A short synthesis of the tricyclic 6-6-6 and 6-7-6 ring systems of the abietane- and icetexane-type diterpenoids from a common intermediate is presented, using alkylation and acid-catalyzed cyclization as key steps.
Nineteen diterpenoids, including saldigitin A(1) bearing an unprecedented 10-methylated 6/7/6 carbon ring system, two new icetexanes(2, 3), and two new nor-abietanes(5, 6) were characterized from the roots of Salvia d...Nineteen diterpenoids, including saldigitin A(1) bearing an unprecedented 10-methylated 6/7/6 carbon ring system, two new icetexanes(2, 3), and two new nor-abietanes(5, 6) were characterized from the roots of Salvia digitaloides. Their structures were elucidated by the analysis of the spectroscopic data,X-ray crystallography, and TDDFT calculations of ECD spectra. The novel architecture of 1 should be biogenetically derived through the cleavage and re-cyclization of the B/C rings from the normal abietane skeleton. Biologically, 1–5 exhibited noticeable inhibitions on Ca_(v)3.1 low voltage-gated Ca2+channel(LVGCC), with IC50values in the range of 3.43–11.70 μmol/L. They are the first example of diterpenoids with 6/7/6 carbon rings system as Ca_(v)3.1 antagonists.展开更多
基金the financial support provided by the National Science Foundation of China(No.30873147)
文摘A short synthesis of the tricyclic 6-6-6 and 6-7-6 ring systems of the abietane- and icetexane-type diterpenoids from a common intermediate is presented, using alkylation and acid-catalyzed cyclization as key steps.
基金financially supported by the National Natural Science Foundation of China (Nos. 32070392 and 32070393)the Second Tibetan Plateau Scientific Expedition and Research(STEP) Program (Nos. 2019QZKK0502-0303 and 2019QZKK0502-0304)+2 种基金Natural Science Foundation of Yunnan Province (Nos.202001AS070040 and 202101AV070010)Yunnan Young&Elite Talents Project (No. YNWR-QNBJ-2020-277)CAS “Light of West China” Program (2021)。
文摘Nineteen diterpenoids, including saldigitin A(1) bearing an unprecedented 10-methylated 6/7/6 carbon ring system, two new icetexanes(2, 3), and two new nor-abietanes(5, 6) were characterized from the roots of Salvia digitaloides. Their structures were elucidated by the analysis of the spectroscopic data,X-ray crystallography, and TDDFT calculations of ECD spectra. The novel architecture of 1 should be biogenetically derived through the cleavage and re-cyclization of the B/C rings from the normal abietane skeleton. Biologically, 1–5 exhibited noticeable inhibitions on Ca_(v)3.1 low voltage-gated Ca2+channel(LVGCC), with IC50values in the range of 3.43–11.70 μmol/L. They are the first example of diterpenoids with 6/7/6 carbon rings system as Ca_(v)3.1 antagonists.
