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Citation: YANG Xiang-Yan, ZHANG Yi-Heng, DING Lan, WANG Han-Qing. Cytotoxic Activity of a Natural ProductWangzaozin A[J]. Acta Physico-Chimica Sinica, ;2009, 25(09): 1749-1755. doi: 10.3866/PKU.WHXB20090824 shu

Cytotoxic Activity of a Natural ProductWangzaozin A

1.
College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, Shandong Province, P. R. China

Received Date: 24 January 2009
Available Online: 30 June 2009

Wangzaozin A (1) is an ent-kaurane diterpenoid isolated from Isodon racemosa (Hemsl) Hara. This natural product exhibits significant cytotoxicity against human Bel-7402 and HO-8910 tumor cells. The structural parameters of compound 1 from X-ray diffraction were compared with those from theoretical calculations at B3LYP/6-31G(d) level compound and the theoretical results were found to be in accordance with the experimental data. The 1H and 13C NMR chemical shifts of compound 1 were also calculated using the gauge independent atomic orbital (GIAO) method at the B3LYP level with the 6-31G(d), 6-31G(d,p), 6-31+G(d,p), and 6-31++G(d,p) basis sets. Results showed that the calculated NMR data for the geometrical conformation optimized using the B3LYP/6-31G(d) basis set are the most accurate by comparison to experimental data. The geometrical conformation optimized using the B3LYP/6-31G(d) basis set, therefore, approximates the real geometric structure of compound 1 most accurately. Statistical error analysis for the theoretically predicted δH and δC values versus experimentally observed values for compound 1 was conducted. A molecular electrostatic potential (MEP) map was used in an attempt to identify key features of the diterpenoid Wangzaozin A to account for its anti-tumor activity. MEP investigations reveal that compound 1, which shows anti-tumor activity, possesses electron-rich regions that extend over the hydroxyl and carbonyl groups of compound 1.
- Density functional theory,
- Protonation,
- Wangzaozin A,
- Nuclear magnetic resonance,
- Molecular electrostatic potential
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