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1.
J Ethnopharmacol ; 248: 112360, 2020 Feb 10.
Artigo em Inglês | MEDLINE | ID: mdl-31676403

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: In folkloric medicine the dried rhizome of the Jamaican sarsaparilla (Smilax ornate Lem.), is given as a decoction to treat chronic rheumatism and rheumatoid arthritis. This particular claim has been scientifically validated; however, the mechanism for its anti-inflammatory activity is still unknown and hence, it forms the reason for this investigation. OBJECTIVE: The objective of this study is to investigate the mechanism of the anti-inflammatory activity of the methanol extract of Smilax ornate Lem. METHOD: The methanol extract was prepared using the soxhlet apparatus. The preliminary mechanism of action was investigated using models of oedema induced by histamine, bradykinin and prostaglandin E2. RESULTS: For the histamine-induced oedema model, the methanol extract (400 mg/kg) reduced the oedema formation, however, it was not significant (P > 0.05). For the bradykinin-induced oedema model, the methanol extract (400 mg/kg) exhibited significant (P < 0.05) anti-inflammatory activity when compared with that of the control (saline) group, with an onset on 60 min and a duration of 2 h. For the prostaglandin-induced oedema model, the methanol extract (400 mg/kg) exhibited significant (P < 0.05) anti-inflammatory activity when compared with that of its control group, with an onset on 120 min and a duration of 1.5 h. CONCLUSION: The methanol extract of Smilax ornata Lem. produced significant anti-inflammatory activity in the bradykinin-induced and prostaglandin-induced oedema models. It is possible that the mechanism by which it acts is by reducing the concentration or blocking the action of these mediators.


Assuntos
Anti-Inflamatórios/farmacologia , Edema/prevenção & controle , Inflamação/prevenção & controle , Metanol/química , Extratos Vegetais/farmacologia , Smilax , Solventes/química , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/toxicidade , Bradicinina , Dinoprostona , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/patologia , Histamina , Inflamação/induzido quimicamente , Inflamação/patologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/toxicidade , Ratos Sprague-Dawley , Rizoma , Smilax/química , Smilax/toxicidade
2.
J Ethnopharmacol ; 240: 111830, 2019 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-31063818

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: Smilax ornata Lem. is used in folklore medicine to treat rheumatoid arthritis and rheumatic pain. This particular claim has never been scientifically validated before in this plant species and hence, it forms the reason for this investigation. OBJECTIVE: To investigate whether the methanol and ethyl acetate extracts of Smilax ornata Lem. possess anti-inflammatory and analgesic properties in Sprague-Dawley rats. METHODS: The anti-inflammatory and analgesic activities were investigated using carrageenan-induced paw oedema model and the tail-flick model respectively. RESULTS: The methanol extracts (200 and 400 mg/kg) and the ethyl acetate extract (400 mg/kg) exhibited significant (P < 0.05) anti-inflammatory activity when compared with that of their control groups (saline and vegetable oil respectively), with an onset of 150 min and a duration of 2.5 h. The methanol extract (200 mg/kg) exhibited significant (P < 0.05) analgesic activity, with an onset of 60 min and a duration of 2 h. Also, the methanol and the ethyl acetate extracts (400 mg/kg) exhibited significant (P < 0.05) analgesic activity when compared with that of their control groups (saline and vegetable oil respectively), with an onset of 30 min and a duration of 2.5 h. CONCLUSION: The present study provided scientific justification that the extracts of Smilax ornata Lem. possess significant anti-inflammatory and analgesic activities.


Assuntos
Analgésicos/uso terapêutico , Anti-Inflamatórios/uso terapêutico , Edema/tratamento farmacológico , Dor/tratamento farmacológico , Extratos Vegetais/uso terapêutico , Animais , Carragenina , Edema/induzido quimicamente , Temperatura Alta/efeitos adversos , Fitoterapia , Ratos Sprague-Dawley , Rizoma , Smilax
3.
Phytochemistry ; 82: 61-6, 2012 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-22818358

