Studies On The Chemical Constituents From Stem Barks Of Vernonia Cumingiana Benth & Studies On Chemical Constituents From The Endophyte

The thesis included two parts of studies on the chemical constituents from stem barks of Vernonia cumingiana Benth and from the endophyte.Vernonia cumingiana Benth belongs to the genus of Vernonia in the family of Compositae, and is widely distributed in the south and southeast of Yunnan, the southwest of Sichuan and Guizhou, Guangxi, Guangdong Provinces, etc, in China. It has been used for curing rheumatic arthritis, lumbocrural pain, fracture and malaria in China. In addition, there is only few report on its chemical constituents and biological activities until now. In order to find bioactive new compounds, the ethanol extract of stem barks of V. cumingiana collected from Guangxi was investigated, and 27 compounds including 14 stigmastane-type steroids, 4 caffeoylquinates, 3 sterols, 1 triterpene and 5 other compounds were isolated and identified. Through spectroscopic methods and chemical methods, their structures were established as 3β, 24 (R), 28 (R)-trihydroxy-stigmasta-7, 9 (11)-dien-21-oic acid-3, 28-di-O-β-D-glucopyranoside (1), 3β, 24 (R), 28 (R)- trihydroxy-stigmasta-7, 9 (11)-dien-21-oic acid-28-O-β-D-gluco pyranosyl-3-O-β-D-galactopyrano-syl-(1→2)-β-D-glucopyranoside (2), 3β, 24 (R), 28 (R)-trihydroxy-stigmasta-7, 9 (11)-dien-21-oic acid-3-O-β-D-glucopyranoside (3), 3β, 24 (R), 28 (R)-trihydroxy-stigmasta-7, 9 (11)-dien-21-oic acid-3-O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranoside (4), 3β, 24 (R), 28 (β)-trihydroxy-stigmasta-7, 9 (11)-dien-21-oic acid-3-O-α-L- arabopyranosyl-(1→2)-β-D-glucopyranoside (5), 3β, 24 (R), 28 (R)- trihydroxy-stigmasta-7, 9 (11)-dien-21-oic acid-28-O-β-D-glucopyranosyl-3-O-α-L-arabopyranosyl-(1→2)-β-D-glucopyranoside(6), 3β, 24 (R), 28 (R)-trihydroxy-stigmasta-8, 9-ene-11-keto-21-oic acid-3, 28-di-O-β-D-glucopyranoside (7), 3β, 24 (R), 28 (R)-trihydroxy-stigmasta-7, 9 (11)-dien-21, 24-lactone-3-O-β-D-glucopyranoside (8), 3β, 24 (R), 28 (R)-trihydroxy-stigmasta-7, 9 (11)-dien-21, 24-lactone-3-O-β-D- galactopyranosyl-(1→2)-β-D-glucopyra noside (9), 3β24 (R), 28 (R)-trihydroxy-stigmasta-7, 9 (11)-dien-21, 24-lactone-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (10), 3β, 24 (R), 28 (R)-trihydroxy-16β-acetoxy-stigmasta-7, 9 (11)-dien-21, 24-lactone-3-O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranoside(11), 3β, 24 (R), 28 (R)-trihydroxy-stigmasta-7, 9 (11)-dien-3, 28-di-O-β-D-glucopyranoside (12), 3β, 16β, 24 (R), 28 (R)-tetrahydroxy-stigmasta-7, 9 (11)-dien-21-ol-3, 28-di-O-β-D-glucopyranoside (13), 3β, 16α, 24 (β), 28 (R)-tetra- hydroxy-stigmasta-7, 9 (11)-dien-21-ol-3, 28-di-O-β-D-glucopyranoside (14), methyl 3, 4-dicaffeoylquinate (15), methyl 3, 5-dicaffeoylquinate (16), ethyl 3, 4-dicaffeoylquinate (17), methyl 3, 4, 5-tricaffeoylquinate (18), stigmasterol (19),α-spinasterol (20),β-sitosterol (21), 24-methylene-lanosta-9 (11)-en-3β-acetate (22), ethyl gallate (23), di-n-butyl-phthalate (24), 1, 2, 3-benzenetriol (25), steric acid (26), palmitic acid (27). There are 14 new compounds (1-14) and respectively named as vernocuminosides A-N, while compounds 15-18 are known and isolated from this genus for the first time, and some compounds were assayed for anti-inflammatory and cytotoxic activities. Moreover, the structural and spectroscopic characteristics of steroids were summarized, and in view of the vicinal diols (vic-diols) in the steroids, the absolute configurations of vic-diols were determined by circular dichroism (CD) method using transition metal chelate reagent Mo₂(OAc)₄.The genus Lysidice consists of two species, L. rhodostegia Hance and L. brevicalyx Wei. The chemical constituents from roots of L. rhodostegia has been studied previously, leading to the isolation of some phloroglucinols, stilbenes and flavanoids. Meanwhile, a series of endophytes were isolated from the roots of L. rhodostegia. According to the cytotoxic activity and chemical screening results, the bioactive strain LJJ032 was selected for scale-up fermentation, and the EtOAc extract of its broth was then chemically investigated, leading to the isolation of 9 compounds including 3 monoterpenes, 5 phenols and 1 monoglyceride. Through spectroscopic methods, their structures were respectively established as: E-1-(4β-hydroxytetrahydro-2H-pyran-2β-yl)-pent-3-en-2-one (28), 3-(1E)-1-propen-2-yl-(1S, 2R, 5S, 6R)-7-oxabicyclo [4.1.0] hept-3-ene-2, 5-diol (29), [3, 5-dihydroxy-2-(7-hydroxy-octanoyl)]-ethylphenylacetate (30), (3, 5-dihydroxy-2-octanoyl)-ethyl phenylacetate (31), (5, 7-dihydroxy-9-heptyl)-isobenzo pyran-3-one (32), 3-(hydroxymethyl)-4-(1E)-1-propen-1-yl-(1R, 2S, 5R, 6S)-7-oxabicyc-lo[4.1.0] hept-3-ene-2, 5-diol (33), (5E, 1E)-2, 3-dihydroxypropyloctadeca-5, 7-dienoate (34), (E)-2-methoxy-3-(prop-l-enyl) phenol (35) and p-hydroxylphenylethanol (36). There are 2 new compounds (28 and 29). The compounds were all assayed for cytotoxic activities.