Production of new ent-hardwickiic acid derivatives by microbial transformation and their antifungal activity
Copyright © 2023 Elsevier B.V. All rights reserved..
Ent-hardwickiic acid is the major compound of Copaifera pubiflora Benth oleoresin traditionally used in Brazilian folk medicine as an antimicrobial agent. Microbial transformation of ent-hardwickiic by Cunninghamella elegans ATCC 10028b resulted in two and five antifungal derivatives (four new ones) produced in the Czapek modified and Koch's K1 media, respectively. The derivatives were isolated and their structures were determined by spectral analysis, namely 1D/2D NMR and HR-ESIMS. All compounds were tested for cytotoxic and antifungal activities and they were not cytotoxic to the tested cell lines, but all derivatives showed fungicidal activity against Candida glabrata and Candida krusei, which have emerged as resistant to fluconazole. One of the yet unreported biotransformation products displayed the strongest activity with minimum fungicidal concentration values smaller than the other compounds, including fluconazole.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:173 |
|---|---|
| Enthalten in: |
Fitoterapia - 173(2024) vom: 16. Feb., Seite 105810 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Teixeira, Maria V S [VerfasserIn] |
|---|
| Links: |
|---|
| Anmerkungen: |
Date Completed 14.02.2024 Date Revised 14.02.2024 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1016/j.fitote.2023.105810 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM366540823 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM366540823 | ||
| 003 | DE-627 | ||
| 005 | 20240214233042.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240108s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.fitote.2023.105810 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1293.xml |
| 035 | |a (DE-627)NLM366540823 | ||
| 035 | |a (NLM)38163448 | ||
| 035 | |a (PII)S0367-326X(23)00385-4 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Teixeira, Maria V S |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Production of new ent-hardwickiic acid derivatives by microbial transformation and their antifungal activity |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 14.02.2024 | ||
| 500 | |a Date Revised 14.02.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2023 Elsevier B.V. All rights reserved. | ||
| 520 | |a Ent-hardwickiic acid is the major compound of Copaifera pubiflora Benth oleoresin traditionally used in Brazilian folk medicine as an antimicrobial agent. Microbial transformation of ent-hardwickiic by Cunninghamella elegans ATCC 10028b resulted in two and five antifungal derivatives (four new ones) produced in the Czapek modified and Koch's K1 media, respectively. The derivatives were isolated and their structures were determined by spectral analysis, namely 1D/2D NMR and HR-ESIMS. All compounds were tested for cytotoxic and antifungal activities and they were not cytotoxic to the tested cell lines, but all derivatives showed fungicidal activity against Candida glabrata and Candida krusei, which have emerged as resistant to fluconazole. One of the yet unreported biotransformation products displayed the strongest activity with minimum fungicidal concentration values smaller than the other compounds, including fluconazole | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Antifungal compounds | |
| 650 | 4 | |a Biotransformation | |
| 650 | 4 | |a Candida glabrata | |
| 650 | 4 | |a Candida krusei | |
| 650 | 4 | |a Cunninghamella elegans | |
| 650 | 4 | |a Ent-hardwickiic acid | |
| 650 | 7 | |a Antifungal Agents |2 NLM | |
| 650 | 7 | |a Fluconazole |2 NLM | |
| 650 | 7 | |a 8VZV102JFY |2 NLM | |
| 650 | 7 | |a hardwickic acid |2 NLM | |
| 650 | 7 | |a 24470-47-1 |2 NLM | |
| 650 | 7 | |a Diterpenes |2 NLM | |
| 700 | 1 | |a Fernandes, Lívia M |e verfasserin |4 aut | |
| 700 | 1 | |a de Paula, Vinícius S |e verfasserin |4 aut | |
| 700 | 1 | |a Ferreira, Antonio G |e verfasserin |4 aut | |
| 700 | 1 | |a Pires, Loren M |e verfasserin |4 aut | |
| 700 | 1 | |a Santos, Raquel A |e verfasserin |4 aut | |
| 700 | 1 | |a Furtado, Niege A J C |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Fitoterapia |d 1948 |g 173(2024) vom: 16. Feb., Seite 105810 |w (DE-627)NLM106553100 |x 1873-6971 |7 nnns |
| 773 | 1 | 8 | |g volume:173 |g year:2024 |g day:16 |g month:02 |g pages:105810 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.fitote.2023.105810 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 173 |j 2024 |b 16 |c 02 |h 105810 | ||