Molecules 2012, 17(12), 14310-14322; doi:10.3390/molecules171214310
Article

Antimicrobial and Cytotoxic Isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) Callus and Cell Suspension Culture

Harilaos Damianakos 1 email, Nadine Kretschmer 2 email, Katarzyna Sykłowska-Baranek 3 , Agnieszka Pietrosiuk 3 email, Rudolf Bauer 2 email and Ioanna Chinou 1,* email
1 Department of Pharmacy, Institute of Pharmacognosy & Chemistry of Natural Products, University of Athens, Zografou 15771, Athens, Greece 2 Department of Pharmacognosy, Institute of Pharmaceutical Sciences, Karl-Franzens University, Universitätsplatz 4, 8010 Graz, Austria 3 Department of Biology and Pharmaceutical Botany, Medical University of Warsaw, Banacha Street 1, 02-097 Warsaw, Poland
* Author to whom correspondence should be addressed.
Received: 13 September 2012; in revised form: 27 November 2012 / Accepted: 28 November 2012 / Published: 3 December 2012
(This article belongs to the Section Natural Products)
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Abstract: The phytochemical investigation of the n-hexane extract from callus and cell suspension culture of Arnebia euchroma (Royle) Jonst. resulted in the isolation of nine isohexenylnaphthazarins: deoxyalkannin (1), alkannin (2), acetylalkannin (3), isobutyrylalkannin (4), β-hydroxyisovalerylalkannin (5), 2''-(S)-α-methylbutyrylalkannin (6), propionylalkannin (7), teracrylalkannin (8) and acetylshikonin (9). Their structures were determined by MS and NMR spectroscopy. Pigments 2–8 are isolated for the first time from Arnebia in vitro cultures, 4 and 7 are reported in the present work as novel metabolites within the Arnebia genus, while 9 is a known constituent of both natural roots and in vitro cultures of A. euchroma. Moreover, methyl jasmonate and 1-monoglyceryl olate, palmitate and stearate are reported for the first time within the Boraginaceae family. The antimicrobial and cytotoxic activities of all isolated pigment compounds were tested, revealing a very interesting profile.
Keywords: Arnebia euchroma; Boraginaceae; callus culture; cell suspension culture; isohexenylnaphthazarins; cytotoxic; antimicrobial

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MDPI and ACS Style

Damianakos, H.; Kretschmer, N.; Sykłowska-Baranek, K.; Pietrosiuk, A.; Bauer, R.; Chinou, I. Antimicrobial and Cytotoxic Isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) Callus and Cell Suspension Culture. Molecules 2012, 17, 14310-14322.

AMA Style

Damianakos H, Kretschmer N, Sykłowska-Baranek K, Pietrosiuk A, Bauer R, Chinou I. Antimicrobial and Cytotoxic Isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) Callus and Cell Suspension Culture. Molecules. 2012; 17(12):14310-14322.

Chicago/Turabian Style

Damianakos, Harilaos; Kretschmer, Nadine; Sykłowska-Baranek, Katarzyna; Pietrosiuk, Agnieszka; Bauer, Rudolf; Chinou, Ioanna. 2012. "Antimicrobial and Cytotoxic Isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) Callus and Cell Suspension Culture." Molecules 17, no. 12: 14310-14322.

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