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 networking
- GNPS Molecular Networking jobs: (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=1abcf2c49b9a43cf85e19b8573eeb8a7) (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=2794a93e36724eaebafa0e1c3fb1aeb9) (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=430bfc8c34974e418156d8c6e711bd35).
- CMB-F585 molecular networking
- GNPS Molecular Networking job: (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=ae56648aefa54f789e04cfc314cb59fc).
- CMB-F115 molecular networking
- GNPS Molecular Networking job: (https://gnps.ucsd.edu/ProteoSAFe/status.jsp?task=e90bdf9596ff4bbfb9e4eb200435a2b1).
- CMB-F458 molecular networking
- 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