Unprecedented Antimicrobial and Cytotoxic Polyketides from Cultures of Diaporthe africana sp. nov.
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experimental Procedures
2.2. Fungal Isolation and Identification
2.3. Fermentation and Extraction
2.4. Isolation of Compounds 1–8
2.5. Determination of Amino Acid Stereochemistry
2.6. Antimicrobial and Cytotoxic Activities
3. Results and Discussion
3.1. Molecular Phylogeny and Taxonomy
3.2. Structural Elucidation of Compounds 1–8
3.3. Physicochemical Data for Compounds 1–4, 7
3.4. Biological Activities of Compounds 1–8
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Species | Isolates 1 | GenBank Accession Numbers 2 | References | ||||
---|---|---|---|---|---|---|---|
ITS | tub2 | his3 | tef1 | cal | |||
Diaporthe acuta | PSCG 047T | MK626957 | MK691225 | MK726161 | MK654802 | MK691125 | Guo et al. [23] |
D. africana | CBS 150080T | OR198681 | OR225229 | OR225231 | OR225227 | OR225233 | Present study |
STMA 18294 | OR198680 | OR225230 | OR225232 | OR225228 | OR225234 | Present study | |
D. amygdali | CBS 126679T | KC343022 | KC343990 | KC343506 | KC343748 | KC343264 | Gomes et al. [24] |
D. anhuiensis | CNUCC 201902T | MN219727 | MN227009 | MN224550 | MN224669 | MN224556 | Zhou and Hou [25] |
D. annellsiae | BRIP 59731aT | OM918687 | OM960614 | - | OM960596 | - | Tan and Shivas [26] |
D. arecae | CBS 161.64T | KC343032 | KC344000 | KC343516 | KC343758 | KC343274 | Gomes et al. [24] |
D. arengae | CBS 114979T | KC343034 | KC344002 | KC343518 | KC343760 | KC343276 | Gomes et al. [24] |
D. aseana | MFLUCC 12-0299aT | KT459414 | KT459432 | - | KT459448 | KT459464 | Hyde et al. [27] |
D. australiana | BRIP 66145T | MN708222 | MN696530 | - | MN696522 | - | Wrona et al. [28] |
D. averrhoae | SCHM 3605T | AY618930 | - | - | - | - | Chang et al. [29] |
D. bounty | BRIP 59361aT | OM918690 | OM960617 | - | OM960599 | - | Tan and Shivas [26] |
D. camelliae-oleiferae | HNZZ 027T | MZ509555 | MZ504718 | MZ504696 | MZ504707 | MZ504685 | Yang et al. [30] |
D. ceratozamiae | CBS 131306T | JQ044420 | - | - | - | - | Crous et al. [31] |
D. cercidis | CFCC 52565T | MH121500 | MH121582 | MH121460 | MH121542 | MH121424 | Yang et al. [32] |
D. cf. heveae | CBS 681.84 | KC343117 | KC344085 | KC343601 | KC343843 | KC343359 | Gomes et al. [24] |
D. chiangmaiensis | MFLUCC 18-0544T | OK393703 | - | - | OL439483 | - | de Silva et al. [33] |
D. chrysalidocarpi | SAUCC 194.35T | MT822563 | MT855760 | MT855532 | MT855876 | MT855646 | Huang et al. [34] |
