New Cytotoxic Diarylheptanoids from the Rhizomes of Alpinia officinarum

Abstract

Bioassay-guided fractionation of the cytotoxic MeOH extract from the rhizomes of Alpinia officinarum Hance led to the isolation of two new diarylheptanoids named alpinoid D (1) and E (2), together with fifteen known diarylheptanoids (3 - 17). The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic data and chemical evidence. The cytotoxic activity of the isolated diarylheptanoids was evaluated against the IMR-32 human neuroblastoma cell line. Among the tested compounds, 11, 12 and 14 exhibited the most potent activities with IC (50) values of 0.83, 0.23 and 0.11 microM, respectively.

Synthesis of Two Natural Furan‐Cyclized Diarylheptanoids via 2‐Furaldehyde

“…(2));141.5, 138.7 (C(1'), (C(1''));1 28.9, 128.67 (C(2'/6'), C(2''/6''));1 28.62, 128.56 (C(3'/5'), C(3''/5''));1 26.6, 126.2 (C(4'), C(4''));107.0 (C(4));106.0 (C(3)); 34.8 (PhCH 2 ); 34.6 (PhCH 2 ); 30.2 (furylÀCH 2 ). The 1 H-and 13 C-NMRdata are in agreement with the datagiven for isolated 1 in [7].…”

“…However, furancyclized naturald iarylheptanoids were only recently discovered, and there are only two examples of them in the literature (Fig.). Sun et al [7]isolated two furan-cyclized diarylheptanoids 1 and 2 from rhizomes of Alpinia officinarum Hance (Zingiberaceae) as minor components in milligram quantities and reported compound 2 as having moderate cytotoxic activity against the IMR-32h uman neuroblastomac ell line.I na different study, An et al[8] also isolated compound 2 from rhizomes of Alpinia officinarum.T othe bestofour knowledge,there is no described synthetic methodfor the preparation of compounds 1 1 )and 2.W eassumethat asynthetic methodology for the preparation of compounds 1 and 2 would facilitate furtherchemical and biological studies on these compounds.Therefore,weherein present asynthetic methodology for preparation of compounds 1 and 2. …”

“…-Diarylheptanoids,bearing two aryl groups at C(1) and C(7) of aC 7 chain, are as pecial classo fn atural products.S of ar, over 400 naturally occurring diarylheptanoids have been isolated from nature and reviewed in different articles [1 -6]. In general, diarylheptanoids are classified into three categories: i)l inear diarylheptanoids, ii)m acrocyclic biarylheptanoids,a nd iii)m acrocyclic diaryl ether heptanoids.B esidest hese three classes,t herea re also few C 7 chain-cyclized diarylheptanoids.I np articular, pyran-cyclizedn atural diarylheptanoids with the structure of 2-arylethyl-6-aryl-tetrahydro-2H-pyran have been long known.…”

Induction of Apoptosis in Human Leukemia Cell (Jurkat) by Neolignans Isolated from Seeds of Licaria puchury-major

“…7,8) Over the past few decades, much attention has been focused on natural products as potential sources of novel anticancer drugs. [9][10][11][12][13][14] The therapeutic application of apoptosis has currently been used as a model for developing anticancer drugs, 15) because many chemotherapeutic drugs have been shown to induce apoptosis in cancer cells. 16) Thus, the identification of potential chemotherapeutic agents using mechanism-based study holds great promise for elucidating mechanisms and devising more specific and effective treatments for cancer-related diseases.…”

Three new antibacterial active diarylheptanoids from Alpinia officinarum

“…A. officinarum, a pungent and aromatic rhizome was used as a traditional Chinese medicine with anti-inflammatory [1], antioxidant [2], anti-proliferative [3], anticancer [4] and antiemetic [5] activities. In the chemical studies of the rhizomes, the isolation and structure determination of essential oils [6], monoterpenes [7], diarylheptanoids [8][9][10][11][12][13][14], flavonoids [15][16][17][18] and phenylpropanoids [19,20] have been reported so far. Diarylheptanoids were among the characteristic constituent found in the rhizomes.…”