Induction of Apoptosis by Diterpenes from the Soft Coral, Xenia Elongata

Supporting Information

Induction of Apoptosis by Diterpenes from the Soft Coral, Xenia elongata

Eric H. Andrianasolo†, Liti Haramaty†, Kurt Degenhardt‡, Robin Mathew§,, Eileen White‡, §, , Richard Lutz† and Paul Falkowski†*

† Center for Marine Biotechnology, Institute of Marine and Coastal Sciences, Rutgers, The State University of New Jersey NJ 08901-8521

‡Center for Advanced Biotechnology and Medicine, Department of Molecular Biology and Biochemistry, Rutgers, The State University of New Jersey, 679 Hoes Lane, Piscataway, New Jersey 08854

§University of Medicine and Dentistry of New Jersey, Robert Wood Johnson Medical School, 675 Hoes Lane, Piscataway, New Jersey 08854

The Cancer Institute of New Jersey, 195 Little Albany Street, New Brunswick, New Jersey 08903

Spectral Data for Compound (1) in CDCl3

Figure S1.300 MHz 1H NMR spectrum of compound (1) in CDCl3

Figure S2.75 MHz 13C NMR spectrum of compound (1) in CDCl3

Figure S3.300 MHz 1H NMR spectrum of compound (1) in CDCl3 (partial view of the two acetate signals)

Figure S4.300 MHz 1H-1H COSY spectrum of compound (1) in CDCl3

Figure S5 300 MHz Multiplicity-edited HSQC spectrum of compound (1) in CDCl3

Figure S6 300 MHz Multiplicity-edited HSQC spectrum of compound (1) in CDCl3 (partial view of the two acetate signals)

Figure S7 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (1) in CDCl3

Figure S8 300MHz ROESY spectrum of compound (1) in CDCl3 (ROESY cross peak between H-1 and H-4a)

Spectral Data for Compound (2) in CDCl3

Figure S9 300 MHz 1H NMR spectrum of compound (2) in CDCl3

Figure S10 300 MHz 1H-1H COSY spectrum of compound (2) in CDCl3

Figure S11 300 MHz Multiplicity-edited HSQC spectrum of compound (2) in CDCl3

Figure S12 300 MHz Multiplicity-edited HSQC spectrum of compound (2) in CDCl3(partial view of the signal belonging to the proton between 1.40 to 2.7 ppm)

Figure S13 75 MHz 13C NMR spectrum of compound (2) in CDCl3(partial view of the carbonyl signals)

Figure S14 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (2)

Figure S15300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (2) (observed correlation to the two carbonyls)

Figure S16 75 MHz 13C NMR spectrum of compound (2) in CDCl3(partial view of the olefinic regions)

Figure S17 75 MHz 13C NMR spectrum of compound (2) in CDCl3(partial view of the signal between 10 to 70 ppm)

Figure S18 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (2) (Vinyl methyl correlations)

Figure S19 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (2) (Terminal CH2 correlations to C-11a and C-9)

Figure S20 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (2) (Observed correlation to C-4 and C-4a)

Figure S21 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (2) (Observed correlation to C-8 and C-11)

Figure S22 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (2) (Observed correlation to C-12)

Figure S23 300MHz ROESY spectrum of compound (2) in CDCl3 (ROESY cross peak between H-9 and H-18)

Figure S24 300MHz ROESY spectrum of compound (2) in CDCl3 (ROESY cross peak between H-3 and H-11a)

Figure S25 300MHz ROESY spectrum of compound (2) in CDCl3 (ROESY cross peak between H-13 and H-4a)

Figure S26 300MHz ROESY spectrum of compound (2) in CDCl3 (ROESY cross peak between H-3 and H-12)

Figure S27 300MHz ROESY spectrum of compound (2) in CDCl3 (ROESY cross peak between H-14 and H-17)

Spectral Data for Compound (3) in CDCl3

Figure S28 300 MHz 1H NMR spectrum of compound (3) in CDCl3

Figure S29 300 MHz 1H-1H COSY spectrum of compound (3) in CDCl3

Figure S30 300 MHz 1H-1H COSY spectrum of compound (3) in CDCl3 (Observed correlation of the E-diene system)

Figure S31 300 MHz Multiplicity-edited HSQC spectrum of compound (3) in CDCl3

Figure S32 300 MHz Multiplicity-edited HSQC spectrum of compound (3) in CDCl3 (partial view of the signal belonging to the terminal CH2)

Figure S33 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (3) (Observed correlation to C-1 attachment of two O-methyl groups)

Figure S34 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (3) (Observed correlation to C-15 attachment of two methyl groups)

Figure S35 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (3) (Vinyl methyl correlations and presence of acetate group)

Figure S36 300MHz ROESY spectrum of compound (3) in CDCl3 (ROESY cross peak between H-3 and H-11a)

Figure S37 300MHz ROESY spectrum of compound (3) in CDCl3 (ROESY cross peak between H-12 and H-3)

Figure S38 300MHz ROESY spectrum of compound (3) in CDCl3 (ROESY cross peak between H-13 and H-4a and H1 and H4a )

Spectral Data for Compound (4) in CDCl3

Figure S39 300 MHz 1H NMR spectrum of compound (4) in CDCl3

Figure S40 300 MHz 1H-1H COSY spectrum of compound (4) in CDCl3

Figure S41 75 MHz 13C NMR spectrum of compound (4) in CDCl3 (partial view of the signal between 10 to 80 ppm)

Figure S42 75 MHz 13C NMR spectrum of compound (4) in CDCl3 (partial view of the signal between 110 to 180 ppm)

Figure S43 300 MHz Multiplicity-edited HSQC spectrum of compound (4) in CDCl3

Figure S44 300 MHz Multiplicity-edited HSQC spectrum of compound (4) in CDCl3 (partial view of the olefinic regions)

Figure S45 300 MHz HMBC spectrum (optimized for J = 8Hz ) of compound (4) in CDCl3

Figure S46 300MHz ROESY spectrum of compound (4) in CDCl3 (ROESY cross peak between H-3 and H-11a)

Figure S47 300MHz ROESY spectrum of compound (4) in CDCl3 (ROESY cross peak between H-12 and H-4a)

HPLC traces

Figure S48 HPLC trace of the fraction originally extracted by Methanol

Figure S49 HPLC trace of the fraction originally extracted by CH2Cl2