scholarly journals Xanthone Derivatives from the Fermentation Products of an Endophytic Fungus Phomopsis sp

2015 ◽  
Vol 10 (2) ◽  
pp. 1934578X1501000
Author(s):  
Yanlin Meng ◽  
Yuchun Yang ◽  
Ying Qin ◽  
Congfang Xia ◽  
Min Zhou ◽  
...  

Three new xanthones, 1-hydroxy-3-hydroxyethyl-5-methoxy-6-methoxycarbonylxanthone (1), 1,4-dihydroxy-3-hydroxyethyl-5-methoxy-6-methoxycarbonyl-xanthone (2), and 1-hydroxy-3-hydroxyethyl-4-methoxy-8-methoxycarbonylxanthone (3), together with five known xanthones (4–8) were isolated from the fermentation products of an endophytic fungus Phomopsis sp.. Their structures were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR spectroscopic techniques. Compounds 1–3 and 7 were also tested for their cytotoxicity against five human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7) by the MTT method, with paclitaxel used as the positive control. Compound 1 showed cytotoxicity against A549 and PC3 cells with IC50 values of 3.2 and 2.5 μM, respectively, 2 showed potential, with an IC50 value of 3.6 μM, and 3 showed cytotoxicity against A549 cells with an IC50 value of 3.5 μM.

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 252 ◽  
Author(s):  
Yin-Ping Song ◽  
Feng-Ping Miao ◽  
Xiang-Hong Liu ◽  
Xiu-Li Yin ◽  
Nai-Yun Ji

Seven previously unreported cyclonerane derivatives, namely, 3,7,11-trihydroxycycloneran-10-one, cycloneran-3,7,10,11-tetraol, cycloneran-3,7,11-triol, 11,12,15-trinorcycloneran-3,7,10-triol, 7,10S-epoxycycloneran-3,15-diol, 7,10R-epoxycycloneran-3,15-diol, and (10Z)-15-acetoxy-10-cycloneren-3,7-diol, were isolated in addition to the known (10Z)-cyclonerotriol, (10E)-cyclonerotriol, catenioblin C, and chokol E from the culture of Trichoderma asperellum A-YMD-9-2, an endophytic fungus obtained from the marine red alga Gracilaria verrucosa. The structures of previously unreported compounds were established by spectroscopic techniques, including 1D/2D NMR, MS, and IR. The isolation of these new cyclonerane derivatives greatly adds to the structural diversity of unusual cyclonerane sesquiterpenes, and several isolates exhibit potent inhibition against some marine phytoplankton species.


2006 ◽  
Vol 1 (7) ◽  
pp. 1934578X0600100 ◽  
Author(s):  
Kuiwu Wang ◽  
Yuanjiang Pan

A new (1) and a known (2) β-dihydroagarofuran sesquiterpene polyol esters were isolated from Celastrus rosthornianus and their structures were established by 1D- and 2D-NMR spectroscopic techniques. The two compounds exhibited anti-tumor activities against a panel of human tumor cell lines.


2010 ◽  
Vol 5 (10) ◽  
pp. 1934578X1000501
Author(s):  
Ning Li ◽  
Wan Xiao ◽  
Bailing Hou ◽  
Xian Li

Two new cycloartane glycosides were isolated from the whole herbs of Camptosorus sibiricus Rupr. By means of chemical and spectroscopic methods (1D and 2D NMR, HRMS, ESIMS), the structures were established as (24 R)-3β,7β,24,25,30-pentahydroxycycloartane-30- O-coumaroyl-3- O-β-D-glucopyranosyl-24- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1) and (24 R)-3β,7β,24,25,30-pentahydroxy-1-ene-cycloartane 24- O-β-D-glucopyranoside (2). The two new compounds were inactive in vitro against A375-S2 and Hela human tumor cell lines using the MTT method.


2008 ◽  
Vol 3 (6) ◽  
pp. 1934578X0800300
Author(s):  
Peng Zhang ◽  
Yiyu Cheng ◽  
Zhongjun Ma

Two new cycloartane glycosides were isolated from the whole herbs of Camptosorus sibiricus Rupr.. By means of chemical and spectroscopic methods (IR, 1D- and 2D- NMR, HRMS, ESI-MS), the structures were established as (24 R)-3β,7β,24,25,30-pentahydroxycycloartane 3- O-β-D-glucopyranosyl-24- O-β-D-glucopyranosyl-30- O-β-D-glucopyranoside (1), and (24 R)-3β,7β,24,25,30-pentahydroxycycloartane 3- O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-24- O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranoside (2). The two new compounds were tested for their cytotoxicity in vitro against human tumor cell lines (A375-S2, Hela) using the MTT method, but both compounds were inactive.


Antibiotics ◽  
2020 ◽  
Vol 9 (11) ◽  
pp. 753
Author(s):  
Elodie Gisèle M. Anoumedem ◽  
Bel Youssouf G. Mountessou ◽  
Simeon F. Kouam ◽  
Abolfazl Narmani ◽  
Frank Surup

Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.


