11-Methoxyviburtinal, a new iridoid fromValeriana jatamansi

Chen, Ye‐Gao; Yu, Lili; Huang, Rong; Lv, Yuanda; Gui, Shi-Hong

doi:10.1007/bf02972980

Cited by 32 publications

(17 citation statements)

References 12 publications

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“…The known compounds, valtrate hydrin B8 ( 3 ) (Demirezer et al, 1999), volvaltrate B ( 4 ) (Lin et al, 2010b), deoxido-didrovaltrate ( 5 ) (Bounthanh et al, 1983), baldrinal ( 6 ) (Denee et al, 1979), homobaldrinal ( 7 ) (Denee et al, 1979), desacylbaldrinal ( 8 ) (Georg and Michael, 1979), 11-methoxyviburtinal ( 9 ) (Chen et al, 2005), jatamanvaltrate R ( 10 ) (Dong et al, 2015), jatamanvaltrate S ( 11 ) (Dong et al, 2015) rupesin E ( 12 ) (Lin et al, 2010a), (1S, 3R, 5S, 7S, 8S, 9S)-3, 8-epoxy-7-hydroxy-1-methoxy-4, 11-dihydronepetane ( 13 ) (Thies, 1970), valeriananoid B ( 14 ) (Ming et al, 1997), valeriananoid C ( 15 ) (Ming et al, 1997), valeriananoid D ( 16 ) (Dong et al, 2015), and valeriananoid E ( 17 ) (Dong et al, 2015) were identified by analysis of their spectroscopic data and comparison with the literature values. This is the first isolation of iridoids with fatty acid esters ( 2 ) from the family of Valerianaceae.…”

Section: Resultsmentioning

confidence: 99%

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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Section: Resultsmentioning

confidence: 99%

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 position of β-D-glucose at C-2 (δC 80.4) was confirmed based on the HMBC correlation ( Fig.1) from anomeric proton δH 4.33 (1H, d, J = 7.8 Hz) to C-2 (δC 80.4). A detailed analysis of HMQC, HMBC and 1 H-1 H COSY spectrum (Fig.1) In addition to the two new compounds 1 and 2, the known iridoids and sesquiterpenoid were identified by comparison of spectroscopic data with those reported in the literature as 8-methoxy-3-methoxy-10-methylene-2,9-dioxatricyclo[4.3.1.0 3,7 ]decan-4-ol (3) (Inouye et al, 1974), vibutinal (4) , baldrinal (5) (Chen et al, 2005), 11-ethoxyviburtinal (6) (Boros et al,1991), jatamanvaltrate E (7) (Lin et al, 2009), jatamanvaltrate A (8) (Lin et al, 2009), jatamanvaltrate F (9) (Lin et al, 2009), valeriotetrate C (10) ( Lin et al, 2010), chlorovaltrate A (11) ( Lin et al, 2013).…”

Section: Resultsmentioning

confidence: 91%

A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity

Tan

Yong

Dong

et al. 2016

Phytochemistry Letters

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A new secoiridoid glycoside, isopatrinioside (1) and a new sesquiterpenoid glycoside, valeriananoid F (2), together with nine known compounds, were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was an unusual monocyclic iridoid glycoside ring-opened between C-1 and C-2 produced by the cleavage of the pyran ring. Of the eleven isolates, compounds 1 and 4 exhibited moderate neuroprotective effects against CoCl2-induced neuronal cell death in PC12 cells.

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“…By analyzing the NMR spectroscopic data of compounds 3-6, and comparing their physical and spectroscopic data with those reported in the literature, the known iridoids were identified as rupesin B (3) [16], homobaldrinal (4) [17], baldrinal (5) [18], and 11-methoxyviburtinal (6) [18].…”

Section: Resultsmentioning

confidence: 96%

Iridoids from the roots ofValeriana jatamansi

Fang

et al. 2012

Journal of Asian Natural Products Research

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Two new iridoids, jatamanvaltrates N (1) and O (2), together with four known compounds (3-6), were isolated from the roots of Valeriana jatamansi. Their structures and relative configurations were elucidated by spectroscopic methods (IR, ESI-MS, HR-ESI-MS, 1D, and 2D NMR) and by comparison of their NMR spectral data with those of related compounds. All the isolated compounds were evaluated for their neuroprotective effects, and only compound 1 showed weak neuroprotective activities.

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11-Methoxyviburtinal, a new iridoid fromValeriana jatamansi

Cited by 32 publications

References 12 publications

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

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

A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity

Iridoids from the roots ofValeriana jatamansi

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