Co-reporter:Shu-Shan Gao, Xiao-Ming Li, Katherine Williams, Peter Proksch, Nai-Yun Ji, and Bin-Gui Wang
Journal of Natural Products 2016 Volume 79(Issue 8) pp:2066-2074
Publication Date(Web):July 27, 2016
DOI:10.1021/acs.jnatprod.6b00403
Genome mining of the fungus Mucor irregularis (formerly known as Rhizomucor variabilis) revealed the presence of various gene clusters for secondary metabolite biosynthesis, including several terpene-based clusters. Investigation into the chemical diversity of M. irregularis QEN-189, an endophytic fungus isolated from the fresh inner tissue of the marine mangrove plant Rhizophora stylosa, resulted in the discovery of 20 structurally diverse indole-diterpenes including six new compounds, namely, rhizovarins A–F (1–6). Among them, compounds 1–3 represent the most complex members of the reported indole-diterpenes. The presence of an unusual acetal linked to a hemiketal (1) or a ketal (2 and 3) in an unprecedented 4,6,6,8,5,6,6,6,6-fused indole-diterpene ring system makes them chemically unique. Their structures and absolute configurations were elucidated by spectroscopic analysis, modified Mosher’s method, and chemical calculations. Each of the isolated compounds was evaluated for antitumor activity against HL-60 and A-549 cell lines.
Co-reporter:Xiao-Rui Liang, Feng-Ping Miao, Yin-Ping Song, Xiang-Hong Liu, Nai-Yun Ji
Bioorganic & Medicinal Chemistry Letters 2016 Volume 26(Issue 20) pp:5029-5031
Publication Date(Web):15 October 2016
DOI:10.1016/j.bmcl.2016.08.093
•Citrinovirin was isolated and identified from algicolous Trichoderma citrinoviride.•Citrinovirin represents a new norditerpene with an unprecedented carbon skeleton.•Citrinovirin is active to Staphylococcus aureus.Citrinovirin (1), a novel norditerpene with an unprecedented carbon skeleton along with three known compounds, cyclonerodiol (2), 3-(2-hydroxypropyl)-4-(hexa-2E,4E-dien-6-yl)furan-2(5H)-one (3), and 5-hydroxy-3-hydroxymethyl-2-methyl-7-methoxychromone (4), was isolated from the culture of a marine brown alga-endophytic strain (cf-27) of Trichoderma citrinoviride. The structure and relative configuration of 1 were identified by spectroscopic methods, including 1D/2D NMR and MS. Its absolute configuration was established by analysis of ECD spectrum, aided by quantum chemical calculations. A plausible biogenetic pathway is proposed for 1, and it was evaluated to be active against Staphylococcus aureus.
Co-reporter:Nai-Yun Ji;Yin-Ping Song;Feng-Ping Miao;Xiao-Rui Liang
Magnetic Resonance in Chemistry 2016 Volume 54( Issue 1) pp:88-90
Publication Date(Web):
DOI:10.1002/mrc.4319
Keywords:
- NMR;
- 1H NMR;
- 13C NMR;
- two-dimensional NMR;
- Dictyopteris divaricata;
- cadinane;
- sesquiterpene;
- norsesquiterpene
Co-reporter:Nai-Yun Ji, Xiao-Ming Li, Lan-Ping Ding, Bin-Gui Wang
Biochemical Systematics and Ecology 2016 Volume 64() pp:1-5
Publication Date(Web):February 2016
DOI:10.1016/j.bse.2015.11.010
•Four new and five known halogenated terpenes have been obtained from Laurencia pinnata.•The isolates support the taxonomic position of this alga under the genus Laurencia.•Eudesmane derivatives may be taken as the chemotaxonomic markers for L. pinnata.Chemical investigation of the marine red alga Laurencia pinnata collected from Nanji Island of China resulted in the isolation and identification of three new eudesmane (selinane) sesquiterpenes, 1β-bromoselin-11-en-4α-ol (1), 1β-bromo-4α,5α-epoxyselinane (2), and 1β-bromoselin-3,11-diene (3), and one new 6,8-cycloeudesmane sesquiterpene, 1β-bromo-6,8-cycloselin-4(15)-ene (4), together with one known eudesmane sesquiterpene, 1β-bromoselin-4(15),11-diene (5), two known chamigrane sesquiterpenes, 2,10-dibromo-3-chlorochamigr-7-ene (6) and 2,10-dibromo-3-chlorochamigr-7-en-9-ol (7), one kahukuane diterpene, kahukuene B (8), and one parguerane diterpene, 15-bromoparguer-9(11)-en-16-ol (9). These halogenated isolates were found in L. pinnata for the first time, and they support the taxonomic position of this species under the genus Laurencia. Eudesmane derivatives (1–5) are predominant and rarely reported from this genus, and they may be taken as chemotaxonomic markers for L. pinnata in the future.
