Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi
Abstract
1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Fungal Strain Isolation and Taxonomy
3.3. Scale up Cultivation of Scopulariopsis sp. CMB-F458
3.4. Scale-Up Cultivation of Beauveria sp. CMB-F585
3.5. Scale-Up Cultivation of Scopulariopsis sp. CMB-F115
3.6. Metabolite Charcterization
- Scopularide A (1); white powder; [α]D22.8 − 34.9 (c 0.25, MeOH); NMR (600 MHz, MeOH-d4) see Table S1, Figures S6 and S7; NMR (600 MHz, DMSO-d6) see Table S2, Figures S8 and S9; ESI(+)MS m/z 672 [M + H]+; HRESI(+)MS m/z 694.4149 [M + Na]+ (calcd. for C36H57N5O7Na, 694.4150); GNPS library CCMSLIB00005436489.
- Scopularide B (2); white powder; [α]D22.2 − 19.8 (c 0.05, MeOH); NMR (600 MHz, MeOH-d4) see Table S3, Figures S10 and S11; NMR (600 MHz, DMSO-d6) see Table S4, Figures S12 and S13; ESI(+)MS m/z 644 [M + H]+; HRESI(+)MS m/z 666.3842 [M + Na]+ (calcd. for C34H53N5O7Na, 666.3837); GNPS library CCMSLIB00005436490.
- Scopularide C (3); white powder; [α]D22.2 − 32.0 (c 0.13, MeOH); NMR (600 MHz, DMSO-d6) see Table 1 and Table S5, Figures S14–S18; ESI(+)MS m/z 714 [M + H]+; HRESI(+)MS m/z 736.4638 [M + Na]+ (calcd. for C39H63N5O7Na, 736.4620); GNPS library CCMSLIB00005436483.
- Scopularide D (4); white powder; [α]D21.9 − 40.9 (c 0.13, MeOH); NMR (600 MHz, DMSO-d6) see Table 1 and Table S6, Figures S19–S23; ESI(+)MS m/z 666 [M + H]+; HRESI(+)MS m/z 688.4620 [M + Na]+ (calcd. for C35H63N5O7Na, 688.4620); GNPS library CCMSLIB00005436484.
- Scopularide E (5); white powder; [α]D21.6 − 19.2 (c 0.13, MeOH); NMR (600 MHz, DMSO-d6) see Table 1 and Table S7, Figures S24–S28; ESI(+)MS m/z 638 [M + H]+; HRESI(+)MS m/z 660.4313 [M + Na]+ (calcd. for C33H59N5O7Na, 660.4307); GNPS library CCMSLIB00005436485.
- Scopularide F (6); white powder; [α]D24.2 − 17.5 (c 0.1, MeOH); NMR (600 MHz, DMSO-d6) see Table 2 and Table S8, Figures S29–S33; ESI(+)MS m/z 728 [M + H]+; HRESI(+)MS m/z 750.4787 [M + Na]+ (calcd. for C40H65N5O7Na, 750.4776); GNPS library CCMSLIB00005436486.
- Scopularide G (7); white powder; ESI(+)MS m/z 680 [M + H]+; HRESI(+)MS m/z 702.4789 [M + Na]+ (calcd. for C36H65N5O7Na, 702.4776) GNPS library CCMSLIB00005436487.
- Scopularide H (8); white powder; [α]D22.2 − 31.0 (c 0.15, MeOH); NMR (600 MHz, DMSO-d6) see Table 2 and Table S9, Figures S34–S38; ESI(+)MS m/z 700 [M + H]+; HRESI(+)MS m/z 722.4464 [M + Na]+ (calcd. for C38H61N5O7Na, 722.4463); GNPS library CCMSLIB00005436488.
3.7. C3 Marfey’s Analyses
3.8. Global Natural Product Social (GNPS) Molecular Networking
- Fish microbial library molecular networkingMASSIVE: MSV000084190 (https://massive.ucsd.edu/ProteoSAFe/dataset.jsp?task=479a543e9b45408bbe93414769058784).
