Antiinflammatory and ulcerogenic activities of Salvia triloba extracts.

In continuation of our research on Salvia triloba, acute and chronic antiinflammatory and ulcerogenic activities of chloroform, ethanol, butanol and water extracts were detected at 25 mg/kg p.o. The chloroform extract showed the highest antiinflammatory activity in both acute and chronic models, while the ulcerogenic effects of all tested extracts were found to be less than that of acetyl salicylic acid.

Phytochemical studies and effect on urine volume of Glossostemon bruguieri Desf. constituents.

Two new flavonoids, takakin 7-O-glucoside (1) and (2) bucegin 7-O-glucoside, and six other known compounds (3-8), takakin, isosctullarien, its 7-O-glucoside, takakin 8-O-glucoside, xanthotoxin and esculetin, were separated and identified from Glossostemon bruguieri. The new compounds were characterized using modern spectroscopic techniques, including UV spectroscopy, proton nuclear resonance (1HNMR), carbon thirteen nuclear resonance (13CNMR), homomolecular quantum coherance (HMQC), heteromolecular bonding connectivity (HMBC) and chemical ionization mass spectra (CI). The effect on rats urine volume of the plant powder, its ethanolic extract, (500 mg kg(-1)) along with four of the purified compounds (1,4-6), (100 mg kg(-1)) are described. Eight groups of albino rats (200-300 g body weight) (n=5 for each group) were used in the tests for a one-time treatment, and other seven groups (150-180 g body weight) (n=5 for each group) were tested using the same dose with repeated administration for 15 days. The rat sera were collected and used to determine liver and kidney functions based on alanine amino transferase (ALT) and aspartate amino transferase (AST) for both single and repeated administration. Levels of urea, creatinine and uric acid were determined for both sets of experiments. The toxic effects of both the powder and its alcoholic extract were also studied on mice to determine their LD50, both materials proved to be non-toxic up to 2500 mg kg(-1) body weight.

Phenolic constituents from the leaves of the carnivorous plant Nepenthes gracilis.

Plumbagin, isoshinanolone, epishinanolone, shinanolone, quercetin and kaempferol were isolated from the leaves of Nepenthes gracilis. Spectral data of shinanolone are presented.

Constituents from Salvia triloba.

Twelve hydrocarbons, four sterols, three triterpenes, nineteen fatty acids, two phenolic acids, and five flavonoids have been detected and identified in Salvia triloba. Among the isolated flavonoids, 8-methoxygenistein 7-O-alpha-L-rhamnoside 4'-O-beta-D-glucoside (1), is reported for the first time.

Kaempferol triosides from Reseda muricata.

A flavonoid trioside and its coumaryl ester together with seven known flavonoids and five phenolic acids were isolated from the leaves of Reseda muricata. Their structures were elucidated by spectroscopic methods including UV, FAB MS, 1H, 13C and 2D-NMR, DEPT, HMBC and HMQC experiments. The two compounds were identified as kaempferol 3-O-beta-D-glucopyranosyl-(1''' --> 2'')-O-alpha-L-rhamnopyranoside 7-O-beta-D-glucopyranoside and kaempferol 3-O-beta-D-glucopyranosyl-(1''' --> 2'')-O-alpha-L rhamnopyranoside 7-O-beta-D-(6''''-O-E-coumarylglucopyranoside), respectively.

15alpha-acetoxycleomblynol A from Cleome amblyocarpa.

Reinvestigation of the MeOH-CH(2)Cl(2) extract of the aerial parts of Cleome amblyocarpa led to isolation of a new dammarane triterpenoid, 15alpha-acetoxycleomblynol A, whose structure was determined to be 11alpha,15alpha-diacetoxybrachycarpon-22(23)-ene (1) by NMR data interpretation and X-ray analysis.

Selected topics from forty years of natural products research: betalains to flavonoids, antiviral proteins, and neurotoxic nonprotein amino acids.

The elucidation by NMR and chemical methods of the unique structure of betanidin, the aglycon of the red-violet beet pigment betanin, forty years ago at the University of Zürich, Switzerland, was the beginning of my plant chemistry research program. Many of the same chemical and spectral techniques developed in Zürich have been used at The University of Texas at Austin for the structure analysis of members of many other classes of natural products including especially flavonoids, terpenoids, and alkaloids. Investigations at UT-Austin have concerned many topics such as biochemical and molecular systematics, biosynthetic pathways, structure-activity relationships, and the medicinal importance of natural products and included studies of antiviral proteins in the genus Phytolacca and neurotoxic nonprotein amino acids from cycads and other sources. Following the betalain story and an account of the early development of my UT-Austin biochemical systematic program, the Phytolacca and neurotoxin investigations are discussed herein.

Nonprotein amino acids from Cycas revoluta.

Two nonprotein amino acids, cycasindene and cycasthioamide, along with eight known nonprotein amino acids, were isolated from the seeds of Cycas revoluta Thunb. The structures of cycasindene and cycasthioamide were elucidated as 3-[3'-amino-indenyl-2]-alanine (1) and N-[glycinyl-alaninyl-11-thio]-5-one-pipecolic acid (2) by chemical and spectral methods.

Clerodane diterpenoids, long chain esters of coumaric acid and other compounds from Baccharis myrsinites.

A new clerodane diterpenoid and two new long chain esters of trans- and cis-coumaric acid, in addition to known triterpenoids and one known clerodane diterpenoid, have been isolated and characterized from Baccharis myrsinites. The structures were determined by spectroscopic techniques.

A new derivative of glucose and 2-C-methyl-D-erythritol from Ferula sinaica.

