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PubMedDate not supplied

Method validation for determination of alkaloid content in goldenseal root powder.

A fast, practical ambient extraction methodology followed by isocratic liquid chromatography (LC) analysis with UV detection was validated for the determination of berberine, hydrastine, and canadine in goldenseal (Hydrastis canadensis L.) root powder. The method was also validated for palmatine, a major alkaloid present in the possible bioadulterants Coptis, Oregon grape root, and barberry bark. Alkaloid standard solutions were linear over the evaluated concentration ranges. The analytical method was linear for alkaloid extraction using 0.3-2 g goldenseal root powder/100 mL extraction solvent. Precision of the method was demonstrated using 10 replicate extractions of 0.5 g goldenseal root powder, with percent relative standard deviation for all 4 alkaloids < or = 1.6. Alkaloid recovery was determined by spiking each alkaloid into triplicate aliquots of neat goldenseal root powder. Recoveries ranged from 92.3% for palmatine to 101.9% for hydrastine. Ruggedness of the method was evaluated by performing multiple analyses of goldenseal root powder from 3 suppliers over a 2-year period. The method was also used to analyze Coptis root, Oregon grape root, barberry bark, and celandine herb, which are possible goldenseal bioadulterants. The resulting chromatographic profiles of the bioadulterants were significantly different from that of goldenseal. The method was directly transferred to LC with mass spectrometry, which was used to confirm the presence of goldenseal alkaloids tetrahydroberberastine, berberastine, canadaline, berberine, hydrastine, and canadine, as well as alkaloids from the bioadulterants, including palmatine, jatrorrhizine, and coptisine.

Alkaloids↗
PubMed2005

Alkaloids of Haloxylon salicornicum (Moq.) Bunge ex Boiss. (Chenopodiaceae).

Haloxylon salicornicum is a desert plant that contains several alkaloids. From the aerial parts a new piperidyl alkaloid, haloxynine, was isolated and characterized on the basis of mass spectrometry, 1H and 13C NMR. A GLC/MS analysis revealed the presence of 17 additional known alkaloids of which piperidine, halosaline, anabasine, hordenine, N-methyltyramine, haloxine and aldotripiperideine had been previously reported in this genus. Among the 18 identified alkaloids, ten alkaloids were recorded for the first time from this plant and the genus Haloxylon. Haloxynine, halosaline, haloxine, anabasine, and smipine figure as major alkaloids with a relative abundance of more than 5% of total alkaloids. Some of these alkaloids are known be strong agonists at nicotinic acetylcholine receptors and it is thus likely that they serve as chemical defencecompounds against insects and mammalian herbivores.

Alkaloids↗
PubMed1994

[Veratrum alkaloids. I].

Alkaloids represent an important group of therapeutically significant secondary metabolites. The plants of the genus Veratrum contain alkaloids with an antihypertensive effect. Also the genera Schoenocaulon and Zygadenus are sources of veratrum alkaloids. The present paper presents a survey of isolated alkaloids from the underground and aerial parts of 17 species of the genus Veratrum. The alkaloids occur as glycosides, aglycones or in the form of esters with various acids. In conformity with the IUPAC regulations for the nomenclature of steroids, Veratrum alkaloids were divided into 7 groups. The present paper lists the compounds of the first two groups, i.e. (1) alkaloids of the jervanine and veratranine types (I-XXIII), and (2) alkaloids with the cevanine skeleton (XXIV-XXXV). The individual compounds are characterized by their physico-chemical constants (melting point, optical rotation).

Veratrum Alkaloids↗
PubMed1994

A novel O-tigloyltransferase for alkaloid biosynthesis in plants. Purification, characterization, and distribution in Lupinus plants.