D. delonicis | MFLU 16-1059T | MT215490 | MT212209 | - | - | - | Perera et al. [35] |
D. drenthii | BRIP 66524T | MN708229 | MN696537 | - | MN696526 | - | Wrona et al. [28] |
D. endocitricola | ZHKUCC 20-0012T | MT355682 | MT409290 | - | MT409336 | MT409312 | Dong et al. [36] |
D. eres | CBS 138594T | KJ210529 | KJ420799 | KJ420850 | KJ210550 | KJ434999 | Udayanga et al. [37] |
D. eucalyptorum | CBS 132525T | JX069862 | - | - | - | - | Crous et al. [38] |
D. eugeniae | CBS 444.82 | KC343098 | KC344066 | KC343582 | KC343824 | KC343340 | Gomes et al. [24] |
D. fraxini-angustifoliae | BRIP 54781T | JX862528 | KF170920 | - | JX852534 | - | Tan et al. [39] |
D. fujianensis | JZB 320149T | MW010212 | MW056008 | - | - | MW205212 | Manawasinghe et al. [40] |
D. fulvicolor | PSCG 051T | MK626859 | MK691236 | MK726163 | MK654806 | MK691132 | Guo et al. [23] |
D. fusiformis | JZB 320156T | MW010218 | MW056014 | - | MW205234 | MW205218 | Manawasinghe et al. [40] |
D. gossiae | BRIP 59730aT | OM918693 | OM960620 | - | OM960602 | - | Tan and Shivas [26] |
D. guangxiensis | JZB 320094T | MK335772 | MK500168 | - | MK523566 | MK736727 | Manawasinghe et al. [41] |
D. hongkongensis | CBS 115448T | KC343119 | KC344087 | KC343603 | KC343845 | KC343361 | Gomes et al. [24] |
D. howardiae | BRIP 59697aT | OM918695 | OM960622 | - | OM960604 | - | Tan and Shivas [26] |
D. huangshanensis | CNUCC 201903T | MN219730 | MN227011 | MN224558 | MN224678 | - | Zhou and Hou [25] |
D. hunanensis | HNZZ 023T | MZ509550 | MZ504713 | MZ504691 | MZ504702 | MZ504680 | Yang et al. [30] |
D. krabiensis | MFLUCC 17-2481T | MN047101 | MN431495 | - | MN433215 | Dayarathne et al. [42] | |
D. limonicola | CBS 142549T | MF418422 | MF418582 | MF418342 | MF418501 | MF418256 | Guarnaccia and Crous [43] |
D. liquidambari | SCHM 3621T | AY601919 | - | - | - | - | Chang et al. [29] |
D. litchicola | BRIP 54900T | JX862533 | KF170925 | - | JX862539 | - | Tan et al. [39] |
D. lithocarpi | CGMCC 3.15175T | KC153104 | KF576311 | - | KC153095 | - | Gao et al. [44] |
D. meliae | CFCC 53089T | MK432657 | MK578057 | ON081662 | ON081654 | - | Cao et al. [45] |
D. melitensis | CBS 142551T | MF418424 | MF418584 | MF418344 | MF418503 | MF418258 | Guarnaccia and Crous [43] |
D. millettiae | GUCC 9167T | MK398674 | MK502089 | - | MK480609 | MK502086 | Long et al. [46] |
D. musigena | CBS 129519T | KC343143 | KC344111 | KC343627 | KC343869 | KC343385 | Gomes et al. [24] |
D. norfolkensis | BRIP 59718aT | OM918699 | OM960626 | - | OM960608 | - | Tan and Shivas [26] |
