The relevant literature is supplemented with complete NMR assignments and revisions for the 29 previously reported compounds. BI0327, BI0383, BI0618, BI0918, and BI0980, isolated from marine sediments collected in the Aegean and Ionian seas, were subjected to repetitive chromatographic fractionations to yield three new natural products, namely 317.0661 and 319.0629 having a ratio of 3:1, characteristic for the presence of one chlorine atom in the molecule. of one chlorine atom in the molecule. The HSQC and HMBC experiments exposed 14 carbon signals, which corresponded to five non-protonated carbon atoms, among which two carbonyls resonating at orientation and assigned the relative construction of 15 that was identified as in ppm, in Hz) 1 of compounds 1C8. (b) 1H NMR data (in ppm, in Hz) 1 of compounds 9C16. (c) 1H NMR data (in ppm, in Hz) 1 of compounds 17C24. (d) 1H NMR data (in ppm, in Hz) 1 of compounds 25C32. (a) in ppm) 1 of compounds 1C16. (b) 13C NMR data (in ppm) 1 of compounds 17C32. (a) 317.0657 and 319.0627 having a percentage of 3:1 (HRESIMS), was isolated while white sound. The spectroscopic characteristics of 16 (Table 1 and Table 2 and Numbers S7CS12) were rather much like those of 15. Specifically, the NMR spectra of 16 exposed the same structural characteristics of a DKP moiety, including a proline amino acid and a 1,2,4-trisubstituted aromatic ring. Probably the most prominent difference was that H-3 (4.13 ppm) and H-6 MANOOL (3.22 ppm) resonated in higher fields, which, in combination with the absence of an NOE correlation between them, indicated that compound 16 was the isomer of 15. The COSY cross-peaks and the HMBC correlations observed for 16 (Number 3), in accordance to those observed for compound 15, were in agreement with the proposed structure of 276 and a fragmentation pattern identical to that of 310 and 312 with an isotopic percentage of 3:1, suggesting that 31 was a monochlorinated compound. Comparison of the 1H NMR data of the mixture with that of 3.90) and H-6 (4.19) to the people of compound 30 indicated their orientation. Therefore, compound 31 was identified as pairs 4/5, 6/7, 8/9, 11/12, and 15/16, it can be observed the chemical shifts of C-3 and C-10 are consistently deshielded by 3 and 3.5C4.5 ppm, respectively, in the DKP isomers. Compounds 15 and 16 were evaluated for his or her antifungal activity against and (ppm) level using TMS as internal standard. High-resolution electrospray ionization (ESI) mass spectra were measured on a Thermo Scientific LTQ Orbitrap Velos mass spectrometer (Thermo Fisher Scientific, Bremen, Germany). Low-resolution electron ionization (EI) mass spectra were measured on a Hewlett-Packard 5973 mass spectrometer (Agilent Systems, Santa Clara, CA, USA) or on a Thermo Electron Corporation DSQ mass spectrometer (Thermo Electron Corporation, Austin, TX, USA). Normal- and reversed-phase column chromatography separations were performed with Kieselgel Si 60 (Merck, Darmstadt, Germany) and Kieselgel RP-18 (Merck, Darmstadt, Germany), respectively. HPLC separations were carried out on (i) a Cecil 1100 Series liquid FLT3 chromatography pump (Cecil Devices Ltd., Cambridge, UK) equipped with a GBC LC-1240 refractive index detector (GBC Scientific Products, Braeside, VIC, Australia), (ii) a Pharmacia LKB 2248 liquid chromatography pump (Pharmacia LKB Biotechnology, Uppsala, Sweden) equipped with an RI-102 Shodex refractive index detector (ECOM spol. s r.o., Prague, Czech Republic), (iii) an Agilent 1100 liquid chromatography system equipped with refractive index detector (Agilent Systems, Waldbronn, Germany), (iv) a Waters 600 liquid chromatography pump (Waters, Milford, MA, USA) having a Waters 410 refractive index detector (Waters, Milford, MA, USA), or (v) a Waters 515 liquid chromatography pump (Waters, Milford, MA, USA) equipped with a Shimadzu RID-20A refractive index detector (Shimadzu Europa GmbH, Duisburg, Germany), using the following columns: (i) Econosphere C18 10u (250 10 mm, Elegance, Columbia, MD, USA), (ii) Kromasil 100-7-C18 (250 10 mm, Akzonobel, Eka Chemicals AB, Separation Products, Bohus, Sweden), (iii) Luna C18 (2) 100A 10u (250 10 mm, Phenomenex, Torrance, CA, USA), (iv) Econosphere Silica 10u (250 10 mm, Elegance, Columbia, MD, USA), (v) MANOOL Kromasil 100-10-SIL (250 10 mm, Akzonobel, Eka Chemicals AB, Separation Products, Bohus, Sweden), or (vi) Supelcosil SPLC-Si 5 m (250 10 mm, Supelco, Bellefonte, PA, USA). TLC was performed with Kieselgel 60 F254 aluminum-backed plates (Merck, Darmstadt, Germany) and places were visualized after spraying with 15% (v/v) H2SO4 in MeOH