Citation: Yang YANG, Jian-Ping YONG, Zacchaeus Olatunde OLAGOKE, Can-Zhong LU. First Isolation and Confirmation of Sterol Based on β-sitosterol Skeleton from the Leaves of Podocarpusnagi Planted in Fujian, Preliminary in vitro Anticancer Activity and the Crystal Structure[J]. Chinese Journal of Structural Chemistry, ;2021, 40(5): 653-658. doi: 10.14102/j.cnki.0254–5861.2011–2981 shu

First Isolation and Confirmation of Sterol Based on β-sitosterol Skeleton from the Leaves of Podocarpusnagi Planted in Fujian, Preliminary in vitro Anticancer Activity and the Crystal Structure

Yang YANG ^{a, b, d, e} ,
Jian-Ping YONG ^c,, ,
Zacchaeus Olatunde OLAGOKE ^{a, e} ,
Can-Zhong LU ^{a, c, e,,}

a.
Fujian Institute of Research on the Structure of Matter, Haixi Institute, Chinese Academy of Sciences, Fuzhou 350002, China
b.
Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, China
c.
Xiamen Institute of Rare-earth Materials, Haixi Institute, Chinese Academy of Sciences, Xiamen 361021, China
d.
ShanghaiTech University, Shanghai 201210, China
e.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Jian-Ping YONG, jpyong@fjirsm.ac.cn Can-Zhong LU, czlu@fjirsm.ac.cn
Received Date: 14 September 2020
Accepted Date: 23 November 2020

Fund Project: the National Natural Science Foundation of China 21875252Self-created Area Project of Major Science Technology Innovation Platform of Xiamen 3502ZCQ20171002

Figures(3)

