Novel sesquiterpene and copyrine alkaloids from Anaxagorea javanica Blume

Husain, Khairana; Zakaria, Siti Mariam; Lajis, Nordin H.; Shaari, Khozirah; Ismail, Intan Safinar; Israf, Daud Ahmad; Paetz, Christian

doi:10.1016/j.phytol.2012.09.003

Cited by 10 publications

(17 citation statements)

References 14 publications

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“…The comparison of these 1D NMR spectral data with those of nordine isolated from A. javanica suggested that compound 1 was a macrocyclic humulene-type sesquiterpenoid as shown in Chart . In the HMBC spectrum, the correlations observed from H-10 to C-14, C-15, C-1, C-8, and C-9 and from H 2 -1 to C-2 and C-3 localized a Δ 2(3) olefinic double bond (Figure ).…”

Section: Resultsmentioning

confidence: 96%

“…The genus Anaxagorea (Annonaceae) comprises 30 species distributed in the neotropics and tropical Asia . Previous phytochemical studies with plants of this genus revealed the presence of xanthones, flavonoids, − neolignans, terpenoids, and alkaloids, − with some of them exhibiting remarkable biological activities. The analysis of the essential oil from the leaves of Anaxagorea brevipes has revealed the presence of mono- and sesquiterpenes such as α-, β-, and γ-eudesmol, guaiol, and caryophyllene oxide.…”

Section: Introductionmentioning

confidence: 99%

“…An interesting sesquiterpene called nordine besides copyrine alkaloids has been isolated from A. javanica, and some of these compounds have been assayed for nitric oxide (NO) inhibition A.…”

Section: Introductionmentioning

confidence: 99%

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Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

et al. 2020

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Six sesquiterpenoids with unprecedented macrocyclic humulene-type structures, namely, dolichocarpols A-E (1− 5) with ether-bridged bicyclic rings between C-10 and C-2, C-10 and C-7, C-10 and C-6 (×2), and C-6 and C-3 and dolichocarpol F (6) cyclized between C-7 and C-2 and with an ether bridge between C-10 and C-3, were isolated from Anaxagorea dolichocarpa roots. The structures of the compounds were elucidated by NMR, MS, and IR data. Absolute configurations of compounds 1−3 and 6 were established on the basis of data from electronic circular dichroism, whereas relative configurations of compounds 4 and 5 were suggested by the NOESY spectrum. In addition, a putative biosynthetic pathway of the compounds is proposed. Furthermore, the cytotoxicity of 3, 4, and 6 against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) was evaluated.

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

et al. 2020

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“…Other seven isolated compounds were identified as quercetin ( 3 ) [26], kaempferol ( 4 ) [27, 28], β-sitosterol-3- O -glucoside ( 5 ) [29], oleic acid ( 6 ) [30], glucomoringin ( 7 ) [31], 2,3,4-trihydroxybenzaldehyde ( 8 ) [32] and stigmasterol ( 9 ) [33, 34] based on the MS and NMR comparison with the respective literatures (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

In vitro anti-allergic activity of Moringa oleifera Lam. extracts and their isolated compounds

Rani

Kumolosasi

Jasamai

et al. 2019

BMC Complement Altern Med

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BackgroundMoringa oleifera Lam. is a commonly used plant in herbal medicine and has various reported bioactivities such as antioxidant, antimicrobial, anticancer and antidiabetes. It is rich in nutrients and polyphenols. The plant also has been traditionally used for alleviating allergic conditions. This study was aimed to examine the anti-allergic activity of M. oleifera extracts and its isolated compounds.MethodM. oleifera leaves, seeds and pods were extracted with 80% of ethanol. Individual compounds were isolated using a column chromatographic technique and elucidated based on the nuclear magnetic resonance (NMR) and electrospray ionisation mass spectrometry (ESIMS) spectral data. The anti-allergic activity of the extracts, isolated compounds and ketotifen fumarate as a positive control was evaluated using rat basophilic leukaemia (RBL-2H3) cells for early and late phases of allergic reactions. The early phase was determined based on the inhibition of beta-hexosaminidase and histamine release; while the late phase was based on the inhibition of interleukin (IL-4) and tumour necrosis factor (TNF-α) release.ResultsTwo new compounds; ethyl-(E)–undec-6-enoate (1) and 3,5,6-trihydroxy-2-(2,3,4,5,6-pentahydroxyphenyl)-4H-chromen-4-one (2) together with six known compounds; quercetin (3), kaempferol (4), β-sitosterol-3-O-glucoside (5), oleic acid (6), glucomoringin (7), 2,3,4-trihydroxybenzaldehyde (8) and stigmasterol (9) were isolated from M. oleifera extracts. All extracts and the isolated compounds inhibited mast cell degranulation by inhibiting beta-hexosaminidase and histamine release, as well as the release of IL-4 and TNF-α at varying levels compared with ketotifen fumarate.ConclusionThe study suggested that M. oleifera and its isolated compounds potentially have an anti-allergic activity by inhibiting both early and late phases of allergic reactions.

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“…[8][9][10] Das espécies do gênero investigadas até o presente momento, foram identificados principalmente alcaloides, terpenoides, xantonas, flavonoides e lignoides. [11][12][13][14][15][16] Ao passo que em Anaxagorea dolichocarpa Sprague & Sandwith, estudos fitoquímicos prévios permitiram o isolamento de alcaloides azafenantrenos e aporfínicos. 11,17 Diversos compostos dessas duas subclasses de alcaloides já foram testados em ensaios de atividade citotóxica e antitumoral, alguns deles apresentando resultados positivos, sendo por isso considerados promissores.…”

Section: Introductionunclassified

DOIS NOVOS ALCALOIDES AZAFENANTRENO DE Anaxagorea dolichocarpa Sprague & Sandwith

et al. 2020

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TWO NEW AZAPHENANTHRENE ALKALOIDS FROM Anaxagorea dolichocarpa Sprague & Sandwith. A chemical investigation of Anaxagorea dolichocarpa Sprague & Sandwith, a member of Annonaceae family, was carried out. The ethanolic extract from the roots of this plant led, by chromatography tecniches, to isolation of the new azaphenanthrene alkaloids dolichocarpine (1) and 9-methoxyeupolauramine (2), besides the known alkaloids eupolauramine (3), 3-methoxyeupolauridine (4), eupolauramine (5) and 4-methylsampangine (6). The structures of isolated compounds were established by 1D and 2D NMR, HRESIMS, tandem MS n and IR data. The cytotoxicity of compounds 1-5 was evaluated against HCT-116 (human colorectal carcinoma) and L929 (murine fibroblast) cell lines.

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Novel sesquiterpene and copyrine alkaloids from Anaxagorea javanica Blume

Cited by 10 publications

References 14 publications

Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

Dolichocarpols A-F, Unprecedented Macrocyclic Humulene-Type Sesquiterpenoids from Anaxagorea dolichocarpa

In vitro anti-allergic activity of Moringa oleifera Lam. extracts and their isolated compounds

DOIS NOVOS ALCALOIDES AZAFENANTRENO DE Anaxagorea dolichocarpa Sprague & Sandwith

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