A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Microorganism
3.4. Extraction and Isolation of Euphoboetirane A (3) and Epoxyboetirane A (4)
3.5. Preparation of Epoxyboetirane A (4) by Epoxidation of Euphoboetirane A (3)
3.6. Preparation of Premyrsinane 5 by Cyclization of Epoxyboetirane A (4) with Cp2TiIIICl
3.7. Biotransformation of Premyrsinane 5 by Mucor circinelloides NRRL3631
3.8. Extraction, Isolation, and Characterization of Biotransformation Products
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Position | 5 | 6 | 7 | |||
---|---|---|---|---|---|---|
δH, Mult (J in Hz) | δC, Type | δH, Mult (J in Hz) | δC, Type | δH, Mult (J in Hz) | δC, Type | |
1α | 3.36, dd (15.1, 9.1) | 42.3, CH2 | 3.35, dd (15.1, 8.9) | 42.3, CH2 | 3.35, dd (15.1, 8.9) | 42.4, CH2 |
1β | 1.54, dd (15.1, 11.1) | 1.55, dd (15.1, 11.2) | 1.55, dd (15.1, 11.2) | |||
2 | 2.14–2.06, m | 37.0, CH | 2.11–2.06, m | 37.0, CH | 2.13–2.06, m | 37.3, CH |
3 | 5.34, t (3.6) | 78.5, CH | 5.34, t (3.5) | 78.4, CH | 5.35, t (3.5) | 78.4, CH |
4 | 2.65, dd (11.4, 3.6) | 51.9, CH | 2.66, dd (11.4, 3.5) | 51.9, CH | 2.63, dd (11.4, 3.5) | 51.8, CH |
5 | 5.41, d (11.4) | 74.7, CH | 5.42, d (11.4) | 74.7, CH | 5.50, d (11.4) | 75.1, CH |
6 | - | 44.1, C | - | 44.1, C | - | 48.0, C |
7α | 1.40, dt (14.1, 6.4) | 30.6, CH2 | 1.45, dd (13.8, 5.9) | 30.5, CH2 | 1.92, dd (13.8, 7.6) | 39.2, CH2 |
7β | 1.15–1.09, m | 1.12–1.05, m | 1.02, dd (13.8, 11.6) | |||
8α | 1.76–1.63, m | 15.8, CH2 | 1.80–1.70, m | 15.4, CH2 | 4.37, dt (11.6, 7.6) | 64.9, CH |
8β | 1.33–1.22, m | 1.40–1.33, m | - | |||
OH-8 | - | - | - | - | 1.31, d (5.2) | - |
9 | 0.70, ddd (9.4, 7.9, 4.5) | 21.7, a CH | 0.85, ddd (9.6, 7.5, 3.9) | 18.2, CH | 1.06, dd (9.4, 7.6) | 26.3, CH |
10 | - | 18.0, C | - | 24.3, C | - | 20.7, C |
11 | 0.11, dd (9.4, 6.7) | 27.1, CH | 0.34, dd (9.6, 6.2) | 24.0, CH | 0.40, dd (9.4, 4.8) | 32.0, CH |
12 | 1.76–1.63, m | 38.0, CH | 1.75, dd (11.4, 6.2) | 37.5, CH | 1.88, dd (11.7, 4.8) | 38.9, CH |
13 | 2.72–2.61, m | 50.6, CH | 2.73, dq (11.4, 7.5) | 51.0, CH | 2.58, dt (11.7, 7.4) | 50.7, CH |
14 | - | 209.0, C | - | 208.7, C | - | 208.3, C |
15 | - | 91.8, C | - | 91.7, C | - | 91.4, C |
16 | 0.87, d (6.7) | 14.1, CH3 | 0.87, d (6.7) | 14.0, CH3 | 0.88, d (6.7) | 13.9, CH3 |
17a | 3.84, d (11.3) | 63.2, CH2 | 3.87, dd (11.3, 2.5) | 62.8, CH2 | 3.86, dd (11.7, 2.5) | 61.8, CH2 |
17b | 3.68, d (11.3) | 3.71, dd (11.3, 6.9) | 3.67, dd (11.7, 8.2) | |||
OH-17 | - | - | 1.67, dd (6.9, 2.5) | - | 1.68, dd (8.2, 2.5) | - |
18a | 1.03, s | 28.2, CH3 | 3.41, d (10.4) | 72.8, CH2 | 1.12, s | 29.5, CH3 |
18b | 3.30, d (10.4) | |||||
19 | 0.99, s | 16.1, CH3 | 1.11, s | 11.7, CH3 | 1.24, s | 17.4, CH3 |
20 | 1.10, d (7.5) | 19.7, CH3 | 1.13, d (7.5) | 19.7, CH3 | 1.12, d (7.4) | 20.3, CH3 |
OCO-3 | - | 171.0, C | - | 170.0, C | - | 171.0, e C |
OCOMe-3 | 2.04, s | 21.0, b CH3 | 2.03, s | 21.0, c CH3 | 2.04, s | 21.2, d CH3 |
OCO-5 | - | 170.0, C | - | 171.0, C | - | 170.0, e C |
OCOMe-5 | 2.03, s | 21.2, b CH3 | 2.04, s | 21.2, c CH3 | 2.04, s | 21.0, d CH3 |
OCO-15 | - | 169.7, C | - | 169.7, C | - | 170.0, C |
OCOMe-15 | 2.12, s | 21.6, a CH3 | 2.14, s | 21.6, CH3 | 2.15, s | 21.6, CH3 |
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Escobar-Montaño, F.; Macías-Sánchez, A.J.; Botubol-Ares, J.M.; Durán-Patrón, R.; Hernández-Galán, R. A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity. Plants 2024, 13, 842. https://doi.org/10.3390/plants13060842
Escobar-Montaño F, Macías-Sánchez AJ, Botubol-Ares JM, Durán-Patrón R, Hernández-Galán R. A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity. Plants. 2024; 13(6):842. https://doi.org/10.3390/plants13060842
Chicago/Turabian StyleEscobar-Montaño, Felipe, Antonio J. Macías-Sánchez, José M. Botubol-Ares, Rosa Durán-Patrón, and Rosario Hernández-Galán. 2024. "A Biomimetic Approach to Premyrsinane-Type Diterpenoids: Exploring Microbial Transformation to Enhance Their Chemical Diversity" Plants 13, no. 6: 842. https://doi.org/10.3390/plants13060842