A novel acyltransferase for alkaloid metabolism, tigloyl-CoA: (-)-13 alpha-hydroxymultiflorine/(+)-13 alpha-hydroxylupanine O-tigloyltransferase (HMT/HLTase), a monomeric 50-kDa protein, was purified to homogeneity from 10-day-old Lupinus termis seedlings. There were two isoforms of this acyltransferase with the same molecular mass (50 kDa) but slightly different isoelectric points (pI 7.8 and 7.6). These two isoforms showed the same catalytic activity of tigloyl transfer from tigloyl-CoA to (-)-13 alpha-hydroxymultiflorine and (+)-13 alpha-hydroxylupanine, which belong to the same (7S, 9S) enantiomeric series of tetracyclic quinolizidine alkaloids; whereas no activity was detected toward an antipodal (7R, 9R) alkaloid, (-)-baptifoline, or to bicyclic quinolizidine alkaloids, (+)-epilupinine and (-)-lupinine. The Km values for HMTase activity were determined to be 21 microM and 46 microM for (-)-13 alpha-hydroxymultiflorine and tigloyl-CoA, respectively; and for HLTase activity, 27 microM and 52 microM for (+)-13 alpha-hydroxylupanine and tigloyl-CoA, respectively. The activity was inhibited by CoASH in a competitive manner, and by (+)-lupanine and (+)-epilupinine in a partially noncompetitive manner. The enzyme showed the highest activity around pH 8.0 and was inactivated by heat treatment and by the addition of sulfhydryl blocking reagents. Such tigloyltransferases for quinolizidine alkaloid metabolism are distributed in some Lupinus species and Cytisus scoparius, in which tigloyl alkaloids are accumulated in addition to non-ester-type alkaloids, but not in other lupin plants, in which only non-ester-type alkaloids are present.

Acyltransferases↗
PubMedDate not supplied

Chiral gas chromatographic determination of ephedrine-type alkaloids in dietary supplements containing Má Huáng.

Má Huáng is a traditional Chinese medicine derived from the aerial parts of several Ephedra species (Ephedraceae). These plants produce (-)-ephedrine, (+)-pseudoephedrine, (-)-norephedrine, (+)-norpseudoephedrine, (-)-N-methylephedrine, and (+)-N-methylpseudoephedrine. Racemic and (-)-ephedrine, (+)-pseudoephedrine, and (+/-)-norephedrine (phenylpropanolamine) are used clinically in the United States and are largely synthetic in origin. Current interest in Má Huáng is spurred by reports describing a "thermogenic" (calorie burning) effect provided by mixtures of ephedrine, caffeine, and aspirin. Products providing the key thermogenic compounds from natural sources are available as dietary supplements in retail outlets. Reports of potentially unsafe levels of the alkaloids, as well as possible fortification of Má Huáng-containing products with synthetic Ephedra alkaloids, prompted the development of a chiral gas chromatographic (GC) method that allows determination of alkaloid patterns and identification of isomerically impure synthetic alkaloids. Nine products were analyzed on a gamma-cyclodextrin capillary GC column. Identity of the alkaloids was verified by GC/mass spectrometry (MS) and GC/matrix isolation/Fourier transform infrared spectroscopy. No synthetic isomers were found in the dietary supplements analyzed. Three products contained only one of the ephedrine-type alkaloids. One product that listed Má Huáng as an ingredient contained no detectable ephedrine-type alkaloid. In products containing measurable quantities of these compounds, total alkaloid levels ranged from 0.3 to 56 mg/g.

Alkaloids↗
PubMed1993

Toxicity study of the main alkaloids of Datura ferox in broilers.

Seeds of the weed Datura ferox are frequent contaminants of raw materials used for animal feed. These seeds produce various toxic effects and contain mainly the alkaloids scopolamine and hyoscyamine. In this 3-month toxicity study, a mixture of scopolamine and hyoscyamine (98:2) was incorporated at four total alkaloid levels (1.5, 15, 75 or 150 mg/kg feed) into a control diet fed to 100 broilers. Alkaloid feeding caused significant reductions in the body weight gain of birds, especially of those fed a dose of 150 mg alkaloid/kg feed. Growth-retarding effects, however, were transient, as no changes in body weight gain were noted after 52 days of alkaloid feeding. Alkaloid-treated broilers showed no significant differences from controls with respect to the cardiac rate and breathing frequency nor in relation to plasma aspartate aminotransferase, alanine aminotransferase and alkaline phosphatase activities. In contrast, plasma leucine aminopeptidase activity was significantly reduced after 3 months in all alkaloid-fed birds. Autopsy and histological examination of tissues by light and electron microscopy revealed no pathological changes associated with alkaloid feeding. Broilers appeared generally healthy and behaved normally throughout. These data should be considered in the formulation of new, improved regulations defining the maximum allowable alkaloid content of D. ferox seeds contaminating raw materials destined for use as broiler feed.