The crystal of (24R)-3β, 5α-dihydroxy-24-ethyl-5α-cholestan-6-one (1) was isolated from the leaves of P. nagi planted in Fujian for the first time with the same skeleton as 26, 27-dinorcholest-5-en-3-β-ol (2) and β-sitosterol (3) that have been reported before. Compound 1 crystallizes in monoclinic, space group P2₁ with a = 10.8482(4), b = 7.3671(3), c = 33.7860(15) Å, β = 93.103(4)°, V = 2696.21(19) Å³, Z = 75, M_r = 446.70, ρ_calc = 1.145 g/cm³, F(000) = 1032, μ = 0.572 mm^–1, GOOF = 1.034, the final R = 0.0467 and wR = 0.1129 for 6989 observed reflections with I > 2σ(I). Compound 2 was selected to evaluate for their preliminary in vitro anticancer activity against four cancer cell lines for the first time. The results showed that compound 2 exhibited great inhibition against gastric cancer, breast cancer MCF-7, lung cancer A549 and Helacell lines with the inhibitions of 89.16% ±1.17, 97.02%±0.53, 47.20% ±2.58 and 36.89%±1.22 respectively at the concentration of 1.4×10^-2 M, which means that we found the new anticancer compound in this plant medicine.
- Podocarpusnagi,
- crystal structure,
- sterols,
- isolation,
- anticancer evaluation
1. [1]
  Liao, Z. Y.; Wei, W. Studies on volatile constituents and their anti-tumor activities from the peel and shell of Podocarpus nagi fruits. Her. Med. 2015, 34, 609–612.
2. [2]
  State administration of traditional Chinese medicine editorial board of Zhong Hua Ben Cao. Zhong Hua Ben Cao. Shanghai Scientific & Technical Publishers, China 1999, p813.
3. [3]
  Dai, B. Chinese Modern Yao Medicine. Nanning: Guangxi Science and Technology Publishers, China 2009, p257.
4. [4]
  Yang, Y.; Yong, J. P.; Lu, C. Z. Chemical and biological progress of Podocarpus nagi. Biomed. Res. Rev. 2019, 2, 1–5.
5. [5]
  Zheng, Y. D.; Bai, G.; Tang, C. P.; Ke, C. Q.; Yao, S.; Tong, L. J.; Feng, F.; Li, Y.; Ding, J.; Xie, H.; Ye, Y. 7α, 8α-Epoxynagilactones and their glucosides from the twigs of Podocarpus nagi: isolation, structures, and cytotoxic activities. Fitoterapia 2018, 125, 174–183. doi: 10.1016/j.fitote.2018.01.007
6. [6]
  Wang, Q. X.; Yang, Z. F.; Peng, W.; Zhang, Y. K.; Chen, Y. G. Study on the constituents of Podocarpus nagi. J. Hainan Normal Univ. (Nat. Sci. ) 2018, 31, 1–5.
7. [7]
  Feng, Z. L.; Zhang, T.; Liu, J. X.; Chen, X. P.; Gan, L. S.; Ye, Y.; Lin, L. G. New podolactones from the seeds of Podocarpus nagi and their anti-inflammatory effect. J. Nat. Med. 2018, 72, 882–889. doi: 10.1007/s11418-018-1219-5
8. [8]
  Yong, J. P.; Lu, C. Z.; Zhang, S. B. Preparation method and use of Podocarpus nagi kernel oil. New Australian Innovation Patent. Application Number: 2020100726.
9. [9]
  Kovganko, N. V.; Kashkan, Z. N. Synthesis of natural phytosteroids of the 6-ketostigmastane series and compounds related to them. Chem. Nat. Compd. 1990, 26, 656–660. doi: 10.1007/BF00630075
10. [10]
  Subash-Babu, S.; Ignacimuthu, S.; Agastian, P.; Varghese, B. Partial regeneration of β-cells in the islets of Langerhans by Nymphayol a sterol isolated from Nymphaea stellata (Willd.) flowers. Bioorg. Med. Chem. 2009, 17, 2864–2870. doi: 10.1016/j.bmc.2009.02.021
11. [11]
  Klingberg, S.; Andersson, H.; Mulligan, A.; Bhaniani, A.; Welch, A.; Bingham, S.; Khaw, K. T.; Andersson, S.; Ellegård, L. Food sources of plant sterols in the EPIC Norfolk population. Eur. J. Clin. Nutr. 2008, 62, 695–703. doi: 10.1038/sj.ejcn.1602765
12. [12]
  Kovganko, N. V.; Kashkan, Z. N.; Borisov, E. V.; Batura, E. V. ¹³C NMR spectra of β-sitosterol derivatives with oxidized rings A and B. Chem. Nat. Compd. 1999, 5, 646–649.
13. [13]
  Kovganko, N. V.; Kashkan, Z. N.; Borisov, E. V. ¹³C NMR spectra of functionally substituted 3β-chloroderivatives of cholesterol and β-sitosterol. Chem. Nat. Compd. 2000, 36, 595–598. doi: 10.1023/A:1017519926605
14. [14]
  Wu, X. Y.; Chao, Z. M.; Wang, C.; Sun, W.; Zhang, G. F. Extraction and crystal structure of β-sitosterol. Chin. J. Struct. Chem. 2014, 33, 801–806.
15. [15]
  Li, W. H.; Chang, S. T.; Chang, S. C.; Chang, H. T. Isolation of antibacterial diterpenoids from Cryptomeria japonica bark. Nat. Prod. Res. 2008, 22, 1085–1093. doi: 10.1080/14786410802267510
16. [16]
  Tasyriq, M.; Najmuldeen, I. A.; In, L. L. A.; Mohamad, K.; Awang, K.; Hasima, N.; Olajide, O. A. 7α-Hydroxy-β-sitosterol from Chisocheton tomentosus induces apoptosis via dysregulation of cellular Bax/Bcl-2 ratio and cell cycle arrest by downregulating ERK1/2 activation. Evid. -based Complement Altern. Med. 2012, 2012.
17. [17]
  Wang, L.; Yang, Y. J.; Chen, S. H.; Ge, X. R.; Xu, C. J.; Gui, S. Q. Effects of beta-sitosterol on microtubular systems in cervical cancer cells. Natl. Med. J. Chin. 2006, 86, 2771–2775.
18. [18]
  Tominaga, H.; Ishiyama, M.; Ohseto, F.; Sasamoto, K.; Hamamoto, T.; Suzuki, K.; Watanabe, M. A water-soluble tetrazolium salt useful for colorimetric cell viability assay. Anal. Commun. 1999, 36, 47–50.
19. [19]
  Sheldrick, G. M. SHELXL-2014/7, Program for Refinement of Crystal Structures. Institute for Inorganic Chemistry. University of Gottingen: Gottingen, Germany 2014.
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