Cyclonerane Derivatives from the Algicolous Endophytic Fungus Trichoderma asperellum A-YMD-9-2

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.

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Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Marine Drugs ◽

10.3390/md19010009 ◽

2020 ◽

Vol 19 (1) ◽

pp. 9

Author(s):

Ya-Ping Liu ◽

Sheng-Tao Fang ◽

Zhen-Zhen Shi ◽

Bin-Gui Wang ◽

Xiao-Nian Li ◽

...

Keyword(s):

Deep Sea ◽

Spectroscopic Data ◽

2D Nmr ◽

Penicillium Oxalicum ◽

Marine Phytoplankton ◽

Cold Seep ◽

Phytoplankton Species ◽

X Ray ◽

X Ray Crystallography ◽

Quinazoline Derivatives

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

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Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai

Marine Drugs ◽

10.3390/md17110605 ◽

2019 ◽

Vol 17 (11) ◽

pp. 605 ◽

Cited By ~ 3

Author(s):

Li ◽

Yang ◽

Meng ◽

Li ◽

...

Keyword(s):

Endophytic Fungus ◽

Density Functional ◽

Aspergillus Terreus ◽

Optical Rotation ◽

2D Nmr ◽

Red Alga ◽

Spectrometric Data ◽

Phenol Derivatives ◽

First Time ◽

Laurencia Okamurai

Three new prenylated phenol derivatives, terreprenphenols A–C (1–3), along with four known related compounds (4–7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, and optical rotation (OR). The corresponding relationship between absolute configuration and optical rotation for known compounds anodendroic acid (4) and asperterreusine C (5) was ambiguous in literature, and their absolute configurations were therefore discussed and confirmed for the first time by time-dependent density functional (TDDFT) ECD and OR calculations. Compounds 1–7 inhibited some common aquatic bacteria with MIC values ranging from 2 to 64 μg/mL.

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Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Antibiotics ◽

10.3390/antibiotics9110753 ◽

2020 ◽

Vol 9 (11) ◽

pp. 753

Author(s):

Elodie Gisèle M. Anoumedem ◽

Bel Youssouf G. Mountessou ◽

Simeon F. Kouam ◽

Abolfazl Narmani ◽

Frank Surup

Keyword(s):

Endophytic Fungus ◽

2D Nmr ◽

In Vitro Cytotoxicity ◽

Coupling Constants ◽

Broth Culture ◽

Spectroscopic Techniques ◽

Cytotoxic Effects ◽

Relative Configuration ◽

Planar Structures

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.

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A New Pyrrolidine Derivative and Steroids from an Algicolous Gibberella zeae Strain

Natural Product Communications ◽

10.1177/1934578x1100600908 ◽

2011 ◽

Vol 6 (9) ◽

pp. 1934578X1100600 ◽

Cited By ~ 2

Author(s):

Xiang-Hong Liu ◽

Xiao-Zhen Tang ◽

Feng-Ping Miao ◽

Nai-Yun Ji

Keyword(s):

Cell Lines ◽

Green Alga ◽

Endophytic Fungus ◽

2D Nmr ◽

Gibberella Zeae ◽

Spectroscopic Techniques ◽

Codium Fragile ◽

Relative Stereochemistry ◽

Marine Green Alga

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.

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Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173

Biomolecules ◽

10.3390/biom10081187 ◽

2020 ◽

Vol 10 (8) ◽

pp. 1187

Author(s):

Xinqian Shen ◽

Xiaozheng Wang ◽

Tingting Huang ◽

Zixin Deng ◽

Shuangjun Lin

Keyword(s):

Antibacterial Activity ◽

Biosynthetic Pathway ◽

Biological Activities ◽

Structural Diversity ◽

2D Nmr ◽

Chemical Diversity ◽

Spectroscopic Techniques ◽

Amino Group ◽

Streptomyces Sp ◽

Resolution Mass

Naphthoquinone-based meroterpenoids are hybrid polyketide-terpenoid natural products with chemical diversity and a broad range of biological activities. Here, we report the isolation of a group of naphthoquinone-containing compounds from Streptomyces sp. B9173, and their structures were elucidated by using a combination of spectroscopic techniques, including 1D, 2D NMR, and high-resolution mass (HRMS) analysis. Seven flaviogeranin congeners or intermediates, three of which were new, have been derived from common naphthoquinone backbone and subsequent oxidation, methylation, prenylation, and amino group incorporation. Both flaviogeranin B1 (1) and B (2) contain an amino group which was incorporated into the C8 of 1,3,6,8-terhydroxynaphthalene (THN). Flaviogeranin D (3) contains an intact C-geranylgeranyl residue attached to the C2 of THN, while the O-geranylgeranyl group of 2 links with the hydroxyl on the C2 site of THN. Four compounds were selected and tested for antibacterial activity and cytotoxicity, with 3 and flaviogeranin C2 (5) displaying potent activity against selected bacteria and cancer cell lines. In light of the structure features of isolated compounds and the biosynthetic genes, a biosynthetic pathway of naphthoquinone-based flaviogeranins has been proposed. These isolated compounds not only extend the structural diversity but also represent new insights into the biosynthesis of naphthoquinone-based meroterpenoids.