2011 ◽  
Vol 6 (9) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Xiang-Hong Liu ◽  
Xiao-Zhen Tang ◽  
Feng-Ping Miao ◽  
Nai-Yun Ji

A new pyrrolidine derivative, 3-hydroxy-5-(hydroxymethyl)-4-(4′-hydroxyphenoxy)pyrrolidin-2-one (1), and eight known steroids, (22 E,24 R)-7β,8β-epoxy-3β,5α,9α-trihydroxyergosta-22-en-6-one (2, a reassigned structure of (22 E,24 R)-5α,6α-epoxy-3β,8β,14α-trihydroxyergosta-22-en-7-one), (22 E,24 R)-3β,5α,9α-trihydroxyergosta-7,22-dien-6-one (3), (22 E,24 R)-3β,5α-dihydroxyergosta-7,22-dien-6-one (4), (22 E,24 R)-ergosta-7,22-dien-3β,5α,6β-triol (5), (22 E,24 R)-ergosta-5,22-dien-3β-ol (6), (22 E,24 R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (7), (22 E,24 R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol (8), and (22 E,24 R)-1(10→6)- abeo-ergosta-5,7,9,22-tetraen-3α-ol (9), were isolated from the cultures of Gibberella zeae, an endophytic fungus isolated from the marine green alga Codium fragile. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. Compound 1 showed cytotoxicity against A-549 and BEL-7402 cell lines.


2021 ◽  
Vol 16 (10) ◽  
pp. 1934578X2110477
Author(s):  
Le Thi Huyen ◽  
Nguyen Thi Thu Hau ◽  
Hoang Son Vu ◽  
Nguyen Thi Lan Huyen ◽  
Bui Huu Tai ◽  
...  

A new β-carboline alkaloid, 10-hydroxy-capitelline (1) together with three known anthraquinones, hedanthroside B (2), hedanthroside C (3), and rubiadin (4) were isolated from the aerial part methanol extract of Hedyotis capitellata. Their structures were established by spectroscopic data (one-dimensional, two-dimensional nuclear magnetic resonance (1D, 2D-NMR) and high-resolution-electrospray ionization-mass spectrometry, HR-ESI-MS) and comparison with those reported in the literature. The anti-inflammatory activity of the isolated compounds is evaluated by their inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. At a concentration of 20 µM, compounds 1 to 4 showed weak inhibitory effects on NO production with inhibitory values ranging from 1.2% to 23.9% compared to a value of 74.5% for the positive control compound, NG-monomethyl-L-arginine (L-NMMA).


Marine Drugs ◽  
2021 ◽  
Vol 19 (10) ◽  
pp. 580
Author(s):  
Zhi-Hui He ◽  
Jia Wu ◽  
Lin Xu ◽  
Man-Yi Hu ◽  
Ming-Ming Xie ◽  
...  

A systematic chemical investigation of the deep-sea-derived fungus Penicillium solitum MCCC 3A00215 resulted in the isolation of one novel polyketide (1), two new alkaloids (2 and 3), and 22 known (4–25) compounds. The structures of the new compounds were established mainly on the basis of exhaustive analysis of 1D and 2D NMR data. Viridicatol (13) displayed moderate anti-tumor activities against PANC-1, Hela, and A549 cells with IC50 values of around 20 μM. Moreover, 13 displayed potent in vitro anti-food allergic activity with an IC50 value of 13 μM, compared to that of 92 μM for the positive control, loratadine, while indole-3-acetic acid methyl ester (9) and penicopeptide A (10) showed moderate effects (IC50 = 50 and 58 μM, respectively).


2021 ◽  
Vol 53 (2) ◽  
pp. 231-242
Author(s):  
Dayar Arbain ◽  
Amri Bakhtiar ◽  
Nova Syafni ◽  
Nofrizal - ◽  
Goldha Faroliu ◽  
...  

Balanophora elongata (Balanophoraceae) is a tropical parasitic flowering plant 9 cm in height. Four known phenyl acrylic acid derivatives, methyl caffeate (1), caffeic acid (2), 1,6-di-O-caffeoyl-β-D-glucopyranose (3), and coniferin (4), were isolated from this plant. Structural elucidation of the isolated compounds was determined by IR, LC-ESI-MS, 1D and 2D NMR.  Extracts and isolated compounds were tested toward some standard human pathogenic bacteria using the agar disk diffusion method. Their inhibition zones were compared to that of chloramphenicol as positive control. Compound 1 showed inhibition toward Streptococcus mutans, while compound 3 and 4 inhibited Staphylococcus aureus.


2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110403
Author(s):  
Jing Qin ◽  
Da-Wei Kang ◽  
Xue-mei Zhang ◽  
Li-ling Mo ◽  
Ying-dong Zhang ◽  
...  

1-Hydroxymethyl goshuyuamide II (1), a new derivative of evodiamine with a quinazolinocarboline skeleton, along with nine known evodiamine derivatives were isolated from the dried and nearly ripe fruits of Tetradium ruticarpum (A. Jussieu) T. G. Hartley using several different chromatographic separations. Their structures were elucidated on the basis of extensive spectroscopic techniques, including 1D and 2D NMR spectra. Putative biosynthetic pathways toward 1 are proposed. Compounds 1 and 2 and 4 to 10 exhibited cytotoxic activity against six human tumor lines, and compounds 4 and 7 to 10 exhibited moderate inhibitory activity against nitric oxide production in LPS-activated RAW264.7 cells.


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