William C. Evans's research while affiliated with University of Nottingham and other places
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Publications (19)
Twenty-six tropane alkaloids were identified from the root-bark of Erythroxylum monogynum by GC and GC-MS and twenty of these alkaloids had not previously been reported as constituents of the root-bark. 3α-(3′,4′,5′-Trimethoxybenzoyloxy) tropane was the main base and in addition, three new alkaloids were identified as 3α-isobutyryloxynortropane, 3α...
Twenty-seven alkaloids were identified from the stem-bark of Erythroxylum zambesiacum by GC and GC-MS. The characteristic alkaloids were tropane derivatives, together with nicotine. In addition to known substances previously isolated from the root-bark, a further 20 alkaloids were identified in the stem-bark. The principal base was 3α-(3′,4′,5′-tri...
From the in vitro hairy root cultures of a Datura candida hybrid, 19 tropane alkaloids have been identified using capillary gas-liquid chromatography and mass spectrometry. As in the parent plants, scopolamine is the major alkaloid. Two hitherto undescribed alkaloids have been detected and their structure tentatively characterised on the basis of t...
Fifteen alkaloids were characterized from the leaves of Erythroxylum hypericifolium; the majority are esters of cinnamic and benzoic acids. 3α-Cinnamoyloxytropan-6β-ol is the main base. New alkaloids reported are 3β- cinnamoyloxytropane, 3α, 6β-dicinnamoyloxytropane, 3-cinnamoyloxynortropan-6-ol, 6β-acetoxy-3α-cinnamoyl- oxytropane and, tentatively...
Hairy root cultures were obtained following inoculation of the stems of sterile plantlets of aDatura candida hybrid withAgrobacterium rhizogenes. The scopolamine and hyoscyamine content was quantified by HPLC and compared with the non-transformed plants. The alkaloid yield (0.68% dry weight) obtained with the hairy roots was 1.6 and 2.6 times the a...
From the leaves of Erythroxylum cuneatum, a new alkaloid (±)-3α,6β-dibenzoyloxytropane was isolated as principal alkaloid; four other benzoyl- and tigloyl-esters were obtained, together with nicotine. Three of these bases were also detected in the stem-bark. Tropacocaine was the principal alkaloid of E. ecarinatum leaves. Erythroxylum australe root...
Erythroxylum macrocarpum and E. sideroxyloides, two closely related species indigenous to Mauritius, contain a similar range of alkaloids consisting mainly of benzoyl esters of tropan-3α-ol, tropan-3β-ol, and tropan-3α,6β-diol together with their nor-derivatives. 3α-Benzoyloxytropan-6β-ol (E. sideroxyloides) and 3α-benzoyloxynortropane and 3β-benzo...
The root-bark of Erythroxylum hypericifolium contains the new bases tropan-3α-yl 3-hydroxyphenylacetate, (+)-tropane-3α,6β-diol 3-phenylacetate, tropane-3α,6β-diol 3-phenylacetate 6-acetate, tropane-3α,6β,7β-triol 3-phenylacetate, and nortropan-3-yl phenylacetate; tropan-3α-yl phenylacetate was also isolated. Chemotaxonomic implications are discuss...
A new steroidal lactone of the withanolide group has been isolated from two Datura species and three hybrids and characterized as (20R,22R-5α,12α-dihydroxy-1-oxo-6α, 7α-epoxywitha-2,24-dienolide. The distribution of six withanolides throughout section Stramonium of the genus has been investigated.
Recent research suggests that, in addition to the well-documented occurrence of significant quantities of cocaine and related alkaloids in a limited number of species, the genus Erythroxylon will prove to be a rich source of tropane alkaloids. These bases are esters of a range of acids with tropine, 3 alpha, 6 beta-dihydroxytropane and 3 alpha, 6 b...
Of the 49 species of Solanum studied, cuscohygrine has been detected in 25, solamine and related amines in 17 and solamine-derived amides in 16. Five species of Cyphomandra examined all contained both amines and amides. From roots of Margaranthus solanaceus cuscohygrine has been isolated which probably occurs, too, in roots of Lycianthes rantonnett...
1 αH, 5αH-Tropan-3α-yl isovalerate is the principal alkaloid of the root-bark of Erythroxylum dekindtii; other new bases characterised are 1 αH, 5αH-tropan-3α-yl phenylacetate and 1αH, 5αH-tropan-3α-yl 2-furoate. The root bark also contains methylecgonidine, valeroidine, poroidine, isoporoidine, and tropine.
Ethyl N, N-bis(4-dimethylaminobutyl) carbamate (solaurethine), a new urethane derivative of solamine, has been isolated from the roots of Solanum carolinense. Other compounds reported for the first time in this species include solamine (principal base), cuscohygrine and anabasine. The chemotaxonomic significance of these compounds is noted.
Datura innoxia plants were fed via the roots with cinnamic acid-[214C], (±)-phenyllactic (2-hydroxy-3-phenylpropanoic) acid-[214C] and phenylalanine-[2-14C]. In each case apohyoscine, hyoscine, hyoscyamine and littorine were isolated from the aerial parts, and hyoscine, hyoscyamine and littorine from the roots. Cinnamic acid was not incorporated in...
