Structural Determination of 3β,11β-Dihydroxyfriedelane from Maytenus Robusta (Celastraceae) by 1D and 2D NMR

Abstract

A new pentacyclic triterpene, 3β,11β-dihydroxyfriedelane was isolated from leaves of Maytenus robusta Reissek (Celastraceae) together with other four known compounds: 3-oxofriedelane (friedelin), 3β-hydroxyfriedelane, 3-oxo-29-hydroxyfriedelane and 3-oxo-11β-hydroxyfriedelane. The structure and chemical conformation of the new friedelane triterpene were established by 1 H and 13 C NMR, including the 2D experiments, HSQC, HMBC, COSY and NOESY.

Chemical constituents of industrial hemp roots and their anti-inflammatory activities

“…Thirty-two phytochemicals (1–32) were isolated from the hemp roots extract, and their chemical structures (Fig. 1 ) were elucidated on the basis of spectroscopic analysis (by NMR and MS) and comparisons of the literature reported values as follows: cannabinol (1) (Wang et al, 2017 ); (9 R ,10 S )-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydro-6 H -benzo[ c ]chromene-1,9,10-triol (2) (Li et al, 2020 ); (-)-7 R -cannabicoumarononic acid A (3) (Radwan et al, 2009 ); (9 R ,10 S )-6,6,9-trimethyl-3-propyl-7,8,9,10-tetrahydro-6 H -benzo[ c ]chromene-1,9,10-triol (4) (Li et al, 2020 ); cannabivarin (5) (Wang et al, 2017 ); cannabidiol (6) (Marchetti et al 2019 ); 4-hydroxy-3-methoxybenzaldehyde (7) (Ito et al, 2001 ); 4-hydroxybenzaldehyde (8) (Bouaicha et al, 1994 ); 4-hydroxy-3,5-dimethoxybenzaldehyde (9) (Xue et al, 2013 ); syringic acid (10) (Queirós et al, 2020 ); vanillic acid (11) (Xu et al 2022 ); 2,6-dimethoxyphenol (12) (Goda et al, 1987 ); (2 E )-3-(4-hydroxyphenyl)-2-propenoic acid (13) (Seal, 2013 ); (3 S )-3-hydroxy- β -ionone (14) (DellaGreca et al, 2004 ); (-)-dihydrovomifoliol (15) (Bennett et al, 1990 ); 1 H -indole-3-carboxaldehyde (16) (Wang et al, 2012 ); 3-(4-hydroxyphenyl)-2-propenoic acid ethyl ester (17) (Pizzolatti et al, 2006 ); 4-hydroxyphenethyl trans-ferulate (18) (Fujita et al, 1995 ); 1,2-diguaiacyl-1-ethoxy-3-propanol (19) (Mohammed et al, 2022 ); (+)-4-ketopinoresinol (20) (Chen et al, 2012 ); dadahol A (21) (Devanathan and Stalin 2020 ); (+)-oleanolic acid (22) (He et al, 2021 ), epipseudotaraxastanediol (23) (Hinge et al, 1966 ); 3-epifriedelinol (24) (Sousa et al, 2012 ); 9,12-octadecadienoic acid (9 Z ,​12 Z )​-​friedelin (25) (Zhou & Guo, 2009 ); β -sitosterol (26) (Kadowaki et al, 2003 ); 5 α ,8 α -epidioxy-(22 E ,24 R )-ergosta-6,22-dien-3 β -ol (27) (Gao et al, 2007 ); stigmast-​4-​en-3-one (28) (Smania et al, 2003 ); 9,​12-​octadecadienoic acid (9 Z ,​12 Z )​-​methyl ester (29) (Huh et al, 2010 ); α -linolenic acid (30) (Kishino et al, 2003 ); linoleic acid (31) (Yoon et al, 2015 ); and dotriacont-1-ene (32) (Chen et al, ...…”