Co-reporter:Nai-Yun Ji;Bin-Gui Wang
Fungal Diversity 2016 Volume 80( Issue 1) pp:301-342
Publication Date(Web):2016 September
DOI:10.1007/s13225-016-0358-9
Marine algicolous fungi refer to the fungi inhabiting or associated with marine algae, which have attracted a great attention for natural product researchers due to their chemical diversity and biological activity during the past two decades. Up to the end of 2014, a total of 366 new natural products, including polyketides, terpenoids, polyketide-terpenoids, peptides, alkaloids, and shikimate derivatives, have been characterized from them. Among these metabolites, 240 compounds feature cytotoxic, antibacterial, antifungal, antimicroalgal, zooplankton-toxic, antiprotozoal, antioxidative, enzyme-modulatory, and/or some other activities. This review gives a comprehensive coverage of both chemical and biological aspects of the secondary metabolites from marine algicolous fungi.
Co-reporter:Feng-Ping Miao ; Xiao-Rui Liang ; Xiang-Hong Liu
Journal of Natural Products 2014 Volume 77(Issue 2) pp:429-432
Publication Date(Web):February 5, 2014
DOI:10.1021/np401047w
Through addition of suberoylanilide hydroxamic acid, two new aromatic norditerpenes, aspewentins A (1) and B (2), along with an oxygenated derivative, aspewentin C (3), were obtained from the culture of an Aspergillus wentii strain (na-3) isolated from the tissue of the brown alga Sargassum fusiforme. The structures and absolute configurations were unambiguously elucidated by spectroscopic analyses and quantum chemical calculations. Aspewentins A–C were produced before sporulation and exhibited potent bioactivities against some marine-derived organisms.
Co-reporter:Nai-Yun Ji, Xiao-Rui Liang, Ran-Ran Sun and Feng-Ping Miao
RSC Advances 2014 vol. 4(Issue 15) pp:7710-7715
Publication Date(Web):10 Jan 2014
DOI:10.1039/C3RA47055E
Bianthrones have occurred widely in drug and material developments, but the stereochemistry remains in chaos so far due to the meso, racemic, and axis-rotating phenomena. Based on the computational and experimental results, an effective rule to distinguish between cis and trans bianthrones by 1H NMR is concluded, which applies to both homo- and heterobianthrones.
Co-reporter:Xiao-Dong Li;Feng-Ping Miao;Xiao-Rui Liang
Magnetic Resonance in Chemistry 2014 Volume 52( Issue 5) pp:247-250
Publication Date(Web):
DOI:10.1002/mrc.4049
One new meroterpene, arisugacin K (1), and four known ones, arisugacin J (2), arisugacin G (3), arisugacin C (4), and territrem C (5), were isolated from the culture of Penicillium echinulatum pt-4, an endophytic fungus isolated from the marine red alga Chondrus ocellatus. The structure and the absolute configuration of 1 were unambiguously elucidated by spectroscopic analyses and quantum chemical calculations, which further resulted in the assignments of absolute configurations for the other arisugacins and territrems. Compound 1 showed inhibitory activity against Escherichia coli with an inhibition diameter 8 mm at 30 µg/disk and 4 exhibited lethality against Artemia salina with an LC50 of 48.6 µg/ml. Copyright © 2014 John Wiley & Sons, Ltd.