D. oculi | HHUF 30565T | LC373515 | LC373519 | - | LC373517 | - | Ozawa et al. [47] |
D. osmanthi | GUCC 9165T | MK398675 | MK502090 | - | MK480610 | MK502087 | Long et al. [46] |
D. pandanicola | MFLUCC 17-0607T | MG646974 | MG646930 | - | - | - | Tibpromma et al. [48] |
D. pascoei | BRIP 54847T | JX862532 | KF170924 | - | JX862538 | - | Tan et al. [39] |
D. perseae | CBS 151.73 | KC343173 | KC344141 | KC343657 | KC343899 | KC343415 | Gomes et al. [24] |
D. pescicola | MFLUCC 16-0105T | KU557555 | KU557579 | - | KU557623 | KU557603 | Dissanayake et al. [49] |
D. phyllanthicola | SCHM 3680T | AY620819 | - | - | - | - | Chang et al. [29] |
D. podocarpi-macrophylli | CGMCC 3.18281T | KX986774 | KX999207 | KX999246 | KX999167 | KX999278 | Gao et al. [50] |
D. pseudomangiferae | CBS 101339T | KC343181 | KC344149 | KC343665 | KC343907 | KC343423 | Gomes et al. [24] |
D. pseudooculi | HHUF 30617T | LC373515 | LC373519 | - | LC373517 | - | Ozawa et al. [47] |
D. pseudophoenicicola | CBS 462.69T | KC343184 | KC344152 | KC343668 | KC343910 | KC343426 | Gomes et al. [24] |
D. pterocarpicola | MFLUCC 10-0580a | JQ619887 | JX275441 | - | JX275403 | JX197433 | Udayanga et al. [51] |
D. rhodomyrti | CFCC 53101T | MK432643 | MK578046 | MK442990 | MK578119 | MK442965 | Cao et al. [45] |
D. salinicola | MFLU 18-0553T | MN047098 | - | - | MN077073 | - | Dayarathne et al. [42] |
D. schimae | CFCC 53103T | MK432640 | MK578043 | MK442987 | MK578116 | MK442962 | Yang et al. [52] |
D. searlei | BRIP 66528T | MN708231 | MN696540 | - | - | - | Wrona et al. [28] |
D. sennae | CFCC 51636T | KY203724 | KY228891 | - | KY228885 | KY228875 | Yang et al. [53] |
D. spinose | PSCG 383T | MK626849 | MK691234 | MK726156 | MK654811 | MK691129 | Guo et al. [23] |
D. taoicola | MFLUCC 16-0117T | KU557567 | KU557591 | - | KU557635 | - | Dissanayake et al. [49] |
D. tectonigena | MFLUCC 12-0767T | KU712429 | KU743976 | - | KU749371 | KU749358 | Doilom et al. [54] |
D. viniferae | JZB 320071T | MK341551 | MK500112 | - | MK500107 | MK500119 | Manawasinghe et al. [41] |
D. xishuangbanica | CGMCC 3.18282T | KX986783 | KX999216 | KX999255 | KX999175 | - | Gao et al. [50] |
1 | |||
---|---|---|---|
No. | δC, Type | δH (J in Hz) | |
Fragment A | 1 | 169.3, C | - |
2 | 40.1, CH2 | 3.69, dd (17.7, 4.9) 3.94, dd (17.7, 7.3) | |
3-NH | - | 8.36, dd (6.9, 5.1) | |
4 | 168.6, C | - | |
5 | 41.6, CH2 | 3.77, d (4.9) | |
6-NH | - | 7.43, t (5.0) | |
Fragment B | 7 | 170.4, C | - |
8 | 58.6, CH | 3.98, dd (7.8, 2.9) | |
9-NH | - | 7.85, d (7.8) | |
24 | 65.3, CH | 4.18, qd (6.3, 2.8) | |
24-OH | - | 5.02, br s | |
