Extractives of Cedrela odorata L. Part II. The structures of the Cedrela tetracyclic triterpenes, odoratol, iso-odoratol, and odoratonen

Abstract

Three triterpenes have been isolated from Cedrela odorata L. These are shown by chemical and spectroscopic evidence to be derivatives of tirucallol in which the side chain has been modified to a dihydroxytetrahydrofuran. , , 3312 cm.-l (OH) (Found: C, 75.9; H, 10-4; 0, 13.7. C30H5004 requires C, 75.9; H, 10.6; 0, 13.5%). Acetylation of the Cedrela Triterpenes.-This was done, in the standard way, with acetic anhydride and pyridine overnight a t room temperature. The products were isolated by dilution with water and filtration. Odoratol triacetate (V) was amorphous, v , , 1754 (OAc) cm.-l, 6 5.27 (lH, m, H-7), 5.12 (lH, q, J6.5 and 5.5 c./sec., H-23), 4-85 (lH, d, J 6.5 c./sec., H-24), 4-69 (lH, m, W J 5 c./sec., H-3), 4.02 (lH, d, J 5.5 c./sec., H-22), and 2.07 and 2.09 (6H and 3H respectively, each s, 3 x OAc) . Odoratone diacetate (11; R2 = Ac) gave needles, m.p. 222-224" (from methanol), vmx. 1754 (OAc) and 1710 (cyclohexanone) cm.-l, 6 5.34 ( l H , m, H-7), 5.13 ( l H , q, J 6-5 and 6.0 c./sec., H-23), 4.87 (lH, d, J -6.5 c./sec., H-24), 4.03 (lH, d, J 6.0 c./sec., H-22), and 2.08 and 2.11 (each 3H, s, 2 x OAc)

Triterpenes and limonoids of Cedrela: Distribution, biosynthesis, and 1H and 13C NMR data

“…An exhaustive revision of the chemical reports for Cedrela plants shows only 11 studied species: C. angustifolia, [9] C. ciliolate, [54] C. degussi, [55] C. fissilis, [8,[56][57][58][59] C. glazziovi, [39,43] C. mexicana, [60,61] C. montana, [22] C. odorata, [10,17,19,24,26,[44][45][46][47]53,[62][63][64][65][66][67][68][69][70][71][72] C. salvadorensis, [55,[73][74][75][76][77] C. sinensis, [33,52,[78][79][80] and C. toona. [81] C. odorata is the most studied with 21 chemical analysis, including two studies where it is grafted with Toona ciliata.…”

“…The cycloartanes 1-7, the tirucallane 15, and the butyrospermanes 16-36 were reported for the first time for C. odorata grafted with Toona ciliata, [10,17] being uncertain to stablish if these compounds are biosynthesized by Cedrela species, were translocated from Toona to Cedrela, or were biosynthesized as result of the graft of both species. However, the isolation of the cycloartane 5 of C. fissilis [8] and of the butyrospermanes 16, 20-36 of C. fissilis, [8] C. glaziovii, [39,43] C. sinensis, [33] and C. odorata [24,26,[44][45][46][47] contributes to suspect its origin from Cedrela. According with its triterpene content, Cedrela species biosynthesized primarily tetracyclic triterpenes (compounds 1-7 and 15-72), being the pentacyclic triterpenes (compounds 8-14) the second type isolated from these natural products (Figure 1; Table 1).…”

“…C. odorata [44][45][46][47] -, [44,45] heartwood [46,47] -, [44,45] C 6 H 6 [46,47] C. odorata grafted with T. ciliata [17] --33 iso-odoratol C. fissilis [8] stems MeOH C. glaziovii [43] heartwood EtOAc (CHCl 3 sf)…”

“…C. odorata [46] heartwood C 6 H 6 C. fissilis [21] roots CH 2 Cl 2 34 odoratone C. fissilis [8] stems MeOH 400 CDCl 3 [48] 100 CDCl 3 [48] C. glaziovii [43] heartwood EtOAc (CHCl C. odorata [44][45][46][47] -, [44,45] heartwood [46,47] -, [44,45] C 6 H 6 [46,47] 35 bourjotinolone A C. sinensis [33] cortex MeOH 60 CDCl 3 [50] 22.63 CDCl 3 [50] 36 sapelin B C. odorata [26] twigs and leaves EtOH (EtOAc sf) 500 CD 3 OD [51] 125 CD 3 OD [51] Apotirucallanes (Table 8 and 9) 37 nr (21R-aposinensin A) a C. sinensis [33] cortex MeOH 500 CDCl 3 [33] 125 CDCl 3 [33] 38 nr (21S-aposinensin A) a C. sinensis [33] cortex MeOH 500 CDCl 3 [33] 125 CDCl 3 [33] 39 nr (21R-aposinensin B) a C. sinensis [33] cortex MeOH 500 CDCl 3 [33] 125 CDCl 3 [33] 40 nr (21S-26-hydroxy-aposinensin B) a C. sinensis [33] cortex MeOH 500 CDCl 3 [33] 125 CDCl 3 [33] 41 nr (21R,24S-aposinensin C) a C. sinensis [52] leaves, seeds, stems MeOH 600 CDCl 3 [52] 150 CDCl 3 [52] 42 nr (2 0 ,3 0 -dihydro-21R,24Saposinensin C) a C. sinensis [52] leaves, stems MeOH 500 CDCl 3…”

Impairment of Photosystem II Donor Side by the Natural Product Odoratol

“…Odoratol was obtained from a CHCl3/methanolic extract (1:1) of C. odorata L. (Meliaceae) wood. The structure of this natural product was established using spectrometric and spectroscopic (IR and NMR) methods (Chan et al, 1968). Odoratol (1) afforded triacetate (2) upon treatment with acetic anhydride and pyridine.…”