Chrysomycins A-C, antileukemic naphthocoumarins from Streptomyces sporoverrucosus

Transcription

1 This journal is The Royal Society of Chemistry 23 ELECTRONIC SUPPORTING INFORMATION (ESI) Chrysomycins A-C, antileukemic naphthocoumarins from Streptomyces sporoverrucosus Shreyans K. Jain, ab Anup S. Pathania, c Rajinder Parshad, d Chandji Raina, d Asif Ali, ab Ajai P. Gupta, e Manoj Kushwaha, e Subrayashastry Aravinda, f Shashi Bhushan, bc Sandip B. Bharate, bf * Ram A. Vishwakarma abf * a Natural Products Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu-8, India. b Academy of Scientific and Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi-, India c Cancer Pharmacology Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu-8, India d Fermentation Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu-8, India. e Quality control and quality assurance division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu- 8, India. f Medicinal Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu-8, India * ram@iiim.ac.in; sbharate@iiim.ac.in IIIM Publication number IIIM/556/23 Fax: ; Tel:

2 This journal is The Royal Society of Chemistry 23 CONTENTS S. H -NMR Spectrum of chrysomycin A () in CD 3 OD S2. HRMS Spectrum of chrysomycin A () S3. H -NMR Spectrum of chrysomycin B (2) in CD 3 OD S4. HRMS Spectrum of chrysomycin B () S5. S6. H -NMR Spectrum of chrysomycin C (3) in CD 3 OD 3 C-NMR Spectrum of chrysomycin C (3) in CD 3 OD S7. DEPT 35 Spectrum of chrysomycin C (3) in CD 3 OD S8. COSY Spectrum of chrysomycin C (3) in CD 3 OD S9. HSQC Spectrum of chrysomycin C (3) in CD 3 OD S. HMBC spectrum of chrysomycin C (3) in CD 3 OD S. HRMS of chrysomycin C (3) S2. HRMS of chrysomycin D (4) S3. LCMS of active fraction S4. Screenshot of DNP database search during dereplication S5. Screenshot of DNP substructure search using basic naphthocoumarin skeleton 2

3 This journal is The Royal Society of Chemistry 23 S H -NMR Spectrum of chrysomycin A () in CD 3 OD 29-jul-shreyan-h SS-Peak-II f (ppm)

4 This journal is The Royal Society of Chemistry 23 S2. HRMS Spectrum of chrysomycin A () 4

5 This journal is The Royal Society of Chemistry 23 S3 H -NMR Spectrum of chrysomycin B (2) in CD 3 OD 29-jul-shreyan-h SS-Peak-I f (ppm)

6 This journal is The Royal Society of Chemistry 23 S4. HRMS Spectrum of chrysomycin B (2) 6

7 This journal is The Royal Society of Chemistry 23 S5 H -NMR Spectrum of chrysomycin C(3) in CD 3 OD Jul22-23 SS-P-III Jul22-23 SS-P-III f (ppm) f (ppm)

8 This journal is The Royal Society of Chemistry 23 S6. 3 C NMR Spectrum of chrysomycin C (3) in CD 3 OD Jul22-23 SS-P-III f (ppm)

9 This journal is The Royal Society of Chemistry 23 S7. DEPT 35 Spectrum of chrysomycin C (3) in CD 3 OD Jul22-23 SS-P-III f (ppm)

10 This journal is The Royal Society of Chemistry 23 S8. COSY Spectrum of chrysomycin C (3) in CD 3 OD Jul22-23 SS-P-III f (ppm) f2 (ppm)

11 This journal is The Royal Society of Chemistry 23 S9. HSQC Spectrum of chrysomycin C (3) in CD 3 OD Jul22-23 SS-P-III f (ppm) f2 (ppm) 3 2 -

12 This journal is The Royal Society of Chemistry 23 S. HMBC spectrum of chrysomycin C (3) in CD 3 OD Jul22-23 SS-P-III f (ppm) f2 (ppm)

13 This journal is The Royal Society of Chemistry 23 S. HRMS of chrysomycin C (3) 3

14 This journal is The Royal Society of Chemistry 23 S2. HRMS of chrysomycin D (4) 4

15 This journal is The Royal Society of Chemistry LCMS of active fraction 3. LC chromatogram at 28 nm.4.3 AU Minutes 3.2. LCMS chromatogram in TIC mode x 5 +/-ESI BPC Scan Frag=35.V SP4.d Smooth CHRYSOMYCIN -D CHRYSOMYCIN -E CHRYSOMYCIN-B CHRYSOMYCIN-A CHRYSOMYCIN-C Counts vs. Acquisition Time (min) 3.3. MS spectras of chrysomycins A-E x 3 -ESI Scan:2 (53.3 min) Frag=35.V SP4.d x ESI Scan: (53.3 min) Frag=35.V SP4.d Counts vs. Mass-to-Charge (m/z) 5

16 This journal is The Royal Society of Chemistry 23 x 3 -ESI Scan:2 (58.8 min) Frag=35.V SP4.d 523. x +ESI Scan: (58.8 min) Frag=35.V SP4.d x Counts vs. Mass-to-Charge (m/z) -ESI Scan:2 (64.9 min) Frag=35.V SP4.d 495. x ESI Scan: (64.9 min) Frag=35.V SP4.d x Counts vs. Mass-to-Charge (m/z) -ESI Scan:2 (7.8 min) Frag=35.V SP4.d x +ESI Scan: (7.7 min) Frag=35.V SP4.d Counts vs. Mass-to-Charge (m/z) 49. 6

17 This journal is The Royal Society of Chemistry 23 S4. Screenshots of DNP database search during dereplication 7

18 This journal is The Royal Society of Chemistry 23 8

19 This journal is The Royal Society of Chemistry 23 9

20 This journal is The Royal Society of Chemistry 23 S5. Screenshots of DNP substructure search using basic naphthocoumarin skeleton 2