Supporting information New Diketopiperazine Derivatives from a Deep-Sea-Derived
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1 Supporting information New Diketopiperazine Derivatives from a Deep-Sea-Derived Nocardiopsis alba SCSIO Qingbo Zhang 1,3, Sumei Li 1, Yuchan Chen 2, Xinpeng Tian 1, Haibo Zhang 1, Guangtao Zhang 1, Yiguang Zhu 1, Si Zhang 1, Weimin Zhang 2, and Changsheng Zhang 1* 1 CAS Key Laboratory of Marine Bio-resources Sustainable Utilization, RNAM Center for Marine Microbiology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou , China 2 Guangdong Institute of Microbiology, 100 Central Xianlie Road, Guangzhou , China 3 Graduate University of the Chinese Academy of Sciences, Beijing , China Correspondence: Prof. Changsheng Zhang, South China Sea Institute, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou , P. R. China czhang2006@gmail.com. S1
2 Content Figure S1 Phylogenetic dendrogram of Nocardiopsis sp. SCSIO and its closest relations reconstructed on the basis of 16S rrna gene sequences by Neighbor-Joining methods... S3 Figure S2 Spectral data of compound 1... S4 Figure S3 Spectral data of compound 2... S7 Figure S4 Spectral data of compound 3... S11 Figure S5 Spectral data of compound 4... S14 Figure S6 Spectral data of compound 5... S17 Figure S7 Spectral data of compound 6... S20 Figure S8 Spectral data of compound 7... S21 Figure S9 Spectral data of compound 8... S24 Figure S10 The determination of the absolute configuration of compound 2... S27 Figure S11 The determination of the absolute configuration of compounds 3 and 4... S28 S2
3 Figure S1 Phylogenetic dendrogram of Nocardiopsis sp. SCSIO and its closest relations reconstructed on the basis of 16S rrna gene sequences by Neighbor-Joining methods Nocardiopsis exhalans ES10.1 T (AY036000) 100 Nocardiopsis valliformis T (AY336503) Nocardiopsis metallicus KBS6 T (AJ420769) Nocardiopsis ganjiahuensis HBUM T (AY336513) Nocardiopsis prasina DSM T (X97884) Nocardiopsis listeri DSM T (X97887) 73 Nocardiopsis alkaliphila DSM T (AY230848) Nocardiopsis terrae YIM T (DQ387958) Nocardiopsis umidischolae 66/93 T (AY036001) 100 Nocardiopsis tropica VKM Ac-1457 T (AF105971) SCSIO Nocardiopsis alba DSM T (X97883) Nocardiopsis aegyptia DSM T (AJ539401) Nocardiopsis lucentensis DSM T (X97888) Nocardiopsis flavescens SA6 T (GU997639) Nocardiopsis dassonvillei subsp. albirubida DSM T (X97882) Nocardiopsis synnemataformans IMMIB D-1215 T (Y13593) Nocardiopsis dassonvilleisubsp. dassonvilleidsm T (ABUI ) Nocardiopsis halotolerans DSM T (AJ290448) Nocardiopsis sinuspersici HM6 T (EU410476) 100 Nocardiopsis arvandica HM7 T (EU410477) Nocardiopsis nikkonensis YU T (AB491226) Nocardiopsis salina YIM T (AY373031) Nocardiopsis xinjiangensisyim T (AF251709) Nocardiopsis litoralis JSM T (EU583726) Nocardiopsis kunsanensis HA-9 T (AF195412) Nocardiopsis trehalosi VKM_Ac-942 T (AF105972) Nocardiopsis composta KS9 T (AF360734) 99 Nocardiopsis potens IMMIB L-21 T (FM253114) S3
4 Figure S2 Spectral data of compound 1 (A) The 1 H NMR spectrum of compound 1 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 1 (CDCl 3 ) S4
5 Figure S2 Spectral data of compound 1 (continued) (C) The HSQC spectrum of compound 1 (CDCl 3 ) (D) The 1 H- 1 H COSY spectrum of compound 1 (CDCl 3 ) S5
6 Figure S2 Spectral data of compound 1 (continued) (E) The HMBC spectrum of compound 1 (CDCl 3 ) (F) The UV spectrum of compound 1 S6
7 Figure S3 Spectral data of compound 2 (A) The 1 H NMR spectrum of compound 2 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 2 (CDCl 3 ) S7
8 Figure S3 Spectral data of compound 2 (continued) (C) The HSQC spectrum of compound 2 (CDCl 3 ) (D) The 1 H- 1 H COSY spectrum of compound 2 (CDCl 3 ) S8
