Terpenoids of Alisma orientale rhizome and the crude drug alismatis rhizoma

Nakajima, Yoshijiro; Satoh, Yohko; Katsumata, Masumi; Tsujiyama, Kazuko; Ida, Yoshiteru; Shoji, Jun

doi:10.1016/s0031-9422(00)97024-9

Cited by 79 publications

(61 citation statements)

References 11 publications

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“…The fraction was subjected to further bioactivity-guided purification using repeated flash column chromatography on silica gel and normal and reverse-phase preparative high performance liquid chromatography. Finally, the compounds in the purified active fraction were deduced by comparing their 1 H and 13 C nuclear magnetic resonance spectroscopic data with those of known Alisma components (22,23) and were identified to be alisol A 23-acetate and alisol A 24-acetate (Fig. 1A), compounds that are known to interconvert rapidly (24).…”

Section: A Gfp-lc3 Screening Assay To Identify Inducers Of Autophagymentioning

confidence: 99%

Alisol B, a Novel Inhibitor of the Sarcoplasmic/Endoplasmic Reticulum Ca2+ ATPase Pump, Induces Autophagy, Endoplasmic Reticulum Stress, and Apoptosis

Law

Wang

et al. 2010

Molecular Cancer Therapeutics

140

120

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Emerging evidence suggests that autophagic modulators have therapeutic potential. This study aims to identify novel autophagic inducers from traditional Chinese medicinal herbs as potential antitumor agents. Using an image-based screen and bioactivity-guided purification, we identified alisol B 23-acetate, alisol A 24-acetate, and alisol B from the rhizome of Alisma orientale as novel inducers of autophagy, with alisol B being the most potent natural product. Across several cancer cell lines, we showed that alisol B-treated cells displayed an increase of autophagic flux and formation of autophagosomes, leading to cell cycle arrest at the G 1 phase and cell death. Alisol B induced calcium mobilization from internal stores, leading to autophagy through the activation of the CaMKK-AMPK-mammalian target of rapamycin pathway. Moreover, the disruption of calcium homeostasis induces endoplasmic reticulum stress and unfolded protein responses in alisol B-treated cells, leading to apoptotic cell death. Finally, by computational virtual docking analysis and biochemical assays, we showed that the molecular target of alisol B is the sarcoplasmic/endoplasmic reticulum Ca 2+ ATPase. This study provides detailed insights into the cytotoxic mechanism of a novel antitumor compound. Mol Cancer Ther; 9(3); 718-30. ©2010 AACR.

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Section: A Gfp-lc3 Screening Assay To Identify Inducers Of Autophagymentioning

confidence: 99%

Alisol B, a Novel Inhibitor of the Sarcoplasmic/Endoplasmic Reticulum Ca2+ ATPase Pump, Induces Autophagy, Endoplasmic Reticulum Stress, and Apoptosis

Law

Wang

et al. 2010

Molecular Cancer Therapeutics

140

120

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“…The correlations from H-5 to H 2 -15 suggested that these protons were all in α-configuration. Thus, compound 1 was the 10-methoxyl derivative of compound 7, and finally concluded to be 4α,15-dihydroxy-10β-methoxy-1β, 5α(H)-guai-6 (7) Tables 1, 2) showed signals of a guaiane sesquiterpene skeleton, which was close to 10-O-methyl-alismoxide, 14) except the replacement of the methoxyl group with an ethoxyl group [δ H 3.36 (2H, m), 1.13 (3H, t, 7.0); δ C 55.9 (t), 16.3 (q)]. Two oxygenated quaternary carbons at δ C 80.3 (s) and 79.0 (s) were assigned to be C-4 and C-10, respectively, according to the HMBC correlations of H-6/C-4, H-1/C-10, H-8/C-10, H-9/C-10 and Me-15/C-10.…”

