New sesquiterpenoids from Aglaia odorata var. microphyllina and their cytotoxic activity

Liu, Shuai; Liu, Shou-Bai; Zuo, Wei; Guo, Zhi‐Kai; Mei, Wen‐Li; Dai, Hao‐Fu

doi:10.1016/j.fitote.2013.10.013

Cited by 29 publications

(33 citation statements)

References 21 publications

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“…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.…”

Section: Resultsmentioning

confidence: 99%

“…The coupling constants of J H-1, H-5 (11.7 Hz) and J H-5, H-6 (0 Hz) revealed that the A/B ring junction was trans-oriented. 12,13) The nuclear Overhauser effect (NOE) correlation from H-1, assumed to be β oriented, to Me-14, suggested that Me-14 was in β-configuration. The correlations from H-5 to H 2 -15 suggested that these protons were all in α-configuration.…”

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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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

Fan

Xue

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…This genus distributed in Indo-Malaysian region, especially in tropical and subtropical forest [1]. Previous phytochemical investigation in this genus reported contain interesting secondary metabolites with biological activity, including antifungal and antitumor sesquiterpenoid [5,6], cytotoxic and antiinflammatory diterpenoid [7], cytotoxic and anti-retroviral triterpenoid [3,[8][9][10][11], cytotoxic steroid [4], cytotoxic alkaloid [12,13], anti-inflammatory and cytotoxic rocaglamide [14][15][16]. During the course of our continuing search for anticancer compounds from Indonesia Aglaia plant, the methanolic extract from the stembark of Aglaia elliptica showed moderate cytotoxic activity against P-388 murine leukemia cells.…”

Section: Introductionmentioning

confidence: 99%

New Cytotoxic Pregnane-type Steroid from the Stem Bark of Aglaia elliptica (Meliaceae)

Farabi¹,

Harneti²,

Nurlelasari³

et al. 2018

Rec.Nat.Prod.

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A new pregnane-type steroid, 2α-hydroxy-3α-methoxy-5α-pregnane (1), together with three known dammarane-type triterpenoid, 3β-acetyl-20S,24S-epoxy-25-hydroxydammarane (2), 20S,24S-epoxy-3α,25-dihydroxydammarane (3), and eichlerianic acid (4) have been isolated from the stem bark of Aglaia elliptica. The structures were determined by spectroscopic methods including the 2D-NMR techniques. Compound 1-4 showed moderate cytotoxic activity against P-388 murine leukemia cells.

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“…Aglaia species are mainly distributed in the tropical rainforest of Southeast Asia and on the Pacific islands (Leong et al, 2016;Hidayat et al, 2017b). Phytochemical studies on Aglaia species have led to the identification of main compounds such as sesquiterpenoids (Joycharat et al, 2010;Liu et al, 2014;Pan et al, 2014), diterpenoids (Cai et al,, 2010;Yodsaoue et al, 2012), rocaglate derivatives (Nugroho et al, 1999;Farabi et al, 2017;Hidayat et al, 2017a), lignans (Sianturi et al, 2016), dammarane-type triterpenoids (Xie, et al, 2007;Zhang, et al, 2010;Harneti et al, 2012;Farabi et al, 2017), cycloartane-type triterpenoids and steroids (Harneti et al, 2014;Zhang et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

“…Some sesquiterpenes such as α-farnesene can be effective against the bacteria that cause tooth decay (Ishnava et al 2013). Liu et al (2014) isolated and discribed four guaian sesquiterpenes and an eudesmene sesquiterpene from the twigs of Aglaia odorata var. microphyllina.…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpenoid Compounds from The Stembark of Aglaia minahassae (Meliaceae)

Kurniasih

Milawati

Fajar

et al. 2018

Molekul

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Two sesquiterpenoid compounds, 4(15)-eudesmen-1,6-diol (1) and spathulenol (2) have been isolated from the stembark of Aglaia minahassae belong to Meliaceae family. The chemical structures of 1 and 2 were identified on the basis of spectroscopic evidence including UV, IR, NMR 1D, NMR 2D as well as mass spectra and by comparison with those previously reported spectra data. This compounds were isolated from this plant for the first time.

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New sesquiterpenoids from Aglaia odorata var. microphyllina and their cytotoxic activity

Cited by 29 publications

References 21 publications

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

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

New Cytotoxic Pregnane-type Steroid from the Stem Bark of Aglaia elliptica (Meliaceae)

Sesquiterpenoid Compounds from The Stembark of Aglaia minahassae (Meliaceae)

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