Revision of the Structures of 1,5-Dihydroxy-3,8-epoxyvalechlorine, Volvaltrate B, and Valeriotetrate C from <i>Valeriana jatamansi</i> and <i>V. officinalis</i>

Lin, Sheng; Shen, Yun‐Heng; Zhang, Zhongxiao; Li, Hui‐Liang; Shan, Lei; Liu, Runhui; Xu, Xiuru; Zhang, Weidong

doi:10.1021/np100426j

Cited by 48 publications

(17 citation statements)

References 15 publications

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“…Therefore, the planar structure of 1 was established. The stereochemistry including the absolute configuration of valepotriates has been well elucidated by NOE experiments, chemical transformation, and X-ray analysis in the previous reports [7,14]. The singlet of H-1 and H-9 in 1 suggested that the dihedral angle of these two protons is close to 908.…”

Section: Resultsmentioning

confidence: 80%

“…These observations, coupled with biogenetic grounds, suggested that 2 has the same configuration of iridoid nucleus as 1. The R configuration of the a-(isovaleroxy)isovaleroxy moiety was established by basic hydrolysis of 2, which yielded R-a-(isovaleroxy)isovaleric acid on the basis of its optical rotation data {½a 20 D þ 8.2 (c ¼ 0.10, CHCl 3 )} [7]. Therefore, 2 was defined as valtral B.…”

Section: Resultsmentioning

confidence: 99%

“…The mixture was resolved by Sephadex LH -20 chromatography eluting with petroleum ether -CHCl 3 -MeOH (5:5:1) and then preparative TLC using CHCl 3 -MeOH (20:1) as developing solvent to yield (R)-a-(isovaleroxy)isovaleric acid (1.2 mg) on the basis of its optical rotation data {½a 20 D þ 8.2 (c 0.10, CHCl 3 )} [7].…”

Section: Basic Hydrolysis Of Valtral B (2)mentioning

confidence: 99%

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Three decomposition products of valepotriates fromValeriana jatamansiand their cytotoxic activity

Lin

Chen

et al. 2015

Journal of Asian Natural Products Research

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Three new decomposition products of valepotriates, valtrals A-C (1-3), and two known products, baldrinal and homobaldrinal, are formed during the isolation procedure of the ethanol extract of the whole plants of Valeriana jatamansi. Their structures were determined by spectroscopic methods including IR, MS, 1D, and 2D NMR experiments. Compounds 1-3 showed selective cytotoxicity against metastatic prostate cancer (PC-3M) and colon cancer (HCT-8) cell lines.

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Section: Resultsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

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Three decomposition products of valepotriates fromValeriana jatamansiand their cytotoxic activity

Lin

Chen

et al. 2015

Journal of Asian Natural Products Research

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“…The relative configuration of 1 was further established by ROESY experiment ( Figure 2 and Supplementary Figures S8, S9 ) and comparison the spectroscopic data with those reported valepotriates (Demirezer et al, 1999; Tang et al, 2002; Wang et al, 2008, 2014; Lin et al, 2010b, 2013). Generally, naturally occurring iridoids display α-orientation for H-1 and β-orientation for H-9.…”

Section: Resultsmentioning

confidence: 88%

Valepotriates From the Roots and Rhizomes of Valeriana jatamansi Jones as Novel N-Type Calcium Channel Antagonists

Fan

Jiang²,

Liu

et al. 2018

Front. Pharmacol.