RESUMO

The insecticidal sesquiterpenes cadina-4,10(15)-dien-3-one and aromadendr-1(10)-en-9-one were administered to the fungus Cyathus africanus ATCC 35853. Biotransformation of the former produced (4R)-9α-hydroxycadin-10(15)-en-3-one, while the latter gave 2ß-hydroxyaromadendr-1(10)-en-9-one, 2α-hydroxyaromadendr-1(10)-en-9-one and 10α-hydroxy-1ß,2ß-epoxyaromadendran-9-one. The bioconversion of santonin led to the production of two analogues, 11,13-dihydroxysantonin and the hitherto unreported 8α,13-dihydroxysantonin, while cedrol yielded 3ß,8ß-dihydroxycedrane and 3α,8ß-dihydroxycedrane. Stemod-12-ene, a diterpene, was transformed to 2-oxostemar-13-ene, a hitherto unknown analogue with a rearranged carbon framework. When methyl betulonate, a triterpenoid belonging to the lupane family, was supplied to the fungus 18α-ursane and 18α-oleanane derivatives, namely 19ß-hydroxy-3-oxo-18α-oleanan-28-oic acid and 19α-hydroxy-3-oxo-18α-ursan-28-oic acids, were generated. There are no previous reports of fungal transformation of a triterpene in which a skeletal rearrangement occurred. All substrate administration experiments were done in the presence of the terpene cyclase inhibitor chlorocholine chloride (CCC), using the single phase - pulse feed method.


Assuntos
Cyathus/metabolismo , Terpenos/metabolismo , Biotransformação
4.
Steroids ; 77(1-2): 85-90, 2012 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-22064215

RESUMO

Transformation reactions on 3ß,17ß-dihydroxyandrost-5-ene using free fungal cells were compared with those carried out by macerated mycelia, immobilized in calcium alginate beads. Six fungi were utilized in this study, namely Rhizopus oryzae ATCC 11145, Mucor plumbeus ATCC 4740, Cunninghamella echinulata var. elegans ATCC 8688a, Aspergillus niger ATCC 9142, Phanerochaete chrysosporium ATCC 24725 and Whetzelinia sclerotiorum ATCC 18687. The results show, for the first time, that encapsulated mycelial fragments essentially carry out the same bioconversions as those observed with growing cells. As the immobilized cells were "resting", the products formed were free of contamination by natural products, and this greatly aided the purification of the metabolites. Conditions for bead preparation were optimized. Furthermore, it was noted that the beads could be reused, once they had been subjected to a rejuvenation process.


Assuntos
Alginatos/química , Androstenos/química , Células Imobilizadas/enzimologia , Fungos/enzimologia , Micélio/enzimologia , Biocatálise , Biotransformação , Células Imobilizadas/química , Fermentação , Fungos/química , Ácido Glucurônico/química , Ácidos Hexurônicos/química , Micélio/química , Reciclagem
5.
Phytochemistry ; 72(18): 2361-8, 2011 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-21940022

RESUMO

A series of analogues, derived from the antiviral and cytotoxic diterpene stemodin, were prepared and evaluated for their lipid peroxidation (LPO), cyclooxygenase enzyme-1 (COX-1) and -2 (COX-2), and tumour cell proliferation inhibitory activities. Oxidation of stemodin produced stemodinone, which was then converted to stemod-12-en-2-one. Reaction of the latter under Petrow conditions (bromine; silver acetate/pyridine) yielded mainly dibrominated abeo-stachanes. Solvolysis of the dibromo compounds gave products of hydrolysis, some with rearranged skeleta. In the lipid peroxidation inhibitory assay three of the compounds exhibited prominent activity. Interestingly, all the analogues showed higher COX-1 enzyme inhibition than COX-2. Although a few of the diterpenes limited the growth of some human tumour cell lines, most compounds induced proliferation of such cells.


Assuntos
Antineoplásicos Fitogênicos/química , Inibidores de Ciclo-Oxigenase/química , Diterpenos/química , Peroxidação de Lipídeos/efeitos dos fármacos , Scrophulariaceae/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Inibidores de Ciclo-Oxigenase/isolamento & purificação , Inibidores de Ciclo-Oxigenase/farmacologia , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Humanos , Oxirredução
6.
Steroids ; 76(12): 1317-30, 2011 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-21763336

