Dysoticans F-H: three unprecedented dimeric cadinanes from (Osbeck) Kosterm. stem bark

• Published in: RSC advances 2023-03, Vol.13 (14), p.937-9376
• Main Authors: Naini, Al Arofatus, Mayanti, Tri, Maharani, Rani, Fajriah, Sofa, Kabayama, Kazuya, Shimoyama, Atsushi, Manabe, Yoshiyuki, Fukase, Koichi, Jungsuttiwong, Sirriporn, Supratman, Unang
• Format: Article
• ISSN: 2046-2069
• DOI: 10.1039/d3ra01085f

An asymmetrical true-dimeric cadinane via ketonic bridge [C-15/C-3′], dysotican F ( 1 ), two symmetrical pseudo-cadinane dimers through an O -ether linkage [C-3/C-3′], dysoticans G ( 2 ) and H ( 3 ), as well as three known sesquiterpenoids 4-6 were obtained from the stem bark of Dysoxylum parasiticum (Osbeck) Kosterm. (Meliaceae). Their structures were determined by spectroscopic and quantum chemical calculations of 13 C NMR shifts using a GIAO method and electronic circular dichroism (ECD) using a TDDFT method. A possible biogenetic pathway for 1-3 beginning from the known compounds ( i-ii ) was proposed. Cytotoxic evaluation showed that 2 as a new lead compound is the most potent against the MCF-7 and HeLa cell lines with IC 50 values of 12.07 ± 0.17 μM and 9.29 ± 0.33 μM, while 1 has moderate inhibition with IC 50 values of 31.59 ± 0.34 μM and 27.93 ± 0.25 μM. Furthermore, 3 is a selective inhibitor against the HeLa cell growth with an IC 50 value of 39.72 ± 0.18 μM. A brief structure-activity relationship analysis of all isolated compounds 1-6 was also provided, including comparison with the coexisting molecules in the previous report. Dysoxylum parasiticum 's stem bark produces an asymmetrical and two symmetrical dimers ( 1-3 ), dysoticans F-H, with a novel cadinene dimer skeleton.