Biotransformation of the Diterpene<i>Ent</i>-18,19-dihydroxytrachylobane by<i>Rhizopus stolonifer</i>

Vasconcelos, Daniely H. P.; Mafezoli, Jair; Uchôa, Paula K. S.; Saraiva, Natália N; Lima, Mary Anne Sousa; Júnior, José N. Silva; Barbosa, Francisco Geraldo; Mattos, Marcos Carlos de; Oliveira, Maria C. F. de; Lima, Cristiano Souza; Pessoa, Maria Nenmaura Gomes

doi:10.5935/0103-5053.20150070

Cited by 4 publications

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“…Both products showed a double triplet at δ 0.57 ppm, typical of H-12 present in the cyclopropane ring of the starting material skeleton (Vasconselos et al 2015). Structure elucidation of the products was accomplished after careful analysis of 1 H and 13 C NMR spectra and by correlations found in HSQC, COSY, NOESY and HMBC spectra (Table I).…”

Section: Resultsmentioning

confidence: 99%

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

Santos

Takahashi

2017

An. Acad. Bras. Ciênc.

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The in vitro metabolism of a widespread natural product, trachyloban-19-oic acid (1), by the fungal species Mucor plumbeus was studied in a sucrose-yeast liquid medium. Two products were isolated, and their structures were determined by spectroscopic means as 7β-hydroxytrachyloban-19-oic acid (5) and trachyloban-19-O-β-D-glucopyranosyl ester (6). To the best of our knowledge, compound 6 is herein reported by the first time in the literature. These compounds were assayed for acetylcholinesterase inhibition along with some related compounds. Compound 6 showed the highest acetylcholinesterase inhibitory activity at 10000 µg/mL among the tested compounds, a result (92.89%) comparable to the activity of the positive control, galanthamine (94.21%). Therefore, biotransformation of the natural product 1 by M. plumbeus produced a novel compound with potential as a new lead to develop anti-Alzheimer medicines.

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Section: Resultsmentioning

confidence: 99%

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

Santos

Takahashi

2017

An. Acad. Bras. Ciênc.

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“…The fungus Rhizopus stolonifer was used in the biotransformation of the diterpene ent -18,19-dihydroxytrachylobane (compound 15 in Figure 16 ) and yielded the new ent -11β,18,19-trihydroxytrachylobane ( 15.1 ) via C-11 hydroxylation of precursor 15 [ 64 ]. The biotransformation of 15 , which is an ent -trachyloban type diterpene, also yielded the new ent -kaurene type diterpenes ent -16α,18,19-trihydroxykaur-11-ene ( 15.2 ) and ent -18,19-dihydroxy-16α-methoxykaur-11-ene ( 15.3 ) ( Figure 16 ).…”

Section: Biotransformation Of Diterpenesmentioning

confidence: 99%

“… Chemical structures of 15 and its derivatives 15.1 , 15.2 and 15.3 obtained by biotransformation with Rhizopus stolonifer [ 64 ] . …”

Section: Figurementioning

confidence: 99%

An Overview of Biotransformation and Toxicity of Diterpenes

2018

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Diterpenes have been identified as active compounds in several medicinal plants showing remarkable biological activities, and some isolated diterpenes are produced at commercial scale to be used as medicines, food additives, in the synthesis of fragrances, or in agriculture. There is great interest in developing methods to obtain derivatives of these compounds, and biotransformation processes are interesting tools for the structural modification of natural products with complex chemical structures. Biotransformation processes also have a crucial role in drug development and/or optimization. The understanding of the metabolic pathways for both phase I and II biotransformation of new drug candidates is mandatory for toxicity and efficacy evaluation and part of preclinical studies. This review presents an overview of biotransformation processes of diterpenes carried out by microorganisms, plant cell cultures, animal and human liver microsomes, and rats, chickens, and swine in vivo and highlights the main enzymatic reactions involved in these processes and the role of diterpenes that may be effectively exploited by other fields.

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“…This is not surprising, since the literature is full of works that demonstrate the enzymatic versatility of microorganisms, such as fungi, for example, against the most different substrates. Hydrolytic enzymes from yeasts [23][24][25] of skills between fungus and host plant, also contribute to knowledge secondary metabolites from this fungi.…”

Section: Issnmentioning

confidence: 99%

Terpenoids and Phytosterols Isolated From Plumeria Rubra L., Form Acutifolia (Ait) Woodson and Its Fungus Parasite Colesporium Plumeriae

Resende

Pinto

et al. 2018

Asian J Pharm Res Dev

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The hexane and ethyl acetate extracts of the leaves from Plumeria rubra L., form acutifolia (Ait) Woodson and the methanolic extract from the fungus Coleosporium plumeriae Pat. were analized by high resolution gas chromatography (HRGC) and by high resolution gas chromatography coupled to mass spectrometes (GC-MS). The identification of the chemical constituintes is these extracts has been made by the automatic comparison of the mass spectra obtained standards within the NBS, Wiley and Wiley 275T librarys supplied with the mass spectrometer and by analized of the principal fragmentations. Phytochemical studies of the hexane and ethyl acetate extracts of the leaves showed nine terpenoids (5-ergosten-3b-ol, 5,22-stigmastadien-3b-ol, 4-stigmasten-3-one, 5-stigmasten-3b-ol, 12-ursen-3b-ol, 12-oleanen-3b-ol, 12-oleanen-3-one-28-oic acid, ursolic acid and 3b-acetoxy-12-oleanen-28-oic acid). The compounds 5-ergosten-3b-ol, 4-stigmasten-3-one, 12-oleanen-3-one-28-oic acid, ursolic acid and 3b-acetoxy-12-oleanen-28-oic acid have been described for the first time from Plumeria rubra L., forma acutifolia (Ait) Woodson. From the methanolic extract of spores of the fungus Coleosporium plumeriae Pat were isolated 5-stigmasten-3b-ol, methyl esters of long chain fatty acids (C18:0, principally) and one aromatic compound, N-methyl toluenesulfonamide. No previous phytochemical studies of this fungus have been reported.

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Biotransformation of the DiterpeneEnt-18,19-dihydroxytrachylobane byRhizopus stolonifer

Cited by 4 publications

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A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

An Overview of Biotransformation and Toxicity of Diterpenes

Terpenoids and Phytosterols Isolated From Plumeria Rubra L., Form Acutifolia (Ait) Woodson and Its Fungus Parasite Colesporium Plumeriae

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