Co-reporter:Nai-Yun Ji;Bin-Gui Wang
Phytochemistry Reviews 2014 Volume 13( Issue 3) pp:653-670
Publication Date(Web):2014 September
DOI:10.1007/s11101-013-9326-0
The marine red algae of the genus Laurencia have produced more 700 secondary metabolites and exhibited high molecular diversity and intriguing bioactivity. Since the halogenated structures have been comprehensively reviewed previously, this review, covering up to the end of 2012, mainly focuses on the source, structure elucidation, and bioactivity of nonhalogenated organic molecules from Laurencia spp. as well as the relationship between nonhalogenated and halogenated products. Overall, 173 new or new naturally occurring compounds with 58 skeletons, mainly including sesquiterpenes, diterpenes, triterpenes, and C15-acetogenins, are described.
Co-reporter:Nai-Yun Ji, Xiang-Hong Liu, Feng-Ping Miao, and Ming-Feng Qiao
Organic Letters 2013 Volume 15(Issue 10) pp:2327-2329
Publication Date(Web):May 7, 2013
DOI:10.1021/ol4009624
A novel carbamate- and cyano-containing alkaloid, aspeverin (1), was isolated from the culture of an algicolous Aspergillus versicolor strain (dl-29). The structure and absolute configuration were unambiguously identified by NMR, IR, ECD, and mass spectrometric methods as well as quantum chemical calculations. 1 exhibited potent bioactivities against some marine-derived organisms.
Co-reporter:Xiao-Dong Li, Feng-Ping Miao, Xiao-Rui Liang, Bin-Gui Wang and Nai-Yun Ji
RSC Advances 2013 vol. 3(Issue 6) pp:1953-1956
Publication Date(Web):04 Dec 2012
DOI:10.1039/C2RA23101H
Two new chamigrane sesquiterpenes, yicterpenes A (1) and B (2) each with an unprecedented halogenation at C-9 and a hemiketal unit at C-10, were isolated from the marine red alga Laurencia composita. The structures and absolute configurations of them were identified by NMR, ECD, and mass spectrometric methods as well as quantum chemical calculations. Compound 1 with a chlorination at C-9 was more active against some tested marine-derived organisms than 2 with a bromination at C-9.
Co-reporter:Xiang-Hong Liu, Feng-Ping Miao, Ming-Feng Qiao, Robert H. Cichewicz and Nai-Yun Ji
RSC Advances 2013 vol. 3(Issue 2) pp:588-595
Publication Date(Web):09 Nov 2012
DOI:10.1039/C2RA22701K
One new meroterpene, 1,2-dihydroterretonin F (2), five new sesterterpenes, (6α)-21-deoxyophiobolin G (3), (6α)-16,17-dihydro-21-deoxyophiobolin G (4), ophiobolin U (5), ophiobolin V (6), and ophiobolin W (7), two new sesquiterpenes, (6-strobilactone-B) esters of (E,E)-6,7-epoxy-2,4-octadienoic acids (13 and 14), and twelve known terpenes (1, 8–12, and 15–20) were isolated from Aspergillus ustus, a fungus from the fresh tissue of marine green alga Codium fragile. Their structures and absolute configurations were identified by NMR and mass spectroscopic methods as well as quantum chemical calculations. Some of the isolates exhibited antibacterial activity and brine shrimp toxicity.
