Spectrophotometry of glycosides of oleanolic acid and hederagenin in concentrated sulfuric acid

Summary The UV spectra in concentrated sulfuric acid of hederagenin and oleanolic acid and their glycosides has been studied. For analytical purposes it is proposed to use the extremum at a wavelength of 405 nm, which is distinguished by constancy of position and intensity of absorption for the genins and their glycosides.A spectrophotometric method is proposed for the determination of the triterpene glycosides in a preparation from the bulbs ofLeontice ewersmannii Bge.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 220–227, March–April, 1977.     

Secondary-emission mass spectrometry of hederagenin glycosides and medicagenic acid glycosides

The secondary emission (SE) spectra of six glycosides of medicagenic acid (MA) and of hederagenin have been studied. The (M + H)⁺ ions were observed in the secondary ion spectra (LSIMS) of mono- and biosides of MA and also of a triand a tetraoside of hederagenin in a glycerol matrix. The (M + Na)⁺ ions were recorded in the spectra of tri- and tetraosides of MA. In the majority of cases processes involving the successive splitting out of the carbohydrate units were revealed. Positive- and negative-ion spectra have been obtained on the ionization by bombardment with fast atoms — FAB + and FAB – — of a trioside and a tetraoside of MA. The FAB – spectra are the most characteristic: They show intense peaks of the (M - H)^– ions and of the products of the sequential elimination of the sugar residues.Institute of the Chemistry of Plant Substances, Uzbekstan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 98–102, January–February, 1992.     

Ananasic acid: A new trihydroxytriterpenecarboxylic acid from pineapple stems

From the stems of commercially grown pineapple (Ananas comosus var Cayenne) we have isolated 3β,11α,15α-trihydroxycycloart-24-en-26-oic (ananasic) acid (6) and determined its structure by spectral determinations and by comparison with the known 3β-hydroxycycloart-24-en-26-oic (mangiferolic) acid (3a).     

A new coruleoellagic acid derivative from stems of Rhodamnia dumetorum

A new coruleoellagic acid derivative, 3,3′,4,4′,5′-pentamethylcoruleoellagic acid (1) together with nine known compounds, hexamethylcoruleoellagic acid (2), 3,4,3′-tri-O-methylellagic acid (3), heptaphylline (4), 7-methoxymukonal (5), dentatin (6), sinapaldehyde (7), gallic acid (8), 2,6-dimethoxy-4H-pyran-4-one (9) and β-sitosterol (10) were isolated from the stems of Rhodamnia dumetorum. Their structures were identified by physical and spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds 1, 2 and 7-10 were tested for antibacterial activity against six pathogenic bacterial strains (Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica serovar Typhimurium, Staphylococcus aureus, and Methicillin resistant S. aureus (MRSA)).     

High-Speed Separation of Oleanolic acid and Ursolic acid from the Fruit of Ligustrum Lucidum ait and Crataegus by Cyclodextrin-Modified Micellar Electrokinetic Chromatography

ABSTRACT

A cyclodextrin-modified micellar electrokinetic chromatography (CD-MEKC) technique for determining oleanolic acid and ursolic acid in the fruit of Ligustrum lucidum Ait and Crataegus was developed. The two bio-active components were successfully separated within 4 minutes using a pH 8.5 sodium borate buffer containing 60mM SDS and 2mM γ-CD. The correlation coefficients of the linear calibration graphs for the analyses exceeded 0.9980. The effects of pH, SDS, γ-CD, sodium borate and temperature on separation were also investigated.     

Polysaccharides from the stems ofAlthea nudiflora

From the heart of the stems of the hollyhockAlthea nudiflora (Lindl.) Boiss., growing on the territory of Southern Kazakhstan we have isolated a polysaccharide (yield 5%) containing residues of glucuronic and galacturonic acids (totalling 42%), and also of glucose, rhamnose, galactose, arabinose, xylose (traces) and mannose (traces). From the bark of the stems of this plant we have isolated a polysaccharide (yield 1.8%) consisting of a branched polymer composed of residues of rhamnose, glucose, and arabinose (22:17:2) and also of glucuronic and galacturonic acids (totalling 30%). In the products of the methylation of this polysaccharide previously reduced at the COOH groups we have established the presence of 2,3,4-tri-O-methylrhamnose, 3,4-di-O-methylrhamnose, 2,3,4,6-tetra-O-methylglucose, 2,6-di-O-methylglucose, and a mixture of 2,3,6-tri-O-methylglucose and 2,3,6-tri-O-methylgalactose (1:10:14:5:7).V. L. Komarov Botanical Institute, Academy of Sciences of the USSR, Leningrad. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 145–148, March–April, 1980.     

