Two new secondary metabolites from a mangrove-derived fungus Cladosporium sp. JJM22

Article abstract of DOI:10.1080/14786419.2018.1431634

Two new compounds (1 and 2), together with six known compounds (3–8), were obtained from the Cladosporium sp. JJM22, an endophytic fungus isolated from the stem bark of the mangrove plant Ceriops tagal collected in South China Sea. Their structures were elucidated on the basis of detailed spectroscopic analysis. The absolute configurations of 1 and 2 were confirmed by the comparison of optical rotation and the CD data with those of known compounds. The inhibitory activities of the isolated compounds against six terrestrial pathogenic bacteria and human cervical carcinoma Hela cell line were evaluated. Compound 3 exhibited a broad spectrum of antibacterial activities.

Full text of DOI:10.1080/14786419.2018.1431634

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
Two new secondary metabolites from a mangrove-
derived fungus Cladosporium sp. JJM22
Jia-Ting Wu, Cai-Juan Zheng, Bin Zhang, Xue-Ming Zhou, Qi Zhou, Guang-Ying
Chen, Zhuo-Er Zeng, Jin-Long Xie, Chang-Ri Han & Ji-Xing Lyu
To cite this article: Jia-Ting Wu, Cai-Juan Zheng, Bin Zhang, Xue-Ming Zhou, Qi Zhou, Guang-
Ying Chen, Zhuo-Er Zeng, Jin-Long Xie, Chang-Ri Han & Ji-Xing Lyu (2018): Two new secondary
metabolites from a mangrove-derived fungus Cladosporium sp. JJM22, Natural Product Research,
DOI: 10.1080/14786419.2018.1431634
To link to this article: https://doi.org/10.1080/14786419.2018.1431634
View supplementary material
Published online: 01 Feb 2018.
Submit your article to this journal
View related articles
View Crossmark data
Full Terms & Conditions of access and use can be found at
http://www.tandfonline.com/action/journalInformation?journalCode=gnpl20

Natural Product research, 2018
https://doi.org/10.1080/14786419.2018.1431634
Two new secondary metabolites from a mangrove-derived
fungus Cladosporium sp. JJM22
Jia-Ting Wua, Cai-Juan Zhenga, Bin Zhanga, Xue-Ming Zhoua, Qi Zhoua,
Guang-Ying Chena, Zhuo-Er Zenga, Jin-Long Xiea, Chang-Ri Hanb and Ji-Xing Lyua
aKey laboratory of tropical Medicinal Plant chemistry of Ministry of education, college of chemistry and
chemical engineering, hainan Normal university, haikou, P. r. china; bKey laboratory of Medicinal and edible
Plants resources of hainan Province, school of chemical and Material engineering, hainan Institute of science
and technology, haikou, P. r. china
ABSTRACT
ARTICLE HISTORY
received 12 september 2017
accepted 18 January 2018
Two new compounds (1 and 2), together with six known compounds
(3–8), were obtained from the Cladosporium sp. JJM22, an endophytic
fungus isolated from the stem bark of the mangrove plant Ceriops tagal
collected in South China Sea. Their structures were elucidated on the
basis of detailed spectroscopic analysis. The absolute configurations
of 1 and 2 were confirmed by the comparison of optical rotation
and the CD data with those of known compounds. The inhibitory
activities of the isolated compounds against six terrestrial pathogenic
bacteria and human cervical carcinoma Hela cell line were evaluated.
Compound 3 exhibited a broad spectrum of antibacterial activities.
KEYWORDS
Ceriops tagal; endophytic
fungus; ribofuranose phenol;
naphthalene derivative;
antibacterial activity
1. Introduction
It is acknowledged that there is a wealthy source of structurally unique and biologically
potent secondary metabolites from marine-derived fungi (Li et al., 2017; Vinale et al. 2017).
Recently, the mangrove-derived fungus has become an important source for the discovery
of new natural compounds. In our search for new bioactive metabolites from mangrove-
derived fungi, some bioactive compounds have been found (Zhou et al. 2014; Huang et al.
2016; He et al. 2017). Recently, the fungus Cladosporium sp. JJM22 isolated from the stem
bark of C. tagal captured our attention because the EtOAc extract of rice medium of the
fungus exhibited antimicrobial activity against Staphylococcus aureus. Moreover, a literature
CONTACT Guang-Ying chen
chgying123@163.com; chang-ri han
hchr116@126.com
supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2018.1431634.
© 2018 Informa uK limited, trading as taylor & Francis Group