- CMB-F585 molecular networkingMASSIVE: MSV000084191 (https://massive.ucsd.edu/ProteoSAFe/dataset.jsp?task=4dee2595568c4296a1c4393de4758b24).
- GNPS Molecular Networking job: (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=ae56648aefa54f789e04cfc314cb59fc).
- CMB-F115 molecular networkingMASSIVE: MSV000084192 (https://massive.ucsd.edu/ProteoSAFe/dataset.jsp?task=74da14126ec24f2ca62ba443a05af7d2).
- GNPS Molecular Networking job: (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=e90bdf9596ff4bbfb9e4eb200435a2b1).
- CMB-F458 molecular networkingMASSIVE: MSV000084193 (https://massive.ucsd.edu/ProteoSAFe/dataset.jsp?task=4b0ec7ee53c34a299fe1828588ead84d).
- GNPS Molecular Networking: (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=3c2af674f0a248c39149993d91a8149e)
3.9. X-Ray Analysis of Scopularides C (3) and H (8)
3.10. Antibacterial Assay
3.11. Antifungal Assay
3.12. Cytotoxicity Assay
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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(3) | (4) | (5) | ||||
---|---|---|---|---|---|---|
Position | δH, mult (J in Hz) | δC | δH, mult (J in Hz) | δC | δH, mult (J in Hz) | δC |
l-Phe1 | l-Val1 | l-Ala1 | ||||
1 | --- | 170.8 | --- | 170.7 | --- | 171.7 g |
2 | 4.38, q (7.1) | 54.2 | 4.15, dd (7.8, 5.3) | 57.3 | 4.13, dq (7.4, 6.0) | 48.1 |
3 | a 3.01, dd (13.9, 6.1) b 2.93, d (13.9, 8.7) | 36.7 | 2.08, m | 29.7 | 1.28, d (7.4) | 16.7 |
4 | --- | 137.2 | 0.87, d (6.8) | 19.0 | ||
5/9 | 7.25, m | 129.0 | 0.85a, d (7.0) | 17.4 | ||
6/8 | 7.28, m | 128.2 | ||||
7 | 7.20, m | 126.5 | ||||
NH | 7.96, d (7.1) | --- | 7.41, d (7.1) | --- | 7.80, d (6.0) | --- |
l-Ala2 | l-Ala2 | l-Ala2 | ||||
1 | --- | 171.7f | --- | 171.8 | --- | 171.5 |
2 | 4.16, dq (7.4, 7.1) | 47.6 | 4.19, dq (8.0, 7.1) | 47.9 | 4.18, dq (7.1, 6.5) | 47.5 |
3 | 1.15, d (7.1) | 17.6 | 1.21, d (7.1) | 17.5 | 1.19, d (7.1) | 17.4 |
NH | 7.84, d (7.4) | --- | 8.03, d (8.0) | --- | 7.89, d (6.5) | --- |
d-Leu3 | d-Leu3 | d-Leu3 | ||||
1 | --- | 171.0 | --- | 171.3 | --- | 171.1 |
2 | 4.03, m | 52.0 | 4.04, dd (10.1, 6.5) | 51.9 | 4.03, dd (11.4, 6.3) | 51.8 |
3 | 1.46, m | 38.7 | 1.48, m | 38.7 | a 1.49, m b 1.47 a, m | 38.6 |
4 | 1.63, m | 24.1 | 1.63, m | 24.1 | 1.63, m | 24.1 |
5 | 0.88, d (6.5) | 22.9 | 0.89 b, d (6.7) | 22.9 | 0.89, d (6.7) | 23.0 |
