1

Supporting Information

Rec. Nat. Prod. 7:2 (2013) 114-118

Maroccanin: a new γγγγ-lactone and other constituents from

Centaurea maroccana Ball. (Asteraceae)

Sabrina Bicha1, Pierre Chalard2,3, Leila Hammoud1, Francisco León4, Ignacio Brouard4,

Victor Perez Garcia4, Annelise Lobstein5, Ali Bentamene1, Samir Benayache6, Jaime Bermejo4

and Fadila Benayache1*

1Laboratoire de Phytochimie et Analyses Physico-Chimiques et Biologiques, Université Mentouri,

Route de Aïn El Bey, 25000 Constantine, Algeria. 2Institut de Chimie de Clermont-Ferrand (ICCF), Ecole Nationale Supérieure de Chimie de Clermont-

Ferrand (ENSCCF), BP10448, F-63000 Clermont-Ferrand (France) 3 UMR 6296, ICCF – CNRS. F-63171 Aubière

4Instituto de Productos Naturales y Agrobiología-CSIC, 3Instituto Universitario de Bio-orgánica

"Antonio González", Avda. Astrofísico Francisco Sánchez, 3, 38206 La Laguna, Tenerife, Spain. 5Laboratoire d’innovation thérapeutique UMR-CNRS 7200, Université de Strasbourg, Faculté de

Pharmacie, 74 Route du Rhin, 67401 Illkirch, France. 6Laboratoire de Valorisation des Ressources Naturelles et Synthèse de Substances Bioactives,

Université Mentouri, Route de Aïn El Bey, 25000 Constantine, Algeria

Table of contents Page

S1 : 13C and DEPT -NMR spectrum (CDCl3, 125 MHz) of Compound 1 (Maroccanin) 3

S2: 1H-NMR spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin) 4

S3: Expansion, 1H-NMR spectrum (CDCl3, 500 MHz) of Compound 1(Maroccanin) 5

S4: Expansion, 1H-NMR spectrum (CDCl3, 500 MHz) of Compound 1(Maroccanin) 6

S5 : COSY spectrum (CDCl3, 500 MHz) of Compound 1(Maroccanin) 7

S6 : Expansion, COSY spectrum (CDCl3, 500 MHz) of Compound 1(Maroccanin) 8

S7 : Expansion COSY spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin) 9

2

S8 : HSQC spectrum (CDCl3, 500 MHz) of compound 1(Maroccanin) 10

S9 : Expansion HSQC spectrum (CDCl3, 500 MHz) of compound 1(Maroccanin) 11

S10: HMBC spectrum (CDCl3, 500 MHz ) of Compound 1(Maroccanin) 12

S11: Expansion HMBC spectrum (CDCl3, 500 MHz ) of Compound 1 (Maroccanin) 13

S12: Expansion HMBC spectrum (CDCl3, 500 MHz ) of Compound 1 (Maroccanin) 14

S13: Expansion HMBC spectrum (CDCl3, 500 MHz ) of Compound 1 (Maroccanin) 15

S14: NOESY spectrum (CDCl3, 500 MHz) of Compound 1(Maroccanin) 16

S15 : High resolution Mass Spectrum (ESI+) of compound 1(Maroccanin) 17

3

S1: 13C and DEPT -NMR spectra (CDCl3, 125 MHz) of Compound 1 (Maroccanin)

C-1 C-13 C-9

C-1

1

C-12 C-10 C-1

4

C-5 C-6

C-4

C-2 C-7

C-3

C-8

4

S2: 1H-NMR spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin)

5

S3: Expansion, 1H-NMR spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin)

H-10 H-14

H-3 H-4

H-7

H-5’ H-5 H-6’ H-6

6

S4: Expansion, 1H-NMR spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin)

H-11 H-12 H-2

7

S5 : COSY spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin)

8

S6 : COSY spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin)

H-2-H-3

H-7-H-11

H-11-H-12

9

S7 : Expansion, COSY spectrum (CDCl3, 500 MHz) of Compound 1 (Maroccanin)

H-3-H-4

H-4-H-5 H-4-H-5’

H-5

-H-6

H-5

-H-6

’

10

S8 : HSQC spectrum (CDCl3, 500 MHz) of compound 1 (Maroccanin)

C-7-H-7

11

S9 : Expansion, HSQC spectrum (CDCl3, 500 MHz) of compound 1 (Maroccanin)

12

S10: HMBC spectrum (CDCl3, 500 MHz ) of Compound 1 (Maroccanin)

H-2-C-9

H-11-C-13 H-14-C-13

13

S11: Expansion, HMBC spectrum (CDCl3, 500 MHz) of Compound 1(Maroccanin)

H-10-C-9

H-6

-C-1

H-6

’-C

-1

H-3

-C1

H-7-C-9

H-7-C-11

14

S12: Expansion, HMBC spectrum (CDCl3, 500 MHz ) of Compound 1 (Maroccanin)

15

S13: Expansion, HMBC spectrum (CDCl3, 500 MHz ) of Compound 1(Maroccanin)

H-5-C-7 H-5

’-C

-7

H-4

-C-7

H-3

-C-7

16

S14: NOESY spectrum (CDCl3, 500 MHz) of Compound 1(Maroccanin)

H-2

-H-7

H

-10

-H-4

H-3

-H-7

17

S15 : High resolution (ESI+) Mass Spectrum of compound 1(Maroccanin)