P (2), were isolated from leaves of Solanum torvum. Their structures were completely and unambiguously assigned by one‐ and two‐dimensional NMR techniques (¹H NMR, ¹³C NMR, TOCSY, HSQC, ROESY and HMBC), ESI‐MS spectrometry and chemical methods. Copyright © 2009 John Wiley & Sons, Ltd.     

Involvement of central noradrenaline, serotonin and dopamine system in the antidepressant activity of fruits of Solanum torvum (Solanaceae)

The methanolic extract (ME) of Solanum torvum seeds and its ethyl acetate fraction (EAF) were investigated for their antidepressant activity using behavioral (forced swim test, FST and tail suspension test, TST) and biochemical (monoamine oxidase, MAO reduced activity) tests. ME (10, 30 and 100?mg?kg(-1)) and EAF (10 and 30?mg?kg(-1)) dose dependently inhibited the immobility period, increased noradrenaline, serotonin and dopamine levels and inhibited the MAO enzymes in FST and TST using mice. Furthermore, we have observed antagonism between the threshold dose of ME (30 and 100?mg?kg(-1)) and EAF (10 and 30?mg?kg(-1)) with antagonists on behaviour mediated by neurotransmitters noradrenaline, serotonin and dopamine. MAO-A inhibition was more prominent as compared to MAO-B inhibition. The study provides evidence for antidepressant actions of S. torvum.     

Studies on the constituents of solanaceous plants. (46). Steroidal glycosides from the fruits of Solanum anguivi

Three new glycosides named anguiviosides A-C were isolated from the fruits of Solanum anguivi and characterized as follows:3-O-beta-chacotrioside (1), 3-O-[4-O-maloyl-alpha-L-rhamnopyranosyl(1-->2)]-alpha-L-rhamnopyra nosyl(1-->4)-beta-D-glucopyranoside (2) and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-xylopyranosyl(1-->3)]-beta-D-+ ++glucopyranoide (3), of (25R,26R)-spirost-5-en-3beta,26-diol.     

Cucurbitane glycosides from unripe fruits of Lo Han Kuo (Siraitia grosvenori)

From the unripe fruits of Lo Han Kuo (Siraitia grosvenori), a Chinese medicinal plant, two new cucurbitane triterpene glycosides, 20-hydroxy-11-oxomogroside IA(1) (1) and 11-oxomogroside IIE (2), were isolated along with five known cucurbitane glycosides, 11-oxomogroside IA(1) (3), mogroside IIE (4), mogroside III (5), mogroside IVA (6), and mogroside V (7), and two flavonoid glycosides, kaempferol 7-O-alpha-L-rhamnopyranoside (8) and kaempferol 3,7-di-O-alpha-L-rhamnopyranoside (9). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods and by comparing with literature values. This paper describes the first investigation of unripe bitter Lo Han Kuo fruits.     

(2-Nitro ethyl)phenyl and cyanophenyl glycosides from the fruits of Diploclisia glaucescens

Chemical investigation of polar fractions of the methanol extract of the fruits of Diploclisia glaucescens of the family Menispermaceae furnished two new phenyl glycosides, 4-(2-nitroethyl)phenyl-beta-D-xylopyranosyl-(l approximately 6)-beta-D-glucopyranoside, and 4-cyanophenyl-beta-D-xylopyranosyl-(l approximately 6)-beta-D-glucopyranoside.     

Steroidal glycosides from the underground parts of Solanum sodomaeum

A new steroidal glycoside has been isolated from the underground parts of Solanum sodomaeum L., along with seven known steroidal glycosides. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence, and the structure of one known pregnane type glycoside was corrected. In addition, their antiproliferative activity against human promyelocytic leukemia (HL-60) cells was investigated, and five compounds exhibited stronger activity than cisplatin.     

Cucurbitane glycosides from unripe fruits of Siraitia grosvenori

Studies on the constituents of the unripe fruits of Siraitia grosvenori led to the isolation of three new cucurbitane triterpene glycosides, 11-oxomogroside III (10), 11-dehydroxymogroside III (11), and 11-oxomogroside IV A (12). Their structures were determined on the basis of detailed analyses of 1D, 2D-NMR spectroscopic methods. All of the compounds isolated from the unripe fruits of S. grosvenori were tested for cytotoxic activities against tumor cells, HCT-116 and SMMC-7721.     

Distinction of absolute configuration at C-22 of C-23-hydroxyspirostane and C-23-hydroxyspirosolane glycosides

It has been revealed that the absolute configurations at C-22 of 23-hydroxyspirostane and 23-hydroxyspirosolane could be unambiguouly judged by the (1)H- and (13)C-NMR spectroscopies.     

Antibacterial,antifungal and in vivo anticancer activities of chitin-binding lectins from Tomato (Solanum lycopersicum) fruits