The distribution of tropane alkaloids in organs of Anthocercis littorea and A. viscosa is reported. The following alkaloids have been isolated: atropine (hyoscyamine), apoatropine, noratropine (norhyoscyamine), littorine, hyoscine, norhyoscine, meteloidine, 3α, 6β-ditigloyloxytropan-7β-ol, 6β-tigloyloxytropan-3α-ol, 3α-tigloyloxytropane, tigloidine...
Citations
... After a thorough biochemical analysis, high-yielding hairy root lines are selected for further scientific endeavors. Other studies which substantiate this fact include establishment and selection of high tropane alkaloid-yielding hairy root lines of Datura candida, D. stramonium, and somatic hybrid of Hyoscyamus albus and H. muticus (Christen et al. 1989;Zehra et al. 1998;. In Atropa hairy roots, several clones have been selected and characterized as high alkaloid-yielding root clones (Eskandari-Samet et al. 2012). ...
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... However, a fragmentation pattern similar to the major alkaloid with signs at m/z 156 [M + -71; C 4 H 7 O] with an intensity of 8%, at m/z 140 [M + -87; C 4 H 7 O 2 ] with an intensity of 11%, and at m/ z 96 with an intensity of 67%, revealed together the presence of OH substituent in C-3, and an ester group in C-6. (El-Bazaoui and Bellimam, 2011;Christen, et al., 1990;Cinelli and Jones, 2021). In turn, the base peak of compound 2 was observed at m/z 43 (C 3 H 7 ), suggesting a typical fragmentation of an ester group with four carbon atoms. ...
... fastuosa, D. leichhardtii, and D. ferox [40]. It is found in only low amounts in D. ceratocaula [73], but it is reported to be the most abundant alkaloid in D. discolor roots (around 20% of the total alkaloid content) [130]. Cuscohygrine (13) is also found in root cultures derived from D. stramonium, D. ferox, D. wrightii, and D. inoxia, and is 10% of the total alkaloid content in the last species [118,128]. ...
... Protocatechuic, caffeic, chlorogenic, gentisic, p-coumaric, p-hydroxybenzoic, phydroxyphenylacetic, ferulic, vannilic, syringic, benzoic and salicylic acids were detected in the phenolic acids fraction. Flavonoids including kaempferol, quercetin and their glycosides were isolated from the plant (248)(249)(250)(251)(252)(253)(254) . ...
... Despite claims to the contrary [22, 701 we [34] have been unable to sub- stantiate the incorporation of phenyl-The benzoyl moiety of cocaine is acetic acid into tropic acid. Several groups [17,431 have reported that cinnamic acid does not serve as a precursor of tropic acid. We also found that cinnamoyltropine is not converted directly to the tropane alkaloids of atb bra stramonium. ...
... These three species biosynthesize closely structurally related withanolides, which in addition to the α,β-unsaturated ketone at ring A and the δ-lactone at the side chain, have an α-hydroxy group at C-5 and a C-6α, C-7α epoxy group, which can be open as in the daturalactones 5 and 6, isolated from D. ferox [10]. In most of these compounds, a hydroxy or ketone group is present at C-12 and the δ-lactone can be α,β-unsaturated or possess a 24,25-epoxy group [10][11][12][13][14][15][16][17]. In the present work, we report the isolation and structural elucidation of five withanolides from D. quercifolia, and the results of the evaluation of their antioxidant and cytotoxic activities. ...
... In addition, erythrobezerrine C (103) showed moderate cytotoxicity activity on HCT-116 and NCI-H460, with IC 50 values of 3.38 and 5.43 μM, respectively [55]. TAs with antimicrobial [12] and diuretic [92,93] activities have also been reported. In 1984, Novak [94] reported the bioactivities of TAs from E. coca and E. novogranatense contained stimulant activity, inhibiting effect on dopamine uptake, and cholinolytic action. ...
... Asteraceae Rosin weed tonic plant [15] Leaves Roots: ethyl N,N-bis(4-dimethylaminobutyl) carbamate (solaurethine). Other compounds reported for the first time in this species include solamine (principal base), cuscohygrine and anabasine [482] Solidago odora Aiton Asteraceae Goldenrod bee stings, sore throat flowers [15] S. odora Aiton fo. odora ...
... The eight known constituents isolated included the tropane alkaloids 6β,7β-dibenzoyloxy-3α-hydroxytropane (2), 6β,7β-dihydroxy-3α-(phenylacetoxy)tropane (3) (Al-Said et al., 1986), 3α-benzoyloxy-6β, 7β-dihydroxytropane (4) (Griffin, 1978), 6β-benzoyloxy-3α-(4-hydroxy-3,5-dimethoxybenzoyloxy)tropane (5) (Oliveira et al., 2011); the glycosylated flavonoid ombuin-3-rutinoside-5-glucoside (6) (González-Guevara et al., 2006); and the triterpenes lupeol (7), taraxerol (8) (Mahato and Kundu, 1994) and lupenone (9) (Nasser et al., 2013). These substances (2-9) were identified by comparing their 1 H and 13 C NMR data with those reported in the literature. ...
... Considering all samples analyzed, six tropane alkaloids (3, 7, 9, 11, 14, and 15), in addition to nine alkaloids previously reported in E. pungens (1, 2, 4-6, 8, 10, 12, and 13), were identified [5]. The tentative characterization was based on literature reports on alkaloids in Erythroxylaceae [13][14][15][16][17], a GC-MS library search (NIST), and mass spectra analysis (▶ Fig. 1 and Figs. 1S-15S, Supporting Information). ...