2
J.-T. WU ET AL.
survey revealed that a series of biologically active compounds have been reported from the
marine fungus Cladosporium sp. including isoindolone derivatives and alkaloids with antiviral
activities (Peng et al. 2013), cladospolides E and F with potent lipid-lowering activity in HepG2
hepatocytes (Zhu et al. 2015), 3α-hydroxy-7-ene-6,20-dione with antiviral activities against
respiratory syncytial virus (RSV) (Yu et al. 2017). In this study, chemical investigation on the
EtOAc extract of the fermentation broth led to the identification of one new ribofuranose
phenol derivative, 4-O-α-D-ribofuranose-3-hydroxymethyl-2-pentylphenol (1), one new
naphthalene derivative, (-)-trans-(3R,4R)-3,4,8-trihydroxy-6,7-dimethyl-3,4- dihydronaphtha-
len-1(2H)-one (2), together with six known compounds, (3S)-3,8-dihydroxy-6,7-dimethyl-α-
tetralone (3) (Kongyen et al. 2015), (3R,4R)-3,4-dihydro-3,4,8-trihydroxy-1(2H)-napthalenone
(4) (Borgschulte et al. 1992), (-)-(4R)-regiolone (5) (Talapatra et al. 1988), 1,8-dimethoxynaph-
thalene (6) (Allport and Bu’Lock 1960), (2S)-5-hydroxy-2-methyl-chroman-4-one (7) (Nadeau
and Sorensen 2011) and (2R*,4R*)-3,4-dihydro-5-methoxy-2-methyl-1(2H)-benzopyran-4-ol
(8) (Zheng et al. 2016) (Figure 1). Herein, we report the isolation, structure elucidation and
pharmacological activities of all compounds.
2. Results and discussion
Compound 1 was obtained as a brown oil. Its molecular formula was determined by HRESIMS
(m/z 343.1751 [M + H]+, calcd 343.1751) to be C17H26O7, including five degrees of unsatura-
tion. In the 1H NMR spectrum of 1, two aromatic protons at δH 6.89 (1H, d, J = 8.8 Hz, H-6)
and 6.68 (1H, d, J = 8.8 Hz, H-5) indicated the presence of 1,2,3,4-tetrasubstituted benzene
ring. In addition, a hydroxymethyl proton signal at δH 4.69 (2H, s, H-12), four signals for eight
methylene protons at δH 2.72 (2H, dd, J = 10.0, 8.0 Hz, H-7), 1.38 (2H, overlapped, H-9), 1.38
Figure 1. the structures of compounds 1–8.