Co-reporter:Feng-Ping Miao, Xiao-Rui Liang, Xiu-Li Yin, Gang Wang, and Nai-Yun Ji
Organic Letters 2012 Volume 14(Issue 15) pp:3815-3817
Publication Date(Web):July 23, 2012
DOI:10.1021/ol3014717
Harzianone (2), a new harziane diterpene, was isolated from an alga-endophytic isolate of Trichoderma longibrachiatum. The structure and absolute configuration of 2 were unambiguously identified by NMR and mass spectrometric methods as well as quantum chemical calculations. The absolute configuration of harziandione (1) was supported by calculation of optical rotation, and the structure of isoharziandione was revised to 1 on the basis of 13C NMR data comparison and calculation.
Co-reporter:Yi Zhang, Xiao-Ming Li, Zhuo Shang, Chun-Shun Li, Nai-Yun Ji, and Bin-Gui Wang
Journal of Natural Products 2012 Volume 75(Issue 11) pp:1888-1895
Publication Date(Web):November 13, 2012
DOI:10.1021/np300377b
Penicillium sp. MA-37, which was obtained from the rhizospheric soil of the mangrove plant Bruguiera gymnorrhiza, exhibited different chemical profiles in static and shaken fermentation modes. Three new meroterpenoid derivatives, 4,25-dehydrominiolutelide B (1), 4,25-dehydro-22-deoxyminiolutelide B (2), and isominiolutelide A (3), together with three known ones were characterized from its static fermentation, while three new diphenyl ether derivatives, namely, Δ1′,3′-1′-dehydroxypenicillide (4), 7-O-acetylsecopenicillide C (5), and hydroxytenellic acid B (6), along with five related metabolites were isolated from the shaken culture. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the structure of compound 2 was confirmed by X-ray crystallographic analysis. The absolute configurations of 1–3 and 6 were determined by ECD and modified Mosher’s method, respectively. All isolated compounds were evaluated for brine shrimp lethality and antibacterial activity.
Co-reporter:Xiao-Dong Li;Wei Ding;Feng-Ping Miao
Magnetic Resonance in Chemistry 2012 Volume 50( Issue 2) pp:174-177
Publication Date(Web):
DOI:10.1002/mrc.2870
Three new halogenated chamigrane sesquiterpenes, laurokamin A (1), laurokamin B (2), and laurokamin C (3), and four known halogenated chamigrane sesquiterpenes, 10-bromo-α-chamigrene (4), 10-bromo-β-chamigrene (5), 2,10-dibromo-3-chloro-β-chamigrene (6), and obtusane (7), were isolated from the marine red alga Laurencia okamurae collected from the coast of Rongcheng, China. The structures of these compounds were unambiguously identified by one- and two-dimensional NMR and mass spectroscopic methods. The antimicrobial activity of compounds 1–3 was evaluated. Copyright © 2012 John Wiley & Sons, Ltd.
Co-reporter:Ming-Feng Qiao;Feng-Ping Miao;Xiu-Li Yin
Magnetic Resonance in Chemistry 2011 Volume 49( Issue 6) pp:366-369
Publication Date(Web):
DOI:10.1002/mrc.2748
Abstract
A new oxylipin, (8E,12Z)-10,11-dihydroxyoctadeca-8,12-dienoic acid (1), a new steroid, 3β,4α-dihydroxy-26-methoxyergosta-7,24(28)-dien-6-one (2), and four known steroids, episterol (3), (22E,24R)-ergosta-7,22-dien-3β,5α,6α-triol (4), (22E,24R)-ergosta-5,22-dien-3β-ol (5), and (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), were isolated from the cultures of Aspergillus flavus, an endophytic fungus isolated from the marine red alga Corallina officinalis. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. 1 and 2 exhibited low activity to inhibit acetylcholinesterase and no activity against plant pathogenic fungi Colletotrichum lagenarium and Fusarium oxysporum. Copyright © 2011 John Wiley & Sons, Ltd.
