Prenylated 9,10-dihydrophenanthrenes from Macaranga javanica

2015 ◽  
Vol 70 (9) ◽  
pp. 659-663 ◽  
Author(s):  
Aulia Ilmiawati ◽  
Euis H. Hakim ◽  
Yana M. Syah

AbstractPhytochemical investigation of the acetone extract of Macaranga javanica leaves afforded three new prenylated 9,10-dihydrophenanthrenes, macajavanicins A–C (1–3). Structures of these compounds were elucidated mainly by NMR and mass spectral data. Along with compounds 1–3, two known prenylated dihydrostilenes, laevifolins A and B (4, 5), were also isolated. The presence of these new 9,10-dihydrophentanthrene derivatives is the first time in the genus Macaranga, and its chemotaxonomic significances are briefly discussed. The antibacterial properties of compounds 1–5 against eight pathogenic bacteria are also described.

2020 ◽  
Vol 75 (1-2) ◽  
pp. 1-5
Author(s):  
Ni Komang T. Dharmayani ◽  
Tsuyoshi Yoshimura ◽  
Elvira Hermawati ◽  
Lia D. Juliawaty ◽  
Yana M. Syah

AbstractA new phenolic sesquiterpene, dysoxyphenol (1), and the known sesquiterpene, 7R,10S-2-hydroxycalamenene (2), were isolated from the acetone extract of Dysoxylum densiflorum seeds. The structures of these compounds were determined based on physical, Nuclear Magnetic Resonance, and mass spectral data. Both compounds were evaluated for their antibacterial and antifungal properties against seven pathogenic bacteria and two wood-rotting fungi, respectively. The results showed that both compounds have significant antibacterial properties only against Bacillus subtilis (Minimum Inhibitory Concentration 28 μM), while in the antifungal evaluation compound 1 was found to be more active than compound 2. Therefore, compound 1 has promising antifungal properties that can be developed further for finding new antifungal agents.


2016 ◽  
Vol 11 (9) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Tita Juwitaningsih ◽  
Lia D Juliawaty ◽  
Yana M. Syah

A new pyrone derivative, malakavalactone (2), was isolated from the acetone extract of Alpinia malaccensis fruits, along with a known compound kavalactone (1). The structure of the new compound was determined based on NMR and mass spectral data. Compounds 1 and 2 showed weak antibacterial activities against eight pathogenic bacteria.


2014 ◽  
Vol 69 (9-10) ◽  
pp. 375-380 ◽  
Author(s):  
Muhamad S. Fareza ◽  
Yana M. Syah ◽  
Didin Mujahidin ◽  
Lia D. Juliawaty ◽  
Iis Kurniasih

Abstract Previously we had isolated two prenylated flavanones and two prenylated dihydrochalcones, macatrichocarpins A-D (1 - 4), from the acetone extract of the leaves of Macaranga trichocarpa. Reexamination of the fractions containing minor components resulted in the isolation of four more flavonoid derivatives, including two new prenylated dihydrochalcones, oxymacatrichocarpin C (5) and isomacatrichocarpin C (6). The structures of these compounds were determined by the analysis of UV, NMR, and mass spectral data. The eight isolated flavonoids were tested on eight pathogenic bacteria and found to be mostly moderate antibacterial agents, with the lowest MIC value of 26.5 μM achieved by the flavanone macatrichocarpin A (1) against Bacillus subtilis.


2008 ◽  
Vol 12 (02) ◽  
pp. 116-122 ◽  
Author(s):  
Ergün Gonca ◽  
Ümmü Gülsüm Baklaci ◽  
Hatice Akin Dinçer

Magnesium porphyrazinates substituted with eight (p-tolyl) and (o-tolyl) units on the peripheral positions have been synthesized for the first time by cyclotetramerization of 1,2-bis(p-tolyl)maleonitrile and 1,2-bis(o-tolyl)maleonitrile in the presence of magnesium butanolate. Their demetalation by the treatment with trifluoroacetic acid resulted in partially oxidized products, namely, octakis(p-tolyl)-2-seco-porphyrazine-2,3-dione and octakis(o-tolyl)-2-seco-porphyrazine-2,3-dione. Further reactions of these products with copper(II) acetate, zinc(II) acetate and cobalt(II) acetate have led to the metallo derivatives, [octakis(p-tolyl)-2-seco-2,3-dioxoporphyrazinato] M(II) and [octakis(o-tolyl)-2-seco-2,3-dioxoporphyrazinato] M(II) ( M = Cu , Zn , Co ). These novel compounds have been characterized by elemental analysis, together with FT-IR, 1H NMR, UV-vis and mass spectral data.