NATURAL PRODUCT RESEARCH
3
(2H, overlapped, H-10), 1.52 (2H, m, H-8) and four oxygenated methine proton signals at δH
5.55 (1H, d, J = 8.8 Hz, H-1′), 4.19 (1H, overlapped, H-4′), 4.16 (1H, overlapped, H-2′), 4.09 (1H,
dd, J = 6.4, 2.4 Hz, H-3′), and two non-equivalent oxygenated methylene protons at δH 3.69
(1H, dd, J = 12.0, 3.6 Hz, H-5′a) and 3.65 (1H, dd, J = 12.0, 4.0 Hz, H-5′b) and one methyl group
signal at δH 0.94 (3H, t, J = 7.2 Hz, H-11), were observed. The 13C NMR and DEPT spectra (Table
S1) exhibited 17 carbon resonances distributed into 1,2,3,4-tetrasubstituted benzene ring,
four oxygenated methines, six methylenes including two oxygenated methylenes and one
methyl group. The proton spin system [δH 5.55 (H-1′), 4.19 (H-4′), 4.16 (H-2′), 4.09 (H-3′), 3.69
(H-5′a) and 3.65 (H-5′b)], together with chemical shift values of the related carbons [δC 103.2
(C-1′), 87.9 (C-4′), 73.6 (C-2′), 71.5 (C-3′) and 63.3 (C-5′)] were typical of a ribofuranose moiety
(Sharma et al. 2012).
The protons that were directly attached to carbons were assigned with the aid of HMQC
spectrum. The 1H–1H COSY data showed proton connectivities of H-5 and H-6; of H-7, H-8,
H-9, H-10 and H-11; H-1′, H-2′, H-3′, H-4′ and H-5′ (Figure S8). The HMBC correlations from
H-12 to C-2, C-3 and C-4 established the attachment of the hydroxy methyl group at C-3.
The long-range coupling observed H-7 to C-1, C-2 and C-3 indicated that a n-pentyl group
was located at C-2. The HMBC correlations from H-1′ to C-4 established the attachment of
the ribofuranose group at C-4 and the doublet at δH 5.55 (d, J = 8.8 Hz) indicated an α ori-
entation of H-1′ (Sharma et al. 2012). The absolute configuration of D-ribose obtained from
acid hydrolysis of compound 1 was established by comparison of its optical rotation ([ꢀ]D25
−19.0, c 0.1, H2O) with that of D-ribose previously reported (Robert et al. 1954). Hence, the
compound 1 was identified as 4-O-α-D-ribofuranose-3-hydroxymethyl-2-pentyl- phenol.
Compound 2 was obtained as needle-like crystals. The molecular formula of 2 was deter-
mined to be C12H14O4 on the basis of HRESIMS. The 1H-NMR spectrum displayed signals for
an aromatic group at δH 6.95 (1H, s), two oxymethine groups at δH 4.55 (1H, d, J = 7.2 Hz)
and 4.05 (1H, ddd, J = 8.0, 7.2, 4.0 Hz), one methylene group at δH 3.07 (1H, dd, J = 17.2,
4.0 Hz), 2.69 (1H, dd, J = 17.2, 8.0 Hz) and two methyl singals at δH 2.33 (s) and 2.14 (s). The
13C-NMR (Table S2) and DEPT spectra exhibited an aromatic ring (δC 161.3, 148.0, 142.2, 124.9,
121.3, 114.3), two methine carbons (δC 73.2 and 71.9), one methylene carbon (δC 44.3), two
methyl groups (δC 20.9 and 10.8) and a ketone carbon (δC 203.8). The 1H NMR and 13C NMR
spectra of compound 2 were similar to those of cis-(3R*, 4S*) 3,4,8-trihydroxy-6,7-dimethyl-
3,4dihydronaphthalen-1(2H)-one (Isaka et al. 2009) expect for the coupling constant data.
A small coupling constant of 3JH-3, H-4 = 3.4 Hz observed in cis-(3R*, 4S*) 3,4,8-trihydroxy-6,7-di-
methyl-3,4dihydronaphthalen-1(2H)-one, a large coupling constant of 3JH-3, H-4 = 7.2 Hz was
observed in 2 which showed H-3 and H-4 has trans diaxial relationship. Furthermore, com-
paring the CD data and optical rotation of 2 with those of 4 (Peng et al. 2013), they showed
similar features in the 200–500 nm range (Figure S16), therefor 2 was determined as 4R. In
conclusion, compound 2 was elucidated as (-)-trans-(3R,4R)-3,4,8-trihydroxy-6,7-dimethyl-3,4-
dihydronaphthalen- 1(2H)-one.
By comparing physical and spectroscopic data with literature values, six known com-
pounds
were
identified
as
(3S)-3,8-dihydroxy-6,7-dimethyl-α-tetralone
(3),
(-)-trans-(3R,4R)-3,4-dihydro-3,4,8-trihydroxy-1(2H)-napthalenone (4), (-)-(4R)- regiolone (5),
1,8-dimethoxy naphthalene (6), (2S)-5-hydroxy-2-methyl-chroman-4- one (7) and (2R*,4R*)-
3,4-dihydro-5- methoxy-2-methyl-1(2H)-benzo pyran-4-ol (8) in Figure 1.
Compounds 1–3 were evaluated for cytotoxic activity against the human cervical carci-
noma Hela cell line. However, in the assay all IC50 values obtained were higher than 10 μM