6 | 0.81, d (6.6) | 21.0 | 0.81, d (6.6) | 21.0 | 0.81, d (6.5) | 21.1 |
NH | 8.62, d (6.1) | --- | 8.63, d (6.5) | --- | 8.64, d (6.3) | --- |
l-Val4 | l-Val4 | l-Val4 | ||||
1 | --- | 171.7f | --- | 171.6 | --- | 171.6 g |
2 | 4.10, dd (8.6, 7.6) | 58.3 | 4.06 c, m | 58.6 | 4.11, dd (8.2, 6.6) | 58.1 |
3 | 1.88, m | 29.8 | 1.86, m | 29.5 | 1.85, m | 29.9 |
4 | 0.87, d (6.4) | 18.9 | 0.88 b, d (6.8) | 19.0 | 0.87, d (6.9) | 18.8 |
5 | 0.83, d (6.6) | 18.7 | 0.83 d, d (6.8) | 18.7 | 0.83, d (6.7) | 18.7 |
NH | 7.92 a, d (7.6) | --- | 8.06, d (7.8) | --- | 7.87, d (6.6) | --- |
Gly5 | Gly5 | Gly5 | ||||
1 | --- | 168.9 | --- | 169.0 | --- | 168.8 |
2 | a 4.07, dd (16.7, 6.6) b 3.41, dd (16.7, 3.9) | 42.3 | a 4.06 c, m b 3.44, dd (17.1, 3.8) | 42.0 | a 4.06, dd (16.5, 6.6) b 3.43, dd (16.5, 4.0) | 42.3 |
NH | 7.91 a, dd (6.5, 3.9) | --- | 7.90, dd (5.8, 3.8) | --- | 7.82, dd (6.1, 4.0) | --- |
HDMLA | HDMLA | HDMLA | ||||
1′ | --- | 169.8 | --- | 170.0 | --- | 169.8 |
2′ | a 2.51, dd (15.2, 9.8) b 2.25, d (15.2, 1.4) | 37.7 | a 2.52, dd (14.5, 9.6) b 2.23, dd (14.5, 1.4) | 38.0 | a 2.53, dd (14.7, 10.1) b 2.24, dd (14.7, 1.8) | 37.7 |
3′ | 4.94, ddd (9.1, 5.1, 1.8) | 74.8 | 4.92, ddd (9.3, 4.8, 1.4) | 75.2 | 4.97, ddd (10.1, 4.8, 1.8) | 74.2 |
4′ | 1.68, m | 33.7 | 1.79, m | 33.9 | 1.75, m | 33.8 |
5′ | a 1.18 b, m b 0.75, m | 39.5h | a 1.29, m b 0.87, m | 39.6h | a 1.26, m b 0.84, m | 39.6 h |
6′ | 1.41, m | 29.3 | 1.44, m | 29.3 | 1.46 a, m | 29.2 |
7′ | a 1.19 b, m b 0.95, m | 35.7 | a 1.22 e, m b 0.98, m | 36.0 | a 1.23 b, m b 0.99, m | 35.8 |
8′ | 1.20 b, m | 26.1 | a 1.26, m b 1.16, m | 26.1 | a 1.24, m b 1.16, m | 26.1 |
9′ | 1.22 c, m | 29.1 | a 1.22 e, m b 1.19, m | 29.1 | 1.23 b, m | 29.0 |
10′ | 1.22 c, m | 31.3 | 1.23 e, m | 31.3 | 1.23 b, m | 31.3 |
11′ | 1.24, m | 22.1 | 1.25, m | 22.1 | 1.26, m | 22.1 |
12′ | 0.84, t (6.9) | 13.9 | 0.85 a, t (7.9) | 13.9 | 0.85, t (7.1) | 13.9 |
4′-Me | 0.70, d (6.7) | 14.8 | 0.84 d, d (8.0) | 15.1 | 0.82, d (6.4) | 15.0 |
6′-Me | 0.80, d (6.6) | 20.2 | 0.83 d, d (7.4) | 20.0 | 0.83, d (6.7) | 20.2 |
(6) | (8) | |||
---|---|---|---|---|
Position | δH, mult (J in Hz) | δC | δH, mult (J in Hz) | δC |
l-Phe1 | l-Phe1 | |||
1 | --- | 170.9 | --- | 170.8 |
2 | 4.38, m | 54.3 | 4.34, q (7.4) | 54.5 |
3 | a 2.97, dd (13.9, 6.1) b 2.95, dd (13.9, 8.4) | 36.7 | 2.98, m | 36.7 |
