72963-56-5Relevant academic research and scientific papers
Synthesis of ent-Cleistanthane Diterpenoid Spruceanol: Construction of an Aromatic C Ring via Lewis Acid-Controlled Regioselective Diels-Alder Cycloaddition
Cai, Wei,Huang, Sujie,Wu, Jiajia,Song, Zhiqiang,Xin, Zhengyuan,Li, Jiabin,Xue, Xiaowen
, p. 6709 - 6718 (2020)
The first synthesis of ent-cleistanthane-type diterpenoid spruceanol with significant anticancer activity is described. A chiral pool approach was employed with a linear sequence of 13 steps beginning from readily available and inexpensive andrographolide. The approach features the construction of an aromatic ring with hydroxyl and methyl groups at C-12 and C-13 of the target compound, respectively, via Lewis acid-controlled regioselective Diels-Alder cycloaddition and the regioselective removal of the primary hydroxyl group of the Diels-Alder adduct.
Terpenoids with potent antimycobacterial activity against Mycobacterium tuberculosis from Trigonostemon reidioides roots
Kaemchantuek, Praphakorn,Chokchaisiri, Ratchanaporn,Prabpai, Samran,Kongsaeree, Palangpon,Chunglok, Warangkana,Utaipan, Tanyarath,Chamulitrat, Walee,Suksamrarn, Apichart
, p. 1594 - 1601 (2017)
Phytochemical investigation of Trigonostemon reidioides roots led to the isolation of fourteen compounds. These included six new diterpenoids, trigonoreidons A?F (1?6), together with eight known diterpenoids 7?14. The structures of the new compounds were elucidated by spectroscopic techniques and the absolute configuration at the asymmetric carbon was determined by the modified Mosher's method. The structure of trigonoreidon B (2) was confirmed by X-ray crystallographic analysis. The known compounds were identified by comparison of the spectroscopic and physical data with those of reported values. The isolated compounds were evaluated for antimycobacterial activity against Mycobacterium tuberculosis. Among the compounds that exhibited antimycobacterial activity, the diterpenoids rediocide C (12) and rediocide G (14) were the most active compounds, with the MIC value of 3.84?μM.
Isolation and confirmation of the proposed cleistanthol biogentic link from Croton insularis
Maslovskaya, Lidia A.,Savchenko, Andrei I.,Gordon, Victoria A.,Reddell, Paul W.,Pierce, Carly J.,Parsons, Peter G.,Williams, Craig M.
supporting information; experimental part, p. 1032 - 1035 (2011/04/27)
The proposed cleistanthol biosynthetic intermediate en route to spruceanol, and other related family members, was isolated for the first time from Croton insularis, confirming the Jacobs-Reynolds hypothesis. Anticancer evaluation of the new isolates and their aerial oxidation products is also reported.(Figure Presented)