4
J.-T. WU ET AL.
and were defined as inactive. Compounds 1–8 were evaluated for their antibacterial activities
against six pathogenic bacteria, including S. aureus, Bacillis cereus, Escherichia coli, Vibrio
alginolyticus, Vibrio parahemolyticus, Methicillin-resistant Staphylococcus aureus. The results
illustrated that only 3 exhibited a broad spectrum of antibacterial activities against six path-
ogenic bacteria at a concentration of 20 μM.
3. Experimental
3.1. General
Melting points were determined on an X-6 micromelting point apparatus and were uncor-
rected. Optical rotation was measured on a JASCO P-1020 digital polarimeter. IR spectra
were recorded on a Thermo Nicolet 6700 (using KBr discs) spectrophotometer (Thermo
Scientific, Madison, WI, USA). 1D and 2D NMR spectra were measured on a Bruker AV-400
(Bruker Corporation, Switzerland) instrument with TMS as the internal standard. HRESIMS
spectra were made on the Bruker Daltonics Apex-Ultra 7.0 T (Bruker Corporation, Billerica,
MA, USA). Semi-preparative HPLC was performed on an Agilent 1260 LC series with a DAD
detector using an Agilent Eclipse XDB-C18 column (9.4 × 250 mm, 5 μm). Sephadex LH-20
(Pharmacia Co. Ltd, Sandwich, UK) and silica gel (200–300 mesh, 300–400 mesh Qingdao
Marine Chemical Factory, Qingdao, China) were used for column chromatography (CC). All
solvents were purchased from Xilong Chemical Reagent Factory (Guangzhou, China).
3.2. Fungal materials
The fungus Cladosporium sp. JJM22 was isolated from the mangrove plant C. tagal, which
was collected from Dongzhaigang of Hainan Province in China in July, 2016. The strain was
deposited in the Key Lab of Tropical Medicinal Plant Chemistry of Ministry of Education,
College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou, P.R.
China. It was cultured in 200 mL of potato dextrose broth at 30 °C on a rotary shaker (120 rpm)
for 7 days to prepare the seed culture. Large-scale fermentation was carried out in 200
Erlenmeyer flasks (1000 mL), each containing rice (65 g), sea salt (1.35 g) and purified water
(45 mL), which were soaked overnight before autoclaving at 121 °C for 20 min. Those
Erlenmeyer flasks were added 3-mL seed broth, respectively, after cooling to room temper-
ature, furthermore, which were maintained at room temperature for 25 days in stationary
phase.
3.3. Identification of fungus
The strain was identified as Cladosporium sp. according to morphologic traits and molecular
identification, whose 497 base pair ITS sequence had 99% sequence identity to that of
Cladosporium sp. The sequence data have been submitted to GenBank with the accession
number MF593626.
3.4. Extraction and isolation
The fungal culture was extracted with EtOAc (3 × 20 L, 24 h each), which was filtered through
cheesecloth. The extract was concentrated in vacuo to yield an oily residue (20.8 g), which