RESUMO

The potential of Fusarium oxysporum var. cubense UAMH 9013 to perform steroid biotransformations was reinvestigated using single phase and pulse feed conditions. The following natural steroids served as substrates: dehydroepiandrosterone (1), pregnenolone (2), testosterone (3), progesterone (4), cortisone (5), prednisone (6), estrone (7) and sarsasapogenin (8). The results showed the possible presence of C-7 and C-15 hydroxylase enzymes. This hypothesis was explored using three synthetic androstanes: androstane-3,17-dione (9), androsta-4,6-diene-3,17-dione (10) and 3α,5α-cycloandrost-6-en-17-one (11). These fermentations of non-natural steroids showed that C-7 hydroxylation was as a result of that position being allylic. The evidence also pointed towards the presence of a C-15 hydroxylase enzyme. The eleven steroids were also fed to Exophialajeanselmei var. lecanii-corni UAMH 8783. The results showed that the fungus appears to have very active 5α and 14α-hydroxylase enzymes, and is also capable of carrying out allylic oxidations. Ceratocystis paradoxa UAMH 8784 was grown in the presence of the above-mentioned steroids. The results showed that monooxygenases which effect allylic hydroxylation and Baeyer-Villiger rearrangement were active. However, redox reactions predominated.


Assuntos
Androstanos/metabolismo , Exophiala/enzimologia , Fusarium/enzimologia , Esteroide Hidroxilases/metabolismo , Androstanos/química , Biotransformação , Hidroxilação , Esteroide Hidroxilases/química
7.
Nat Prod Commun ; 4(6): 789-90, 2009 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-19634323

RESUMO

This is the first report of a phytochemical investigation of Jamaican populations of a local folk medicinal plant Salvia coccinea (Lamiaceae/Labiatae). Apart from the presence of 3-sitosterol, phytochemical profiling of the aerial parts yielded compounds other than those previously reported from Indian and Italian populations. The triterpenes betulinic acid and betulin, the phytosterols beta-sitosterol and beta-sitosterol-3-O-beta-D-glucopyranoside, as well as the steroid precursor squalene were isolated. The structures of the compounds were established by comparison of NMR spectroscopic data with those reported in literature.


Assuntos
Salvia/química , Jamaica , Fitosteróis/química , Triterpenos/química
8.
Steroids ; 72(9-10): 713-22, 2007 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-17628623

RESUMO

The fungi Whetzelinia sclerotiorum ATCC 18687, Phanerochaete chrysosporium ATCC 24725 and Mucor plumbeus ATCC 4740 were examined for their ability to perform steroid biotransformations under single phase, pulse feed conditions. The steroids 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone) (1), 17beta-hydroxyandrost-4-en-3-one (testosterone) (5), 3beta-hydroxypregn-5-en-20-one (pregnenolone) (3), pregn-4-ene-3,20-dione (progesterone) (9), 17alpha,21-dihydroxypregn-4-ene-3,11,20-trione (cortisone) (11), 17alpha,21-dihydroxypregna-1,4-diene-3,11,20-trione (prednisone) (14), and 3-hydroxyestra-1,3,5(10)-trien-17-one (estrone) (15) were fed to each fungus. The production of a number of novel metabolites is reported. Of the fungi investigated W. sclerotiorum performed the most interesting biotransformations and had a clear propensity for 2beta, 6beta/7beta and 15beta/16beta hydroxylations. P. chrysosporium was more prone functionalize steroids in the allylic position. Oxygen insertion at C-14 by M. plumbeus is reported for the first time. All three micro-organisms exhibited redox activity.


Assuntos
Fungos/metabolismo , Mucor/metabolismo , Phanerochaete/metabolismo , Esteroides/metabolismo , Biotransformação , Hidroxilação , Esteroides/química , Esteroides/isolamento & purificação
9.
Phytochemistry ; 67(11): 1088-93, 2006 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-16725164

RESUMO

Stemodane and stemarane diterpenes isolated from the plant Stemodia maritima and their dimethylcarbamate derivatives were fed to growing cultures of the fungi Cunninghamella echinulata var. elegans ATCC 8688a and Phanerochaete chrysosporium ATCC 24725. C. echinulata transformed stemodin (1) to its 7alpha-hydroxy- (2), 7beta-hydroxy- (3) and 3beta-hydroxy- (4) analogues. 2alpha-(N,N-Dimethylcarbamoxy)-13-hydroxystemodane (6) gave 2alpha-(N,N-dimethylcarbamoxy)-6alpha,13-dihydroxystemodane (7) and 2alpha-(N,N-dimethylcarbamoxy)-7alpha,13-dihydroxystemodane (8). Stemodinone (9) yielded 14-hydroxy-(10) and 7beta-hydroxy- (11) congeners along with 1, 2 and 3. Stemarin (13) was converted to the hitherto unreported 6alpha,13-dihydroxystemaran-19-oic acid (18). 19-(N,N-Dimethylcarbamoxy)-13-hydroxystemarane (14) yielded 13-hydroxystemaran-19-oic acid (17) along with the two metabolites: 19-(N,N-dimethylcarbamoxy)-2beta,13-dihydroxystemarane (15) and 19-(N,N-dimethylcarbamoxy)-2beta,8,13-trihydroxystemarane (16). P. chrysosporium converted 1 into 3, 4 and 2alpha,11beta,13-trihydroxystemodane (5). The dimethylcarbamate (6) was not transformed by this microorganism. Stemodinone (9) was hydroxylated at C-19 to give 12. Both stemarin (13) and its dimethylcarbamate (14) were recovered unchanged after incubation with Phanerochaete.