1978 ◽  
Vol 56 (18) ◽  
pp. 2467-2471 ◽  
Author(s):  
Herbert L. Holland ◽  
Donald W. Hughes ◽  
David B. MacLean ◽  
Russell G. A. Rodrigo

The 13C magnetic resonance spectrum of cancentrine is reported. Assignments of chemical shifts have been made by comparison of the cancentrine spectrum with the published spectra of codeine, codeinone, and cularine and with the spectra reported here for the first time of 9,10-dihydrocancentrine methine-O-methyl ether and 10-oxocodeinone. The spectral data so obtained have been used to interpret the 13C spectrum of 10-oxocancentrine, a new alkaloid of the cancentrine family, and to verify the structure deduced for it from 1H nmr, ir, uv, and mass spectral data.


2013 ◽  
Vol 8 (11) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Indra Prakash ◽  
Venkata Sai Prakash Chaturvedula ◽  
Avetik Markosyan

From the extract of the leaves of Stevia rebaudiana Bertoni, a diterpene glycoside was isolated which was identified as 13-[(2- O-β-D-glucopyranosyl-3- O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2- O-β-D-glucopyranosyl-3- O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester (1). The complete 1H and 13C NMR assignment of 1 is reported for the first time, from extensive NMR (1H and 13C, COSY, HSQC, and HMBC) and mass spectral data. Also, we report the sensory evaluation of 1 against sucrose for the sweetness property of this molecule.


2012 ◽  
Vol 67 (1-2) ◽  
pp. 8-14 ◽  
Author(s):  
Ahmed El Bazaoui ◽  
My Ahmed Bellimam ◽  
Abdelmajid Soulaymani

Fifty three alkaloids were identified in the organs (roots, stems, leaves, flowers, and seeds) of Datura innoxia by GC/MS. Seventeen of them are reported for the first time for this species and one nor-derivative, 3-phenylacetoxynortropane (28), for the genus Datura. Furthermore, four new tropane esters were tentatively identified as 3-acetoxy-6,7-epoxytropane (acetylscopine) (10), 3-acetoxy-6-propionyloxy-7-hydroxytropane (15), 6,7-dehydro- 3-phenylacetoxy tropane (25), and 3-(2´-phenylpropionyloxy)-6,7-epoxynortropane (dihydroaponorscopolamine) (37) on the basis of their mass spectral data. Hyoscyamine (44) and scopolamine (48) figure as main alkaloids in the roots and aerial parts, respectively


2019 ◽  
Vol 31 (9) ◽  
pp. 1895-1898
Author(s):  
Relangi Siva Subrahmanyam ◽  
Venkateswara Rao Anna

We report here an easy, efficient and green synthetic protocol for the (E)-1-aryl-3-(2-morpholinoquinolin-3-yl)prop-2-en-1-ones by the Claisen-Schmidt condensation of 2-morpholinoquinoline-3-carbaldehyde and different substituted acetophenones by using 1-butyl-3-methylimidazolium tetrafluoroborate (Bmim)BF4. The compounds were characterized by using 1H NMR, 13C NMR and mass spectral data and screened there in vitro antimicrobial activity against different bacterial and fungal organisms.


Molbank ◽  
10.3390/m1187 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1187
Author(s):  
Stanimir Manolov ◽  
Iliyan Ivanov ◽  
Dimitar Bojilov

The title compound was obtained in high yield in the reaction between tryptamine and naproxen. The newly synthesized naproxen derivative was fully analyzed and characterized via 1H, 13C-NMR, UV, IR, and mass spectral data.


Molbank ◽  
10.3390/m1199 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1199
Author(s):  
Milene A. G. Fortunato ◽  
Filipa Siopa ◽  
Carlos A. M. Afonso

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.


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