Smenamides A and B, Chlorinated Peptide/Polyketide Hybrids Containing a Dolapyrrolidinone Unit from the Caribbean Sponge Smenospongia aurea. Evaluation of Their Role as Leads in Antitumor Drug Research
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structural Elucidation
Z-Conformer | E-Conformer | ||||||
---|---|---|---|---|---|---|---|
Position | δH [Mult., J (Hz)] | δC [Mult.] | δH [Mult., J (Hz)] | δC [Mult.] | COSY | HMBC | |
1 | − | 135.6 (C) | − | 135.6 (C) | |||
2/6 | 6.99 (m) | 130.8 (CH) | 6.99 (m) | 130.8 (CH) | 3/5 | 4 | |
3/5 | 7.23 (ovl) | 129.4 (CH) | 7.23 (ovl) | 129.4 (CH) | 2/6 | 1 | |
4 | 7.23 (ovl) | 128.3 (CH) | 7.23 (ovl) | 128.3 (CH) | 2/6 | ||
7 | a | 3.37 (ovl) | 34.8 (CH2) | 3.37 (ovl) | 34.8 (CH2) | 7b, 8 | 1, 2/6, 8, 9 |
b | 3.19 (m) | 3.19 (m) | 7a, 8 | 2/6 | |||
8 | 5.02 (ovl) | 60.5 (CH) | 5.02 (ovl) | 60.5 (CH) | 7a, 7b | ||
9 | − | 179.5 (C) | − | 179.5 (C) | |||
10 | 5.04 (br. s) | 95.5 (CH) | 5.02 (br. s) | 95.5 (CH) | 8, 11 | ||
11 | − | 170.7 (C) | − | 170.7 (C) | |||
12 | − | 172.3 (C) | − | 172.2 (C) | |||
13 | − | 132.1 (C) | − | 132.1 (C) | |||
14 | 1.77 (d, 1.5) | 13.7 (CH3) | 1.78 (d, 1.5) | 13.7 (CH3) | 15 | 12, 13, 15 | |
15 | 5.36 (br. d, 10.2) | 144.1 (CH) | 5.36 (br. d, 10.2) | 144.1 (CH) | 14, 16 | ||
16 | 2.45 (m) | 33.4 (CH) | 2.48 (m) | 33.4 (CH) | 15, 17, 18a | ||
17 | 0.98 (d, 6.5) | 20.4 (CH3) | 1.00 (d, 6.5) | 20.6 (CH3) | 16 | 15, 18, 19 | |
18 | a | 1.51 (ovl) | 36.1 (CH2) | 1.52 (ovl) | 35.9 (CH2) | 16, 19a, 19b | 19 |
b | 1.28 (ovl) | 1.30 (ovl) | 19a, 19b | ||||
19 | a | 2.19 (ovl) | 33.2 (CH2) | 2.23 (ovl) | 33.2 (CH2) | 18a, 18b, 19b, 21 | 20, 21 |
b | 2.06 (ovl) | 2.05 (ovl) | 18a, 18b, 19a, 21 | 20 | |||
20 | − | 143.1 (C) | − | 142.8 (C) | |||
21 | 5.93 (br. s) | 113.9 (CH) | 5.97 (br. s) | 114.1 (CH) | 19a, 19b | 20, 22 | |
22 | a | 2.22 (m) | 28.1 (CH2) | 2.26 (m) | 28.0 (CH2) | 22b, 23 | 20, 21 |
b | 2.15 (m) | 2.18 (m) | 22a, 23 | 20 | |||
23 | 1.64 (m) | 25.9 (CH2) | 1.70 (m) | 26.6 (CH2) | 22a, 22b, 24 | ||
24 | 3.36 (ovl) | 48.6 (CH2) | 3.33 (ovl) | 51.5 (CH2) | 23 | 22, 23, 25, 27 | |
25 | − | 172.9 (C) | − | 172.7 (C) | |||
26 | 2.08 (s) | 21.7 (CH3) | 2.07 (s) | 21.1 (CH3) | 27 | 25 | |
27 | 3.03 (s) | 36.6 (CH3) | 2.88 (s) | 33.7 (CH3) | 26 | 24, 25 | |
OMe | 3.97 (s) | 59.7 (CH3) | 3.97 (s) | 59.7 (CH3) | 9 |
2.2. 16S rRNA Metagenomic Analysis
2.3. In Vitro Evaluation of Cytotoxic Activity of Smenamides
3. Experimental Section
3.1. General Experimental Procedures
3.2. Collection, Extraction, and Isolation
3.3. Smenamide A (1)
3.4. Smenamide B (2)
3.5. DNA Isolation
3.6. PCR Amplification and Clone Library Construction
3.7. Cell Culture
3.8. MTT Assay
3.9. Apoptosis assay
3.10. Accession Codes
4. Conclusion
Acknowledgments
Conflicts of Interest
References
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Teta, R.; Irollo, E.; Della Sala, G.; Pirozzi, G.; Mangoni, A.; Costantino, V. Smenamides A and B, Chlorinated Peptide/Polyketide Hybrids Containing a Dolapyrrolidinone Unit from the Caribbean Sponge Smenospongia aurea. Evaluation of Their Role as Leads in Antitumor Drug Research. Mar. Drugs 2013, 11, 4451-4463. https://doi.org/10.3390/md11114451
Teta R, Irollo E, Della Sala G, Pirozzi G, Mangoni A, Costantino V. Smenamides A and B, Chlorinated Peptide/Polyketide Hybrids Containing a Dolapyrrolidinone Unit from the Caribbean Sponge Smenospongia aurea. Evaluation of Their Role as Leads in Antitumor Drug Research. Marine Drugs. 2013; 11(11):4451-4463. https://doi.org/10.3390/md11114451
Chicago/Turabian StyleTeta, Roberta, Elena Irollo, Gerardo Della Sala, Giuseppe Pirozzi, Alfonso Mangoni, and Valeria Costantino. 2013. "Smenamides A and B, Chlorinated Peptide/Polyketide Hybrids Containing a Dolapyrrolidinone Unit from the Caribbean Sponge Smenospongia aurea. Evaluation of Their Role as Leads in Antitumor Drug Research" Marine Drugs 11, no. 11: 4451-4463. https://doi.org/10.3390/md11114451