Planta Med 2019; 85(18): 1485
DOI: 10.1055/s-0039-3399887
Main Congress Poster
Poster Session 1
© Georg Thieme Verlag KG Stuttgart · New York

Identification of new labdane diterpenoids from the aerial parts of Otostegia persica utilizing NMR and circular dichroism calculations

M Alilou
1 Pharmacy/Pharmacognosy and Center for Molecular Biosciences Innsbruck (CMBI),, Innrain 80-82, Innsbruck 6020, Austria
,
S Schwaiger
1 Pharmacy/Pharmacognosy and Center for Molecular Biosciences Innsbruck (CMBI),, Innrain 80-82, Innsbruck 6020, Austria
,
H Stuppner
1 Pharmacy/Pharmacognosy and Center for Molecular Biosciences Innsbruck (CMBI),, Innrain 80-82, Innsbruck 6020, Austria
› Author Affiliations
Further Information

Publication History

Publication Date:
20 December 2019 (online)

 

The genus Otostegia (Lamiaceae) encompasses 33 species growing worldwide [1]. The Iran flora, comprises three species of this genus, which are growing in tropical and subtropical regions. In traditional medicine, Otostegia persica is used for the treatment of malaria, headache, diabetes, stomachache, and rheumatoid arthritis, but also to promote wound healing [2],[3]. Phytochemical investigations of a petroleum ether subfraction of O. persica extract resulted in isolation of three new labdane diterpenes with spiro skeleton (1-3) and two derivatives comprising a furan ring (4 and 5). The relative configuration of the isolated compounds was established by analysis of NOESY correlations along with 1H and 13C NMR and DP4+ probability calculations, while the absolute configuration was determined by quantum chemical calculation methods and comparison of calculated and experimentally obtained ECD spectra.

Therefore, the isolated compounds were identified as (2ʹ’S,3R,4a’’S,5R,5ʹR,6ʹ’R,8a’’S)-6ʹ’-hydroxy-5-methoxy-2ʹ’,5ʹ’,5ʹ’,8a’’-tetramethyldecahydro-2H,2ʹ’H-dispiro[furan-3,2ʹ-furan-5ʹ,1ʹ’-naphthalen]-3ʹ’(4ʹ’H)-one (1), (2ʹ’S,3R,4ʹ’S,4a’’S,5R,5ʹR,6ʹ’R,8a’’S)-4ʹ’,6ʹ’-dihydroxy-5-methoxy-2ʹ’,5ʹ’,5ʹ’,8a’’-tramethyldecahydro -2H,2ʹ’H-dispiro[furan-3,2ʹ-furan-5ʹ,1ʹ’-naphthalen]-3ʹ’(4ʹ’H)-one (2), (2ʹ’S,3S,4a’’S,5R,5ʹR,6ʹ’R, 8a’’S)-6ʹ’-hydroxy-5-methoxy-2ʹ’,5ʹ’,5ʹ’,8a’’-tetramethyldecahydro-2H,2ʹ’H-dispiro[furan-3,2ʹ furan-5ʹ,1ʹ’-naphthalene]-2,3ʹ’(4ʹ’H)-dione (3), (4aS,7R,8aR)-4-(2-(furan-3-yl)ethyl)-7-hydroxy-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one (4), (1S,4aS,7R,8aR)-4-(2-(furan-3-yl)ethyl)-1,7-dihydroxy-3,4a,8,8-tetramethyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one (5).

 
  • References

  • 1 Khan A, Ahmad VU, Farooq U, Bader S, Arshad S. Two new flavonol glycosides from otostegia limbata BENTH. Chem Pharm Bull 2009; 57: 276-279
  • 2 Tofighi Z, Alipour F, Hadavinia H, Abdollahi M, Hadjiakhoondi A, Yassa N. Effective antidiabetic and antioxidant fractions of Otostegia persica extract and their constituents. Pharm Biol 2014; 52 , 961-966
  • 3 Sadeghi Z, Akaberi M, Valizadeh J. Otostegia persica (Lamiaceae): a review on its ethnopharmacology, phytochemistry, and pharmacology. Avicenna J Phytomed 2014; 4: 79-88