Section: Resultsmentioning

confidence: 97%

“…The Extensive analysis of the above data suggested that compound 5 was a norsesquiterpenoid derivatived from alismol (6). 10,11,14) The significant difference included the obvious presence of the carbonyl group and the lack of the isopropyl group. The HMBC correlations (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Guaiane-Type Sesquiterpenoids from Alismatis Rhizoma and Their Anti-inflammatory Activity

Fan

Xue

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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Twelve guaiane-type sesquiterpenoids, including four new ones, 10-O-methyl-orientalol A (1), 10-Oethyl-alismoxide (2), 3β,4β-expoxy-chrysothol (3), orientalol G (4), and a new norsesquiterpenoid, orientalol H (5), were isolated from Chinese Alismatis Rhizoma, the dried rhizome of Alisma orientale. The structures of new compounds were elucidated on the basis of spectroscopic data. Moreover, the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells of all compounds was tested.Key words Alismatis Rhizoma; Alisma orientale; guaiane-type sesquiterpenoid; anti-inflammatory Alismatis Rhizoma ("Zexie" in Chinese), a Chinese crude drug prepared from dried rhizome of the aquatic plant Alisma orientale (SAM.) JUZEP. (Alismataceae) widely cultivated in China and Japan, has been used as a diuretic agent used to "remove dampness and promote water metabolism" in the body according to Chinese medicinal principles.1-5) Previous phytochemical and pharmacological study on Alismatis Rhizoma reported the isolation of prostane-type triterpenes and guaiane-type sesquiterpenes, which exhibited a series of bioactivities, such as diuretic, anti-hepatitis B virus (HBV), antibacterial, anti-hypertentive, hypolipidemic, anti-inflammatory, positive hypocholesterolemic activity, and repairing action to cholinergic acetyltransferase, etc.1-3,6-10) With the aim of discovering more structurally unique and bioactive terpenoids from natural resource, five new guaiane-type sesquiterpenes (1-5) along with seven known ones (6-12) (Fig. 1) were isolated from Alismatis Rhizoma. Furthermore, all compounds were examined for their anti-inflammatory potential and compounds 6 and 12 showed moderate inhibition of nitric oxide (NO) production with IC 50 values of 36.997 and 48.602 µM, respectively. Herein, we report the isolation, structural elucidation and biological evaluation of the isolated compounds. Results and DiscussionThe powdered Alismatis Rhizoma was extracted with 95% EtOH, and the concentrated extract was suspended in H 2 O followed by partition with EtOAc. The EtOAc fraction was purified using various column chromatographies to yield twelve guaiane-type sesquiterpenoids (1-12).Compound 1, colorless oil, gave rise to a quasi-molecular ion peak at m/z 291.1935 ([M+Na] + ) in the positive high resolution-electrospray ionization (HR-ESI)-MS, which corresponded to the molecular formula C 16 H 28 O 3 , in combination with its 13 C-NMR and distortionless enhancement by polarization transfer (DEPT) analysis. The IR spectrum exhibited a broad absorption at 3420 cm −1 due to hydroxyl group. The 1 H-NMR spectrum (Table 1) showed the presence of a tertiary methyl [δ H 1.09 (3H, s)], a hydroxymethyl [δ H 3.80 (1H, dd,

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“…Protostane-type triterpenes are the principal active constituents of Rhizoma Alismatis and more than 50 unique protostane-type triterpenes, including alisols A, B and their monoacetates, have been isolated from this herbal drug. [1][2][3] As the bioactive "marker compounds" of Rhizoma Alismatis, protostane-type triterpenes, including alisol A 24-acetate, which is one of the main active triterpenoid compounds isolated from Rhizoma Alismatis, have been determined for the quality control of Rhizoma Alismatis. 4,5) However, during the course of our research on the quantification of alisol A 24-acetate, it was found that alisol A 24-acetate was unstable and could be transformed into other compounds in methanol.…”

