SUPPORTING INFORMATION (1)

Hirsutosterols A–G, Polyoxygenated Steroids from a

Formosan Soft Coral Cladiella hirsuta

Bo-Wei Chen,a Shu-Ming Chang,a Chiung-Yao Huang,a Jui-Hsin Su,b Zhi-Hong Wen,a Yang-Chang Wu,c and Jyh-Horng Sheu*a,d

aDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan bTaiwan Coral Research Center, National Museum of Marine Biology & Aquarium, Checheng, Pingtung 944,Taiwan cGraduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan dAsia-Pacific Ocean Research Center, National Sun Yat-sen University, Kaohsiung 804,Taiwan

Corresponding author: sheu@mail.nsysu.edu.tw

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

List of Supporting Information: S2. 1H NMR spectrum of 1 in CDCl3 at 300 MHz.

S3. 13C NMR spectrum of 1 in CDCl3 at 75 MHz.

S4. HRESIMS spectrum of 1.

S5. 1H NMR spectrum of 2 in CDCl3 at 400 MHz.

S6. 13C NMR spectrum of 2 in CDCl3 at 100 MHz.

S7. HRESIMS spectrum of 2.

S8. 1H NMR spectrum of 3 in CDCl3 at 500 MHz.

S9. 13C NMR spectrum of 3 in CDCl3 at 125 MHz.

S10. HRESIMS spectrum of 3.

S11. 1H NMR spectrum of 4 in CDCl3 at 400 MHz.

S12. 13C NMR spectrum of 4 in CDCl3 at 100 MHz.

S13. HRESIMS spectrum of 4.

S13. 1H NMR spectrum of 5 in CDCl3 at 300 MHz.

S14. 13C NMR spectrum of 5 in CDCl3 at 75 MHz.

S15. HRESIMS spectrum of 5.

S16. 1H NMR spectrum of 6 in CDCl3 at 400 MHz.

S17. 13C NMR spectrum of 6 in CDCl3 at 100 MHz.

S18. HRESIMS spectrum of 6.

S19. 1H NMR spectrum of 7 in CDCl3 at 500 MHz.

S20. 13C NMR spectrum of 7 in CDCl3 at 125 MHz.

S21. HRESIMS spectrum of 7.

S1

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S

2. 1 H

NM

R s

pect

rum

of

1in

CD

Cl 3

at 3

00 M

Hz.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S

313

C N

MR

spe

ctru

m o

f 1

in C

DC

l 3at

75

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S4

HR

ES

IMS

spe

ctru

m o

f 1.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S5.

1 H N

MR

spe

ctru

m o

f 2

in C

DC

l 3 a

t 400

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S6.

13C

NM

R s

pect

rum

of

2in

CD

Cl 3

at 1

00M

Hz.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S7

HR

ES

IMS

spe

ctru

m o

f 2.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S8.

1 H N

MR

spe

ctru

m o

f 3

in C

DC

l 3 a

t 500

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S9.

13C

NM

R s

pect

rum

of

3 in

CD

Cl 3

at 1

25M

Hz.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S

10. H

RE

SIM

Ssp

ectr

um o

f 3.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S

11. 1 H

NM

R s

pect

rum

of

4in

CD

Cl 3

at 4

00 M

Hz.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S

12. 13

C N

MR

spe

ctru

m o

f 4

in C

DC

l 3 a

t 100

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S13

HR

ES

IMS

spe

ctru

m o

f 4.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S14

. 1 H N

MR

spe

ctru

m o

f5

in C

DC

l 3 a

t 300

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S15

. 13C

NM

R s

pect

rum

of

5in

CD

Cl 3

at 7

5 M

Hz.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S15

HR

ES

IMS

spe

ctru

m o

f 5.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S16

. 1 H N

MR

spe

ctru

m o

f 6

in C

DC

l 3 a

t 400

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S

17. 13

C N

MR

spe

ctru

m o

f 6

in C

DC

l 3 a

t 100

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S18

HR

ES

IMS

spe

ctru

m o

f 6.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S19

. 1 H N

MR

spe

ctru

m o

f 7

in C

DC

l 3 a

t 500

MH

z.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S20

. 13C

NM

R s

pect

rum

of

7in

CD

Cl 3

at 1

25M

Hz.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011

S

21 H

RE

SIM

S s

pect

rum

of

7.

Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is (c) The Royal Society of Chemistry 2011