Diterpenoid Hydroperoxides from the Far-Eastern Brown Alga Dictyota dichotoma

2009 ◽  
Vol 62 (9) ◽  
pp. 1185 ◽  
Author(s):  
Sophia A. Kolesnikova ◽  
Ekaterina G. Lyakhova ◽  
Anatoly I. Kalinovsky ◽  
Pavel S. Dmitrenok ◽  
Sergei A. Dyshlovoy ◽  
...  

Two new compounds, dictyohydroperoxide 1 and hydroperoxyacetoxycrenulide 2, (Scheme 1) containing hydroperoxyl groups rarely found in algal terpenoids were isolated from the Russian population of brown alga Dictyota dichotoma. The known compounds acetoxycrenulide 4 and squalene were also found in this algal species for the first time. Some of the isolated compounds showed moderate cytoxicity against human cancer cell lines.

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2736 ◽  
Author(s):  
Liu ◽  
Zhang ◽  
Wu ◽  
Chen ◽  
Li ◽  
...  

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.


2016 ◽  
Vol 7 (5) ◽  
pp. 2204-2212 ◽  
Author(s):  
V. C. Graça ◽  
Lillian Barros ◽  
Ricardo C. Calhelha ◽  
Maria Inês Dias ◽  
Ana Maria Carvalho ◽  
...  

The phytochemical characterization, antioxidant activity and in vitro cytotoxicity against human cancer cell lines of Geranium molle L. extracts are reported for the first time.


2017 ◽  
Vol 12 (7) ◽  
pp. 1934578X1701200
Author(s):  
Marina V. Veselova ◽  
Sergey A. Fedoreyev ◽  
Darya V. Tarbeeva ◽  
Nadezda I. Kulesh ◽  
Anatoliy I. Kalinovskiy ◽  
...  

Two new prenylated flavanones, isomaackiaflavanone A (1), isomaackiaflavanone B (2) and a new prenylated stilbene maackiastilbene (3), along with five known flavanones were isolated from the root bark of Maackia amurensis using repeated column chromatography on silica gel, Sephadex LH-20 and octadecyl silica (ODS-A) sorbents. The structures of the new compounds were elucidated by HPLC–PDA–MS, HR-ESI-MS, 1H, 13C, 1H–1H COSY, HSQC, ROESY and HMBC NMR analyses. The cytotoxicity of compounds 1–2, 4–8 against two human cancer cell lines HeLa and SK-MEL-5 was tested using the MTS method. Compounds 4, 6 and 8 showed the strongest cytotoxic activity among the compounds tested with IC50 values of 6.5, 8.8 and 7.7 μM, against SK-MEL-5 cells and 8.2, 18.8 and 12 μM against HeLa cells, respectively.


2009 ◽  
Vol 64 (3-4) ◽  
pp. 193-196 ◽  
Author(s):  
Peng Zhang ◽  
Dong Liang ◽  
Wenrong Jin ◽  
Haibin Qu ◽  
Yiyu Cheng ◽  
...  

A new thiophene, echinothiophenegenol (1), together with seven known thiophenes was isolated from the crude ethanol extract of roots of Echinops grijisii Hance. The structure of 1 was elucidated on the basis of spectroscopic data. Compounds 2 and 5, isolated from the plant for the first time, and compounds 1 - 7 were tested for their cytotoxicity against two human cancer cell lines, HL60 and K562. The thiophenes showed better activity than the bithiophenes


2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701
Author(s):  
Liping Liu ◽  
Junqi Zhang ◽  
Xiaoyang Wang ◽  
Hongbing Wang

Two new glycoglycerolipids (1 and 2), along with three known compounds (3-5) were isolated from Stellera chamaejasme. The structure of the new compounds was elucidated by chemical and spectroscopic data analysis. The cytotoxic activity of 1-3 was evaluated and showed no activity against the assayed human cancer cell lines.


2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800
Author(s):  
Zushang Su ◽  
Ping Wang ◽  
Wei Yuan ◽  
Shiyou Li

A new glycoxyuracil and 15 known compounds were isolated from the fruit body of Chlorophyllum molybdites. The structures were determined from their NMR and MS data and by comparison with literature data. Compounds 2–5, 10–11, 13, and 15–16 were isolated from the genus Chlorophyllum for the first time. Compounds (1–9) did not show cytotoxicity against two human cancer cell lines, A549 and Panc-28 (GI50 > 50 μM).


Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 840 ◽  
Author(s):  
Yeon-Ju Lee ◽  
Su Kim ◽  
Hansol Choi ◽  
Hyi-Seung Lee ◽  
Jong Lee ◽  
...  

Three furan-containing scalarane sesterterpenoids (1–3) and a novel pyrrole-containing analog (4) were isolated from the sponge Scalarispongia species. Compound 3, reported in the literature as a synthetic derivative of furoscalarol 2, was for the first time isolated from a natural source. During the separation performed using a silica column in the presence of methanol, 16-methoxy derivatives (5, 6) were obtained from the unintended reaction of 2. The isolated natural products 3 and 4 and the artifact 5 showed moderate to high cytotoxicity against six human cancer cell lines, whereas compound 6, the C-16 epimer of 5, showed no cytotoxicity at a concentration of 60 μΜ.


2020 ◽  
Vol 18 (48) ◽  
pp. 9883-9894
Author(s):  
Yantao Ma ◽  
Xuan Pan ◽  
Baohe Guan ◽  
Guangyan Zhang ◽  
Zhanzhu Liu

(−)-Homo-renieramycin G and its twenty analogs were designed and synthesized for the first time. The cytotoxicity was evaluated against four human cancer cell lines and the SAR was discussed.


2013 ◽  
Vol 8 (10) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Tian-Shan Wang ◽  
You-Ping Luo ◽  
Jing Wang ◽  
Meng-Xiong He ◽  
Ming-Guo Zhong ◽  
...  

Two new compounds, (+)-rumphiin (3) and polyalthurea (7), together with seven known ones, 3,4,5-trimethoxy benzoic acid (1), (-)-seselinone (2), cannabisin D (4), allantoin (5), oxostephanine (6) and a mixture of β-sitosterol (8) and stigmasterol (9) were isolated from the stems of Polyalthia rumphii. The chemical structures of 3 and 7 were elucidated by the combination of spectroscopic data, and the absolute configuration of 3 at C-2 was determined by the matrix method to be R. All compounds were evaluated for their cytotoxicity on four human cancer cell lines, which demonstrated that 3 was a moderate bioactive lignan, and 6 showed significant anticancer activity against SPC-A-1 and BEL-7402 cell lines with IC50 values of 1.47 and 1.73 μg/mL, respectively.


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