Novel Flavonoids in Dragon's Blood of Daemonorops draco

Abstract

The three novel methylene bis[flavonoids] 1 -3, the novel 2-flavene 4, the new naturally occurring flavan 5, and the new retro-dihydrochalcone 6 were isolated from dragons blood of Daemonorops draco, together with seven known compounds. The structures were elucidated by extensive 1D-and 2D-NMR spectroscopic analysis. In our successive research of the phytochemicals in secretes, we have isolated secobiflavonoids in farinose exudate of Pentagramma triangularis [10] and kamalachalcones in glandular hair of Mallotus philippensis [11], and the chemical constituents in the red resin originated from D. draco were investigated. Herein, the structures of three novel secobiflavonoids, daemonorols A -C 1 ) (1 -3), a novel 2-flavene, daemonorol D

Biomimetic Synthesis of Complex Flavonoids Isolated from Daemonorops “Dragon's Blood”

“…These comprise monomeric flavonoids such as (2S)-5-methoxyflavan-7-ol (1)a nd (2S)-5-methoxy-6-methylflavan-7-ol (2). Themonomeric flavonoids can dimerize in various ways to give rise to nordracorubin (5), dracorubin (6), [8] daemonorol A(7)and C(8), [9] dracooxepine (9), [10] and the diastereomeric dracoflavans C1 (10 a)a nd C2 (10 b). Themonomeric flavonoids can dimerize in various ways to give rise to nordracorubin (5), dracorubin (6), [8] daemonorol A(7)and C(8), [9] dracooxepine (9), [10] and the diastereomeric dracoflavans C1 (10 a)a nd C2 (10 b).…”

“…Their oxidized congeners nordracorhodin (3) and dracorhodin (4), respectively,which are shown here as the anhydrobases,are largely responsible for the intense red color of dragonsblood. Themonomeric flavonoids can dimerize in various ways to give rise to nordracorubin (5), dracorubin (6), [8] daemonorol A (7)and C(8), [9] dracooxepine (9), [10] and the diastereomeric dracoflavans C1 (10 a)a nd C2 (10 b). [11] Recently,W ua nd co-workers isolated the first flavonoid trimers from dragonsblood, namely dragonbloodin A1 (11 a) and A2 (11 b).…”

Antibacterial and Antibiofilm Activity of Daemonorops draco Resin

“…Previous report pointed out that some semipolar and polar constituent has been isolated from D. draco. Dracorhodin, dracorubin, and nordracorubin were isolated from chloroform-methanol extract [9], dracoflavan B1, B2, C1, C2, D1 and D2 were isolated from ethyl acetate extract (Arnone et al, 1997), daemonorol group (A-F) were isolated from acetone extract (Nakashima et al, 2009) and dimethoxyflavan group were isolated from chloroform extract (Hao et al, 2015).…”

Biomimetische Synthese komplexer Flavonoide isoliert aus Daemonorops‐“Drachenblut”

“…Kürzlich hat ein aus Daemonorops draco gewonnenes Harz erneute Aufmerksamkeit als Quelle biologisch aktiver Verbindungen auf sich gezogen. Die monomeren Flavonoide kçnnen über verschiedene Wege zu Nordracorubin (5), Dracorubin (6), [8] Daemonorol A( 7)u nd C( 8), [9] Dracooxepine (9) [10] sowie den diastereomeren Dracoflavanen C1 (10 a)u nd C2 (10 b)d imerisieren. Genauere Untersuchungen der chemischen Zusammensetzung identifizierten eine Vielzahl an Flavonoiden mit variierender Komplexität( Abbildung 1), unter anderem monomere Flavonoide wie (2S)-5-Methoxyflavan-7-ol (1)u nd (2S)-5-Methoxy-6-methylflavan-7-ol (2).…”

“…Ihre direkten Oxidationsprodukte Nordracorhodin (3)u nd Dracorhodin (4), die hier als Anhydrobasen gezeigt sind, sind weitestgehend fürd ie intensive rote Farbe des Drachenbluts verantwortlich. Die monomeren Flavonoide kçnnen über verschiedene Wege zu Nordracorubin (5), Dracorubin (6), [8] Daemonorol A( 7)u nd C( 8), [9] Dracooxepine (9) [10] sowie den diastereomeren Dracoflavanen C1 (10 a)u nd C2 (10 b)d imerisieren. [11] Kürzlich konnte die Gruppe von Wu die ersten Flavonoidtrimere aus Drachenblut isolieren -D ragonbloodin A1 (11 a)u nd A2 (11 b).…”