scholarly journals The Constituents of the Stems of Cissus assamica and Their Bioactivities

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2799 ◽  
Author(s):  
Yu-Yi Chan ◽  
Chiu-Yuan Wang ◽  
Tsong-Long Hwang ◽  
Shin-Hun Juang ◽  
Hsin-Yi Hung ◽  
...  
Keyword(s):  
Spectral Data ◽  
Betulinic Acid ◽  
Small Cell Lung Carcinoma ◽  
Cell Lung Carcinoma ◽  
Pheophytin A ◽  
Mass Spectral ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Hct 116 ◽  
First Time

Fifty-five compounds were isolated from the fresh stems of Cissus assamica, including 14 benzenoids, 11 triterpenes, nine steroids, five tocopherols, five chlorophylls, four flavonoids, two benzoquinones, two tannins, and three other compounds. Their structures were constructed by 1D and 2D nuclear magnetic resonance (NMR) and mass spectral data, and were also identified by a comparison of their spectral data with those reported in the literature. Among these isolates, 1,2-bis-(5--tocopheryl) ethane (51) was reported for the first time from natural sources. Some purified compounds were examined for their anti-inflammatory and anticancer bioactivities. The results indicated that betulinic acid (16) exhibited strong inhibition of superoxide anion generation with IC50 value of 0.2 ± 0.1 μM, while betulinic acid (16) and pheophytin-a (47) inhibited elastase release with IC50 value of 2.7 ± 0.3 and 5.3 ± 1.0 μM, respectively. In addition, betulinic acid (16) and epi-glut-5(6)-en-ol (18) exhibited potential cytotoxicity to non-small-cell lung carcinoma (NCI-H226) and colon cancer (HCT-116) cell lines with IC50 values in the range of 1.6 to 9.1 μM.

scholarly journals New Galloyl Derivative from Winged Sumac (Rhus copallinum) Fruit

2012 ◽  
Vol 7 (1) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Hang Ma ◽  
Tao Yuan ◽  
Antonio González-Sarrías ◽  
Liya Li ◽  
Maxwell E. Edmonds ◽  
...  
Keyword(s):  
Malic Acid ◽  
Betulinic Acid ◽  
Dimethyl Ester ◽  
Human Colon ◽  
Methyl Gallate ◽  
Mass Spectral Data ◽  
Antiproliferative Effects ◽  
Mass Spectral ◽  
Rhus Copallinum ◽  
Hct 116

Twelve compounds were isolated from Winged Sumac ( Rhus copallinum) fruit and their structures were elucidated on the basis of NMR and mass spectral data. The isolates included a new galloyl derivative, (R)-galloyl malic acid dimethyl ester (1), and eleven known compounds, gallic acid (2), methyl gallate (3), glucogallin (4), methyl m-digallate (5), methyl p-digallate (6), quercetin (7), myricetin (8), rhamnazin (9), kaempferol (10), betulinic acid (11), and oleanolic acid (12). All of the compounds were evaluated for antiproliferative effects against human colon tumorigenic (HCT-116, Caco-2) and non-tumorigenic (CCD18-Co) cell lines.

scholarly journals Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 164 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wan Liu ◽  
Runzhu Fan ◽  
Shouye Han ◽  
Yuanli Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Chemical Study ◽  
Positive Control ◽  
Hydroxyl Group ◽  
Etoac Extract ◽  
The Third ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time

A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

scholarly journals Four New ent-Kaurane Diterpene Glycosides from Isodon henryi

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2736 ◽  
Author(s):  
Liu ◽  
Zhang ◽  
Wu ◽  
Chen ◽  
Li ◽  
...  
Keyword(s):  
Cell Lines ◽  
Human Cancer ◽  
Spectroscopic Methods ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Aerial Parts ◽  
Ic50 Values ◽  
Hct 116 ◽  
Relationship Of ◽  
First Time

To obtain diterpene glycosides from an aqueous extract of the aerial parts of Isodon henryi and further investigate their cytotoxicities, in this study, a total of seven compounds were isolated, including six ent-kaurane diterpene glycosides (1–6) and one diterpene aglycon (7). Among the seven ent-kaurane diterpenes obtained, four were novel compounds, including ent-7,20-epoxy- kaur-16-en-1α,6β,7β,15β-tetrahydroxyl-11-O-β-d-glucopyranoside (1), ent-7,20-epoxy-kaur-16-en- 6β,7β,14β,15β-tetrahydroxyl-1-O-β-d-glucopyranoside (2), ent-7,20-epoxy-kaur-16-en-6β,7β,15β- trihydroxyl-1-O-β-d-glucopyranoside (3), and ent-7,20-epoxy-kaur-16-en-7β,11β,14α,15β-tetrahydr- oxyl-6-O-β-d-glucopyranoside (4), and three were isolated from this plant for the first time (5–7). Their structures were elucidated by utilizing spectroscopic methods and electronic circular dichroism analyses. Furthermore, the cytotoxicities of all seven compounds were investigated in four human cancer cell lines, including A2780, BGC-823, HCT-116, and HepG2. The IC50 values of these diterpenes ranged from 0.18 to 2.44 mM in the tested cell lines. In addition, the structure–cytotoxicity relationship of diterpene glycosides was also evaluated to study the effect of glycosylation on the cytotoxicity of diterpene compounds.

