Four New Polyhydroxy Cyclohexanes from the Stems of Fissistigma tientangense
Mei-Zhu Wu
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Mei-Zhu Wu and Ming-Chang Chen contributed equally to this study.
Search for more papers by this authorMing-Chang Chen
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Mei-Zhu Wu and Ming-Chang Chen contributed equally to this study.
Search for more papers by this authorXiao-Zheng Zhang
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorChen Sun
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorGuang-Ying Chen
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorZi-Han Yang
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorCai-Juan Zheng
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorYou-Ping Luo
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorCorresponding Author
Xue-Ming Zhou
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorMei-Zhu Wu
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Mei-Zhu Wu and Ming-Chang Chen contributed equally to this study.
Search for more papers by this authorMing-Chang Chen
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Mei-Zhu Wu and Ming-Chang Chen contributed equally to this study.
Search for more papers by this authorXiao-Zheng Zhang
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorChen Sun
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorGuang-Ying Chen
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorZi-Han Yang
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorCai-Juan Zheng
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorYou-Ping Luo
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorCorresponding Author
Xue-Ming Zhou
Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, 571158 China
Search for more papers by this authorAbstract
Four undescribed polyhydroxy cyclohexanes, fissoxhydrylenes A–D (1–4), together with two known biogenetically related polyhydroxy cyclohexanes (5 and 6) were isolated from the stems of Fissistigma tientangense Tsiang et P. T. Li. Their structures were elucidated by detailed analysis of NMR, HR-ESI-MS, IR, UV and Optical rotations data. The absolute configuration of 1 was confirmed by X-ray crystallographic. The absolute configurations of 2–4 were confirmed by chemical reaction and optical rotations. Compound 4 represent the first example of a no substituent polyhydroxy cyclohexanes from natural products. All isolated compounds were evaluated for their anti-inflammatory activities against the lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells in vitro. Compounds 3 and 4 showed inhibitory activities with the IC50 values of 16.63±0.06 μM and 14.38±0.08 μM, respectively.
Graphical Abstract
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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References
- 1SFDA. In Chinese Herbal Medicine. Shanghai Science and Technology Publishing Co.: Shanghai, 1997, Vol. 3, p. 1594–1595.
- 2J. Q. Chen, C. Jin, B. L. Xu, J. C. Shu, F. Shao, C. J. Yuan, F. Q. Li, L. P. Huang, H. L. Huang, Fitoterapia 2021, 151, 104883.
- 3C. X. Gao, F. X. Lin, Y. X. Luo, X. M. Zhou, Biochem. Syst. Ecol. 2021, 97, 104298.
- 4Y. W. Ge, S. Zhu, M. Y. Shang, X. Y. Zang, X. Wang, Y. J. Bai, L. Li, K. Komatsu, S. Q. Cai, Phytochemistry 2013, 86, 201–207.
- 5Y. Wu, C. C. Zhu, Y. X. Luo, B. Zhang, X. S. Ji, X. M. Song, X. M. Zhou, J. Asian Nat. Prod. Res. 2022, 24, 550–555.
- 6W. L. Zhong, X. M. Zhou, J. L. Yi, X. M. Song, B. Zhang, J. Y. Yang, G. Y. Chen, Nat. Prod. Res. 2022, 36, 3598–3602.
- 7C. Geny, A. Abou Samra, P. Retaileau, B. I. Iorga, H. Nedev, K. Awang, F. Roussi, M. Litaudon, V. Dumontet, J. Nat. Prod. 2017, 80, 3179–3185.
- 8C. Auranwiwat, P. Wongsomboon, T. Thaima, R. Rattanajak, S. Kamchonwongpaisan, A. C. Wills, S. Laphookhieo, S. G. Pyne, T. Limtharakul, J. Nat. Prod. 2019, 82, 101–110.
- 9G. Maeda, J. Wal, A. K. Gupta, J. J. E. Munissi, A. Orthaber, P. Sunnerhagen, S. S. Nyandoro, M. Erdelyi, J. Nat. Prod. 2020, 83, 210–215.
- 10T. Jaipetch, S. Hongthong, C. Kuhakarn, P. Pailee, P. Piyachaturawat, K. Suksen, P. Kongsaeree, S. Prabpai, N. Nuntasaen, V. Reutrakul, Fitoterapia 2019, 139, 104182.
- 11L. Wirasathien, T. Pengsuparp, M. Moriyasu, K. Kawanishi, R. Suttisri, Arch. Pharmacal Res. 2006, 29, 497–502.
- 12A. Kijjoa, J. Bessa, M. M. M. Pinto, C. Anatachoke, A. M. S. Silva, G. Eaton, W. Herz, Phytochemistry 2002, 59, 543–549.
- 13Y. H. Liao, L. Z. Xu, S. L. Yang, J. Dai, Y. S. Zhen, M. Zhu, N. J. Sun, Phytochemistry 1997, 45, 729–732.
- 14A. Kijjoa, J. Bessa, M. M. M. Pinto, C. Anatachoke, A. M. S. Silva, G. Eaton, W. Herz, Phytochemistry 2002, 59, 543–549.
- 15P. C. Stevenson, N. C. Veitch, M. S. J. Simmonds, Phytochemistry 2007, 68, 1579–1586.
- 16X. M. Zhou, C. J. Zheng, Y. Q. Zhang, X. P. Zhang, X. P. Song, W. Xu, G. Y. Chen, Plant. Med. 2017, 83, 217–223.
- 17J. Cai, X. M. Zhou, X. Yang, M. M. Tang, Q. Y. Liao, B. Z. Meng, S. Liao, G. Y. Chen . Bioorg. Chem. 2020, 94, 103362.