Assuntos
Cunninghamella/metabolismo , Diterpenos/metabolismo , Phanerochaete/metabolismo , Scrophulariaceae/química , Biotransformação , Diterpenos/química , Estrutura Molecular , Plantas Medicinais/química
10.
Phytochemistry ; 66(16): 1898-902, 2005 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-16061265

RESUMO

Incubation of stemodin (1) with Mucor plumbeus ATCC 4740 resulted in the formation of 2alpha,6beta,13-trihydroxystemodane (2), 2alpha,3beta,13-trihydroxystemodane (3), 2alpha,11beta,13-trihydroxystemodane (4) and 2alpha,13,14-trihydroxystemodane (5), while stemodinone (7) afforded 6alpha,13-dihydroxystemodan-2-one (8) and 6alpha,12alpha,13-trihydroxystemodan-2-one (9). Metabolites obtained from the bioconversion of stemarin (11) were 8,13,19-trihydroxystemarane (12) and 2alpha,13,19-trihydroxystemarane (13). 19-N,N-Dimethylcarbamoxy-13-hydroxystemarane (14) was not transformed by the fungus. Stemodin (1) was incubated with Whetzelinia sclerotiorum ATCC 18687 to produce 2alpha,7beta,13-trihydroxystemodane (6) and 2alpha,11beta,13-trihydroxystemodane (4). Stemodinone (7) was converted to 7beta,13-dihydroxystemodan-2-one (10). Compounds 2, 4, 9, 10, 12 and 13 have not been previously reported.


Assuntos
Ascomicetos/metabolismo , Diterpenos/metabolismo , Mucor/metabolismo , Meios de Cultura , Hidroxilação
11.
J Agric Food Chem ; 53(12): 4774-7, 2005 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-15941314

RESUMO

The chemical composition of the essential oil obtained by hydrodistillation from the aerial parts of Hyptis verticillata Jacq. was elucidated by a combination of GC and GC-MS analyses. The oil was dominated by the sesquiterpenoids cadina-4,10(15)-dien-3-one (15.1%) (1) and aromadendr-1(10)-en-9-one (squamulosone) (30.7%) (2). The oil exhibited chemosterilant activities against the cattle tick, Boophilus microplus Canest., and toxic action against adult Cylas formicarius elegantulus Summer, the most destructive pest of sweet potato (Ipomoea species).


Assuntos
Hyptis/química , Inseticidas , Óleos Voláteis/química , Animais , Cromatografia Gasosa , Besouros , Cromatografia Gasosa-Espectrometria de Massas , Ixodidae
12.
Phytochemistry ; 66(8): 901-9, 2005 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-15845408

RESUMO

Solvolytic rearrangement of the C/D ring system of the tetracyclic diterpenoid stemodinone (2) afforded the compounds 15(13-->12)abeo-13beta-hydroxystemaran-2-one (5) and 15(8-->9)abeo-8beta(H)-12beta-hydroxystachan-2-one (10). Terpene 5 possesses a novel diterpene skeleton. Oxidation of these compounds yielded their respective diketones. Bioconversion of 5 by Rhizopus oryzae yielded 15(13-->12)abeo-7beta,13beta-dihydroxystemaran-2-one (18) while microbial transformation of 10 provided 15(8-->9)abeo-8beta(H)-6alpha,12beta-dihydroxystachan-2-one (19), 15(8-->9)abeo-8beta(H)-7beta,12beta-dihydroxystachan-2-one (20) and 15(8-->9)abeo-8beta(H)-6alpha,12beta,14beta-trihydroxystachan-2-one (21). A rationale for the formation of the rearranged compounds is proposed.


