5085-72-3Relevant articles and documents
Friedelane triterpenoids: Transformations toward A-ring modifications including 2-: Homo derivatives
Das, Jayanta,Sarkar, Antara,Ghosh, Pranab
, p. 6673 - 6688 (2018/05/07)
Friedelin and its derivatives, commonly known as friedelane triterpenoids, exhibit potential biological effects ranging from antimicrobial to anticancer to anti-HIV. To modify the A-ring of the pentacyclic triterpenoid, various transformative scopes have been utilized. Herein, some simple unprecedented transformative protocols have been accomplished towards furnishing 42 (25 new) A-ring modified pentacyclic friedelane triterpenoids. It is worth noting that the modifications include the all-new 2-homo derivatives. The one-pot BF3·OEt2-mediated oxidative transformation of friedelin to yield friedel-3-enol acetate as the major product was one of the key reactions. A group of isomeric A-ring modifications was produced on the basis of simple transformations on suitable friedelane-based molecules. The syntheses of the novel 2-homofriedelanes were envisioned from the transformative reactions of the designed triterpenoid 3-chlorofriedel-2-ene-2-carbaldehyde, which was isolated as the major product from the reaction of friedelin with the novel Vilsmeier-Haack reagent. New A-ring modified derivatives were also obtained due to further interesting transformations of 3-chlorofriedel-3-ene, isolated as side products from the same reaction. Again, considering the scope of the 3-chloro-2-enal moiety associated with the A-ring of the triterpenoid, some heterocycle-linked- (bonded to C3) 2-homofriedelane triterpenoids were synthesized. Various common reaction strategies were employed on suitable substrates to finally achieve a series of C2,C3-; C3,C4- and C2,C3,C4-functionalized as well as 2-homofriedelane triterpenoids with just one to four efficient steps.
Chemical constituents of Argyreia argentea, Millingtonia hortensis and Pyrostegia venusta
Dinda,De,Bhattacharya,Arima,Sato,Harigaya
, p. 291 - 293 (2007/10/03)
Isolation of five known compounds n-hentriacontanol, β-sitosterol, friedelin, epifriedelinol and epifriedelinol acetate from Argyreia argentea aerial parts; four known compounds nonacosanoic acid, ursolic acid, oleanolic acid and 6-methoxy-5,7,4′-trihydroxyflavone from Millingtonia hortensis flower, and four known compounds lupeol, betulin, betulinic acid and choline chloride from the stem bark of Pyrostegia venusta is reported.
Cytotoxic terpenoids and flavonoids from Artemisia annua
Zheng
, p. 54 - 57 (2007/10/02)
The cytotoxic activity of nine terpenoids and flavonoids isolated from Artemisia annua was tested in vitro on several human tumor cell lines. These compounds are artemisinin, deoxyartemisinin, artemisinic acid, arteannuin-B, stigmasterol, friedelin, friedelan-3β-ol, artemetin, and quercetagetin 6,7,3',4'-tetramethyl ether. Friedelane-type triterpenoids were isolated for the first time from this plant. Artemisinin and quercetagetin 6,7,3',4'-tetramethyl ether showed significant cytotoxicity against P-388, A-549, HT-29, MCF-7, and KB tumor cells.
