Studies On Friedelane Triterpenes Of Celastrus Monospermus Roxb.

Celastrus monospermus Roxb., a evergreen vine, belongs to the Celastraceae family. Previously, abundant friedelane triterpenes have been isolated from Celastrus monospermus. It have been reported that the friedelane derivatives have important pharmacological activities such as anti-tumor, anti-inflammatory, anti-HIV, anti-ulceration, anti-rheumatic, anti-bacteria, and so on. In a continuation of our investigation to find active compounds especially new active friedelane triterpenes, we systematically studied the constituents of Celastrus monospermus. These active components, particularly the friedelane triterpenes, can be used as lead compounds for discovering new drugs.This thesis was consisted of three parts. The extraction and separation of chemical constituents from the stem and the root of Celastrus monospermus Roxb., the review on advances in friedelane triterpenes from natural resources, were reported respectively. Ten compounds were isolated and identified from the stem of Celastrus monospermus in the first part, nine of them were friedelane triterpenes, including four new compounds. Twelve compounds were isolated from the root of Celastrus monospermus in the second part, and ten ones were identified, of them, seven were fiedelane triterpenes comprising a new compound and two nortriterpene quinone methides. The third part was mainly about the advances in friedelane triterpenes from natural resources in recent years.In the first part, studies on chemical constituents extracted from the stem of Celastrus monospermus was carried out through using modern separated and analytical technologies. Ten compounds including nine friedelane triterpenes were extracted and isolated by using column chromatography and recrystallization methods. Their structures were elucidated as 3β-hydroxyolean-12-en (s-1), 3-oxofriedelane (friedelin s-2), 3-oxofriedelan-28-al (canophyllal, s-3), 3,12-dioxofriedelane (prionostemmadione, s-4), 3-oxo-28-hydroxyfriedelane (canophyllol, s-5), 3,12-di- oxofriedelan-28-al (s-6), 3-oxo-11β-hydroxyfriedelane (monospermol, s-7), 3-oxo- 12α-hydroxyfriedelane (s-8), 3,12-dioxo-28-hydroxyfriedelane (s-9) and 3-oxo- 12α,28-dihydroxyfriedelane (s-10), respectively, on the basis of chemical methods and spectral analysis including 2D experiments (HMBC, HSQC, 1H-1H COSY and NOESY) and high resolution mass spectrometry. They were all the friedelane triterpenes excepted s-1, Compounds s-6, s-7, s-9 and s-10 were the new ones, especially. Compounds s-4, s-5 and s-8 were isolated from this genus for the first time, and compound s-1 was separated from Celastrus monospermus for the first time.In the second part, the experiments of isolation and identification had been done by using modern separated and analytical technologies. Twelve compounds were separated from the root of Celastrus monospermus via using column chromatography and recrystallization technologies, and ten of them were identified as 3-oxofriedelane (r-1), 3,12-dioxofriedelane (r-2), 3-oxo-28-hydroxyfriedelane (prionostemmadione, r-3), 3-oxo-11β-hydroxyfriedelane (monospermol, r-4), 3-oxo-12α-hydroxyfriedelane (r-5), 3β-hydroxylcholest-5,22-dien (r-6),β-sitosterol (r-7), pristimerin (r-8), celastrol (r-9), and daucosterol (r-10), respectively, on the basis of physico-chemical properties and spectral data including 2D spectroscopy (HMBC, HSQC, 1H-1H COSY and NOESY) and high resolution mass spectrometry. Compounds r-1, r-2, r-3, r-4, r-5, r-8 and r-9 belonged to friedelane triterpenes; compounds r-1, r-2, r-3, r-4 and r-5 were the 3-oxofriedelane derivatives; compounds r-8 and r-9 were nortriterpene quinone methides. Of them, compound r-4 was a new fredelane triterpene, named as monospermol; compounds r-2, r-3, r-5 and r-6 were obtained from this genus for the first time; compounds r-8, r-9 and r-10 were obtained from this plant for the first time. Structure elucidation of r-2 by 1H and 13C NMR chemical shift assignments and 2D spectroscopy were reported for the first time.The third part is an overview about study on the advances in friedelane triterpenes from natural resources in recent years. It will be helpful in the following study of exploiting the Celastraceae family plants especially Celastrus monospermus that contain abundant friedelane triterpenes.