Color reactions of hederagenin and its glycosides

The spectrophotometric reactions of triterpene compounds with concentrated sulfuric acid, a mixture of sulfuric acid and ethanol, and a mixture of sulfuric and acetic acids has been studied with hederagenin and its glycosides — caulosides A, C, and D, isolated from the Far Eastern plantCaulophyllum robustum Maxim — as examples. Conditions for performing the reaction which exclude the influence of the carbohydrate components of the glycosides from the determination of hederagenin have been suggested. The reaction with a mixture of sulfuric acid and ethanol has been used to determine the amounts of caulosides A and C in a total preparation after their separation by the TLC method. The relative error of the determination did not exceed 5 rel.%. Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 643–646. September–October, 1980.     

Oleanolic triterpene saponins from the roots of Panax bipinnatifidus

Ten oleanane-type saponins (1-10), including three new compounds, namely bifinosides A-C (1-3), were isolated from the roots of Panax bipinnatifidus SEEM. Their structures were elucidated on the basis of chemical and spectroscopic methods.     

Triterpenoids and lignans from the stems of Schisandra glaucescens

Two new triterpenoids, 24(E)-3α,12α-dihydroxyl-lanost-9(11),24-dien-26-oid acid (1) and 3,4-seco-24(Z)-6α,7β-dihydroxyl-cycloart-4(28),24-dien-3,26-dioic-3-methyl ester (2), and ten known ones (3–12), together with eight lignans (13–20), were isolated from the stems of Schisandra glaucescens. Their structures were established on the basis of extensive spectroscopic analyses. Compounds 1–3, 5–7, 9, 11–13 and 15–18 were isolated from this species for the first time. 1 and 2 were evaluated for their in vitro cytotoxicities against the mouse cancer B16 cell line, human cancer HepG2 and MCF7 cell lines by MTT assay.     

Polyoxypregnanes from the stems of Marsdenia tenacissima

From the stems ofMarsdenia tenacissima two new polyoxypregnanes were isolated, their structures were elucidated by 1D, 2D-NMR as 11α,12β-di-O-tigloyl-tenacigenin B （1） and tenacigenoside E （2）.     

Amides from the stems of Cinnamomum burmannii

A novel amide, cinnabutamine (1), along with five known amides, cinnaretamine (2), N-trans-caffeoyl-5-hydroxytyramine (3), N-trans-feruloyltyramine (4), N-trans-feruloyl-5-methoxytyramine (5) and N-cis-feruloyl-5-methoxytyramine (6), were isolated from the stems of Cinnamomum burmannii (Lauraceae). Their structures were characterized and identified by spectral analysis.     

Constituents from the stems of Hibiscus taiwanensis

Five new compounds, hibicuslide A (1), hibicuslide B (2), hibicuslide C (3), hibicutaiwanin (4), hibicusin (5), and fifty-one known compounds have been isolated from the stems of Hibiscus taiwanensis. The structures of these compounds were determined by spectroscopic and chemical transformation methods. Among them, mansonone H (19) and uncarinic acid A (30) inhibited HIV replication in H9 lymphocyte cells. The 9,9'-O-feruloyl-(-)-secoisolaricinresinol (12), myriceric acid C (29), and uncarinic acid A (30) showed cytotoxic activity against human lung carcinoma and breast carcinoma.     

Xanthones from the stems of Cratoxylum cochinchinense

Four new xanthones, 1‐methoxy‐3,7,8‐trihydroxyxanthone (1), 1‐methoxy‐4,7,8‐trihydroxyxanthone (2), 1‐methoxy‐4,7‐dihydroxyxanthone (3), and 1,4‐dimethoxy‐2,7‐dihydroxyxanthone (4) were isolated from the stems of Cratoxylum cochinchinense along with four known xanthones (5–8). The structures of new compounds were determined by extensive spectroscopic analyses, mainly 1D and 2D NMR and HRESIMS data. Copyright © 2012 John Wiley & Sons, Ltd.