A new glucose derivative (1) and 2-C-methyl-D-erythritol (2) were isolated from the leaves of Ferula sinaica. The two structures were elucidated by highfield NMR spectroscopy, and that of 1 was confirmed by X-ray diffraction analysis.

Gallotannins and flavonoids from Haematoxylon campechianum.

Two new compounds, 2,6-bis-O-digalloyl-3-O-galloylglucose and 2-O-trigalloyl-1,3,4,6-tetrakis-O-galloylglucose, along with four known gallotannins, were isolated and identified from the leaves of Haematoxylon campechianum. In addition, four known flavonoid and three simple phenolic compounds were also detected.

Nonprotein amino acids from seeds of Cycas circinalis and Phaseolus vulgaris.

Our chemical studies on Cycas circinalis seeds from Guam has provided two new nonprotein amino acids, N-(3'-one-5'-methyl)-hexylalanine and leucine betaine. N-methylisoleucine, previously reported as a component of naturally occurring peptides, has been isolated as a free amino acid from the seeds of Phaseolus vulgaris (pinto bean), together with S-methylcysteine, pipecolic acid and a dipeptide, gamma-glutamyl-leucine.

An unusual cycloartane triterpenoid from Cimicifuga foetida.

A new cycloartane triterpenoid glycoside has been isolated from the rhizomes of Cimicifuge foetida L. The spectroscopic characteristics of the new compound are different from previously described cycloartane triterpenoids because of the loss of the 24-isopropyl group as well as the presence of a 11 beta-OH group. Based on spectroscopic evidence, including a series of 2D-NMR analyses, the structure of the new triterpene is assigned as 24-des-isopropyl-7-ene-23-one-9,19; 16,24-dicycloart-3 beta,11 beta,16 alpha,24 alpha-tetraol 3-O-beta-D-xylopryanoside, named here as neocimiside. The structure of the aglycone of neocimiside was confirmed by X-ray analysis.

Rapid gas chromatographic screening of edible seeds, nuts and beans for non-protein and protein amino acids.

Water extraction with subsequent picric acid treatment and solvent washing (ethyl acetate and diethyl ether) was employed for the rapid isolation of free amino acids from non-aqueous food samples. The isolated amino acids were subjected to N(O,S)-isobutyloxycarbonylation followed by solid-phase extraction and tert.-butyldimethylsilylation for direct analysis by gas chromatography and gas chromatography-mass spectrometry. When the present method was applied to nineteen food samples (common beans, seeds, and nuts), seventeen protein amino acids and fifteen non-protein amino acids were simultaneously screened. Eleven non-protein amino acids including gamma-aminobutyric acid, pipecolic acid, pyroglutamic acid, alpha-aminobutyric acid, alpha-aminoadipic acid, and beta-alanine were tentatively identified, and four compounds assumed to be non-protein amino acids remained unidentified.

Abietane diterpenes from Lepechinia urbaniana.

Lepechinia urbaniana was investigated with respect to abietane diterpenes. In addition to four widespread diterpenes, two rare compounds were isolated and characterized.

Screening for non-protein amino acids in seeds of the Guam cycad, Cycas circinalis, by an improved GC-MS method.

The non-protein amino acid, beta-N-methyl-amino-L-alanine (L-BMAA) from Cycas circinalis seeds, has been implicated as a causative agent of amyotrophic lateral sclerosis-Parkinsonism dementia complex (ALS-PDC), a disease known from Guam and other areas in the western Pacific. We analyzed C. circinalis seeds for additional free non-protein amino acids by a recently developed GC-MS method. The samples were prepared by water extraction of seed flour. The amino acids present in the extract were derivatized by N(O,S)-isobutyloxycarbonylation of the amine functional groups and then tert-butyldimethylsilylation of the carboxyl functional groups. Peaks for a total of seventeen derivatives of non-protein amino acids were detected by GC-MS. In addition to L-BMAA, four other non-protein amino acids were identified as beta-alanine, gamma-amino-butyric acid, pyroglutamic acid, and alpha-aminoadipic acid.

The magical and medicinal usage of Stangeria eriopus in South Africa.

The underground caudex of the cycad Stangeria eriopus is used extensively by several ethnic groups in South Africa, mainly as an ingredient in magical potions but also as an emetic. An assessment of two main outlets showed that 3410 plants were sold in the month of July 1992; continued usage of this material now threatens the remaining plant populations. A proximate analysis of the caudex material gives high carbohydrate content with only small percentages of fat, protein, fibre and ash. An unusually high content of sodium sulphate may explain the efficacy of Stangeria-containing preparations as an emetic. The phytosterols sitosterol and stigmasterol are present in a 4:1 ratio while the fatty acid component comprises palmitic, oleic, stearic and arachidic acids. Twelve amino acids were identified in the material, including the non-protein amino acids beta-alanine, gamma-aminobutyric acid and pyroglutamic acid. The candidate neurotoxin beta-N-methylamino-L-alanine could not be detected but cycasin is present at the levels of 0.17% and 0.21% in fresh and dry caudex material, respectively and appears to be accompanied by the related toxin, macrozamin.

An acylated flavone C-glycoside from Glycyrrhiza eurycarpa.

A new acylated flavone C-glycoside, apigenin 6-C-alpha-L-rhamnopyranoside-8-C-[6"-(3-hydroxy-3-methyl-glutaroyl )-beta-D-glucopyranoside], was isolated from rhizomes of Glycyrrhiza eurycarpa and its structure was established on the basis of spectroscopic data.

Sesquiterpene glycosides from Calendula arvensis.

The extract of the aerial parts of Calendula arvensis afforded four new sesquiterpene glycosides 1-4 in addition to three known compounds. The structures of the new compounds were established by high field 1H-nmr spectroscopy.