Dammarane-type triterpenes from Cordia spinescens

Traditional uses, phytochemistry and pharmacology of the medicinal species of the genus Cordia (Boraginaceae)

“…As per structural characteristics, they are classified into four classes: (1) oleanane type isolated from C. alliodora, C. cylindrostachya, C. piauhiensis, C. latifolia and C. multispicata [74][75][76][77][78] ; (2) lupane type identified from C. obliqua and C. gilletii [79][80][81] ; (3) ursane type reported from C. retusa, C. obliqua, C. rothii and C. multispicata [80,[82][83][84][85] ; and (4) dammarane type found in C. spinescens, C. multispicata and C. verbenacea. [86][87][88] [58] C. fragrantissima [59] Heartwood Timber Alliodorol (2) C. alliodora [58] Heartwood Allioquinol C (3) C. alliodora [58] Heartwood Cordiachrome A (4) C. alliodora [58] Heartwood Cordiachrome A (5) C. fragrantissima [59] Timber Cordiachrome B (6) C. fragrantissima [59] Timber Cordiachrome C (7)…”

“…obliqua [117] Root Lupeol-3-rhamnoside C. obliqua [80] Seed Lupeol C. gilletii [81] Roots Betulin C. obliqua [80] Seed Ursane-type triterpenoids a-Amyrin C. retusa [82] Aerial parts b-Amyrin C. obliqua [80] C. rothii [83,84] Seed Fruit 3-Epipomolic acid (50) C. multispicata [85] Leaves Cordiaketal A (51) C. multispicata [85] Leaves Cordiaketal B (52) C. multispicata [85] Leaves Cordianal A (53) C. multispicata [85] Leaves Cordianone (54) C. multispicata [85] Leaves Cordianal B (55) C. multispicata [85] Leaves Cordianal C (56) C. multispicata [85] Leaves Icterogenin (57) C. multispicata [85] Leaves Lantadene A (58) C. multispicata [85] Leaves Lantadene B (59) C. multispicata [85] Leaves Lantic acid (60) C. multispicata [85] Leaves Lantanolic acid (61) C. multispicata [85] Leaves Pomonic acid (62) C. multispicata [85] Leaves Ursomic acid (63) C. multispicata [85] Leaves Dammarane-type triterpenes 3a-Acetoxy-6b, 25-dihydroxy-20(S), 24(S)-epoxydammarane (64) C. spinescens [86] Leaves 3a, 6b, 25-Trihydroxy-20(S), 24(S)-epoxydammarane (65) C. spinescens [86] Leaves Cabraleadiol (66) C. spinescens [86] Leaves Cordialin A (67) C. multispicata [87] Leaves Cordialin B (68) C. verbenacea [88] Leaves Cordianol-A (69) C. multispicata [87] Leaves Cordianol-B (70) C. multispicata [87] Leaves Cordianol-C (71)…”

Two Novel abeo‐Dammaranes with a Six‐Membered Acetal Moiety from Aglaia perviridisHiern

“…Together with 1 and 2, the six known dammaranes cabraleone [6], cabraleadiol [7], cabraleadiol 3-acetate [8], cabralealactone [9], cabraleahydroxylactone [10], and cabraleahydroxylactone 3-acetate [11] were isolated from the same extract. Their structures were elucidated by spectral data and comparison with literature values.…”

“…25)abeo-dammaran-3-ol acetate (2). The six known dammaranes cabraleone (¼ (24S)-20,24-epoxy-25-hydroxydammaran-3-one) [6], cabraleadiol (¼ (3a,24S)-20,24-epoxydammarane-3,25-diol) [7], cabraleadiol 3-acetate (¼ (3a,24S)-20,24-epoxydammarane-3,25-diol 3-acetate) [8], cabralealactone (¼ (5a)-20-hydroxy-4,4,8,14-tetramethyl-3-oxo-18-norcholan-24-oic acid g-lactone) [9], cabraleahydroxylactone (¼ (3a,5a)-3,20-dihydroxy-4,4,8,14-tetramethyl-18-norcholan-24-oic acid g-lactone) [10], and cabraleahydroxylactone 3-acetate (¼ (3a,5a)-3-(acetyloxy)-20-hydroxy-4,4,8,14-tetramethyl-18-norcholan-24-oic acid g-lactone) [11], were also isolated from the same extract. According to our knowledge, this is the first report of the chemical constituents from A. perviridis.…”

“…Thus, the side chain of 1 was determined as an epoxy-substituted 2,2,5-trimethyl-1-methoxypentane moiety. The configuration (S) was assigned to C(20), which is the configuration of most of dammarane triterpenes, particularly of those isolated from the Aglaia genus [7]. This was further supported by the correlations of HÀC (13) C-NMR spectra (Table), assigned by means of HMQC and HMBC experiments, and by comparison of the spectral data with those of 1, the structure of 2 was established as (3a,20S,24S)-20,24-epoxy-24-methoxy-23(24 !…”