4 | --- | 137.1 | --- | 137.2 |
5/9 | 7.26, m | 128.9 | 7.26, m | 129.1 |
6/8 | 7.28, m | 128.3 | 7.26, m | 128.2 |
7 | 7.21, m | 126.6 | 7.20, m | 126.5 |
NH | 8.14, d (6.5) | --- | 8.03, d (6.7) | --- |
l-Abu2 | l-Ala2 | |||
1 | --- | 171.0 | --- | 171.8 |
2 | 4.08 a, m | 52.9 | 4.19, dq (8.1, 7.1) | 47.6 |
3 | a 1.74, m b 1.48 b, m | 24.4 | 1.15, d (7.1) | 17.6 |
4 | 0.73, t (7.2) | 9.5 | ||
NH | 7.67, d (8.0) | --- | 7.83, d (8.1) | --- |
d-Leu3 | d-Leu3 | |||
1 | --- | 171.1 | --- | 171.0 |
2 | 4.09 a, m | 51.8 | 4.03, m | 52.0 |
3 | 1.47 b, m | 38.6 | a 1.47, m b 1.44, m | 38.7 |
4 | 1.61, m | 24.1 | 1.63, m | 24.1 |
5 | 0.88, d (6.5) | 22.8 | 0.89, d (6.5) | 22.9 |
6 | 0.81, d (6.8) | 21.2 | 0.82 d, d (6.5) | 21.1 |
NH | 8.62, d (6.3) | --- | 8.63, d (6.0) | --- |
l-Val4 | l-Val4 | |||
1 | --- | 171.6 | --- | 171.7 |
2 | 4.15, dd (8.9, 8.7) | 58.1 | 4.10, dd (8.6, 7.9) | 58.3 |
3 | 1.88, m | 29.9 | 1.87, m | 29.8 |
4 | 0.86, d (6.7) | 18.8 | 0.88 c, d (6.2) | 18.9 |
5 | 0.83 f, d (6.6) | 18.7 | 0.81 d, d (6.1) | 18.7 |
NH | 7.86, d (8.9) | --- | 7.88, d (7.9) | --- |
Gly5 | Gly5 | |||
1 | --- | 168.6 | --- | 168.9 |
2 | a 4.01, dd (16.7, 6.3) b 3.42, dd (16.7, 4.7) | 42.4 | a 4.07, dd (16.6, 6.4) b 3.40, dd (16.6, 4.1) | 42.3 |
NH | 7.85, dd (5.6, 4.7) | --- | 7.93, dd (6.4, 4.1) | --- |
HDMLA | HMLA | |||
1′ | --- | 169.8 | --- | 169.8 |
2′ | a 2.53, dd (14.8, 9.4) b 2.24, dd (14.8, 1.2) | 37.9 | a 2.48, dd (14.9, 9.2) b 2.24, dd (14.9, 1.8) | 37.0 |
3′ | 4.94, ddd (9.1, 3.2, 1.8) | 74.7 | 4.90, ddd (9.2, 5.7, 1.8) | 75.1 |
4′ | 1.66, m | 33.9 | 1.50, m | 36.1 |
5’ | a 1.17 e, m b 0.75, m | 39.6f | a 1.19 b, m b 0.87 c, m | 31.4 |
6′ | 1.41, m | 29.2 | a 1.19 b, m b 1.09, m | 26.5 |
7′ | a 1.19, m b 0.95, m | 35.8 | 1.18 b, m | 29.3 |
8′ | a 1.25 c, m b 1.17 e, m | 26.1 | 1.23 a, m | 28.9 |
9′ | 1.22 d, m | 29.1 | 1.23 a, m | 28.7 |
10′ | 1.22 d, m | 31.3 | 1.23 a, m | 31.3 |
11′ | 1.24 c, m | 22.1 | 1.25, m | 22.1 |
12′ | 0.83 f, t (6.9) | 13.9 | 0.85, t (6.6) | 13.9 |
4′-Me | 0.69, d (6.7) | 14.8 | 0.67, d (6.9) | 14.5 |
6′-Me | 0.80, d (6.8) | 20.1 |
Compound | aa1 | aa2 | aa3 | aa4 | aa5 | Compound | aa1 | aa2 | aa3 | aa4 | aa5 |
---|---|---|---|---|---|---|---|---|---|---|---|
scopularide A [2] | l-Phe | l-Ala | d-Leu | l-Val | Gly | iso-isariin D [17] | l-Ala | l-Ala | d-Leu | l-Val | Gly |
