Biotransformation of an africanane sesquiterpene by the fungus Mucor plumbeus

Fraga, Braulio M.; Díaz, Carmen E.; Amador, Leonardo J.; Reina, Matı́as; López-Rodríguez, Matías; González-Coloma⊥, Azucena

doi:10.1016/j.phytochem.2016.12.015

Cited by 4 publications

(5 citation statements)

References 20 publications

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“…Two benzofuran derivatives, 6-hydroxytremetone β-D-glucoside ( 18 ) and 6,10,11-trihydroxytremetone ( 19 ), have been obtained from the biotransformation of 6-hydroxytremetone ( 1 ) with Mucor plumbeus ( Figure 3 ). This fungus has a broad specificity of substrate and has been used in the biotransformation of sesquiterpenes and diterpenes [ 38 , 39 , 40 ].…”

Section: Resultsmentioning

confidence: 99%

Insect Antifeedant Benzofurans from Pericallis Species

et al. 2023

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In this work, we have studied the benzofurans of Pericallis echinata (aerial parts and transformed roots), P. steetzii (aerial parts and transformed roots), P. lanata (aerial parts), and P. murrayi (aerial parts and roots). This work has permitted the isolation of the new benzofurans 10-ethoxy-11-hydroxy-10,11-dihydroeuparin (10), (-)-eupachinin A ethyl ether (12), 11,15-didehydro-eupachinin A (13), 10,12-dihydroxy-11-angelyloxy-10,11-dihydroeuparin (14), 2,4-dihydroxy-5-formyl-acetophenone (15) isolated for the first time as a natural product, 11-angelyloxy-10,11-dihydroeuparin (16), and 12-angelyloxyeuparone (17), along with several known ones (1–9, 11). In addition, the incubation of the abundant component, 6-hydroxytremetone (1), with the fungus Mucor plumbeus has been studied. Benzofurans in the tremetone series (1, 1a, 2–5, 18, 18a), the euparin series (6, 7, 7a, 8–10, 14, 16), and the eupachinin-type (11, 12) were tested for antifeedant effects against the insect Spodoptera littoralis. The antifeedant compounds (1, 4, 6, 11, 12) were further tested for postingestive effects on S. littoralis larvae. The most antifeedant compounds were among the tremetone series, with 3-ethoxy-hydroxy-tremetone (4) being the strongest antifeedant. Glucosylation of 1 by its biotransformation with Mucor plumbeus gave inactive products. Among the euparin series, the dihydroxyangelate 14 was the most active, followed by euparin (6). The eupachinin-type compounds (11, 12) were both antifeedants. Compounds 4, 11, and 12 showed antifeedant effects without postingestive toxicity to orally dosed S. littoralis larvae. Euparin (6) had postingestive toxicity that was enhanced by the synergist piperonyl butoxide.

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Section: Resultsmentioning

confidence: 99%

Insect Antifeedant Benzofurans from Pericallis Species

et al. 2023

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“…To complement these works, in order also to study their structure-activity relationship as potential pesticides, we expand this research to the sesquiterpenes. Thus, we have investigated the biotransformation of an africanane sesquiterpene by this fungus [ 18 ]. Now, continuing with these studies, and considering the good yield of 3α-hydroxypelenolide isolated from A. absinthium , we have biotransformed it by the fungus M. plumbeus affording two products 9 and 10 .…”

Section: Resultsmentioning

confidence: 99%

“…Biotransformations of terpenoids can modify the biological activities of the starting compounds [9] and are also used to study structure-activity relationships of bioactive compounds [10]. In this context, Mucor plumbeus, with a broad substrate specificity [11,12], has been used in biotransformations of diterpenes to develop models to explain their hydroxylations [13][14][15][16][17] and for the biotransformation of an africanane sesquiterpene to give epoxy Plants 2021, 10, 891 2 of 14 derivatives with improved insect antifeedants and insecticidal effects [18]. In this work we describe three unknown compounds, the sesquiterpene lactones absilactone (1) and hansonlactone (2) and the acetophenone derivative artenol (12) [4], isolated from A. absinthium var.…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpene Lactones from Artemisia absinthium. Biotransformation and Rearrangement of the Insect Antifeedant 3α-hydroxypelenolide

Fraga

Díaz

Bailén

et al. 2021

Plants

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Three new compounds, the sesquiterpenes absilactone and hansonlactone and the acetophenone derivative ajenjol, have been isolated from a cultivated variety of Artemisia absinthium. In addition, the major lactone isolated, 3α-hydroxypelenolide, was biotransformed by the fungus Mucor plumbeus affording the corresponding 1β, 10α-epoxide. A cadinane derivative was formed by an acid rearrangement produced in the culture medium, but not by the enzymatic system of the fungus. Furthermore, 3α-hydroxypelenolide showed strong antifeedant effects against Leptinotarsa decemlineata and cytotoxic activity to Sf9 insect cells, while the biotransformed compounds showed antifeedant postingestive effects against Spodoptera littoralis.

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“…Dry solvents were obtained by distillation with dehydration reagent by appropriate procedure. (14). To a stirred solution of 2-bromopropene (12) (1.51 mL, 12.4 mmol) in Et 2 O (20 mL) was added a 1.60 M pentane solution of t-BuLi (16.0 mL, 24.8 mmol) at À 78 °C.…”

Section: Generalmentioning

confidence: 99%

“…Fraga, González-Coloma, and co-workers reported the insect anti-feedant activities of several africanes that were isolated from transformed root cultures of a plant and exhibited insect cell-selective cytotoxicity. [13,14] Over the more than forty years since africanol (1) was isolated, the potential bioactivity of africanes has been discussed in several reports, [15,16] however, structure-activity relationship (SAR) studies to identify the most crucial functional group or architecture for activity were rarely included.…”

Section: Introductionmentioning

confidence: 99%

Scalable Syntheses and Biological Evaluation of Africane‐Type Sesquiterpenoids

Matsuda

Koyama

Kawano

et al. 2022

Chemistry & Biodiversity

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Practical total syntheses of africane-type sesquiterpenoids were realized by reexamination of a divergent strategy employing optimized three-component coupling followed by ring-closing metathesis and substratecontrolled cyclopropanation. This sequential eight-step conversion provided Δ 9(15) -africanene, a common bicyclo[5.3.0]decane intermediate for the syntheses of africane derivatives, in more than twice the yield as in the previous approach. The scalability and robustness of this improved synthetic route were confirmed by gramscale preparation of Δ 9(15) -africanene. In vitro cell-based assays of the synthesized africane-type sesquiterpenoids disclosed that ester-incorporating derivatives showed cytotoxic activity against HeLa cells. The effect of relative and absolute configuration of africane-9,15-diol monoacetates on the cytotoxicity against HeLa cells was also investigated.

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Biotransformation of an africanane sesquiterpene by the fungus Mucor plumbeus

Cited by 4 publications

References 20 publications

Insect Antifeedant Benzofurans from Pericallis Species

Insect Antifeedant Benzofurans from Pericallis Species

Sesquiterpene Lactones from Artemisia absinthium. Biotransformation and Rearrangement of the Insect Antifeedant 3α-hydroxypelenolide

Scalable Syntheses and Biological Evaluation of Africane‐Type Sesquiterpenoids

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