Bioactive Diterpenes from the Aerial Parts of Anisochilus harmandii (original) (raw)

New Triterpene Glycosides from the Stems of Anomospermum grandifolium

Journal of Natural Products, 2003

Two new dammarane saponins identified as jujubogenin 3-OR -L-arabinofuranosyl(1f2)-[-D-glucopyranosyl(1f6)-D-glucopyranosyl(1f3)]-R-L-arabinopyranoside (2) and jujubogenin 3-OR -L-arabinofuranosyl-(1f2)-{6-O-[3-hydroxy-3-methylglutaryl]-D-glucopyranosyl(1f3)}-R-L-arabinopyranoside (3) and a new lupane saponin, 3-hydroxylup-20(29)-en-27,28-dioic acid 28-O-D-glucopyranosyl(1f2)-[-D-xylopyranosyl(1f3)]-D-xylopyranosyl(1f2)-D-glucopyranoside ester (5), along with the known jujubogenin 3-OR -L-arabinofuranosyl(1f2)-[-D-glucopyranosyl(1f3)]-R-L-arabinopyranoside (1) and 3-hydroxylup-20(29)ene-27,28-dioic acid (4), were isolated from the methanol extract of the stems of Anomospermum grandifolium. The structures of the new compounds were established by spectral analysis. Antimicrobial activity screening of compounds 1-3 revealed antifungal properties against C. albicans ATCC 3153 for compounds 2 and 3. The antibacterial and antifungal activities of the petroleum ether, chloroform, and methanol extracts of A. grandifolium stems were also evaluated.

Bioactive Cembrane Diterpenoids of Anisomeles indica

Journal of Natural Products, 2008

Five new cembrane-type diterpenoids with a trans-fused R-methylene-γ-lactone (1-5), a new flavonoid glucoside (6), and 17 known compounds were isolated from a methanol extract of Anisomeles indica. The structures of 1-6 were elucidated by spectroscopic analysis, and the absolute configuration of compound 1 was determined using the modified Mosher's method. Compound 8 (4,5-epoxovatodiolide) exhibited cytotoxicity against a small panel of human cancer cell lines. Additionally, compounds 4 and 7 (ovatodiolide) exhibited selective antiplatelet aggregation activities toward collagen, while compounds 4, 5, and 8 showed inhibitory effects on antiplatelet aggregation induced by thrombin.

Two New Antiprotozoal Diterpenes From the Roots of Acacia nilotica

Frontiers in Chemistry, 2021

The powdered roots of the medicinal plant Acacia nilotica were extracted with hexane and ethyl acetate, and the extracts were subjected to column chromatography for the isolation of potentially bioactive compounds and their screening against kinetoplastid pathogens. NMR and HREI mass spectrometric analyses identified two new diterpenes, characterized as 16, 19-dihydroxycassa-12-en-15-one (Sandynone, 1) and (5S, 7R, 8R, 9R, 10S, 13Z, 17S)-7,8:7,17:16,17-triepoxy-7,8-seco-cassa-13-ene (niloticane B, 2). The previously reported (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-diene-7,17-diol (3), (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-dien-7-ol-17-al (4), and (5S,7R,8R,9R,10S) -(-)-7,8-seco-7, 8-oxacassa-13,15-dien-7-ol (5) a, mixture of stigmasterol (6a) and sitosterol (6b), and lupeol (7) were also isolated. Several column fractions displayed significant activity against a panel of Trypanosoma and Leishmania spp., and from the most active fraction, compound 4 was isol...

Steriod and Triterpenoid from Anogeissus latifolia

Dhaka University Journal of Pharmaceutical Sciences, 2007

3-?-hydroxy-28-acetyltaraxaren (1) and ?-sitosterol (2) were isolated from an ethyl acetate extract of the stem bark of Anogeissus latifolia. The ethyl acetate and methanol extracts when subjected to antimicrobial screening showed significant inhibitory activity to microbial growth, while the ethyl acetate showed demonstrated significant cytotoxicity to brine shrimp with LC50 of 0.50 ?g/ml. Key words: Anogeissus latifolia, Combretaceae, 3-?-hydroxy-28-acetyltaraxaren, ?-sitosterol, antimicrobial, cytotoxiciy, disc diffusion Dhaka Univ. J. Pharm. Sci. 6(1): 47-50, 2007 (June) The full text is of this article is available at the Dhaka Univ. J. Pharm. Sci. website

Antimicrobial and antiparasitic abietane diterpenoids from the roots of Clerodendrum eriophyllum

