Two new dihydroisocoumarins and terpenoids from Scorzonera longiana Sumbul an endemic species to Turkey and their antimicrobial activity

KORKMAZ B., RENDA G., ERİK İ., BOZDAL G., ÇOŞKUNÇELEBİ K., YAYLI N.

NATURAL PRODUCT RESEARCH, cilt.37, sa.7, ss.1185-1198, 2023 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 37 Sayı: 7
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1080/14786419.2021.2000410
  • Dergi Adı: NATURAL PRODUCT RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Aquatic Science & Fisheries Abstracts (ASFA), Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, CINAHL, EMBASE, Food Science & Technology Abstracts, MEDLINE, Veterinary Science Database
  • Sayfa Sayıları: ss.1185-1198
  • Anahtar Kelimeler: Scorzonera longiana, dihydroisocoumarins, sesquiterpene, triterpenes, PHENOLIC-COMPOUNDS, SECONDARY METABOLITES, ACID-DERIVATIVES, TRITERPENOIDS, HYDRANGENOL, GLYCOSIDES, ROOTS, SESQUITERPENOIDS, CONSTITUENTS, S.L.
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

Two new dihydroisocoumarins (scorzolongin I (1), and scorzolongin II (2)) and nine known compounds (3 ',5 '-dimethoxy hydrangenol (scorzolongin III, 3), cladantholide (4), dammar-24-ene-3 beta-ol (5), taraxasterol (6), beta-sitosterol (7), mangifgerursanone (8), and a mixture of alpha-amyrenone (9a), beta-amyrenone (9b), and dammar-24-ene-3-one (9c) in about 1:1:2 ratio) were identified from the dichloromethane fraction of Scorzonera longiana. The structure of all compounds (1-9a-c) were elucidated by extensive 1D and 2D NMR (H-1, C-13/APT, COSY, HMBC, HSQC, and NOESY) spectroscopy, UV, FT-IR, and LC-QTOF-MS data and by comparison of their NMR data with the literature. These compounds have been isolated from S. longiana for the first time. An antimicrobial assay against eight microorganisms was applied to isolated compounds 1-3. Scorzolongin I, and scorzolongin II, and scorzolongin III showed notable activity against gram (-) (Escherichia coli and Yersinia pseudotuberculosis) and fungi (Candida albicans, Saccharomyces cerevisiae) with 20 mm inhibition zone each. Scorzolongin II (2) exhibited strong activity against E. coli, Y. pseudotuberculosis, Mycobacterium smegmatis C. albicans, S. cerevisiae with MIC value of 33.8 mu g/mL.