Assuntos
Diterpenos/química , Diterpenos/metabolismo , Rhizopus/metabolismo , Scrophulariaceae/química , Biotransformação , Estrutura Molecular
13.
Phytochemistry ; 65(15): 2211-7, 2004 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-15587705

RESUMO

Incubation of 2alpha,13(R)-dihydroxystemodane (3) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(R)-trihydroxystemodane (11) while biotransformation of 13(R)-hydroxystemodan-2-one (5) yielded 6alpha,13(R)-dihydroxystemodan-2-one (12) and 7beta,13(R)-dihydroxystemodan-2-one (13). Bioconversion of 2beta,13(R)-dihydroxystemodane (7) with Rhizopus afforded 2beta,7,13(R)-trihydroxystemodane (14). The results complement data from our previous work and provide more information about the effect of functional groups of stemodane substrates on the site of hydroxylation.


Assuntos
Diterpenos/química , Diterpenos/metabolismo , Oxigênio/química , Rhizopus/metabolismo , Biotransformação , Catálise , Diterpenos/isolamento & purificação , Hidroxilação , Estrutura Molecular , Estereoisomerismo
14.
Steroids ; 69(3): 193-9, 2004 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-15072921

RESUMO

A number of metal trifluoroacetates were reacted with the olefin 3beta-acetoxyandrost-5-en-17-one (6). Palladium(II) trifluoroacetate afforded bis[micro-trifluoroacetato(alpha-5,7-eta-3beta-acetoxyandrostenyl-17-one)palladium(II)] (20), a new ring B pi-allyl steroid-palladium complex, in quantitative yield. Thallium(III) trifluoroacetate gave 3beta-acetoxy-5alpha-hydroxy-6beta-trifluoroacetoxyandrostan-17-one (16), 3beta-acetoxy-6beta-trifluoroacetoxyandrost-4-en-17-one (9), 3beta-acetoxy-4beta-trifluoroacetoxyandrost-5-en-17-one (10), and 3beta-acetoxy-5alpha,6beta-dihydroxyandrostan-17-one (17). Lead(IV) trifluoroacetate yielded 9, 10 and 16. 3beta-Acetoxy-5alpha,6beta-bis(trifluoroacetoxy)androstan-17-one (15), a new compound, was also formed in this reaction. During the course of the lead(IV) studies the dichlorosteroid 21 and the rearranged allylic oxidation product 24 were formed. Their formation was attributed to the generation of lead(IV) chloride in the reaction. Silver(I) and copper(II) trifluoroacetates proved to be unreactive towards 6.


Assuntos
Desidroepiandrosterona/análogos & derivados , Desidroepiandrosterona/química , Chumbo/química , Paládio/química , Tálio/química , Ácido Trifluoracético/química , Cristalografia , Dimerização
15.
Phytochemistry ; 65(6): 701-10, 2004 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-15016566

RESUMO

A new stemodinoside, stemodin-alpha-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2 alpha,7 beta,13(S)-trihydroxystemodane (17) and 2 alpha,3 beta,13(S),16 alpha-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6 alpha,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2 beta,13(S)-dihydroxystemodane (10) by the fungus yielded 2 beta,7 beta,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7 beta,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion.


Assuntos
Diterpenos/química , Diterpenos/metabolismo , Rhizopus/metabolismo , Arabinose/análogos & derivados , Biotransformação , Hidroxilação , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Rhizopus/genética , Scrophulariaceae/química , Triterpenos/química
16.
J Nat Prod ; 67(2): 179-83, 2004 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-14987055

RESUMO

Examination of the aerial portions of Cleome spinosa yielded five new cembranes, named cleospinols A (1), B (3), C (4), and D (5), and the 3'-hydroxy-iso-pentan-10-oate ester of cleospinol A (2). The cleospinols were determined to be derivatives of 10,13-dihydroxy-4,12-dimethyl-1-(1-methylethenyl)-11(E)-cyclotetradecene on the basis of spectroscopic data interpretation.


