Abstract
Three previously undescribed compounds, two prenyleudesmanes (1 and 2), and one hexanorlanostane (3), were isolated from the roots of Lonicera macranthoides. Their structures were established based on 1D and 2D nuclear magnetic resonance (NMR) spectra and high-resolution electrospray ionization mass spectral (HR-ESI-MS) data. The absolute configurations of 1 and 3 were determined by X-ray diffraction. To the best of our knowledge, this is the first time that the absolute configuration of a prenyleudesmane with a trans-decalin system and a hexanorlanostane have been unambiguously confirmed by single-crystal X-ray diffraction with Cu Kα radiation. Thecompounds were tested for their antiproliferative activity on the cancer cell lines (HepG2 and HeLa). The compounds 1–3 exhibited moderate inhibitory effects against two human cancer cell lines.
Highlights
Lonicera macranthoides Hand.-Mazz., a plant of the genus Lonicera in the family Caprifoliaceae, is mainly distributed in the southwest of China [1]
The dried flower buds of L. macranthoides are commonly used as a raw material in traditional Chinese medicine for treating fever, inflammation, and infectious diseases [2]
We report on the isolation and characterization of two new diterpenes, lonimacranthoidin C (1) and lonimacranthoidin D (2), and a novel hexanorlanostane, lonimacranthoidin E (3)
Summary
Lonicera macranthoides Hand.-Mazz., a plant of the genus Lonicera in the family Caprifoliaceae, is mainly distributed in the southwest of China [1]. The dried flower buds of L. macranthoides are commonly used as a raw material in traditional Chinese medicine for treating fever, inflammation, and infectious diseases [2]. Earlier phytochemical studies on the plant have shown the presence of various triterpenoid saponins (e.g., hederagenin saponins, oleanolic acid saponins, 18-oleanene saponins, and lupane saponins) [3,4,5,6], flavonoids [7], phenolic acids [8,9], and iridoids [8,9] in aerial parts and flowers of the plant. Because of our studies of L. macranthoides, we became interested in the diterpenes of this species. We reported the first known occurrence of diterpenes (e.g., labdane, aphidicolane, and syn-pimarane) in the roots of L. macranthoides [10,11,12]. To explore further unknown diterpenes, we reinvestigated the roots of L. macranthoides. Compounds 1–3 were screened for antiproliferative activity against two human cancer cell lines, HepG2 and HeLa
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