A novel caryophyllene type sesquiterpene lactone from Asparagus falcatus (Linn.); Structure elucidation and anti-angiogenic activity on HUVECs

• Published in: European journal of medicinal chemistry 2012, Vol.47 (1), p.601-607
• Main Authors: Ghalib, Raza Murad, Hashim, Rokiah, Sulaiman, Othman, Mehdi, Sayed Hasan, Valkonen, Arto, Rissanen, Kari, Trifunović, Srećko R., Khadeer Ahamed, Mohamed B., Majid, Amin Malik Shah Abdul, Kawamura, Fumio
• Format: Article
• Language: English
• Subjects: Angiogenesis Inhibitors - chemistry; Angiogenesis Inhibitors - isolation & purification; Angiogenesis Inhibitors - pharmacology; Anti-angiogenic activity; Asparagus falcatus (Linn.); Asparagus Plant - chemistry; Aspfalcolide; Biological and medical sciences; Cell Movement - drug effects; Cell Proliferation - drug effects; Crystal structure; General pharmacology; Human Umbilical Vein Endothelial Cells - cytology; Human Umbilical Vein Endothelial Cells - drug effects; Humans; HUVECs; Lactones - chemistry; Lactones - isolation & purification; Lactones - pharmacology; Medical sciences; Models, Molecular; Molecular Conformation; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Sesquiterpenes - chemistry; Vascular Endothelial Growth Factor A - pharmacology
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2011.10.037

In this study the novel caryophyllene type sesquiterpene lactone (aspfalcolide) has been isolated from the leaves of Asparagus falcatus (Linn.) and characterized by IR, 1D NMR, 2D NMR, EI–MS, HR–ESI–MS and X-ray single crystal diffraction analysis. The aspfalcolide crystallizes in the orthorhombic space group P2 12 12 1 with a = 6.37360(10), b = 7.6890(2), c = 27.3281(6) Å, α =  β =  γ = 90 ° and Z = 4. One intermolecular O–H⋯O hydrogen bond enforces these natural molecules to form infinite chains through the crystal. Aspfalcolide was screened for its anti-angiogenic activity in human umbilical vein endothelial cells (HUVECs) and the result showed the remarkable inhibitory effect of aspfalcolide on the proliferation (IC 50 1.82 μM), migration and tube formation of HUVECs. Here is a report of novel caryophyllene type sesquiterpene lactone from Asparagus falcatus (Linn.) with its anti-angiogenic activity on HUVECs. [Display omitted] ► A novel caryophyllene type sesquiterpene lactone (aspfalcolide) has been isolated from A. falcatus (Linn.). ► The new structure has been confirmed by 1D, 2D NMR, EI–MS, HR–EI–MS and X-ray crystal diffraction. ► The compound has been found to have anti-angiogenic activity (IC 50 1.82 μM) on HUVECs.