A mixture of chitin-binding lectins from Tomato (Solanum lycopersicum) fruits, designated as Tomato chitin-binding lectins (TCLs), was isolated through affinity chromatography using an acetylated chitin column. Molecular weights of TCLs were determined to be 30 to 115 KDa which possessed mild toxicity with an LC₅₀ value of 521 µg/ml examined by the brine shrimp nauplii toxicity assay. Strong antibacterial activity of TCLs was found against Escherichia coli, Staphylococcus aureus and Shigella boydii at a concentration of 500 µg/ml by using disc diffusion method. Minimum inhibitory concentrations (MIC) of TCLs against Staphylococcus aureus and Escherichia coli were found to be 200 µg/ml and 140 µg/ml, respectively whereas minimum bactericidal concentrations (MBC) against the same bacterial species were 840 and 600 µg/ml, respectively. TCLs also exerted antibiofilm activity (53.32% at 250 μg/ml) against Escherichia coli. Strong antifungal activity of TCLs against Aspergillus niger was found at 600 µg/ml whereas the lectin mixture agglutinated A. niger spores at 200 µg/ml. TCLs exhibited 19.63% and 59.91% anti-proliferative activity against Ehrlich ascites carcinoma (EAC) cells in vivo in Swiss albino mice when intraperitonealy injected at doses 1.0 mg/kg/day and 2.0 mg/kg/day, respectively for five consecutive days. Morphological changes of apoptosis in EAC cells under fluorescence microscope and alteration of the expression of apoptosis-related genes (Fas, Caspase 8 and Caspase 3) had also been observed. MTT assay showed 27.61%, 38.74% and 49.23% of in vitro anticancer activity of the tomato lectins at concentrations of 37.5, 75 and 150 µg/ml, respectively.     

Synthesis of (22S, 23S)-homobrassinolide and brassinolide from stigmasterol

(22S, 23S)-Homobrassinolide (2α, 3α, 22S, 23S-tetrahydroxy-24S-etyl-B-homo-7-oxa-5α-cholestan-6-one) and brassinolide (2α, 3α 22R, 23R-tetrahydroxy-24S-methyl-B-homo-7-oxa-5α-cholestan-6-one) were synthesized from stigmasterol and shown to promote plant growth.     

Myrseguinosides A-E, five new glycosides from the fruits of Myrsine seguinii

Chemical investigation of the 1-BuOH soluble fraction of the dried fruits of Myrsine seguinii (Myrsinaceae) led to the isolation of five new glycosides, named myrseguinosides A-E (1-5), together with eight known compounds (6-13). The absolute structures of the new glycosides were elucidated by spectroscopic and chemical analyses to be a monoterpene glucoside (1), two flavonol glycosides (2, 3), and two oleanane-type triterpene saponins (4, 5). Myrseguinosides B (2), D (4), and E (5) exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity and growth inhibitory activity toward human cancer cells, respectively.     

Cucurbitane‐type triterpene glycosides from the fruits of Momordica charantia

The chemical study of Momordica charantia fruits led to the isolation of three new cucurbitane triterpene glycosides, momordicosides U, V, and W (1–3). The structures of these compounds were determined to be (19R, 23R)‐5β, 19‐epoxy‐19‐methoxycucurbita‐6,24‐diene‐3β, 23‐diol 3‐O‐β‐D‐allopyranoside (1), (23R)‐5β, 19‐epoxycucurbita‐6,24‐diene‐3β, 23‐diol 3‐O‐β‐D‐allopyranoside (2), and (19R)‐5β, 19‐epoxy‐19,25‐dihydroxycucurbita‐6,23(E)‐diene‐3β‐ol 3‐O‐β‐D‐glucopyranoside (3), by chemical and spectroscopic methods. Copyright © 2010 John Wiley & Sons, Ltd.     

Structure and stereochemistry of the higher bile acid isolated from turtle bile: (22S,25R)-3 alpha,12 alpha,15 alpha,22-tetrahydroxy-5 beta-cholestan-26-oic acid

The structure and stereochemistry of the higher bile acid, tetrahydroxyisosterocholanic acid (TISA), which was previously isolated from the bile of Amyda japonica (turtle) and proposed as a tetrahydroxyisosterocholanic acid, have been established as (22S,25R)-3 alpha,12 alpha,15 alpha,22-tetrahydroxy-5 beta-cholestan-26-oic acid by X-ray crystallographic analysis of its ethyl ester.     

Three new glycosides from Sinopodophyllum emodi (Wall.) Ying.

Tow new aryltetralin-type lignan glycosides: methyl epipodophyllate 7'-O-beta-D-glucopyranoyl-(1-->6)-beta-D-glucopyranoside (1), 4-demethylepipodophyllotoxin 7'-O-beta-D-glucopyranoside (2), and a new phenyl ethanol glycoside: phenyl ethanol 4-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (3), along with three known compounds: junipetriolosides (4), 3,4-dihydroxy-phenyl ethanol (5), and 4-hydroxy-phenyl ethanol (6) were isolated and identified from the n-butanol extract of the roots and rhizomes of Sinopodophyllum emodi (Wall.) Ying. The structures of the above were established by means of spectral data and chemical methods.     

Reaction of a Metallamacrocycle Leading to a Mercury(II)⋅⋅⋅Palladium(II)⋅⋅⋅Mercury(II) Interaction

All wrapped up : The reaction of a 22‐membered macrocycle derived from bis(o‐formylphenyl)mercury and 1,2‐phenylenediamine with palladium(II) results in cleavage of the macrocycle and concomitant formation of a trimetallic complex (see picture; phenyl rings truncated for clarity). The nature of the Hg^II???Pd^II???Hg^II interaction was investigated by theoretical studies.

     

Steroid glycosides from the starfishSolaster dawsoni (Verrill)

Two novel glycosides from the starfishSolaster dawsoni (Verrill) have been isolated and characterized: 24-O-(-D-xylopyranosyl)-5-cholestane-3,6,15,24,26-pentaol (solasteroside S₁) and (24R)-29-O-[-D-galactofuranosyl-(16)--D-galactofuranosyl]-24-ethyl-5-cholestane-3, 6,8,15,16,29-hexaol (solasteroside S₂).Translated fromIzvestiya Akademu Nauk. Seriya Khimicheskaya, No. 5, pp. 980–982, May, 1993.