New seco-Prezizaane-Type Sesquiterpenes, Jiadifenin with Neurotrophic Activity and 1,2-Dehydroneomajucin from Illicium jiadifengpi

Abstract

Two new seco-prezizaane-type sesquiterpenes, 1,2-dehydroneomajucin (1) and jiadifenin (2), were isolated from the methanol extract of the pericarps of Illicium jiadifengpi, indigenous to the southern part of China. Their structures were elucidated on the basis of NMR data. Compound 2, which is an equilibrated mixture of the epimers 2a and 2b on the C-10 acetal carbon, is the first example of a majucin-type seco-prezizaane with an oxo-function at the C-10 position. The proposed structure for 2 was unambiguously confirmed by chemical conversion of the known sesquiterpene (2S)-hydroxy-3,4-dehydroneomajucin (5) to 2. Compounds 2 and 5 were found to significantly promote neurite outgrowth in primary cultures of fetal rat cortical neurons at concentrations from 0.1 to 10 microM.

Formal Total Synthesis of (−)-Jiadifenolide and Synthetic Studies toward seco-Prezizaane-Type Sesquiterpenes

“…was added dropwise in 20 minutes. The reaction mixture was allowed to warm up to rt over 7 h. The yellow solution was treated with pentane (10 mL Methyl (5aR,6R,8aR)- 8a-hydroxy-6-methyl-3-oxo-1,3,4,5,6,7,8,8a-octahydro-5aH-indeno[4,5-c] 5, 173.4, 164.7, 124.8, 80.9, 64.9, 60.2, 52.4, 41.7, 38.5, 32.9, 31.2, 20.4, 18.7; elemental (5aR,6R,8aR)- 3,4,5,6,7,8, 69.5, 61.9, 40.3, 37.7, 31.6, 28.6, 18.8, 17.7; elemental analysis calcd for C 13 H 16 (5aS,6R,8aR,11S)- 5,7,indeno [4,5-c] 2953, 2929, 2874, 2361, 1785, 1725, 1682, 1442, 1359, 1217, 1191, 1133, 1086, 1046, 1022, 967 cm -1 176.3, 172.5, 157.5, 127.8, 87.4, 69.6, 68.9, 56.2, 36.2, 35.9, 30.7, 21.3, 15.8, 14. Methyl (5aR,6R)- 6-methyl-3-oxo-1,3,4,5,6,7-hexahydro-5aH-indeno[4,5-c] 249.1121, found: 249.1119; X-ray crystal structure is given in the supporting information. (5aR,6R,8R,8aS)-8,8a-dihydroxy-6-methyl-3-oxo-1,3,4,5,6,7,8,8a-octahydro-5aH-indeno[4,5-c] 9, 173.5, 162.6, 128.0, 76.9, 71.5, 69.1, 63.3, 51.7, 41.4, 37.5, 22.4, 19. Methyl (3aR,5aR,6R,8R,8aS, 285.1333, found: 285.1334; X-ray crystal structure is given in the supporting information.…”

“…1H),1.04 (d,J = 6.8 Hz,3H); 13 C NMR (101 MHz, CDCl 3 ) δ = 216. 5,171.1,147.0,111.5,76.0,62.7,51.8,40.1,38.8,29.3,28.2,27.7,17.5,15.8;HRMS (ESI) Methyl (1R, 3081,2957,2879,2361,1729,1435,1404,1328,1234,1165,1121,1061,994,924,883,669 6,171.3,140.8,115.1,73.2,62.9,51.9,40.2,38.9,31.6,28.3,27.7,15.9;HRMS (ESI) ( = 3728, 3728, 3703, 3629, 3600, 2956, 2361, 2340, 1749, 1613, 1513, 1459, 1301, 1246, 1174, 1065, 1035, 995, 823, 679 cm −1 ; 1 H NMR (400 MHz, CDCl 3 ) δ = 7. 2H),6.86 (dd,J = 8.8,2.4 Hz,2H),5.69 (ddd,…”

“…2929, 2338, 1734, 1692, 1450, 1409, 1384, 1363, 1284, 1239, 1193, 1105, 1088, 1032, 995, 912, 887, 853, 819, 757, 702, 627 cm -1 6, 170.7, 147.6, 129.6, 75.0, 74.2, 62.2, 56.4, 51.7, 49.9, 42.3, 38.9, 35.8, 26.5, 26.1, 14.7, 14. given in the supporting information. 4R,5aR,6R,2,4,5,6,oxepine-5a, 9-dicarboxylate (57) and 2R,4R,5aR,6R,2,4,5,6,oxepine-5a, 9-dicarboxylate (58): Hydroxy-dicarboxylate 56 (3.48 g, 10.1 mmol, 1.0 eq.) was dissolved in degassed cyclohexane (200 mL, freezethaw method, 3 cycles).…”

Sesquilignans and sesquiterpenoid from the stem barks of Illicium simonsii and their anti-AChE activity

“…After 48 h, the medium is changed to a serum-free medium F12 (10% HS + 5% FBS + 10 mg/mL NGF). 12 Samples at 50 µM and 5 µM are added into F12. The length of axon was measured and calculated by using microscope.…”

New monoterpene phenyl ethers from Illicium micranthum

“…2,3 Phytochemical investigation showed that this genus produced monoterpenoids, 4 sesquiterpene lactones, [5][6][7][8] diterpenoids, 9 triterpenoids, 10 lignans and neolignans, [11][12][13] which showed various bioactivities, such as insecticidal activity, 14 cancer chemopreventive activity, 15 and neurotrophic activity. [16][17][18] Illicium micranthum was a poisonous shrub used as a traditional pesticide. 3 Previous studies on this plant have resulted in the isolation of eight secoprezizaane sesquiterpene lactones, 5 seven phenylpropanoids 19 and several other compounds.…”