New nor-ursane type triterpenoids from Gelsemium elegans.
Five new nor-ursane type triterpenoids, gelse-norursane A-E, together with twenty known compounds, were isolated from the whole plant of Gelsemium elegans. The structures of new compounds were established as (2R,3R,7R,17S,19R)-2,3,7,19-tetrahydroxy-6-oxo-24-norurs-4(23),12-dien-28-oic acid (1), (2R,3R,7R,17S)-2,3,7-trihydroxy-6-oxo-24-norurs-4(23), 12-dien-28-oic acid (2), (2R,3R,7R,17S)-2,3,4-trihydroxy-23-norurs-20(30),12-dien-28-oic acid (3), (2R,3R,30R)-2,3-dihydroxy-24-norurs-4(23),12-dien-30-oic acid (4), and (2R,3R,30R)-2, 3-dihydroxy-24-norurs-4,12-dien-30-oic acid (5), using spectroscopic analysis, including HRESIMS, 1D and 2D NMR. The absolute configurations of 1 and 4 were established through comparison of experimental and calculated ECD spectra. The gelse-norursane A-E are isolated as the 24-nor-ursane type triterpenoids from the family Loganiaceae for the first time. The cytotoxicities of the selected compounds against a panel of four human cancer HL60, Hela, Hep-G2, and Smmc 7221 cell lines were evaluated using the MTT assay in vitro.
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Hong-Ru
HR
Wu
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Xiao-Feng
XF
He
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Xiao-Jie
XJ
Jin
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Hui
H
Pan
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Zhuan-Ning
ZN
Shi
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Dong-Dong
DD
Xu
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.
Xiao-Jun
XJ
Yao
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China. Electronic address: zhuy@lzu.edu.cn.
Ying
Y
Zhu
D045744:Cell Line, Tumor; D031450:Gelsemium / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
D010936:Plant Extracts; D014315:Triterpenes
12-Hydroxy-pregna-4,16-diene-3,20-dione (9 CID 155941); 14-Hydroxygelsenicine (20 CID 14217347); 5α,6β-Dihydroxysitostrerol (11 CID 23427231); 6-Hydroxy-7-methoxycoumarin (16 CID 69894); 8-Hydroxypinoresinol (13 CID 3010930); Absolute configurations; Ethyl caffeate (15 CID 5317238); Ethyl p-coumarate (14 CID 676946); GEIR-2 (17 CID 10398318); Gelsemine (23 CID 23817963); Gelsemium elegans; Gelsenicine (19 CID 21123652); Humantenine (21 CID 44593672); Koumine (22 CID 20056077); Loganiaceae; Nor-ursane triterpenoids; Pinoresinol (12 CID 73399); Ursolic acid (6 CID 3001199)