25 | 20.6, CH3 | 1.02, d (6.4) | |
Fragment C | 10 | 175.3, C | - |
11 | 45.7, CH | 2.37, qd (7.5, 3.2) | |
12 | 70.6, CH | 3.83, m | |
13 | 41.2, CH2 | 1.65, t (6.9) | |
14 | 68.9, CH | 3.57, quin (6.1) | |
14-OH | - | 4.72, br s | |
15 | 36.4, CH2 | 1.38, m 1.48, m | |
16 | 27.5, CH2 | 1.88, m 1.99, m | |
17 | 130.7, CH | 5.45, m | |
18 | 131.6, CH | 5.09, dd (15.4, 8.9) | |
19 | 39.0, CH | 2.32, m | |
20 | 78.5, CH | 4.67, dd (9.6, 2.4) | |
21 | 34.8, CH2 | 1.62, td (7.0, 2.4) | |
22 | 26.4, CH2 | 1.15, m | |
23 | 11.7, CH3 | 0.84, t (7.1) | |
26 | 16.2, CH3 | 1.20, d (7.3) | |
27 | 17.2, CH3 | 0.88, d (6.9) | |
28 | 12.6, CH3 | 0.83, d (7.0) |
2 | 3a | 3b | ||||
---|---|---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
1 | 171.9, C | - | 69.1, C | 4.97, d (12.3) 4.86, d (12.3) | 69.2, C | 4.97, d (12.3) 4.86, d (12.3) |
2 | 109.5, C * | - | 125.3, C | - | 125.3, C | - |
3 | 157.5, C * | - | 149.5, C | - | 149.6, C | - |
4 | 119.0, CH | 7.06, d (8.6) | 114.4, CH | 6.63, d (8.1) | 114.4, CH | 6.59, d (8.1) |
5 | 138.5, CH | 7.46, d (8.6) | 128.7, CH | 6.75, d (8.1) | 128.8, CH | 6.74, d (8.1) |
6 | 129.8, C | - | 125.5, C | - | 125.6, C | - |
7 | 143.5, C * | - | 142.6, C | - | 142.6, C | - |
8 | - | - | 105.8, C | - | 106.0, C | - |
9 | 131.0, C | - | 130.6, C | - | 131.1, C | - |
10 | 140.9, C | - | 139.3, C | - | 139.6, C | - |
11 | 143.3, C | - | 142.6, C | - | 142.5, C | - |
12 | 122.1, CH | 6.9, br s | 117.1, CH | 6.64, d (2.1) | 117.0, CH | 6.64, d (2.1) |
13 | 131.0, C | - | 127.7, C | - | 128.1, C | - |
14 | 122.9, CH | 6.9, br s | 120.2, CH | 7.24, d (2.1) | 120.1, CH | 7.22, d (2.1) |
15 | 20.6, CH3 | 2.24, s | 20.6, CH3 | 2.2, s | 20.7, CH3 | 2.2, s |
1′ | 29.7, CH2 | 3.13, br d (6.7) | 28.0, CH2 | 2.8, m (overlapped) | 28.0, CH2 | 2.8, m (overlapped) |
2′ | 121.4, CH | 5.06, br t (6.7) | 123.6, CH | 4.8, t (7.1) | 123.7, CH | 4.8, t (7.1) |
3′ | 133.9, C | - | 130.2, C | - | 130.2, C | - |
4′ | 17.6, CH3 | 1.50, s | 17.4, CH3 | 1.33, s | 17.4, CH3 | 1.34, s |
5′ | 25.6, CH3 | 1.64, s | 25.5, CH3 | 1.51, s | 25.6, CH3 | 1.52, s |
1″ | 64.2, CH2 | 3.93, t (9.7) 4.37, br d (9.5) | 63.7, CH2 | 4.27, dd (11.1, 2.1) 3.48, br dd (11.1, 9.0) | 64.3, CH2 | 4.27, dd (11.1, 2.0) 3.73, dd (11.1, 9.2) |
2″ | 79.6, CH | 3.99, m | 79.1, CH | 3.60, dd (9.0, 2.3) | 79.0, CH | 3.23, dd (9.2, 1.9) |
3″ | 72.4, C | - | 68.8, C | - | 69.1, C | - |
4″ | 23.5, CH3 | 1.20, s | 22.2, CH3 | 0.35, s | 23.0, CH3 | 0.52, s |
5″ | 25.6, CH3 | 1.30, s | 27.4, CH3 | 0.85, s | 27.2, CH3 | 0.84, s |
No. | 4a | 4b | ||