Natural Product Communications, 2010

Chromatographic separation of the roots of a Kenyan medicinal plant, Clerodendrum eriophyllum, led to the isolation of ten abietane diterpenoids (1-10), one of which (1) was isolated for the first time from a natural source. Using spectroscopic data, the structure of 1 was determined to be 12-hydroxy-8,12-abietadiene-3,11,14-trione. Circular dichroism (CD) spectra showed that the stereochemistry of compounds 1, 3, and 6-8 belongs to the normal series of abietane diterpenes, which confirmed the absolute stereochemistry of the isolated compounds. Compounds 2-10 were evaluated for their in vitro antiplasmodial, antileishmanial, antifungal and antibacterial activities. Compounds 3 and 7 exhibited potent antifungal activity (IC50/MIC 0.58/1.25 and 0.96/2.5 µg/mL, respectively) against C. neoformans, whereas 3, 6 and 7 showed strong antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with IC50/MIC values between 1.33–1.75/2.5–5 and 0.96–1.56/2.5 µg/mL, respectively. In addition, compounds 3 and 9 exhibited potent antileishmanial activity (IC50 0.08 and 0.20 µg/mL, respectively) against L. donovani, while 3 and 7 displayed weak antimalarial activity against Plasmodium falciparum, but 9 was inactive.

Dual-stage triterpenoids from an African medicinal plant targeting the malaria parasite

Bioorganic & Medicinal Chemistry, 2014

Sixteen triterpenoids (1-16), previously isolated from the aerial parts of the African medicinal plant Momordica balsamina or obtained by derivatization, were evaluated for their activity against liver stages of Plasmodium berghei, measuring the luminescence intensity in Huh-7 cells infected with a firefly luciferase-expressing P. berghei line, PbGFP-Luc con. Toxicity of compounds (1-16) was assessed on the same cell line through the fluorescence measurement of cell confluency. The highest activity was displayed by a derivative bearing two acetyl residues, karavoate B (7), which led to a dose-dependent decrease in the P. berghei infection rate, exhibiting a very significant activity at the lowest concentration employed (1 lM) and no toxicity towards the Huh-7 cells. It is noteworthy that, in previous studies, this compound was found to be a strong inhibitor of blood-stages of Plasmodium falciparum, thus displaying a dual-stage antimalarial activity.

Antimicrobial substances from Amazonian Aniba (Lauraceae) species

Natural Product Research

Extracts and six isolated substances from Aniba (Lauraceae) Amazonian species A. parviflora, A. panurensis and A. rosaeodora were analysed in vitro to their antibacterial, antiparasitic and antiplasmodial activities. NMR and MS experiments led to the identification of three styrylpyrones (5,6-dihydrokawain [I], 4-methoxy-11,12-methylenedioxy-6-trans-styryl-pyran-2-one [II] and rel-(6R,7S,8S,5'S)-4'-methoxy-8-(11,12-dimethoxyphenyl-7-[6-(4-methoxy-2pyranyl)]-6-(E)-styryl-1'-oxabicyclo[4,2,0]oct-4'-en-2'-one [III]), a pyridine alkaloid (anibine [IV]) and two kavalactones (tetrahydroyangonin [V] and dihydromethysticin [VI]). The best antibacterial result was observed at the hexane fraction of A. panurensis (MIC 7.8 μg/mL against the three bacteria). Equal MIC were observed by the extract and dichloromethane fraction of A. panurensis against S. simulans and S. aureus; and 15.62 μg/mL against MRSA. Similarly, only A. panurensis extracts showed in vitro activities against Tripanossoma cruzi and Leishmania amazonensis parasites. In Plasmodium falciparum assay, 5,6-dihydrokawain was considered an active antimalarial (14.03 μM), and substances II (132.94 μM) and III (41.84 μM) presented moderate activities.

Yaoundamines A and B, new antimalarial naphthylisoquinoline alkaloids from Ancistrocladus korupensis

Tetrahedron, 1997

Abstrucr: New monomeric naphthylisoquinoline alkaloids, yaoundamines A and 8, were isolated from Ancisrrocludus korupensis and their sttuctures were determined by extensive chemical and spectroscopic analyses. The absolute configuration at C3 was established by chemical degradation, while the axial chkality was deduced by comparison of experimental and calculated CD spectra. Yaoundamine B has an unprecedented glycosylated tiaphthylisoquinoline structure. Yaoundamines A and B are active in vitro against the malaria parasite f'hsmodiumfalciporum. Published by Elsevier Science Ltd.

A New Triterpene from Atalantia retusa Merr

Atalantia retusa Merr. is a rare Philippine endemic shrub which was reported to exhibit high antinociceptive and anti-inflammatory activities. The dichloromethane extract of the air-dried leaves of A. retusa afforded a new triterpene, retusenol (1), and friedelin (2), dischidiol (3), 5,7-dimethoxy-8-(3-methyl-2-oxybutyl)coumarin (4), humulene (5), and β -caryophyllene (6). The structures of 1 -4 were elucidated by extensive 1D and 2D NMR experiments. Friedelin, a known analgesic and antiinflammatory drug, is an active principle of the shrub.