Animal Feed↗
PubMed2005

Spectrometric studies of cytotoxic protoberberine alkaloids binding to double-stranded DNA.

The noncovalent complexes of five cytotoxic protoberberine alkaloids, that is, berberine, palmatine, jatrorrhizine, coptisine, and berberrubine with several double-stranded oligodeoxynucleotides were systematically investigated by using electrospray ionization mass (ESI-MS) and fluorescence spectrometric methods, with the aim of establishing the structure-activity relationships. ESI-MS spectrometric studies indicated that these five alkaloids showed both 1:1 and 1:2 binding stoichiometries with d(AAGAATTCTT)(2), d(AAGGATCCTT)(2), and d(AAGCATGCTT)(2). Their relative binding affinities toward these three double-stranded DNA were semi-quantitatively evaluated by measuring the ratios of the complex signals ([ds+alkaloid-5H](4-)+[ds+2alkaloid-6H](4-)) to those of the duplexes ([ds-4H](4-)) and also by ESI-MS competitive binding experiments. These experiments established the relative binding affinities of five protoberberine alkaloids in the order of palmatine>jatrorrhizine>coptisine>berberine>berberrubine with d(AAGAATTCTT)(2), palmatinecoptisine>jatrorrhizineberberine>berberrubine with d(AAGGATCCTT)(2) and palmatine>jatrorrhizinecoptisine>berberine>berberrubine with d(AAGCATGCTT)(2). Significantly, these alkaloids except berberrubine bound to d(AAGGATCCTT)(2) and d(AAGCATGCTT)(2) with the affinities comparable to Hoechst 33258, a typical DNA minor groove binder. The relative binding preferences of berberine, palmatine, and coptisine with these three double-stranded DNA were further quantitatively assessed by their association constants obtained from fluorescence titration experiments. The values revealed the order of relative binding affinities as berberine>coptisine>palmatine with d(AAGAATTCTT)(2) and coptisine>berberine>palmatine with d(AAGGATCCTT)(2) and d(AAGCATGCTT)(2). These results were not in full agreement with those obtained from ESI-MS experiments, maybe due to the different measuring solution conditions. The results from ESI-MS and fluorescence titration experiments indicated that the sequence selectivities of these five alkaloids were not significant and remarkable AT- or GC-rich DNA binding preferences were not obtained, in contrast to the report that berberine binds preferentially to AT-rich DNA. To provide further insight into the sequence selectivities, the association constants of berberine with d(AAGATATCTT)(2), 5'-AAGTAATCTT-3'/5'-AAGATTACTT-3', d(AAGGGCCCTT)(2), d(AAGGCGCCTT)(2), and 5'-AAGGCCGCTT-3'/5'-AAGCGGCCTT-3', that is double helical DNA from AT-rich to GC-rich sequences, were further measured by fluorescence titration methods. No significant differences in their association constants were observed, suggesting that berberine showed no remarkable sequence selectivities.

Alkaloids↗
PubMed2001

Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.

We compared the effects of four quaternary benzo[c]phenanthridine alkaloids--chelerythrine, chelilutine, sanguinarine, and sanguilutine--and two quaternary protoberberine alkaloids-berberine and coptisine--on the human cell line HeLa (cervix carcinoma cells) and the yeasts Saccharomyces cerevisiae and Schizosaccharomyces japonicus var. versatilis. The ability of alkaloids to display primary fluorescence, allowed us to record their dynamics and localization in cells. Cytotoxic, anti-microtubular, and anti-actin effects in living cells were studied. In the yeasts, neither microtubules nor cell growth was seriously affected even at the alkaloid concentration of 100 microg/ml. The HeLa cells, however, responded to the toxic effect of alkaloids at concentrations ranging from 1 to 50 microg/ml. IC50 values for individual alkaloids were: sanguinarine IC50 = 0.8 microg/ml, sanguilutine IC50 = 8.3 microg/ml, chelerythrine IC50 = 6.2 microg/ml, chelilutine IC50 = 5.2 microg/ml, coptisine IC50 = 2.6 microg/ml and berberine IC50 > 10.0 microg/ml. In living cells, sanguinarine produced a decrease in microtubule numbers, particularly at the cell periphery, at a concentration of 0.1 microg/ml. The other alkaloids showed a similar effect but at higher concentrations (5-50 microg/ml). The strongest effects of sanguinarine were explained as a consequence of its easy penetration through the cell membrane owing to nonpolar pseudobase formation and to a high degree of molecular planarity.