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The roots and rhizomes of Valeriana jatamansi have long been used as folk medicine in Asia and usually named as “Zhizhuxiang” in Chinese for the treatment of abdominal distention and pain. However, its active ingredients and molecular targets for treatment of abdominal pain remain unrevealed. Inhibitors of Ca v 2.2 N-type voltage-gated calcium channels (VGCCs) are actively sought after for their potential in treating pain, especially chronic pain. As far as we know, the method used for seeking analgesic active ingredient from plant material has rarely been reported. The analgesic potentials of the EtOH extract (0.01 mg/ml) of the roots and rhizomes of V. jatamansi and its EtOAc, n -BuOH and H 2 O soluble parts (0.01 mg/ml, respectively) were tested herein on Ca v 2.2, using whole-oocyte recordings in vitro by tow-electrode voltage clamp. The results indicated that the EtOAc-soluble part exhibited the most potent inhibition of Ca v 2.2 peak current (20 mv). The EtOAc-soluble part was then subjected to silica gel column chromatography (CC) and giving 9 fractions. Phytochemical studies were carried out by repeated CC and extensive spectroscopic analyses after the fraction (0.01 mg/ml) was identified to be active and got seventeen compounds ( 1 – 17 ). All isolates were then sent for further bioactive verification ( 1 and 3 at concentration of 10 μM, others at 30 μM). In addition, the selectivity of the active compounds 1 and 3 were tested on various ion channels including Ca v 1.2, Ca v 2.1 and Ca v 3.1 VGCCs and Kv1.2, Kv2.1, Kv3.1 and BK potassium channels. The results indicated that compound 1 and 3 (an abundant compound) inhibited Ca v 2.2 with an EC 50 of 3.3 and 4.8 μM, respectively, and had weaker or no effect on Ca v 1.2, Ca v 2.1 and Ca v 3.1 VGCCs and Kv1.2, Kv2.1, Kv3.1 and BK potassium channels. Compounds 1 and 3 appear to act as allosteric modulators rather than pore blockers of Ca v 2.2, which may play crucial role in attenuating nociception. The results of present research indicated that the ethnopharmacological utilization of V. jatamansi for relieving the abdominal distention and pain may mediate through Ca v 2.2 channel. Our work is the first demonstration of inhibition of Ca v 2.2 by iridoids, which may provide a fresh source for finding new analgesics.

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“…Valtrate, acevaltrate were important sedative-hypnotics chemical bulk drugs. Iridoid esters could also inhibit the growth and proliferation of human tumor cell lines (Lin et al, 2009;Lin et al, 2010), with the mechanism unknown. In addition, valtrate and its analogs are Rev-export inhibitors demonstrated other effects such as anti-HIV (Watanabe et al, 2011), and reversed tumor RESEARCH ARTICLE (Turner et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Induction of Cytotoxicity and Apoptosis in Human Gastric Cancer Cell SGC-7901 by Isovaltrate Acetoxyhydrin Isolated from Patrinia heterophylla Bunge Involves a Mitochondrial Pathway and G2/M Phase Cell Cycle Arrest

Yang

Wang²,

Cheng³

et al. 2013

Asian Pacific Journal of Cancer Prevention

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Background: Our previous study demonstrated cytotoxicity of a crude extract from Patrinia heterophylla Bunge (PHEB). In the present study, we aimed to investigate the effects of isovaltrate acetoxyhydrin (IA) isolated from PHEB on the gastric cancer cell SGC-7901, in order to explore a potential treatment for gastric cancer. Methods: MTT assays were employed to determine the effects of IA on cell vitality and proliferation, with monitoring of cell morphology changes and examination of apoptosis with Annexin V-PI staining. Flow cytometry was used to assess cell cycle progression and mitochondrial membrane potential. The activity of caspase 3, 9 was evaluated by spectrophotometry, and the protein levels of Bax, Bcl2 and Cyclin B1 were analyzed with Western blotting of total proteins extracted from cultured cells. Results: The results demonstrated direct toxicity of IA towards SGC-7901 cells. Evidence of apoptosis included blebbing and chromatin condensation. Annexin V-PI assays revealed early apoptosis, involving rapid depolarization of mitochondrial membranes and activity of caspase 3, 9 signaling pathways. Western blotting showed that Bcl2 and Bax proteins was down-and up-regulated, respectively, and cyclin B1 was up-regulated. Cell cycle analysis further indicated that IA could induce G2/M phase arrest in SGC-7901 cells. Conclusions: In conclusion, we believe that IA induces apoptosis of SGC-7901 cells, therefore providing a potential therapeutic agent for treatment of gastric cancer.

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Revision of the Structures of 1,5-Dihydroxy-3,8-epoxyvalechlorine, Volvaltrate B, and Valeriotetrate C from Valeriana jatamansi and V. officinalis

Cited by 48 publications

References 15 publications

Three decomposition products of valepotriates fromValeriana jatamansiand their cytotoxic activity

Three decomposition products of valepotriates fromValeriana jatamansiand their cytotoxic activity

Valepotriates From the Roots and Rhizomes of Valeriana jatamansi Jones as Novel N-Type Calcium Channel Antagonists

Induction of Cytotoxicity and Apoptosis in Human Gastric Cancer Cell SGC-7901 by Isovaltrate Acetoxyhydrin Isolated from Patrinia heterophylla Bunge Involves a Mitochondrial Pathway and G2/M Phase Cell Cycle Arrest

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