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confidence: 99%

Stability and Structure Studies on Alisol A 24-Acetate

Makabel

Zhao

Wang

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Rhizoma Alismatis, the dried rhizome of Alisma orientalis (SAM.) JUZEP, is a famous Traditional Chinese Medicine (TCM) which has been widely used for diuretic, hypolipidemic, anti-inflammatory and anti-diabetic purposes in China for more than a thousand years. Protostane-type triterpenes are the principal active constituents of Rhizoma Alismatis and more than 50 unique protostane-type triterpenes, including alisols A, B and their monoacetates, have been isolated from this herbal drug. [1][2][3] As the bioactive "marker compounds" of Rhizoma Alismatis, protostane-type triterpenes, including alisol A 24-acetate, which is one of the main active triterpenoid compounds isolated from Rhizoma Alismatis, have been determined for the quality control of Rhizoma Alismatis. 4,5) However, during the course of our research on the quantification of alisol A 24-acetate, it was found that alisol A 24-acetate was unstable and could be transformed into other compounds in methanol.In this paper, the stability of alisol A 24-acetate in different solvents was described in detail. Furthermore, by using LC-MS, NMR, and single crystal X-ray diffraction techniques, the structures of the compounds transformed from alisol A 24-acetate and the single crystal X-ray structure of alisol A 24-acetate were elucidated for the first time. ExperimentalGeneral Experimental Procedures A Shimadzu 10A HPLC system (Tokyo, Japan), equipped with a quaternary pump, a diode array spectrophotometric detector (DAD) and an Altech ELSD-2000ES evaporative light scattering detector (ELSD), was used for HPLC analysis. NMR spectra were recorded on a Bruker DRX-500 NMR spectrometer equipped with 5 mm probes using TMS as internal standard. LC-MS analysis was performed on an Agilent 1000 HPLC system (Palo Alto, CA, U.S.A.) equipped with a MDS SCIEX QSTAR mass spectrometer with an ESI source. A single crystal was mounted on a Japan MAC DIP-2030K area detector diffraction meter (Tokyo, Japan). HPLC-grade acetonitrile (CH 3 CN) and methanol (MeOH) were purchased from Fisher Scientific (Fair Lawn, NJ, U.S.A.). HPLC-grade deionized water (H 2 O) was purified by Milli-Q Water purification system (Millipore, MA, U.S.A. C-and 2D-NMR spectra.HPLC Analysis HPLC analysis was performed on a YMC analytical column (Tokyo, Japan) with 5 mm C18-reversed phase material (250ϫ4.60 mm i.d.) using CH 3 CN/H 2 O (70% or 52%) as the mobile phase with the flow rate of 1.0 ml/min at room temperature. The injection volume was 20 ml. For UV detection, the detection wavelength were set at 210 nm, while for ELSD detection, the tube temperature was set at 90°C, and air was used as the gas with the flow rate of 2.5 l/min. LC-MS Analysis LC-MS analysis was performed on a YMC analytical column (Tokyo, Japan) with 5 mm C18-reversed phase material (250ϫ 4.60 mm i.d.) using CH 3 CN/H 2 O (52%, v/v) as the mobile phase. The flow rate was 1.0 ml/min and split 0.4 ml/min to mass spectrometer. The injection volume was 20 ml. Mass spectra were acquired using a MDS SCIEX QSTAR mass spectrometer equipped with ...

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Terpenoids of Alisma orientale rhizome and the crude drug alismatis rhizoma

Cited by 79 publications

References 11 publications

Alisol B, a Novel Inhibitor of the Sarcoplasmic/Endoplasmic Reticulum Ca2+ ATPase Pump, Induces Autophagy, Endoplasmic Reticulum Stress, and Apoptosis

Alisol B, a Novel Inhibitor of the Sarcoplasmic/Endoplasmic Reticulum Ca2+ ATPase Pump, Induces Autophagy, Endoplasmic Reticulum Stress, and Apoptosis

Guaiane-Type Sesquiterpenoids from Alismatis Rhizoma and Their Anti-inflammatory Activity

Stability and Structure Studies on Alisol A 24-Acetate

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