9 Figure S3 Spectral data of compound 2 (continued) (E) The HMBC spectrum of compound 2 (CDCl 3 ) (F) The 1 H NMR spectrum of compound 2 (DMSO-d 6 ) S9
10 Figure S3 Spectral data of compound 2 (continued) (G) The NOESY spectrum of compound 2 (DMSO-d 6 ) (H) The UV spectrum of compound 2 S10
11 Figure S4 Spectral data of compound 3 (A) The 1 H NMR spectrum of compound 3 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 3 (CDCl 3 ) S11
12 Figure S4 Spectral data of compound 3 (continued) (C) The HSQC spectrum of compound 3 (CDCl 3 ) (D) The 1 H- 1 H COSY spectrum of compound 3 (CDCl 3 ) S12
13 Figure S4 Spectral data of compound 3 (continued) (E) The HMBC spectrum of compound 3 (CDCl 3 ) (F) The UV spectrum of compound 3 S13
14 Figure S5 Spectral data of compound 4 (A) The 1 H NMR spectrum of compound 4 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 4 (CDCl 3 ) S14
15 Figure S5 Spectral data of compound 4 (C) The HSQC spectrum of compound 4 (CDCl 3 ) (D) The 1 H- 1 H COSY spectrum of compound 4 (CDCl 3 ) S15
16 Figure S5 Spectral data of compound 4 (continued) (E) The HMBC spectrum of compound 4 (CDCl 3 ) (F) The UV spectrum of compound 4 S16
17 Figure S6 Spectral data of compound 5 (A) The 1 H NMR spectrum of compound 5 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 5 (CDCl 3 ) S17
18 Figure S6 Spectral data of compound 5 (continued) (C) The HSQC spectrum of compound 5 (CDCl 3 ) (D) The 1 H- 1 H COSY spectrum of compound 5 (CDCl 3 ) S18
19 Figure S6 Spectral data of compound 5 (continued) (E) The HMBC spectrum of compound 5 (CDCl 3 ) S19
20 Figure S7 Spectral data of compound 6 (A) The 1 H NMR spectrum of compound 6 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 6 (CDCl 3 ) S20
21 Figure S8 Spectral data of compound 7 (A) The 1 H NMR spectrum of compound 7 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 7 (CDCl 3 ) S21
22 Figure S8 Spectral data of compound 7 (continued) (C) The HSQC spectrum of compound 7 (CDCl 3 ) (D) The 1 H- 1 H COSY spectrum of compound 7 (CDCl 3 ) S22
23 Figure S8 Spectral data of compound 7 (continued) (E) The HMBC spectrum of compound 7 (CDCl 3 ) S23
24 Figure S9 Spectral data of compound 8 (A) The 1 H NMR spectrum of compound 8 (CDCl 3 ) (B) The 13 C NMR and DEPT 135 spectra of compound 8 (CDCl 3 ) S24
25 Figure S9 Spectral data of compound 8 (continued) (C) The HSQC spectrum of compound 8 (CDCl 3 ) (D) The 1 H- 1 H COSY spectrum of compound 8 (CDCl 3 ) S25
26 Figure S9 Spectral data of compound 8 (continued) (E) The HMBC spectrum of compound 8 (CDCl 3 ) S26
27 Figure S10 The determination of the absolute configuration of compound 2 (A) The determination of the absolute configuration of phenylalanine (Phe) moiety in compound 2 FDAA derivatized hydrolysate of compound 2 (2a) Absorbance (AU) (2b) FDAA derivate of L-Phe standard FDAA derivate of D-Phe standard a b c Retention Time (min) (B) The HPLC analysis of compound 2 on (a) an analytical reverse phase column (Luna C 18 column; 5 μm, mm) and (b) a chiral column (Chiralpak AD-H, mm, 5 μm) Absorbance (AU) 2 (a) Absorbance (AU) 2b Retention Time (min) 2a (b) Retention Time (min) S27
28 Figure S11 The determination of the absolute configuration of compound 3-4 (A) The determination of the absolute configuration of alanine (Ala) moiety in compound 3 FDAA derivatized hydrolysate of compound 3 a FDAA derivate of L-Ala standard b FDAA derivate of D- Ala standard c (B) The determination of the absolute configuration of valine (Val) moiety in compound 4 FDAA derivatized hydrolysate of compound 4 a FDAA derivate of L-Val standard b FDAA derivate of D-Val standard c S28
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