Composite Constituent: Lactucenyl Acetate, a Novel Migrated Lupane Triterpenoid from Lactuca indica Revision of Structure of Tarolupenyl Acetate

Abstract

Lactucenyl acetate (1), a new member of migrated lupane triterpenoids was isolated from Lactuca indica and its structure was elucidated on the basis of spectral analyses. The structure of tarolupenyl acetate was revised as lup-19(21)-en-3b b-yl acetate (2).

The enzymes OSC1 and CYP716A263 produce a high variety of triterpenoids in the latex of Taraxacum koksaghyz

“…Due to low amounts of isolated lup-19(21)-en-3-ol and its ketone, only a limited set of high intensity correlation signals could be observed in COSY, HSQC and HMBC experiments (Supplementary Table S1). Lup-19(21)-en-3-ol and its ketone could be identified based on published NMR data of the acetate derivative 63 .…”

Phytochemical Profile of the Aerial Parts of Sedum sediforme and Anti-inflammatory Activity of Myricitrin

“…The polarity was successively increased to give 28 sub-fractions (a2b1 -a2b28). Sub-fraction a2b6 contained germanicyl formate (24), a2b7 taraxeryl acetate (22), a2b14 lupeol (23), and a2b16 ß-sitosterol (25). Fraction a6 was separated by preparative TLC (CH 2 Cl 2 : MeOH 94:6, v/v) to obtain (2R * , 3R * )-5,7-dihydroxy-2,3-dimethyl-4-chromanone (19) and ß-sitosterol-3-O-glucoside (26).…”

“…gradient fast centrifugal partition chromatography (FCPC) ® , silica gel and Sephadex ® column chromatography (CC), as well as preparative thin layer chromatography. Twenty-six compounds were identified as phlorin (1) [9], picraquassioside D (2) [4], protocatechuic acid (3) [10], phloroglucin-1-O-(6''-galloyl-glucoside) (4) [11], gallincin (5) [12], aesculetin (6) [13], caffeic acid (7) [10], piceol (8) [14], syringic acid ( 9) [15], eriodictyol-4',7-O-diglucoside (10) [16], apocynin (11) [17], eriodictyol-4'-O-glucoside ( 12) [18], myricitrin (13) [19], eriodictyol ( 14) [13], quercitrin (15) [20], myricetin-3-O-(2''galloylrhamnoside) ( 16) [21], myricetin-3-O-(3''-galloyl-rhamnoside) (17) [21], naringenin (18) [22], (2R * , 3R * )-5,7-dihydroxy-2,3-dimethyl-4-chromanone ( 19) [23], quercetin (20) [24], luteolin (21) [24], taraxeryl acetate ( 22) [25], lupeol (23) [26], germanicyl formate (24) [27], ß-sitosterol (25) [10], and ß-sitosterol Compound 27 was identified as the 7-O-ß-D-glucoside of (2R * , 3R * )-5,7-dihydroxy-2,3-dimethyl-4-chromanone, an aglycone which was previously described by Mutanyatta-Comar et al [23]. The 1 H NMR spectrum showed two doublets at δ H 1.19 (3H, J = 7.0 Hz) and δ H 1.48 (3H, J = 6.3 Hz) representing two methyl groups bonded to the sp 3 Also the structure of the new alkyl glycoside 28 was elucidated by means of 1D-and 2D-NMR spectroscopy.…”

Triterpenoids

“…Lactucenyl acetate 388, from Lactuca indica, has a migrated lupane structure which is identical to the structure originally assigned to tarolupenyl acetate. 157 The structure of tarolupenyl acetate has been revised to lup-19(21)en-3b-yl acetate 389. Breynceanothanolic acid 390 is a 25-norceanothic acid derivative from roots of Breynia fruticosa.…”