reagent and heating at 100 C for 1 min. 3.2. Biological Material The bacterial strains were isolated from marine sediments collected from your East Mediterranean Sea and were recognized based on assessment of their 16S ribosomal RNA (rRNA) sequences with data from your Genbank database of the National Center for Biotechnology Info (NCBI) using the Basic Local Positioning Search Tool (BLAST). Specifically, strain BI0327, identified as (GenBank accession quantity “type”:”entrez-nucleotide”,”attrs”:”text”:”DQ485415″,”term_id”:”93117547″,”term_text”:”DQ485415″DQ485415), was isolated from a sediment collected east of Thiorichio in the island of Milos, at a depth of 4 m, in July 2012. Strain BI0383, identified as (GenBank accession quantity “type”:”entrez-nucleotide”,”attrs”:”text”:”KJ573071″,”term_id”:”645175650″,”term_text”:”KJ573071″KJ573071), was isolated from a.and E.I.; writingReview and editing, V.R. 1 of compounds 9C16. (c) 1H NMR data (in ppm, in Hz) 1 of compounds 17C24. (d) 1H NMR data (in ppm, in Hz) 1 of compounds 25C32. (a) in ppm) 1 of compounds 1C16. (b) 13C NMR data (in ppm) 1 of compounds 17C32. (a) 317.0657 and 319.0627 having a percentage of 3:1 (HRESIMS), was isolated while white sound. The spectroscopic characteristics of 16 (Table 1 and Table 2 and Numbers S7CS12) were rather much like those of 15. Specifically, the NMR spectra of 16 exposed the same structural characteristics of a DKP moiety, including a proline amino acid and a 1,2,4-trisubstituted aromatic ring. Probably the most prominent difference was that H-3 (4.13 ppm) and H-6 (3.22 ppm) resonated in higher fields, which, in combination with the absence of an NOE correlation between them, indicated that compound 16 was the isomer of 15. The COSY cross-peaks and the HMBC correlations observed for 16 (Number 3), in accordance to those observed for compound 15, were in agreement with the proposed structure of 276 and a fragmentation pattern identical to that of 310 and 312 with an isotopic percentage of 3:1, suggesting that 31 was a monochlorinated compound. Comparison of the 1H NMR data of the mixture with that of 3.90) and H-6 (4.19) to the people of compound 30 indicated their orientation. Therefore, compound 31 was identified as pairs 4/5, 6/7, 8/9, 11/12, and 15/16, it can be observed that the chemical shifts of C-3 and C-10 are consistently deshielded by 3 and 3.5C4.5 ppm, respectively, in the DKP isomers. Compounds 15 and 16 were evaluated for his or her antifungal activity against and (ppm) level MANOOL using TMS as internal standard. High-resolution electrospray ionization (ESI) mass spectra were measured on a Thermo Scientific LTQ Orbitrap Velos mass spectrometer (Thermo Fisher Scientific, Bremen, Germany). Low-resolution electron ionization (EI) mass spectra were measured on a Hewlett-Packard 5973 mass spectrometer (Agilent Systems, Santa Clara, CA, USA) or on a Thermo Electron Corporation DSQ mass spectrometer (Thermo Electron Corporation, Austin, TX, USA). Normal- and reversed-phase column chromatography separations were performed with Kieselgel Si 60 (Merck, Darmstadt, Germany) and Kieselgel RP-18 (Merck, Darmstadt, Germany), respectively. HPLC separations were carried out on (i) a Cecil 1100 Series liquid chromatography pump (Cecil Devices Ltd., Cambridge, UK) equipped with a GBC LC-1240 refractive index detector (GBC Scientific Products, Braeside, VIC, Australia), (ii) a Pharmacia LKB 2248 liquid chromatography pump (Pharmacia LKB Biotechnology, Uppsala, Sweden) equipped with an RI-102 Shodex refractive index detector (ECOM spol. s r.o., Prague, Czech Republic), (iii) an Agilent 1100 liquid chromatography system equipped with refractive index detector (Agilent Systems, Waldbronn, Germany), (iv) a Waters 600 liquid chromatography pump (Waters, Milford, MA, USA) having a Waters 410 refractive index detector (Waters, Milford, MA, USA), or (v) a Waters 515 liquid chromatography pump (Waters, Milford, MA, USA) equipped with a Shimadzu RID-20A refractive index detector (Shimadzu Europa GmbH, Duisburg, Germany), using the following columns: (i) Econosphere C18 10u (250 10 mm, Elegance, Columbia, MD, USA), (ii) Kromasil 100-7-C18 (250 10 mm, Akzonobel, Eka Chemicals AB, Separation Products, Bohus, Sweden), (iii) Luna C18 (2) 100A 10u (250 10 mm, Phenomenex, Torrance, CA, USA), (iv) Econosphere Silica 10u (250 10 mm, Elegance, Columbia, MD, USA), (v) Kromasil 100-10-SIL (250 10 mm, Akzonobel, Eka Chemicals AB, Separation Products, Bohus, Sweden), or (vi) Supelcosil SPLC-Si 5 m (250 10 mm, Supelco, Bellefonte, PA, USA). TLC was performed with Kieselgel 60 F254 aluminum-backed.