Alkaloids↗
PubMed1982

Selective inhibition of in vitro synthesis of cancer DNA by alkaloids of beta-carboline class.

The high template in vitro activity of native DNA from cancerous mammalian and plant tissues, compared to DNA from healthy tissues, enabled us to select substances which selectively inhibit cancer DNA synthesis. Among them, alstonine, serpentine, sempervirine and flavopereirine, all alkaloids which belong to the Beta-carboline class, distinguish cancer DNA from healthy tissue DNA inhibit DNA in vitro synthesis when native DNA from different cancerous tissues or cells is used as template. They have practically no effect on DNA from healthy tissues. The inhibitory effect of alkaloids is due to their capacity to form an 'alkaloid-cancer DNA' complex which has been characterized by use of the Sephadex column. Evidence is presented showing that these alkaloids inhibit the initiation of DNA synthesis but not chain elongation. The stimulating action caused by carcinogens during cancer DNA in vitro synthesis may be prevented and reversed by alkaloids. Furthermore, the stimulating action of steroids during in vitro synthesis of hormone target tissue DNA might be neutralized by alkaloids. However, at relatively high doses, steroids reversibly compete with alkaloids for binding sites on breast cancer DNA. This is not observed with DNA from nonhormone target tissues.

Alkaloids↗
PubMed1996

Analysis, separation, and bioassay of pyrrolizidine alkaloids from comfrey (Symphytum officinale).

Pyrrolizidine alkaloids have been linked to liver and lung cancers and a range of other deleterious effects. As with many natural toxicants, major problems arise in determining the effects of the different members of the class and the importance of various forms of ingestion. In this study we have investigated the levels of pyrrolizidine alkaloids in comfrey (Symphytum officinale), determined the levels in different parts of the plant and in herbal remedies, separated the alkaloids into two main groups--the principal parent alkaloids and the corresponding N-oxides--and, finally, carried out a simple bioassay based upon the mutagenic capability of the separated compounds in a human cell line. We conclude that the part of the plant ingested is important in terms of alkaloid challenge and that the effect of two of the major groups of alkaloids individually is different from that of alkaloids in the whole plant extract.

Base Sequence↗
PubMed2006

Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways.

Clavines and D-lysergic acid-derived alkaloid amides and alkaloid peptides are two different families of compounds that have the indole-derived tetracyclic metergoline ring system in common. Previous work has shown that D-lysergic acid is biosynthetically derived from clavine alkaloids. Recent cloning and analysis of the ergot alkaloid biosynthesis gene cluster from the D-lysergic acid peptide (ergopeptines)-producing Claviceps purpurea, has shown that it most probably contains all genes necessary for D-lysergic acid synthesis as well as those that encode the assembly of D-lysergic acid peptides, such as ergotamine. To address the role of the oxygenase genes of alkaloid-gene clusters, the only cytochrome P450 monooxygenase gene of this cluster was inactivated by disruption. The resultant mutant accumulated agroclavine, elymoclavine, and chanoclavine in substantial amounts but not ergopeptines. Feeding the mutant with D-lysergic acid restored ergopeptine synthesis; this suggests a block in the conversion of elymoclavine to D-lysergic acid. The gene was designated cloA (for encoding a clavine oxidase, CLOA). Retransformation of the mutant with the intact cloA gene also restored ergopeptine synthesis. These data show that CLOA catalyses the conversion of clavines to D-lysergic acid, it acts as a critical enzyme in the ergot alkaloid gene cluster, and bridges the biosynthesis of the two different families of alkaloids.

Claviceps↗
PubMed1984

Comparative disposition kinetics of two diastereomeric pairs of cinchona alkaloids in the dog.