scopularide B [2] | l-Phe | l-Ala | d-Leu | l-Val | Gly | isariin G2 [15] | l-Ala | l-Ala | d-Leu | l-Val | Gly |
scopularide C | l-Phe | l-Ala | d-Leu | l-Val | Gly | scopularide E | l-Ala | l-Ala | d-Leu | l-Val | Gly |
scopularide H | l-Phe | l-Ala | d-Leu | l-Val | Gly | isariin F1 [15] | Abu/Aib | l-Ala | d-Leu | l-Val | Gly |
chrysogeamide A [6] | l-Val | l-Ala | d-Leu | l-Val | Gly | scopularide F | l-Phe | l-Abu | d-Leu | l-Val | Gly |
chrysogeamide B [6] | l-Val | l-Ala | d-Leu | l-Val | Gly | chrysogeamide C [6] | l-Phe | l-Ala | d-Leu | d-Leu | Gly |
scopularide D | l-Val | l-Ala | d-Leu | l-Val | Gly | chrysogeamide D [6] | l-Phe | l-Ala | d-Leu | d-Leu | Gly |
nodupetide [9] | l-Val | l-Ala | d-Leu | l-Val | Gly | chrysogeamide E [6] | l-Phe | l-Ala | d-Leu | d-Leu | Gly |
isariin A [10,11] | l-Val | l-Ala | d-Leu | l-Val | Gly | chrysogeamide F [6] | l-Phe | l-Ala | d-Leu | l-Pro | Gly |
isariin B [12,13,14] | l-Val | l-Ala | d-Leu | l-Val | Gly | chrysogeamide G [6] | l-Phe | l-Ala | d-Leu | l-Pro | Gly |
iso-isariin B [16] | l-Val | l-Ala | d-Leu | l-Val | Gly | scopularide G | l-Val | l-Abu | d-Leu | l-Val | Gly |
isariin C2 [15] | l-Val | l-Ala | d-Leu | l-Val | Gly | emericellamide A [7] | l-Ala | l-Ala | l-Leu | l-Val | Gly |
isariin E [15] | l-Val | l-Ala | d-Leu | l-Val | Gly | emericellamide B [7] | l-Ala | l-Ala | l-Leu | l-Val | Gly |
isariin F2 [15] | l-Val | l-Ala | d-Leu | l-Val | Gly | emericellamide C [8] | l-Ala | l-Ala | l-Leu | l-Val | Gly |
isariin G1 [15] | l-Val | l-Ala | d-Leu | l-Val | Gly | emericellamide D [8] | l-Ala | l-Ala | l-Leu | l-Val | Gly |
oryzamide A [5] | l-Leu | l-Ala | d-Leu | l-Val | Gly | emericellamide E [8] | l-Ala | l-Ala | l-Leu | l-Val | Gly |
oryzamide B [5] | l-Tyr | l-Ala | d-Leu | l-Val | Gly | emericellamide F [8] | l-Ala | l-Ala | l-Leu | l-Val | Gly |
oryzamide C [5] | l-Met | l-Ala | d-Leu | l-Val | Gly | arenamide A [18] | l-Phe | l-Ala | l-Leu | l-Val | Gly |
isariin C [13,14] | l-Ala | l-Ala | d-Leu | l-Val | Gly | arenamide B [18] | l-Phe | l-Ala | l-Leu | l-Val | Gly |
isariin D [13,14] | l-Ala | l-Ala | d-Leu | l-Val | Gly | arenamide C [18] | l-Met | l-Ala | l-Leu | l-Val | Gly |
Structure a | |||||||||
compound | n | R | compound | n | R | ||||
isariin E * [15] | 1 | H | iso-isariin B * [16] | 3 | Me | ||||