NATURAL PRODUCT RESEARCH
5
was subjected to silica gel CC (petroleum ether/EtOAc v/v, gradient 100:0–0:100) to generate
six fractions (Fr. E1–Fr. E6). Fr. E2 was crystallised from petroleum ether/EtOAc to afford 6
(15.0 mg). Fr. E4 was concentrated and rechromatographed on a silica gel column eluted
with petroleum ether/EtOAc (50:1 to 1:1) to afford seven fractions (E4-1–E4-7). Fr. E4-2 was
evaporated and subjected to Sephadex LH20 column chromatography (CHCl3/MeOH, v/v,
1:1) to afford seven fractions (E4-2-1–E4-2-7). Fr. E4-2-3 was purified by reversed-phase pre-
parative HPLC developed with 40% acetonitrile–water at a flow rate of 1.8 mL min−1 to yield
compounds 2 (7.0 mg), 3 (25.0 mg), 4 (11.0 mg) and 5 (13.0 mg). Fr. E5 was subjected to
reversed-phase HPLC with 35% acetonitrile–water at a flow rate of 2.0 mL min−1 to furnish
compounds 7 (15.0 mg) and 8 (17.0 mg). Compund 1 (15.0 mg) was obtained from fraction
E6 using reversed-phase HPLC with 30% acetonitrile-water at a flow rate of 1.8 mL min−1.
3.5. Physical properties of compounds 1 and 2
Compound 1: brown oiliness; UV (MeOH) λmax (log ε) 292 (0.262), 209 (1.071) nm; IR (KBr)
ν
max 3373, 2928, 1649, 1460, 1043, 479 cm−1; positive HRESIMS m/z 343.1751 [M+H]+ (calcd
for C17H27O7, 343.1751). [ꢀ]2D5−9.8° (c 0.5 MeOH). 1H NMR (400 MHz, CD3OD) δ: 6.89 (1H, d, J
= 8.8 Hz, H-6), 6.68 (1H, d, J = 8.8 Hz, H-5), 5.55 (1H, d, J = 8.8 Hz, H-1′), 4.69 (2H, s, H-12), 4.19
(1H, overlapped, H-4′), 4.16 (1H, overlapped, H-2′), 4.09 (1H, dd, J = 6.4, 2.4 Hz, H-3′), 3.69 (1H,
dd, J = 12.0, 3.6 Hz, H-5′a), 3.65 (1H, dd, J = 12.0, 4.0 Hz, H-5′b), 2.72 (2H, dd, J = 10.0, 8.0 Hz,
H-7), 1.52 (2H, m, H-8), 1.38 (4H, overlapped, H-9,10), 0.94 (3H, t, J = 7.2 Hz, CH3-11); 13C NMR
(100 MHz, CD3OD) δ: 151.4 (C-1), 150.5 (C-4), 131.1 (C-3), 130.6 (C-2), 115.5 (CH-6), 115.1 (CH-
5), 103.2 (CH-1′), 87.9 (CH-4′), 73.6 (CH-2′), 71.5 (CH-3′), 63.3 (CH2-5′), 57.3 (CH2-12), 33.2
(CH2-9), 31.5 (CH2-8), 27.0 (CH2-7), 23.6 (CH2-10), 14.4 (CH3-11).
Compound 2: needle-like crystals; m.p. 174.5-175.5 °C; UV (MeOH) λmax (log ε) 257 (0.98),
212 (5.02) nm; IR (KBr) νmax 3433, 2925, 2851, 1745, 1631, 1161, 520 cm−1; HRESIMS m/z
25
1
223.0971 [M + H]+ (Calcd 223.0964, C12H15O4); [ꢀ]D −35° (c 0.1 MeOH). H NMR (400 MHz,
CD3OD) δ: 6.95 (1H, s, H-5), 4.55 (1H, d, J = 7.2 Hz, H-4), 4.05 (1H, ddd, J = 8.0, 7.2, 4.0 Hz, H-3),
3.07 (1H, dd, J = 17.2, 4.0 Hz, H-2b), 2.69 (1H, dd, J = 17.2, 8.0 Hz, H-2a), 2.33 (3H, s, 9-CH3),
2.14 (3H, s, CH3-10); 13C NMR (100 MHz, CD3OD) δ: 203.8 (C-1), 161.3 (C-8), 148.0 (C-4a), 142.2
(C-6), 124.9 (C-8a), 121.3 (C-5), 114.3 (C-7), 73.2 (CH-4), 71.9 (CH-3), 44.3 (CH2-2), 20.9 (CH3-9),
10.8 (CH3-10); CD (c 0.5 MeOH) Δε −10.28 (217.6 nm), +3.18 (266.9 nm).
3.6. Acid hydrolysis of 1 and determination of the configuration of the
ribofuranose
A solution of 1 (10 mg) in 6 mol/L HCl (1 mL) was reacted 3 h at 100 °C. The reaction mixture
was extracted with EtOAc repeatedly to remove the aglycone fraction. The H2O layer was
then concentrated to furnish the sugar residue (2.0 mg). The rotation recorded for the ribose
isolated in this study was[ꢀ]2D5−19.0 (c 0.1, H O), which closely matched that for the D-ribose
2
(lit.−20) (Lin et al. 1995).
3.7. Biological assays
Cytotoxic activity was evaluated by the MTT method as described previously. Human cervical
carcinoma Hela cell line was used. Epirubicin was used as a positive control (Scudiero et al.

