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of Ajuga salicifolia (L.) Schreber, a new ionone glycoside (3-hy- droxy-7,8-dihydro-4-oxo--ionol-9-O--d-glucopyranoside) was isolated, along with the known compounds, corchoionoside C, 8-O-acetylmioporoside, ajugol, harpagide, 8-O-acetyl- harpagide, lavandulifolioside and leonosides A and B. This is the first report of the occur- rence of ionone glycosides and 8-O-acetylmioporoside in Ajuga species. Ajugol, lavanduli- folioside, leonoside A and B were isolated for the first time from Ajuga salicifolia. The structures were elucidated by means of 1D-, 2D

Chemical Constituents from Pedicularis rex C. B. Clarke Hong-Biao Chua,b, Ning-Hua Tana, and Yu-Mei Zhanga a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China b Graduate School of the Chinese Academy of Sciences, Beijing 100039, China Reprint requests to Prof. Dr. Ning-Hua Tan or Dr. Yu-Mei Zhang. Fax: +86-871-5223800. E-mail:; Z. Naturforsch. 2007, 62b, 1465 – 1470; received June 5, 2007 One new ionone glycoside

–250 . Among them, compounds 247–249 are new. Compound 249 exhibits weak cytotoxic activity against HepG2 and MCF-7 human cell lines [ 109 ]. Four megastigmane derivatives 251–254 and 257 were isolated in 2012 [ 7 ], [ 112 ]. A new ionone glycoside 255 was also isolated from this plant. This is the first report of the occurrence of ionone glycosides in Ajuga species [ 111 ]. Table 6 Sesquiterpenoids. No. Name Source Part Ref. 246 Glecholone A. decumbens aerial part [ 7 ] 247 3 α -Acetoxy-1 α ,8 β -dihydroxyeudesm-7(11)-en-8,12-olide A. forrestii whole plant [ 109

ANNEX List of chiral substanes analyzed by the treated techniques Chiroptical methods Carotenoids 38 Cocaine 38 Codeine 38 3,4-Dihydroxy-ß-ionone glycosides 38 Epinephrine 38 Flavonoids 38 Glucosinolates 38 Glycosides 38 Nicotine 38 Penicillamine 38 Saponins 38 Nuclear magnetic resonance Alcohols 43,44 45,47,48,49 Aldehydes 46 Alkenes 44 Alkynes 48 Allenes 48 Amines, primary and secondary 43, 44, 47, 48,54 a-Amino esters 45 Amino alcohols 45,54 2- Butanol 47 sec-Butylamine 48 Carbonyls 46 Carboxylic acids 45,46,53,54 Cyclohexanones 48

have been published [52]. The exciton chirality method is also useful for the stereochemical analysis of the aglycone part in glycosides. Recently, the determination of the absolute stereo- chemistry of natural 3,4-dihydroxy-ß-ionone glycosides has established the con- figuration as being 3ß,4ß (3S,4R) [53]. Furthermore, a lot of ORD and CD spectroscopy has been done in the field of carotenoid chemistry. In a fundamental paper by Klyne's and Weedon's groups [54] ORD spectra of carotenoids have been studied systematically. Extensive CD studies of carotenoids