Kadcoccinones A–F, New Biogenetically Related Lanostane-Type Triterpenoids with Diverse Skeletons from Kadsura coccinea

Abstract

Six new lanostane-related triterpenoids, kadcoccinones A-F (1-6), were isolated from Kadsura coccinea. Compound 3 possesses a novel 6/6/9-fused carbocyclic core containing a rare oxabicyclo[4.3.1]decane system. Compounds 4 and 5 are isomers representing the first example of the 18(13 → 12)-abeo-26-norlanostane triterpenoid. The absolute configurations of 1 and 4-6 were defined by X-ray diffraction and experimental ECD spectra, and that of 3 was elucidated by quantum chemical calculations. The plausible biogenetic pathway of 1-6 is postulated.

Anti‐gastric cancer activity and mechanism of natural compound “Heilaohulignan C” isolated from Kadsura coccinea

“…For the K562, Bel‐7402, and A549 cell lines, Kadlongilactone A‐B and Longipedlactone A showed high cytotoxicity, with IC50 values of 0.1, 0.1, and 1.0 μmol/L, respectively (Gao et al, 2008). Hu et al (2015) has been reported that kadcoccinones A‐F exhibit cytotoxic activity against six cancer cell lines (HL‐60, SMMC7721, A‐549, MCF‐7, SW‐480, and Hela). The treatment of single Xenopus embryo cells with kadsuracoccinic acid A is reported to be capable of detained cleavage of these cells with an IC50 value of 0.32 μg/ml (H. Li, Wang, Miyata, & Kitanaka, 2008).…”

Natural Products Research in China From 2015 to 2016

“…Kadsura coccinea was also the source of six new lanostane-related triterpenoids, kadcoccinones A–F. Kadcoccinone C ( 619 ) possessed an unprecedented 6/6/9-fused carbocyclic core containing a rare oxabicyclo[4.3.1]decane system, while kadcoccinones D ( 620 ) and E ( 621 ) were two novel 18(13→12)-abeo-26-norlanostane triterpenoids (Hu et al, 2015 ). Neogenkwanines A–H ( 622 - 629 ), daphnane-type diterpenes with a 4,7- or 4,6-oxo bridge, were isolated from Daphne genkwa (Mianyang, Sichuan, China) (Li et al, 2015c ).…”

New Cadinane Sesquiterpenes from the Stems of Kadsura heteroclita

“…In the last few decades, phytochemical work on the family Schisandraceae has resulted in a seminal contribution to novel structural frameworks for triterpenoidal skeletons [1,2,3,4]. Recently, some promising sesquiterpenes has also been reported from the plants of family Schisandraceae [5,6,7,8,9,10].…”