---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
1 | 169.9, C | - | 169.9, C | - |
2 | 115.8, C | - | 115.9, C | - |
3 | 153.2, C | - | 153.3, C | - |
4 | 115.8, CH | 6.73, d (8.2) | 115.6, CH | 6.70, d (8.2) |
5 | 134.1, CH | 7.02, d (8.2) | 134.2, CH | 7.02, d (8.2) |
6 | 127.0, C | - | 127.0, C | - |
7 | 148.0, C | - | 148.0, C | - |
8 | 84.9, C | - | 85.1, C | - |
9 | 127.9, C | - | 127.9, C | - |
10 | 138.6, C | - | 138.8, C | - |
11 | 142.6, C | - | 142.7, C | - |
12 | 117.1, CH | 6.67, d (2.1) | 117.1, CH | 6.67, d (2.1) |
13 | 128.3, C | - | 128.5, C | - |
14 | 120.7, CH | 7.33, br s | 120.7, CH | 7.33, br s |
15 | 20.6, CH3 | 2.23, s | 20.6, CH3 | 2.23, s |
16-NH | - | 8.79, s | - | 9.04, br s |
1′ | 27.8, CH2 | 2.92, m (overlapped) | 27.8, CH2 | 2.92, m (overlapped) |
2′ | 122.9, CH | 4.79, br t (6.6) | 123.0, CH | 4.79, br t (6.6) |
3′ | 130.7, C | - | 130.8, C | - |
4′ | 17.3, CH3 | 1.35, s | 17.3, CH3 | 1.37, s |
5′ | 25.4, CH3 | 1.50, s | 25.5, CH3 | 1.52, s |
1″ | 63.8, CH2 | 3.46, dd (11.2, 9.2) 4.31, m | 64.1, CH2 | 3.68, dd (11.2, 9.2)4.31, m |
2″ | 79.4, CH | 3.56, dd (9.0, 1.8) | 79.4, CH | 3.29, m |
3″ | 68.8, C | - | 68.5, C | - |
4″ | 21.9, CH3 | 0.33, s | 22.7, CH3 | 0.60, s |
5″ | 27.7, CH3 | 0.92, s | 27.4, CH3 | 0.86, s |
No. | 7a | 7b | ||
---|---|---|---|---|
δC, Type | δH (J in Hz) | δC, Type | δH (J in Hz) | |
1 | 144.8, CH | 7.78, d (1.7) | 144.8, CH | 7.83, d (1.7) |
2 | - | - | - | - |
3 | 157.6, C | - | 157.2, C | - |
4 | 105.0, CH | 6.82, s | 105.8, CH | 6.88, s |
4a | 142.6, C | - | 142.5, C | - |
5 | 107.4, C | - | 107.7, C | - |
6 | 185.5, C | - | 185.6, C | - |
7 | 81.9, C | - | 81.9, C | - |
8 | 43.3, CH | 3.54, dd (11.9, 1.7) | 43.1, CH | 3.54, dd (11.9, 1.7) |
8a | 116.2, C | - | 116.2, C | - |
9 | 117.6, CH | 6.51, d (15.9) | 120.2, CH | 6.61, d (15.7) |
10 | 140.8, CH | 7.07, d (15.9) | 132.2, CH | 7.41, d (15.7) |
11 | 132.2, C | - | 130.2, C | - |
12 | 146.5, CH | 5.73, d (9.8) | 144.0, CH | 5.52, d (9.9) |
13 | 34.3, CH | 2.46, m | 33.4, CH | 2.64, m |
14 | 29.6, CH2 | 1.39, m 1.26, m | 29.7, CH2 | 1.39, m 1.26, m |
15 | 11.9, CH3 | 0.82, t (7.4) | 11.9, CH3 | 0.82, t (7.4) |
16 | 20.2, CH3 | 0.96, d (6.6) | 21.0, CH3 | 0.96, d (6.6) |
17 | 12.3, CH3 | 1.81, d (0.9) | 19.9, CH3 | 1.88, d (1.1) |
18 | 18.7, CH3 | 1.20, s | 18.7, CH3 | 1.20, s |
19 | 174.6, C | - | 174.6, C | - |
20 | 47.0, CH | 3.41, br dd (11.9, 5.7) | 47.0, CH | 3.41, br dd (11.9, 5.7) |
21 | 65.7, CH | 4.04, m | 65.6, CH | 4.04, m |
21-OH | - | 5.22, br d (4.4) | - | 5.22, br d (4.4) |