iso-isariin D [17] | 1 | Me | isariin B [12,13,14] | 4 | H | ||||
nodupetide [9] | 1 | Me | isariin C * [13,14] | 4 | H | ||||
chrysogeamide D [6] | 1 | Me | isariin F1* [15] | 4 | H | ||||
isariin C2 * [15] | 2 | H | isariin G1 * [15] | 5 | H | ||||
isariin D * [13,14] | 2 | H | isariin A [10,11,19] | 7 | H | ||||
isariin F2 * [15] | 3 | H | isariin G2 * [15] | 7 | H | ||||
Structure b | |||||||||
compound | n | R1 | R2 | R3 | compound | n | R1 | R2 | R3 |
scopularide B [2] | 1 | H | Me | H | arenamide A [18,20] | 3 | H | Me | H |
chrysogeamide A [6] | 1 | H | Me | H | arenamide C [18,20] | 3 | H | Me | H |
chrysogeamide E [6] | 1 | H | Me | H | emericellamide A [7] | 3 | Me | Me | H |
chrysogeamide F [6] | 1 | H | Me | H | emericellamide C [8] | 3 | Me | H | H |
arenamide B [18,20] | 1 | H | Me | H | emericellamide E [8] | 5 | Me | H | H |
scopularide A [2] | 3 | H | Me | H | emericellamide F [8] | 5 | H | Me | H |
chrysogeamide B [6] | 3 | H | Me | H | scopularide H | 5 | H | Me | H |
chrysogeamide C [6] | 3 | H | Me | H | scopularide C | 5 | H | Me | Me |
chrysogeamide G [6] | 3 | H | Me | H | scopularide D | 5 | H | Me | Me |
oryzamide A [5] | 3 | H | Me | H | scopularide E | 5 | H | Me | Me |
oryzamide B [5] | 3 | H | Me | H | scopularide F | 5 | H | Me | Me |
oryzamide C [5] | 3 | H | Me | H | scopularide G | 5 | H | Me | Me |
emericellamide D [8] | 3 | H | Me | H | emericellamide B [7] | 5 | Me | Me | Me |
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Elbanna, A.H.; Khalil, Z.G.; Bernhardt, P.V.; Capon, R.J. Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi. Mar. Drugs 2019, 17, 475. https://doi.org/10.3390/md17080475
Elbanna AH, Khalil ZG, Bernhardt PV, Capon RJ. Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi. Marine Drugs. 2019; 17(8):475. https://doi.org/10.3390/md17080475
Chicago/Turabian StyleElbanna, Ahmed H., Zeinab G. Khalil, Paul V. Bernhardt, and Robert J. Capon. 2019. "Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi" Marine Drugs 17, no. 8: 475. https://doi.org/10.3390/md17080475
APA StyleElbanna, A. H., Khalil, Z. G., Bernhardt, P. V., & Capon, R. J. (2019). Scopularides Revisited: Molecular Networking Guided Exploration of Lipodepsipeptides in Australian Marine Fish Gastrointestinal Tract-Derived Fungi. Marine Drugs, 17(8), 475. https://doi.org/10.3390/md17080475