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Asporyergosterol, A New Steroid from an Algicolous Isolate of Aspergillus Oryzae

Natural Product Communications ◽

10.1177/1934578x1000501012 ◽

2010 ◽

Vol 5 (10) ◽

pp. 1934578X1000501 ◽

Cited By ~ 1

Author(s):

Ming-Feng Qiao ◽

Nai-Yun Ji ◽

Xiang-Hong Liu ◽

Fang Li ◽

Qin-Zhao Xue

Keyword(s):

Double Bond ◽

Aspergillus Oryzae ◽

Endophytic Fungus ◽

Red Alga ◽

Spectroscopic Techniques ◽

Isolated Structures ◽

Low Activity

Asporyergosterol (1), a new steroid with an E double bond between C-17 and C-20, was identified from the culture extracts of Aspergillus oryzae, an endophytic fungus isolated from the marine red alga Heterosiphonia japonica. Moreover, four known steroids including (22 E,24 R)-ergosta-4,6,8(14),22-tetraen-3-one (2), (22 E,24 R)-3β-hydroxyergosta-5,8,22-trien-7-one (3), (22 E,24 R)-ergosta-7,22-dien-3β,5α,6β-triol (4), and (22 E,24 R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (5) were isolated. Structures of these compounds were unambiguously established by spectroscopic techniques and by comparison with literature values. All the isolates exhibited low activity to modulate acetylcholinesterase (AChE).

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

Natural Product Communications ◽

10.1177/1934578x1501000223 ◽

2015 ◽

Vol 10 (2) ◽

pp. 1934578X1501000

Author(s):

Yanlin Meng ◽

Yuchun Yang ◽

Ying Qin ◽

Congfang Xia ◽

Min Zhou ◽

...

Keyword(s):

Endophytic Fungus ◽

A549 Cells ◽

Human Tumor ◽

2D Nmr ◽

Positive Control ◽

Spectroscopic Techniques ◽

Fermentation Products ◽

Mtt Method ◽

Pc3 Cells ◽

Control Compound

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.

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Halogenated and Nonhalogenated Metabolites from the Marine-Alga-Endophytic Fungus Trichoderma asperellum cf44-2

Marine Drugs ◽

10.3390/md16080266 ◽

2018 ◽

Vol 16 (8) ◽

pp. 266 ◽

Cited By ~ 13

Author(s):

Yin-Ping Song ◽

Feng-Ping Miao ◽

Sheng-Tao Fang ◽

Xiu-Li Yin ◽

Nai-Yun Ji

Keyword(s):

Pathogenic Bacteria ◽

Marine Alga ◽

2D Nmr ◽

Marine Phytoplankton ◽

Trichoderma Asperellum ◽

Spectrometric Data ◽

Naturally Occurring ◽

Quantum Chemical Computations ◽

Marine Brown Alga ◽

Oxazole Derivative

One new bisabolane sesquiterpene, bisabolan-1,10,11-triol (1), one new norbisabolane sesquiterpene, 12-nor-11-acetoxybisabolen-3,6,7-triol (2), two new naturally occurring monoterpenes, (7S)- and (7R)-1-hydroxy-3-p-menthen-9-oic acids (3 and 4), one new naturally occurring trichodenone, dechlorotrichodenone C (5), one new chlorine-containing trichodenone, 3-hydroxytrichodenone C (6), one new diketopiperazine, methylcordysinin A (7), and one new naturally occurring oxazole derivative, 4-oxazolepropanoic acid (8), were isolated from the culture of a marine brown alga-endophytic strain (cf44-2) of Trichoderma asperellum. Their structures and relative configurations were determined by extensive 1D/2D NMR and mass spectrometric data, and the absolute configurations of 3–6 were assigned by analysis of the ECD spectra aided by quantum chemical computations. Compounds 1, 2, 5, and 6 showed growth inhibition of some marine phytoplankton species and pathogenic bacteria.

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