Biologically Active Arborinane-Type Triterpenoids and Anthraquinones from Rubia yunnanensis

Abstract

Twelve new arborinane-type triterpenoids (1-12) and four new anthraquinones (13-16), together with 50 known compounds, were isolated from the roots of Rubia yunnanensis. The structures of 1-16 were elucidated by spectroscopic data analysis and chemical methods. All compounds were evaluated for their cytotoxic, antibacterial, and antifungal activities. Rubiyunnanol C (5) is the first example of an arborinane-type triterpenoid with a double bond at C-8-C-9.

Two New Cinnamyl Isovalerate Derivatives from Sabina gaussenii

“…The NMR data indicated that 1 was a phenylpropanoid, which was very similar with those of 3 [8]. In comparison with 3, the only difference is a hexanoyl (δ C 173.8 (C-1"), 34.3 (C-2"), 24.7 (C-3"), 31.4 (C-4"), 22.4 (C-5"), 14.0 (C-6")) in 1 replaced the isovaleryl (δ C 173.0 (C-1"), 43.4 (C-2"), 25.7 (C-3"), 22.4 (C-4", 5")) in 3. The 1 H-1 H COSY correlations ( Figure 1) between H-2" and H-3", H-3" and H-4", H-4" and H-5", H-5" and H-6", and the HMBC cross-peaks of H-2" with C-1" confirmed the presence of the hexanoyl in 1.…”

“…The NMR data of 2 was closely similar with those of 1, which suggested that 2 was also a phenylpropanoid. The only difference is that a 4"-methyl-hexanoyl (δC 174.0 (C-1"), 32.1 (C-2"), 31.4 (C-3"), 34.0 (C-4"), 29.1 (C-5"), 18.8 (C-6")) in 2 replaced the hexanoyl (δC 173.8 (C-1"), 34.3 (C-2"), 24.7 (C-3"), 31.4 (C-4"), 22.4 (C-5"), 14.0 …”

“…The 1 H-NMR spectrum of 1 showed three methoxy signals (δ H 3.87 (s, 6H), 3.84 (s, 3H)). The 13 C-and DEPT-NMR spectra of 1 revealed 18 carbon signals: a carbonyl (δ C 173.8 (C-1")), a symmetrical benzene (δ C 153.3 (C-3', 5'), 138.0 (C-4'), 132.0 (C-1'), 103.6 (C-2', 6')), a double bond (δ C 134.2 (C-3), 122.9 (C-2)), five methylenes (δ C 64.9 (C-1), 34.3 (C-2"), 31.4 (C-4"), 24.7 (C-3"), 22.4 (C-5")), and four methyls (δ C 56.1 (C-2*OMe), 61.0 (C-OMe), 14.0 (C-6")). The NMR data indicated that 1 was a phenylpropanoid, which was very similar with those of 3 [8].…”

“…The NMR data of 2 was closely similar with those of 1, which suggested that 2 was also a phenylpropanoid. The only difference is that a 4"-methyl-hexanoyl (δ C 174.0 (C-1"), 32.1 (C-2"), 31.4 (C-3"), 34.0 (C-4"), 29.1 (C-5"), 18.8 (C-6")) in 2 replaced the hexanoyl (δ C 173.8 (C-1"), 34.3 (C-2"), 24.7 (C-3"), 31.4 (C-4"), 22.4 (C-5"), 14.0 (C-6"), 11.4 (C-7")) in 1. The 1 H-1 H COSY correlations between H-2" and H-3", H-3" and H-4", H-4" and H-5", H-4" and H-7", H-5" and H-6", and the HMBC cross-peaks of H-2" with C-1", confirmed the presence of the 4"-methyl-hexanoyl portion in 2.…”

“…The cytotoxicities of the 90% acetone extract and compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) against the HeLa, BGC-823, and A549 cancer cell lines were measured using a sulforhodamine B (SRB, Sigma, Saint Louis, MO, USA) assay as described in the literature [24]. Taxol were used as positive controls.…”