Triterpenoids from the twigs and leaves of Rhododendron latoucheae by HPLC‒MS‒SPE‒NMR

Cytotoxic and Anti-inflammatory Terpenoids from the Whole Plant of Vaccinium emarginatum

“…The IR spectrum exhibited absorption bands at 3570 cm −1 (OH); 2400-3300, 1711, and 939 cm −1 (COOH); 1687 cm −1 (C=O); and 1604 and 1514 cm −1 (aromatic ring), respectively. The 1 H and 13 C NMR spectral data of 2 (▶ Table 1) were similar to that of 3β-O-(Z)-feruloyl-19α-hydroxy-urs-12-ene-28-oic acid (4) [10], with the exception of a (Z)-coumaroyl moiety located at C-3 of 2 instead of a (Z)-feruloyl moiety in 4. (OH) and 1638, 980, and 908 cm −1 (vinyl).…”

“…The (E)configuration was deduced from the vinylic proton signals detected at δ H 7.59 and 6.31, with a large coupling constant (J = 15.9 Hz). The overall 1D and 2D NMR data suggested a close structural similarity between 1 and 3β-O-(E)-feruloyl-19α-hydroxy-urs-12-ene-28-oic acid (3) [10], with the exception of the presence of an (E)-coumaroyl moiety at C-3 in 1 instead of an (E)feruloyl moiety at in 3. The HMBC correlations (▶ Fig.…”

“…Its cytotoxicity was associated with the EtOAc-soluble fraction, which more potently inhibited PC-3 proliferation with 35.1 % (± 1.2) inhibition at the same concentration. The phytochemical investigation of the EtOAc-soluble fraction of the V. emarginatum MeOH extract yielded two new Δ 12 ursenetype triterpenoid coumaroyl esters (1 and 2), one new Δ 12 isopimarane-type diterpenoid glycoside (20), and two new irido-δ-lactone-type iridoids (21 and 22), together with 17 known pentacyclic triterpenoids (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)) (▶ Fig. 1).…”

“…1). The known compounds were identified as 3β-O-(E)-feruloyl-19α-hydroxy-urs-12-ene-28-oic acid (3) [10], 3β-O-(Z)-feruloyl-19α-hydroxy-urs-12-ene-28-oic acid (4) [10], 3β-O-(E)-feruloyl oleanolic acid (5) [11], 3β-O-(E)-feruloyl ursolic acid (6) [11], ursolic acid (7) [12], pomolic acid (8) [13], rotundic acid (9) [13], 2α,3α,23-trihydroxyurs-12-en-28-oic acid (10) [14], euscaphic acid (11) [15], myrianthic acid (12) [15], rotundanonic (13) [16], 3-oxo-19,23,24-trihydroxyurs-12-en-28-oic acid (14) [17], maslinic acid (15) [18], arjunolic acid (16) [19], 2α,3α,23-trihydroxyolean-12-en-28-oic acid (17) [20], friedelin (18) [21], and epi-friedelinol (19) [21] based on their spectroscopic data, which were identical to literature values. The structures of compounds 1, 2, and 20-22 were elucidated by detailed analysis of standard spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), IR spectroscopy, and 1D and 2D NMR and by comparison with the spectroscopic data of known analogs.…”

“…The substitution of triterpenoid by coumaroyl and feruloyl moieties played an important role in their bioactivities, including cytotoxicity against several cancer cell lines [33,34], anti-inflammatory properties [34], antiviral activity against HSV-1 [10], and antimycobacterial activity against Mycobacterium tuberculosis [11]. Here, six triterpenoid coumaroyl and feruloyl esters (1-6) were isolated from V. emarginatum, which may provide a rationale for further investigations of bioactive natural products from V. emarginatum.…”