β-Dihydroagarofuran-type sesquiterpenoids from the stems of Celastrus orbiculatus with their cytotoxic activities

2021 ◽  
Vol 19 ◽  
Author(s):  
Yong Hua Lin ◽  
Bao Yan Zhang ◽  
Zhi Chao Chen ◽  
Jian Feng Wei
Keyword(s):  
Cytotoxic Activity ◽  
Human Cancer ◽  
Cytotoxic Activities ◽  
Celastrus Orbiculatus ◽  
Physico Chemical ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Hct 116 ◽  
Hct 116 Cells

Abstract: A new β-dihydroagarofuran-type sesquiterpenoid named 1α,2α,5α,11-tetraacetoxy-8α-(trans-p-coumaroyl)-β-dihydroagarofuran (1), together with five known compounds (2-6) were isolated from the CHCl3-soluble extract of the stems of Celastrus orbiculatus. The structure of new compound was elucidated with spectroscopic physico-chemical analyses. All isolates were evaluated for in vitro cytotoxic activity against four human cancer lines including HepG2, MCF-7, A549 and HCT-116 cells. Among them, compounds 1 and 6 showed potent cytotoxic activities on HepG2 cells with IC50 values of 8.78 ± 2.31 and 10.28 ± 1.15 μM, respectively. In addition, compound 6 exhibited significant cytotoxic activity on HCT-116 cells with IC50 value of 6.37 ± 2.52 μM

Seco-porphyrazines with eight (p-tolyl) and (o-tolyl) units

2008 ◽  
Vol 12 (02) ◽  
pp. 116-122 ◽  
Author(s):  
Ergün Gonca ◽  
Ümmü Gülsüm Baklaci ◽  
Hatice Akin Dinçer
Keyword(s):  
Spectral Data ◽  
Elemental Analysis ◽  
Trifluoroacetic Acid ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
H Nmr ◽  
Ft Ir ◽  
First Time ◽  
Oxidized Products

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.

scholarly journals Dammarane-Type Triterpenoids from The Stembark of Aglaia argentea (Meliaceae)

2018 ◽  
Vol 4 (1) ◽  
pp. 7-13
Author(s):  
Ace Tatang Hidayat ◽  
Kindi Farabi ◽  
Ida Nur Farida ◽  
Kansy Haikal ◽  
Nurlelasari Nurlelasari ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Spectral Data ◽  
Chemical Structure ◽  
2D Nmr ◽  
Leukemia Cells ◽  
Ic50 Values ◽  
First Time ◽  
Murine Leukemia

Two dammarane-type triterpenoids, 20S,24S-epoxy-3α,25-dihydroxydammarane (1) and 3α-acetyl-20S,24S-epoxy-3α,25-dihydroxydammarane (2), have been isolated from the stembark of Aglaia argentea. The chemical structure of compounds (1 and 2) were identified by spectroscopic evidences including UV, IR, 1D-NMR, 2D-NMR and MS as well as by comparing with previously reported spectral data. Those compounds were isolated from this plant for first time. Compounds (1 and 2) showed cytotoxic activity against P-388 murine leukemia cells with IC50 values of 23.96 and 8.14 mM, respectively.DOI:http://dx.doi.org/10.15408/jkv.v4i1.7065

Cancentrine. V. The 13C magnetic resonance spectra of cancentrine and some derivatives; the structure of 10-oxocancentrine

1978 ◽  
Vol 56 (18) ◽  
pp. 2467-2471 ◽  
Author(s):  
Herbert L. Holland ◽  
Donald W. Hughes ◽  
David B. MacLean ◽  
Russell G. A. Rodrigo
Keyword(s):  
Magnetic Resonance ◽  
Spectral Data ◽  
Methyl Ether ◽  
Resonance Spectrum ◽  
Chemical Shifts ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
H Nmr ◽  
First Time ◽  
Magnetic Resonance Spectra

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.

scholarly journals Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3714
Author(s):  
Emmanoel V. Costa ◽  
Liviane do N. Soares ◽  
Jamal da Silva Chaar ◽  
Valdenizia R. Silva ◽  
Luciano de S. Santos ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
Cancerous Cell ◽  
Ic50 Value ◽  
Ic50 Values ◽  
Low Cytotoxicity ◽  
First Time

Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nβ-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol (13). Compound 5 is described for the first time in the literature as a natural product. The cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous cell lines. Among the tested compounds, the most promising results were found for the benzylated dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 µg·mL−1) and low cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 µg·mL−1). Dichamanetin (11) showed cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 µg·mL−1 (33.70 µmol·L−1) and 18.99 µg·mL−1 (40.56 µmol·L−1), respectively while the mixture of uvarinol (12) and isouvarinol (13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 µg·mL−1, and HCT116, with an IC50 value of 17.31 µg·mL−1. These cytotoxic activities can be attributed to the presence of one or more hydroxybenzyl groups present in these molecules as well as the position in which these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been previously established, with liriodenine being the most potent compound.

Prenylated 9,10-dihydrophenanthrenes from Macaranga javanica

2015 ◽  
Vol 70 (9) ◽  
pp. 659-663 ◽  
Author(s):  
Aulia Ilmiawati ◽  
Euis H. Hakim ◽  
Yana M. Syah
Keyword(s):  
Spectral Data ◽  
Pathogenic Bacteria ◽  
Antibacterial Properties ◽  
Acetone Extract ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Phytochemical Investigation ◽  
First Time

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.

scholarly journals Isolation, Characterization and Sensory Evaluation of a Hexa β-D-Glucopyranosyl Diterpene from Stevia rebaudiana

2013 ◽  
Vol 8 (11) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Indra Prakash ◽  
Venkata Sai Prakash Chaturvedula ◽  
Avetik Markosyan
Keyword(s):  
Spectral Data ◽  
Sensory Evaluation ◽  
Nmr Assignment ◽  
Stevia Rebaudiana ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Stevia Rebaudiana Bertoni ◽  
First Time ◽  
C Nmr

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.

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