The comparative disposition kinetics of quinidine, quinine, cinchonine , and cinchonidine were investigated in five male, mongrel dogs after intravenous bolus injections of a 9.2-mmol/kg dose of each alkaloid base. Blood and plasma specimens were obtained at various times up to 6 h postdose and assayed for quinidine and quinine with a TLC-fluorometric procedure and for cinchonine and cinchonidine by HPLC. The plasma alkaloid concentration-time data were analyzed by weighted, nonlinear least-squares regression analysis to obtain the central compartment volume (Vc), disposition rate constants (alpha and beta), and corresponding half-life values (t1/2). Total body clearance (CL) and apparent volume of distribution (Vd) were estimated by nonparametric analysis. In this study, the highest plasma alkaloid concentrations were reached with quinidine and the lowest concentrations with the quinidine congener, cinchonine . The other congeneric pair, quinine and cinchonidine , exhibited plasma alkaloid concentrations that were comparable and intermediate to those of quinidine and cinchonine . With cinchonine and cinchonidine , the plasma and blood concentration-time curves were virtually superimposable. However, with quinidine and quinine, the plasma alkaloid concentrations of these diastereomers were approximately twice the corresponding blood concentrations. The total body clearance rate of quinidine was significantly slower than quinine and cinchonine clearance. No difference in clearance was observed between cinchonine and cinchonidine . The beta and t1/2 beta for quinidine were significantly smaller and larger, respectively, than the corresponding values obtained with the other alkaloids. No significant differences in alpha or Vc and Vd were found between and within the two diastereomeric pairs of alkaloids. The differences in disposition kinetics observed in this study were attributable to an interaction of stereochemical and 6'-methoxy group substitution effects.

Animals↗
PubMed1989

Piperidine alkaloid composition and relation to crooked calf disease-inducing potential of Lupinus formosus.

A congenital deformity condition called crooked calf disease, of widespread occurrence in western North America, is known to be induced by maternal ingestion during gestation of certain members of the Lupinus genus containing the quinolizidine alkaloid teratogen anagyrine. Because some piperidine alkaloids from other sources induce a similar condition, we have investigated the alkaloid composition and teratogenicity of Lupinus formosus, reported by others to be low in quinolizidines but rich in the type of piperidine alkaloids that we have speculated would be teratogenic. GC/MS analysis of L. formosus showed seven major and nine minor components in the total alkaloid fraction. All seven major and five of the nine minor components, representing all but 3% of the fraction, were identified by mass spectrometric fragmentation patterns and GC retention times. They included several potentially teratogenic piperidine alkaloids (including a very large amount of ammodendrine), as well as several nonteratogenic quinolizidine alkaloids plus a trace (at nonteratogenic levels) of the known quinolizidine teratogen anagyrine. The plant induced severe crooked calf disease with limb, spinal, and palate involvement in experimental calves. The deformities are believed to have been induced by ammodendrine.

Abnormalities, Drug-Induced↗
PubMed1975

Disposition of catecholamine-derived alkaloids in mammalian systems.

Tetrahydropapaveroline, the tetrahydroisoquinoline alkaloid derived from dopamine, is converted in vivo by rats and by rat liver and brain preparations to tetrahydroprotoberberine alkaloids. The latter alkaloids have also been identified for the first time in the urine of parkinsonian patients receiving L-dopa therapy. These findings suggest that man, like plants, may have the ability to elaborate several classes of alkaloids with potentially important pharmacological consequences. Thus, this newly demonstrated ability of mammalian systems to evoke the biosynthesis of benzyl-tetrahydroisoquinoline-derived alkaloids - a capability previously considered unique to plants - elects the tetrahydroprotoberberine alkaloids as representative of the first class of a possible constellation of complex mammalian alkaloids elaborated from the neuroamines.

Alkaloids↗
PubMed1978

Isoquinoline alkaloids. Inhibitory actions on cation-dependent ATP-phosphohydrolases.

Representatives of eleven different classes of isoquinoline alkaloids inhibit Na+, K+-ATPase and Mg2+-ATPase in rat brain microsomal preparations. In most cases the Na+, K+-ATPase is more sensitive than Mg2+-ATPase to inhibition by the alkaloids. The classes of alkaloids can be ranked according to potency of inhibition of Na+, K+-ATPase. Protoberberines are most effective, followed in decreasing order by benzophenanthridines, benzylisoquinolines, aporphines, tetrahydroprotoberberines, pavines, protopines, isoquinolines, tetrahydrobenzylisoquinolines, morphinanes, and tetrahydroisoquinolines. As specific representatives of each of the first four classes of alkaloids, berberine, sanguinarine, papaveroline and 1,2,10,11-tetrahydroxyaporphine, respectively, prove most valuable in kinetic studies because they exhibit the greatest inhibitory action on brain Na+, K+-ATPase. Kinetic analyses plotted in double reciprocal form reveal that berberine and 1,2,10,11-tetrahydroxyaporphine are simple linear competitive inhibitors with respect to ATP, whereas sanguinarine and papaveroline are simple linear noncompetitive inhibitors. These four representative alkaloids exhibit non-linear competitive inhibition with respect to Na+-activation. Additionally, these alkaloids significantly inhibit rat brain microsomal K+-activated pNPPase. The results demonstrate that certain members of several classes of isoquinoline alkaloids markedly affect various cation-dependent phosphohydrolases in vitro.

