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19-nor-, 20-nor-, and tetranor-Halimane-Type Furanoditerpenoids from Croton crassifolius.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-01-31 , DOI: 10.1021/acs.jnatprod.9b00634 Rong Wang 1 , Run-Zhu Fan 1 , Fu-Qiang Ni 1 , Jun Sang 1 , Xing-Lin Xie 1 , Si-Yuan Luo 1 , Gui-Hua Tang 1 , Sheng Yin 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-01-31 , DOI: 10.1021/acs.jnatprod.9b00634 Rong Wang 1 , Run-Zhu Fan 1 , Fu-Qiang Ni 1 , Jun Sang 1 , Xing-Lin Xie 1 , Si-Yuan Luo 1 , Gui-Hua Tang 1 , Sheng Yin 1
Affiliation
The phytochemical investigation of the roots of Croton crassifolius led to the isolation of 16 new halimane furanoditerpenoids, crohalifuranes A-P (1-16), along with 15 known analogues, 17-31. The new structures including their absolute configurations were elucidated by NMR and MS data analysis, comparison of experimental and calculated electronic circular dichroism data, single-crystal X-ray diffraction data, and chemical methods. Crohalifuranes A (1) and B (2) are tetranor- and 19-nor-halimane diterpenoids featuring a rare decahydroacenaphthene core, respectively, which might be derived from the accompanying crassifoliusin A by loss of the furan ring or the C-19 substituent. Crohalifurane C (3) represents the first example of a 20-nor-halimane diterpenoid, and crohalifurane D (4) is characterized by an unusual 6,20-δ-lactone moiety. All compounds were examined for their inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide in RAW264.7 cells, and 2 and 23 exhibited moderate inhibition on NO production with IC50 values of 17.2 ± 1.3 and 23.7 ± 1.4 μM, respectively.
中文翻译:
Croton crassifolius的19-nor-,20-nor-和tetranor-Halimane型呋喃二萜类化合物。
对巴豆(Croton crassifolius)根的植物化学研究导致分离出16种新的哈拉曼呋喃呋喃二萜类化合物,crohalifuranes AP(1-16),以及15种已知类似物17-31。通过核磁共振和质谱数据分析,实验和计算的电子圆二色性数据,单晶X射线衍射数据和化学方法的比较,阐明了包括其绝对构型在内的新结构。Crohalifuranes A(1)和B(2)是分别具有罕见的十氢ac庚啶核的四正氟烷和19-正卤烷二萜类化合物,其可能因呋喃环或C-19取代基丢失而由伴随的crassifoliusin A衍生而来。crofurifurane C(3)代表20-正卤代烷二萜的第一个例子,crohalifurane D(4)的特征是不寻常的6,20-δ-内酯部分。
更新日期:2020-02-03
中文翻译:
Croton crassifolius的19-nor-,20-nor-和tetranor-Halimane型呋喃二萜类化合物。
对巴豆(Croton crassifolius)根的植物化学研究导致分离出16种新的哈拉曼呋喃呋喃二萜类化合物,crohalifuranes AP(1-16),以及15种已知类似物17-31。通过核磁共振和质谱数据分析,实验和计算的电子圆二色性数据,单晶X射线衍射数据和化学方法的比较,阐明了包括其绝对构型在内的新结构。Crohalifuranes A(1)和B(2)是分别具有罕见的十氢ac庚啶核的四正氟烷和19-正卤烷二萜类化合物,其可能因呋喃环或C-19取代基丢失而由伴随的crassifoliusin A衍生而来。crofurifurane C(3)代表20-正卤代烷二萜的第一个例子,crohalifurane D(4)的特征是不寻常的6,20-δ-内酯部分。