Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale

Ma, Qingjuan; Han, Li; Bi, Xiaopeng; Wang, Fudi; Mu, Yu; Guan, Peipei; Li, Liya; Huang, Xueshi

doi:10.1016/j.phytochem.2016.08.015

Cited by 41 publications

(35 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…11‐OH and 16‐MeO were both in β ‐orientations based on the ROESY correlations ( SI ) of H–C(11)/Me(30), H–C(16)/Me(30) and MeO/Me(18). Moreover, the relative configurations of C(23) and C(24) were determined as (23 S* ) and (24 S* ) as deduced from the big coupling constant ( J = 7.8 Hz) between H–C(23) and H–C(24), which was consistent with those in alisol E . Therefore, compound 7 was finally determined and named as 16 β ‐methoxyalisol E.…”

Section: Resultsmentioning

confidence: 99%

“…The known compounds were identified as alisol F (13), alisol F 24-acetate (14), [22] alisol B (15), alisol B 23-monoacetate (16), [3] 16b-methoxyalisol B monoacetate (17), [3] [11] alisol A (18), [7] alisol A 24-monoacetate (19), [23] 11-deoxyalisol A (20), [7] 25-O-methylalisol A (21), [7] 16-oxoalisol A (22), [7] 13,17-epoxyalisol A (23), [7] alisol G (24), [20] [24] alisol C 23-acetate (25), [9] 16,23-oxidoalisol B (26), [7] alismalactone 23-acetate (27) [13] and alismaketone-B 23-acetate (28) [25] by comparison of their spectral data with literature values.…”

Section: Structural Elucidationmentioning

confidence: 99%

See 1 more Smart Citation

Protostane‐Type Triterpenoids from Alisma orientale

Chen

Luo

et al. 2017

Chemistry & Biodiversity

View full text Add to dashboard Cite

Twenty-eight protostane triterpenoids, including a new degraded one (1), nine new ones (2 - 10), and two new natural ones (11 and 12), have been isolated from the dried rhizomes of Alisma orientale. Alisol R (1) was the first 20,21,22,23,24,25,26,27-octanorprotostane triterpenoid. The absolute configurations of 25-methoxyalisol F (2) and 16β-hydroperoxyalisol B 23-acetate (3) were determined by X-ray diffraction analysis. In addition, alismaketone-B 23-acetate (28) showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Structural Elucidationmentioning

confidence: 99%

Protostane‐Type Triterpenoids from Alisma orientale

Chen

Luo

et al. 2017

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

“…Compound 4 was isolated as colorless oil, whose molecular formula was determined to be C 15 . The above spectral features suggested 4 to be a guaiane-type sesquiterpenoid, and the exact structure was determined by the following HMBC analysis (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, since no any literature discussed the absolute configuration of guaiane-type sesquiterpenoids, 1,11,13,15) the determination of the absolute stereochemistry of new compounds by calculated methods will be not very reliable. Thus, the absolute configuration of compounds 1-5 was not determined.…”

Section: Resultsmentioning

confidence: 99%

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

Fan

Xue

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

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,

show abstract

“…Cytotoxicity Assay The cytotoxicities of 1-11 were assayed against three human carcinoma cell lines including a human gastric carcinoma cell line (SGC-7901), a human lung carcinoma cell line (H1975), and a human hepatocellular carcinoma cell line (SMMC-7721) in a 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. 26) Etoposide (VP-16) was assayed as a positive control.…”

Section: Inhibition Of No Production Assaymentioning

confidence: 99%

New Iridoids from <i>Scrophularia ningpoensis</i>

Han

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Five new compounds including five iridoids (1-5) and six known compounds were isolated from the rhizomes of Scrophularia ningpoensis. Their structures were determined by extensive NMR and IR, MS spectroscopic data analyses. The anti-inflammatory, antibacterial, antifungal, and cytotoxic activities of the isolated compounds were evaluated. Compound 11 exhibited significant inhibitory effects on lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophage cells.

show abstract

Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale

Cited by 41 publications

References 23 publications

Protostane‐Type Triterpenoids from Alisma orientale

Protostane‐Type Triterpenoids from Alisma orientale

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

New Iridoids from <i>Scrophularia ningpoensis</i>

Contact Info

Product

Resources

About