Adenosine Triphosphatases↗
PubMed1982

Pyrrolizidine alkaloids from Symphytum officinale L. and their percutaneous absorption in rats.

An analysis of a commercial sample of Symphyti radix originating from Poland with a total alkaloid content of 0.07% revealed the presence of 7 pyrrolizidine alkaloid-N-oxides: 7-acetyl intermedine, 7-acetyl lycopsamine as the main constituents and lycopsamine, intermedine, symphytine and traces of 2 further not yet identified alkaloids. The percutaneous absorption of these alkaloids was investigated in rats, using a crude alcoholic extract of the plant corresponding to a dose of 194 mg alkaloid-N-oxides/kg b.wt. The excretion of N-oxides in the urine during 2 days was in the range of 0.1-0.4% of the dose. The dermally absorbed N-oxides are not or only to a small extent converted to the free alkaloids in the organism. The oral application led to a 20-50 times higher excretion of N-oxides and free alkaloids in the urine.

Animals↗
PubMed1983

Alkaloids in ergot found on different Gramineae in The Netherlands.

The alkaloid content and the composition of the alkaloid complex of thirteen samples of ergot sclerotia from different gramineous host species collected in The Netherlands were investigated. Two samples collected in France were also examined. Ergot of Glyceria fluitans (L.) R.Br. did not contain alkaloids. The total alkaloid content of ergot found on the other wild grasses was more than 0.2%. The ratio between the contents of water soluble and water insoluble alkaloids of the investigated ergot sclerotia varies between 1:10 and 1:20. The composition of the alkaloid complex in the sclerotia was studied by quantitative thin-layer chromatography. The sclerotia could be grouped into three main categories: --sclerotia of Lolium perenne L., Festuca arundinacea Schreb. and Arrhenatherum elatius (L.) P.B. ex J. et C. Presl, containing predominantly ergocornine, alpha- and beta-ergokryptine and ergosine; --sclerotia of Dactylis glomerata L., Phalaris arundinacea L., Alopecurus geniculatus L. and Holcus mollis L., containing predominantly ergosine, ergocristine and ergotamine; --sclerotia of Molinia caerulea (L.) Moench, containing predominantly ergocristine, ergosine and ergometrine. A great similarity was found between the composition of the alkaloid complex in ergot of Lolium perenne L. from different locations and also in ergot of Molinia caerulea (L.) Moench from different locations. This similarity was less in ergot of Dactylis glomerata L. collected from different locations.

Chromatography, Thin Layer↗
PubMed1982

Quantitative changes of the alkaloid complex in a submerged culture of Claviceps paspali.

Claviceps paspali FA produced high concentrations of alkaloid under submerged conditions. Their production was found to depend on the developmental stage and treatment of the filamentous culture inoculum. A medium containing Bacto-peptone with a constant composition of amino acids was selected for the preparation of the inoculum. A two-week fermentation in a synthetic medium with mannitol at 24 +/- 1 degrees C resulted in an increased production of total alkaloids from the original value of 100-200 micrograms/mL to more than 2000 micrograms/mL. Addition of tryptophan did not further increase the production of alkaloids but resulted in changes of the spectrum of some metabolites, 2,3-Dihydroxybenzoic acid accompanied the alkaloids in the fermentation medium. alpha-Hydroxyethyllysergamide was the predominant component of extracellular alkaloids (80% in the first days of fermentation). During fermentation the level of this alkaloid continuously decreased while the concentration of the accompanying alkaloids, i.e. lysergamide and the corresponding minor isomers, increased.

Alkaloids↗