Assuntos
Cleome/química , Diterpenos/química , Plantas Medicinais/química , Jamaica , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Estereoisomerismo
17.
Phytochemistry ; 60(5): 475-81, 2002 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-12052513

RESUMO

The naturally occurring sesquiterpene squamulosone (1), isolated from Hyptis verticillata (Labiatae), was synthetically reduced to five analogues that were identified as (1S,10S)-9alpha-hydroxy-allo-aromadendrane (2), (1R,10R)-9beta-hydroxyaromadendrane (3), (1S,10S)-allo-aromadendran-9-one (4), (1R,10R)-aromadendran-9-one (5) and aromadendra-1,9-diene (6). Each congener was incubated with the fungus Curvularia lunata ATCC 12017 in two different growth media. All the substrates except the deoxy compound 6 underwent a simple redox reaction. Ketone 5 additionally experienced remote hydroxylation while analogue 6, possessing a conjugated diene system, was most extensively metabolised. The substrates and products presented here, but one, are all novel.


Assuntos
Fungos/metabolismo , Sesquiterpenos/química , Sesquiterpenos/metabolismo , Meios de Cultura , Fungos/química , Hidroxilação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Oxirredução
18.
Phytochemistry ; 59(5): 479-88, 2002 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-11853742

RESUMO

The sesquiterpenes cadina-4,10(15)-dien-3-one (1) and aromadendr-1(10)-en-9-one (squamulosone) (14) along with the triterpenoid methyl ursolate (21) were incubated with the fungus Mucor plumbeus ATCC 4740. Substrates 1, 14 and ursolic acid (20) were isolated from the plant Hyptis verticillata in large quantities. M. plumbeus hydroxylated 1 at C-12 and C-14. When the iron content of the medium was reduced, however, hydroxylation at these positions was also accompanied by epoxidation of the exocyclic double bond. In total nine new oxygenated cadinanes have been obtained. Sesquiterpene 14 was converted to the novel 2alpha,13-dihydroxy derivative along with four other metabolites. Methyl ursolate (21) was transformed to a new compound, methyl 3beta,7beta,21beta-trihydroxyursa-9(11),12-dien-28-oate (22). Two other triterpenoids, 3beta,28-dihydroxyurs-12-ene (uvaol) (23) and 3beta,28-bis(dimethylcarbamoxy)urs-12-ene (24) were not transformed by the micro-organism, however.


Assuntos
Lamiaceae/química , Mucor/metabolismo , Naftalenos/farmacocinética , Sesquiterpenos/farmacocinética , Triterpenos/farmacocinética , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Ultravioleta
19.
Phytochemistry ; 59(5): 489-92, 2002 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-11853743

RESUMO

Cadina-4,10(15)-dien-3-one (1) was metabolised by Curvularia lunata ATCC 12017 in two different growth media to give three metabolites, one of which, 12-hydroxycadina-4,10(15)-dien-3-one (4), was new. Incubation of 3alpha-hydroxycadina-4,10(15)-diene (2) with the fungus produced three new analogues, namely, (4S)-1alpha,3alpha-dihydroxycadin-10(15)-ene (5), 3alpha,14-dihydroxycadina-4,10(15)-diene (6) and 3alpha,12-dihydroxycadina-4,10(15)-diene (7).


Assuntos
Ascomicetos/metabolismo , Lamiaceae/química , Naftalenos/farmacocinética , Espectroscopia de Ressonância Magnética , Espectrofotometria Ultravioleta
20.
Phytochemistry ; 59(1): 57-62, 2002 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-11754944

RESUMO

Incubation of stemodin (1) in cultures of Aspergillus niger ATCC 9142 resulted in the production of 2alpha,3beta,13-trihydroxystemodane (2), 2alpha,7beta,13-trihydroxystemodane (3) and 2alpha,13,16beta-trihydroxystemodane (4), while stemodinone (5) afforded 13,18-dihydroxystemodan-2-one (6) and 13,16beta-dihydroxystemodan-2-one (7). Four novel metabolites were obtained from the bioconversion of stemarin (8) by the fungus, namely 18-hydroxystemaran-19-oic acid (9), 7beta,18-dihydroxystemaran-19-oic acid (10), 7alpha,18,19-trihydroxystemarane (11) and 1beta-hydroxystemaran-19-oic acid (12). 19-N,N-Dimethylcarbamoxy-13-hydroxystemarane (13) was also transformed to afford 19-N,N-dimethylcarbamoxy-13,17xi,18-trihydroxystemarane (14).


Assuntos
Aspergillus niger/metabolismo , Diterpenos/metabolismo , Plantas Medicinais/química , Biotransformação
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