Chemical and biological comparison of different sections of Uncaria rhynchophylla (Gou-Teng)

Abstract

Uncaria rhynchophylla (Gou-Teng in Chinese) is officially documented in Chinese pharmacopoeia as one of the authentic sources for the crude drug of Gou-Teng which has long been used for mental and cardiovascular diseases. Indole alkaloids are the characteristic constituents responsible for the desired hypotensive effect; however, the psychiatric active constituents of Gou-Teng are still unclear. According to traditional Chinese medicine theory, only the hook-bearing stems of U. rhynchophylla are used as the crude materials for Gou-Teng, while its leaves and fruits are scarcely used. The present study aimed to compare the metabolic fingerprints of different parts (hooks, stems, leaves and fruits) of U. rhynchophylla by LC-DAD-MS/MS analysis and further evaluate their psychiatric activities on HEK293 cell line in vitro. A total of 38 constituents including 26 alkaloids, six flavonoids, two triterpenoids, two chlorogenic acid analogs and two other compounds were characterized. The different parts of U. rhynchophylla can be well differentiated from their chemical profiles. Leaves displayed the most potent activity on both MT₁ and MT₂ receptors, with agonistic rates of 39.7% and 97.6%. For 5-HT_1A and 5-HT_2C receptors, hooks showed the strongest activity with agonistic rates of 92.6% and 83.1%, respectively. This investigation provided valuable information for understanding the chemical divergence between different parts of U. rhynchophylla, and their substantial bases for psychiatric purposes.

Keywords

Gou Teng LC-MS analysis chemical profiles indole alkaloids

Get full access to this article

View all access options for this article.

References

Kinghorn

Lee

et al.

Cancer chemopreventive agents discovered by activity-guided fractionation: an update. Curr Org Chem 2003; 7: 213.

Newman

Cragg

. Natural products as sources of new drugs from 1981 to 2014. J Nat Prod 2016; 79: 629.

Inui

Wang

Pro

et al.

Unbiased evaluation of bioactive secondary metabolites in complex matrices. Fitoterapia 2012; 83: 1218.

Qiu

Cai

Jaki

et al.

Quantitative purity-activity relationships of natural products: the case of anti-tuberculosis active triterpenes from Oplopanax horridus. J Nat Prod 2013; 76: 413.

Prince

Pohnert

. Searching for signals in the noise: metabolomics in chemical ecology. Anal Bioanal Chem 2010; 396: 193.

Yuliana

Khatib

Choi

et al.

Metabolomics for bioactivity assessment of natural products. Phytother Res 2011; 25: 157.

Geng

Chen

Zhou

et al.

LC-MS guided isolation of (±)-sweriledugenin A, a pair of enantiomeric lactones, from Swertia leducii. Org Lett 2014; 16: 370.

Henke

Kelleher

. Modern mass spectrometry for synthetic biology and structure-based discovery of natural products. Nat Prod Rep 2016; 33: 942.

Cui

Abliz

Xia

et al.

On-line identification of phenanthroindolizidine alkaloids in a crude extract from Tylophora atrofolliculata by liquid chromatography combined with tandem mass spectrometry. Rapid Commun Mass Spectrom 2004; 18: 184.

10.

Heitzman

Neto

Winiarz

et al.

Ethnobotany, phytochemistry and pharmacology of Uncaria (Rubiaceae). Phytochemistry 2005; 66: 5–29.

11.

Laus

. Advances in chemistry and bioactivity of the genus Uncaria. Phytother Res 2004; 18: 259.

12.

Ndagijimana

Wang

Pan

et al.

A review on indole alkaloids isolated from Uncaria rhynchophylla and their pharmacological studies. Fitoterapia 2013; 86: 35.

13.

Zhang

Zhao

et al.

Medicinal uses, phytochemistry and pharmacology of the genus Uncaria. J Ethnopharmacol 2015; 173: 48.

14.

Wang

Zhang

et al.

Qualitative and quantitative analyses of alkaloids in Uncaria species by UPLC-ESI-Q-TOF/MS. Chem Pharm Bull 2014; 62: 1100.

15.

Niu

Inada

et al.

Chemical profiling with HPLC-FTMS of exogenous and endogenous chemicals susceptible to the administration of chotosan in an animal model of type 2 diabetes-induced dementia. J Pharm Biomed Anal 2015; 104: 21.

16.

Wang

Wan

et al.

Structural stabilities and transformation mechanism of rhynchophylline and isorhynchophylline by ultra performance liquid chromatography/time-of-flight mass spectrometry (UPLC/Q-TOF-MS). Molecules 2015; 20: 14849.

17.

Wang

Luo

Wang

et al.

New indole glucosides as biosynthetic intermediates of camptothecin from the fruits of Camptotheca acuminata. Fitoterapia 2015; 103: 1.

18.

Kumar

Singh

Bajpai

et al.

Simultaneous determination of bioactive monoterpene indole alkaloids in ethanolic extract of seven Rauvolfia species using UHPLC with hybrid triple quadrupole linear ion trap mass spectrometry. Phytochem Anal 2016; 27: 296.

19.

Pan

Yang

Zhang

et al.

An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS. Anal Bioanal Chem 2015; 407: 6057.

20.

Kushida

Matsumoto

Igarashi

et al.

Metabolic profiling of the Uncaria hook alkaloid geissoschizine methyl ether in rat and human liver microsomes using high-performance liquid chromatography with tandem mass spectrometry. Molecules 2015; 20: 2100.

21.

Gai

Chen

et al.

Analysis of the traditional medicine YiGan San by the fragmentation patterns of cadambine indole alkaloids using HPLC coupled with high-resolution MS. J Sep Sci 2013; 36: 3723.

22.

Szabó

. Rigorous biogenetic network for a group of indole alkaloids derived from strictosidine. Molecules 2008; 13: 1875.

23.

Xie

Shi

Wang

et al.

Systematic identification and quantification of tetracyclic monoterpenoid oxindole alkaloids in Uncaria rhynchophylla and their fragmentations in Q-TOF-MS spectra. J Pharm Biomed Anal 2013; 81: 56.

24.

Singh

Kumar

Bajpai

et al.

Structural characterization of flavonoid C - and O -glycosides in an extract of Adhatoda vasica leaves by liquid chromatography with quadrupole time-of-flight mass spectrometry. Rapid Commun Mass Spectrom 2015; 29: 1095.

25.

Shimada

Goto

Kogure

et al.

Protective effect of phenolic compounds isolated from the hooks and stems of Uncaria sinensis on glutamate. Am J Chinese Med 2001; 29: 173.

26.

Zhao

Geng

et al.

UFLC/MS-IT-TOF guided isolation of anti-HBV active chlorogenic acid analogues from Artemisia capillaris as a traditional Chinese herb for the treatment of hepatitis. J Ethnopharmacol 2014; 156: 147.

27.

Zhang

Yang

Yao

et al.

New triterpenic acids from Uncaria rhynchophylla: chemistry, NO-inhibitory activity, and tandem mass spectrometric analysis. Fitoterapia 2014; 96: 39.

28.

Geng

Chen

et al.

Rapid characterization of chemical constituents in Saniculiphyllum guangxiense by ultra fast liquid chromatography with diode array detection and electrospray ionization tandem mass spectrometry. Int J Mass Spectrom 2014; 361: 9.

29.

Abrous-Belbachir

De Paepe

Tremolieres

et al.

Evidence that norflurazon affects chloroplast lipid unsaturation in soybean leaves (Glycine max L.). J Agric Food Chem 2009; 57: 11434.