22 | 22.7, CH3 | 1.35, d (6.3) | 22.8, CH3 | 1.35, d (6.3) |
MIC (µg/mL) | |||||||||
---|---|---|---|---|---|---|---|---|---|
Test Organisms | 1 | 2 | 3 (3a + 3b) | 4 (4a + 4b) | 5 | 6 | 7 (7a + 7b) | 8 | References |
Acinetobacter baumanii | - | - | - | - | - | - | - | - | 0.26 c |
Bacillus subtilis | - | - | 33.3 | 66.6 | 66.6 | 16.6 | 16.6 | 8.3 | 8.3 o |
Candida albicans | - | - | - | - | - | - | - | - | 16.6 n |
Chromobacterium violaceum | - | - | - | - | - | - | - | - | 0.83 o |
Escherichia coli | - | - | - | - | - | - | - | - | 1.7 o |
Mucor hiemalis | - | - | 66.6 | 33.3 | 66.6 | 16.6 | 8.3 | 66.6 | 8.3 n |
Mycobacterium smegmatis | - | - | - | - | - | - | 16.6 | 8.3 | 1.7 k |
Pseudomonas aeruginosa | - | - | - | - | - | - | - | - | 0.21 g |
Rhodoturula glutinis | - | - | - | 33.3 | 66.6 | 16.6 | - | 66.6 | 4.2 n |
Schizosaccharomyces pombe | - | - | - | 33.3 | 33.3 | 66.6 | - | 33.3 | 8.3 n |
Staphylococcus aureus | - | - | 33.3 | 66.6 | 66.6 | 16.6 | 66.6 | 8.3 | 0.83 o |
Wickerhamomyces anomalus | - | - | - | - | - | 66.6 | - | - | 8.3 n |
IC50 (µM) | |||||||||
---|---|---|---|---|---|---|---|---|---|
Cell Lines | 1 | 2 | 3 (3a + 3b) | 4 (4a + 4b) | 5 | 6 | 7 (7a + 7b) | 8 | Epothilone B |
KB3.1 | - | SI | 32.9 | 31.9 | 22.0 | 20.0 | 5.3 | 2.3 | 4.5 × 10−5 |
L929 | - | - | 51.6 | 59.2 | 54.4 | 49.5 | 12.9 | 2.8 | 4.3 × 10−4 |
A431 | n.t | n.t | n.t | n.t | n.t | 19.3 | 4.1 | 2.4 | 5.5 × 10−5 |
MCF-7 | n.t | n.t | n.t | n.t | n.t | 17.7 | 0.9 | 2.0 | 6.1 × 10−5 |
A549 | n.t | n.t | n.t | n.t | n.t | 20.8 | 2.3 | 2.6 | 6.9 × 10−5 |
SKOV-3 | n.t | n.t | n.t | n.t | n.t | 42.5 | 3.3 | 3.3 | 9.9 × 10−5 |
PC-3 | n.t | n.t | n.t | n.t | n.t | 17.9 | 1.1 | 1.9 | 7.3 × 10−5 |
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Matio Kemkuignou, B.; Lambert, C.; Stadler, M.; Kouam Fogue, S.; Marin-Felix, Y. Unprecedented Antimicrobial and Cytotoxic Polyketides from Cultures of Diaporthe africana sp. nov. J. Fungi 2023, 9, 781. https://doi.org/10.3390/jof9070781
Matio Kemkuignou B, Lambert C, Stadler M, Kouam Fogue S, Marin-Felix Y. Unprecedented Antimicrobial and Cytotoxic Polyketides from Cultures of Diaporthe africana sp. nov. Journal of Fungi. 2023; 9(7):781. https://doi.org/10.3390/jof9070781
Chicago/Turabian StyleMatio Kemkuignou, Blondelle, Christopher Lambert, Marc Stadler, Simeon Kouam Fogue, and Yasmina Marin-Felix. 2023. "Unprecedented Antimicrobial and Cytotoxic Polyketides from Cultures of Diaporthe africana sp. nov." Journal of Fungi 9, no. 7: 781. https://doi.org/10.3390/jof9070781