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[Anthraquinones from the roots of Knoxia valerianoides].
Zhongguo Zhong Yao Za Zhi. 2011 Nov; 36(21):2980-6.ZZ

Abstract

OBJECTIVE

To investigate the chemical constituents of the roots of Knoxia valerianoides and their biological activities.

METHOD

The anthraquinones were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Structures of the isolates were identified by their physical-chemical properties and spectroscopic analysis including 2D NMR and MS. Antioxidant, anti-HIV, neuroprotective, and cytotoxic activities were screened by using cell-based models.

RESULT

Twenty-two constituents were isolated from an ethanolic extract of the roots of K. valerianoides. Their structures were identified as nordamnacanthal (1), ibericin (2), rubiadin (3), damnacanthol (4), 2-ethoxymethylknoxiavaledin (5), 3-hydroxymorindone (6), knoxiadin (7), 2-formyl knoxiavaledin (8), lucidin (9), xanthopurpurin (10), 1, 3-dihydroxy-2-methoxy-9, 10- anthraquinone (11), lucidin(-methyl ether (12), digiferruginol (13), 3-hydroxy-2-methyl-9,10-anthraquinone (14), rubiadin-1-methyl ether (15), 6-methoxylucidin (-ethyl ether (16), 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone (17), 1,3-dihydroxy-2-hydroxy methyl-6-methoxy-9,10-anthraquinone (18), 1,3,6-trihydroxy-2-methoxymethyl-9,10- anthraquinone (19), 3,6-dihydroxy-2- hydroxymethyl-9,10-anthraquinone (20), and 1,6-dihydroxy-2-methyl-9,10-anthra quinone (21). In the in vitro assays, at a concentration of 1 x 10(-5) mol x L(-1), no compounds were active against human cancer cell lines (HCT-8, Bel7402, BGC-823, A549, and A2780), deserum and glutamate induced PC12-syn cell damage, LPS induced NO production in macrophage, Fe2+-cystine induced rat liver microsomal lipid peroxidation, HIV-1 replication, and protein tyrosine phosphatase 1B (PTP1B).

CONCLUSION

Compounds 9-21 were obtained from the roots of K. valerianoides for the first time.

Authors+Show Affiliations

Zhao F
State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Science and Peking Union Medical College, Beijing 100050, China.
Wang S
No affiliation info available
Wu X
No affiliation info available
Yu Y
No affiliation info available
Yue Z
No affiliation info available
Liu B
No affiliation info available
Lin S
No affiliation info available
Zhu C
No affiliation info available
Yang Y
No affiliation info available
Shi J
No affiliation info available

MeSH

AnimalsAnthraquinonesCell LineDrugs, Chinese HerbalHumansMolecular StructurePlant RootsRatsRubiaceae

Pub Type(s)

English Abstract
Journal Article
Research Support, Non-U.S. Gov't

Language

chi

PubMed ID

22308688

Citation

Zhao, Feng, et al. "[Anthraquinones From the Roots of Knoxia Valerianoides]." Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica, vol. 36, no. 21, 2011, pp. 2980-6.
Zhao F, Wang S, Wu X, et al. [Anthraquinones from the roots of Knoxia valerianoides]. Zhongguo Zhong Yao Za Zhi. 2011;36(21):2980-6.
Zhao, F., Wang, S., Wu, X., Yu, Y., Yue, Z., Liu, B., Lin, S., Zhu, C., Yang, Y., & Shi, J. (2011). [Anthraquinones from the roots of Knoxia valerianoides]. Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica, 36(21), 2980-6.
Zhao F, et al. [Anthraquinones From the Roots of Knoxia Valerianoides]. Zhongguo Zhong Yao Za Zhi. 2011;36(21):2980-6. PubMed PMID: 22308688.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - [Anthraquinones from the roots of Knoxia valerianoides]. AU - Zhao,Feng, AU - Wang,Sujuan, AU - Wu,Xiuli, AU - Yu,Yang, AU - Yue,Zhenggang, AU - Liu,Bo, AU - Lin,Sheng, AU - Zhu,Chenggen, AU - Yang,Yongchun, AU - Shi,Jiangong, PY - 2012/2/8/entrez PY - 2012/2/9/pubmed PY - 2012/3/28/medline SP - 2980 EP - 6 JF - Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica JO - Zhongguo Zhong Yao Za Zhi VL - 36 IS - 21 N2 - OBJECTIVE: To investigate the chemical constituents of the roots of Knoxia valerianoides and their biological activities. METHOD: The anthraquinones were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Structures of the isolates were identified by their physical-chemical properties and spectroscopic analysis including 2D NMR and MS. Antioxidant, anti-HIV, neuroprotective, and cytotoxic activities were screened by using cell-based models. RESULT: Twenty-two constituents were isolated from an ethanolic extract of the roots of K. valerianoides. Their structures were identified as nordamnacanthal (1), ibericin (2), rubiadin (3), damnacanthol (4), 2-ethoxymethylknoxiavaledin (5), 3-hydroxymorindone (6), knoxiadin (7), 2-formyl knoxiavaledin (8), lucidin (9), xanthopurpurin (10), 1, 3-dihydroxy-2-methoxy-9, 10- anthraquinone (11), lucidin(-methyl ether (12), digiferruginol (13), 3-hydroxy-2-methyl-9,10-anthraquinone (14), rubiadin-1-methyl ether (15), 6-methoxylucidin (-ethyl ether (16), 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone (17), 1,3-dihydroxy-2-hydroxy methyl-6-methoxy-9,10-anthraquinone (18), 1,3,6-trihydroxy-2-methoxymethyl-9,10- anthraquinone (19), 3,6-dihydroxy-2- hydroxymethyl-9,10-anthraquinone (20), and 1,6-dihydroxy-2-methyl-9,10-anthra quinone (21). In the in vitro assays, at a concentration of 1 x 10(-5) mol x L(-1), no compounds were active against human cancer cell lines (HCT-8, Bel7402, BGC-823, A549, and A2780), deserum and glutamate induced PC12-syn cell damage, LPS induced NO production in macrophage, Fe2+-cystine induced rat liver microsomal lipid peroxidation, HIV-1 replication, and protein tyrosine phosphatase 1B (PTP1B). CONCLUSION: Compounds 9-21 were obtained from the roots of K. valerianoides for the first time. SN - 1001-5302 UR - https://www.unboundmedicine.com/medline/citation/22308688/[Anthraquinones_from_the_roots_of_Knoxia_valerianoides]_ DB - PRIME DP - Unbound Medicine ER -