Co-reporter:Ming-Feng Qiao, Nai-Yun Ji, Xiang-Hong Liu, Ke Li, Qing-Mei Zhu, Qin-Zhao Xue
Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 19) pp:5677-5680
Publication Date(Web):1 October 2010
DOI:10.1016/j.bmcl.2010.08.024
Two new indoloditerpene derivatives asporyzin A (1) and asporyzin B (2), one new indoloditerpene asporyzin C (3), and three known related indoloditerpenes JBIR-03 (4), emindole SB (5), and emeniveol (6) were isolated from an endophytic fungus Aspergillus oryzae, isolated from the marine red alga Heterosiphonia japonica. Their structures were unambiguously established by spectroscopic techniques. In addition, all the isolates were evaluated preliminarily for insecticidal and antimicrobial activities in order to probe into their chemical defensive function. Compound 4 was more active against brine shrimp than the others, and 3 possessed potent activity against Escherichia coli.
Co-reporter:Ling-Hong Meng; Yang Liu; Xiao-Ming Li; Gang-Ming Xu; Nai-Yun Ji;Bin-Gui Wang
Journal of Natural Products () pp:
Publication Date(Web):
DOI:10.1021/acs.jnatprod.5b00450
Citrifelins A (1) and B (2), two citrinin adducts possessing a unique tetracyclic framework, were characterized from a coculture of marine-derived fungal isolates of Penicillium citrinum and Beauveria felina. Neither fungus produced these compounds when cultured alone under the same conditions. The structures of these adducts were elucidated on the basis of spectroscopic analysis, and the absolute configurations were assigned on the basis of TDDFT-ECD calculations. A hypothesis that adducts 1 and 2 might be derived from a citrinin derivative through a non-pericyclic Michael reaction is proposed. Compounds 1, 2, and 5 showed inhibitory activities against several human and aquatic pathogens.
![[9,9'-Bianthracene]-10,10'(9H,9'H)-dione, 4,4',5,5'-tetrahydroxy-2,2'-dimethyl-8,8'-bis[(3-methyl-2-butenyl)oxy]-](http://img.cochemist.com/ccimg/112400/112356-35-1.png)
![[9,9'-Bianthracene]-10,10'(9H,9'H)-dione, 4,4',5,5'-tetrahydroxy-2,2'-dimethyl-8,8'-bis[(3-methyl-2-butenyl)oxy]-](http://img.cochemist.com/ccimg/112400/112356-35-1_b.png)
![4H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione,4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-4,4,6a,12b-tetramethyl-,(4aR,6aR,12aS,12bS)-](http://img.cochemist.com/ccimg/89100/89020-33-7.png)
![4H,11H-Naphtho[2,1-b]pyrano[3,4-e]pyran-1,11(5H)-dione,4a,6,6a,12,12a,12b-hexahydro-4a,12a-dihydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-4,4,6a,12b-tetramethyl-,(4aR,6aR,12aS,12bS)-](http://img.cochemist.com/ccimg/89100/89020-33-7_b.png)
![(1R,2S,3R)-3-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-1,2-dimethylcyclopentanol](http://img.cochemist.com/ccimg/28900/28834-06-2.png)
![(1R,2S,3R)-3-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-1,2-dimethylcyclopentanol](http://img.cochemist.com/ccimg/28900/28834-06-2_b.png)
![[9,9'-Bianthracene]-2,2'-dicarboxylicacid, 9,9',10,10'-tetrahydro-4,4',5,5'-tetrahydroxy-10,10'-dioxo-,(9R,9'S)-rel-](http://img.cochemist.com/ccimg/600/517-44-2.png)
![[9,9'-Bianthracene]-2,2'-dicarboxylicacid, 9,9',10,10'-tetrahydro-4,4',5,5'-tetrahydroxy-10,10'-dioxo-,(9R,9'S)-rel-](http://img.cochemist.com/ccimg/600/517-44-2_b.png)
