Phenolic Compounds of Dragon's Blood from Dracaena draco

Abstract

Three new compounds, 2,4,4'-trihydroxydihydrochalcone (1), 3-(4-hydroxybenzyl)-5,7-dimethoxychroman (2), and 7-hydroxy-3-(4-hydroxybenzyl)chromone (3), were isolated from the resin "Dragon's blood" obtained from Dracaena draco along with 18 known compounds. The structures of 1, 2, and 3 were determined using MS and NMR techniques.

Anti-Helicobacter pyloriand Thrombin Inhibitory Components from Chinese Dragon’s Blood,Dracaena cochinchinensis

“…Comparison of the NMR data of 6 and 7 with those of known biflavonoid derivatives previously reported from Dracaena plants revealed that the structures of 6 and 7 resembled that of cinnabarone, a biflavonoid isolated from D. cinnabari, 21 except for the existence of three methoxy groups in both 6 and 7, instead of only one methoxy group in cinnabarone. The three methoxy groups were deduced to be located at C-2, C-4, and C-2′′ in 6 by 1 H-13 C long-range correlations at H 2 -/C-2, 2-OCH 3 / C-2, H-γ/C-4, 4-OCH 3 /C-4, H 2 -′/C-2′′, and 2′′-OCH 3 /C-2′′ in its HMBC spectrum, and the results were further confirmed by NOE correlations between 2-OCH 3 and H-3, 4-OCH 3 and H-3, and 2′′-OCH 3 and H-3′′, respectively. Likewise, the three methoxy groups in 7 were located at C-2, C-2′′, and C-4′′′ by observation of the HMBC crosspeaks at H 2 -/C-2, 2-OCH 3 /C-2, 4′′′-OCH 3 /C-4′′′, H 2 -′/C-2′′, and 2′′-OCH 3 /C-2′′ as well as NOE correlations between 2-OCH 3 and H-3, 4′′′-OCH 3 and H-3′′′ (H-5′′′), and 2′′-OCH 3 and H-3′′, respectively.…”

“…The UV spectrum exhibited absorption at λ max 328 nm, which was assignable to a stilbene core. The 1 H NMR spectrum of 1 ( 3 carbon; two secondary sp 3 carbons; and four methoxy carbons. The complete assignment of the protonated carbons was made using the HSQC spectrum, while analysis of the HMBC and ROESY spectra of 1 led to the definition of a stilbene moiety and a deoxotetrahydrochalcone residue in the structure of 1 (Figure 2).…”

“…Likewise, the three methoxy groups in 7 were located at C-2, C-2′′, and C-4′′′ by observation of the HMBC crosspeaks at H 2 -/C-2, 2-OCH 3 /C-2, 4′′′-OCH 3 /C-4′′′, H 2 -′/C-2′′, and 2′′-OCH 3 /C-2′′ as well as NOE correlations between 2-OCH 3 and H-3, 4′′′-OCH 3 and H-3′′′ (H-5′′′), and 2′′-OCH 3 and H-3′′, respectively. Therefore, the structures of 6 and 7, given the trivial names cochinchinenins B and C, were established as 1- 3 carbons, and two methoxy carbons ( Table 2). The complete assignments of the protonated carbon resonances were made using the HSQC spectrum of 8, while analysis of the HMBC data led to the definition of the structure of 8 (Figure 1 In addition to the eight new flavonoid derivatives (1-8), 14 known compounds were also isolated and characterized by comparison with literature data as 1-[5-(2-methoxy-4,4′-dihydroxydihydrochalconyl)]-1-(4-hydroxyphenyl)-3-(2-methoxy-4-hydroxyphenyl)propane (9), 22 (2R)-4′-hydroxy-7-methoxy-8-methylflavan (10), 23 (2S)-4′,7-dihydroxy-8-methylflavan (11), 24 7-hydroxy-3-(4-hydroxybenzyl)-8-methoxychroman (12), 25 (2S)-4′,5-dihydroxy-7-methoxy-8-methylflavan (13), 26 4,4′,6-trihydroxy-2-methoxydihydrochalcone (14), 27 4,4′-dihydroxy-2′-methoxychalcone (15), 28 (-)-7-hydroxy-4′-methoxyflavan (16), 29 33 2,4,4′-trihydroxydihydrochalcone (21), 34 and 4,4′-dihydroxy-2,6-dimethoxydihydrochalcone (22).…”

Flavonoid oligomers from Chinese dragon’s blood, the red resins of Dracaena cochinchinensis

“…3 Chemical studies on the dragon's blood from the genus Dracaena (D. draco, D. cinnabari and D. loureiri) have revealed the occurrence of flavonoids, including flavan, flavone, chalcones, homoisoflavanes, and the oligomers of flavonoids. [4][5][6][7][8][9][10][11][12][13][14][15][16] Flavonoid oligomers, composing of one dihydrochalcone unit condensed with one or more chalcone, flavane or homoisoflavane units, [5][6][7] constituted the major identified components of dragon's blood from the genus Dracaena. Furthermore, a series of publications reported the natural product diversity of original plants of dragon's blood from the genus Dracaena.…”

A New Red Pigment from Chinese Dragon's Blood, the Red Resin of Dracaena cochinchinensis

“…2,[5][6][7][8][9][10] Several pigments, such as dracorhodin (2) and dracorubin reported from Daemonorops resin, elucidated the reason that dragon's blood takes on red color. [11][12][13][14] Moreover, HPLC and GC/MS methods were developed to identify pigments and discriminate dragon's blood from different individual species.…”