6
J.-T. WU ET AL.
1988). Antibacterial activity was determined against six terrestrial pathogenic bacteria,
including S. aureus (ATCC 6538), E. coli (ATCC 25,922), B. cereus (ATCC 6633), V. alginolyticus
(ATCC 33,787), V. parahemolyticus (ATCC 17,802), MRSA (CMCC(B) 63,303) (Pierce et al. 2008).
Ciprofloxacin was used as the positive control.
4. Conclusions
In this study, one new ribofuranose phenol derivative 4-O-α-D-ribofuranose-3- hydroxym-
ethyl-2-pentylphenol (1) and one new naphthalene derivative (-)-trans-(3R,4R)-3,4,8-trihy-
droxy-6,7-dimethyl-3,4dihydronaphthalen-1(2H)-one (2), together with six known
compounds (3–8), were obtained from the EtOAc extract of Cladosporium sp. JJM22, an
endophytic fungus isolated from the stem bark of the mangrove plant C. tagal collected in
South China Sea. The absolute configuration of D-ribose obtained from acid hydrolysis of
compound 1 was established by comparison of its optical rotation with that of D-ribose
previously reported. The absolute configuration of 2 was confirmed by the comparison of
CD spectrum analysis with the known compound 4.
Supplementary material
Supplementary material relating to this article is available online, alongside Figures S1–S15, Tables
S1 and S2.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was supported by the Foundation for the National Natural Science Foundation of China
[grant number 21662012]; Ministry of Education Innovation Team Development Plan [grant number
IRT-16R19]; the Hainan Province Natural Science Foundation of Innovatie Research Team Project [grant
number 2016CXTD007].
References
Allport DC, Bu’Lock JD. 1960. 134. Biosynthetic pathways in daldinia concentrica. J Chem Soc. 0:654–662.
Borgschulte K, Rebuffat S, Trowitzsch-Kienast W, Schomburg D, Pinon J, Bodo B. 1992. Isolation and
structure elucidation of hymatoxins B-E and other phytotoxins from Hypoxylon mammatum fungal
pathogen of leuce poplars. Tetrahedron. 47:8351–8360.
He KY, Zhang C, DuanYR, Huang GL, Yang CY, Lu XR, Zheng CJ, Chen GY. 2017. New chlorinated xanthone
and anthraquinone produced by a mangrove-derived fungus Penicillium citrinum HL-5126. J Antibiot.
70(7):823–827.
HuangGL,ZhouXM,MengB,LiuYX,ZhaoYL,LuoYP,NiuYY,ZhengCJ,ChenGY.2016.Dihydroisocoumarins
from the mangrove-derived fungus Penicillium citrinum. Marine Drugs. 14(10):177.
IsakaM,YangchumA,RachtaweeP,KhoyaiklangP,BoonyuenN,LumyongS.2009.Dihydronaphthalenones
from the endophytic fungus Botryosphaeria sp. BCC 8200. Phytochem Lett. 2(4):207–210.
Kongyen W, Rukachaisirikul V, Phongpaichit S, Sakayaroj J. 2015. A new hydronaphthalenone from the
mangrove-derived Daldinia eschscholtzii PSU-STD57. Nat Prod Res. 29(21):1995–1999.

NATURAL PRODUCT RESEARCH
7
Li X, Xia Z, Tang J, Wu J, Tong J, Li M, Ju J, Chen H, Wang L. 2017. Identification and biological evaluation of
secondary metabolites from marine derived fungi-Aspergillus sp. Scsiow 3, cultivated in the presence
of epigenetic modifying agents. Molecules. 22(8):1302–1311.
Lin CN, Lu CM, Lin HC, Ko FN, Teng CM. 1995. Novel antiplatelet naphthalene from rhamnus nakaharai.
J Nat Prod. 58(12):1934–1940.
Nadeau AK, Sorensen JL. 2011. Polyketides produced by Daldinia loculata cultured from northern
manitoba. Tetrahedron. 52(14):1697–1699.
Peng JX, Lin T, Wang W, Xin ZH, Zhu TJ, Gu QQ, Li DH. 2013. Antiviral alkaloids produced by the
mangrove-derived fungus Cladosporium sp. pjx-41. J Nat Prod. 76(6):1133–1141.
Pierce CG, Uppuluri P, Tristan AR, Wormley FL Jr, Mowat E, Ramage G, Lopez-Ribot JL. 2008. A simple and
reproducible 96 well plate-based method for the formation of fungal biofilms and its application
to antifungal susceptibility testing. Nat Protoc. 3(9):1494–1500.
Prado S, Ndoye I, Vallet M, Nay B. 2013. One-step enantioselective synthesis of (4)-isosclerone through
biotranformation of juglone by an endophytic fungus. Tetrahedron. 54(10):1189–1191.
Robert KN, Harry WD, Hewitt GFJ. 1954. New benzoyl derivatives of D-ribofuranose and aldehydo-D-
ribose. The preparation of crystalline 2,3,5-tri-O-benzoyl-β-D-ribose from D-ribose1. J Am Chem
Soc. 76(3):763–767.
Scudiero DA, Shoemaker RH, Paull KD, Monks A, Tierney S, Nofziger TH, Currens MJ, Seniff D, Boyd MR.
1988. Evaluation of a soluble tetrazolium/ formazan assay for cell growth and drug sensitivity in
culture using human and other tumor cell lines. Cancer Res. 48(17):4827–4833.
Sharma RK, Singh S, Tiwari R, Mandal D, Olsen CE, Parmar VS, Parang K, Prasad AK. 2012. O-Arylα, β-D-
ribofuranosides: Synthesis & highly efficient biocatalytic separation of anomers and evaluation of
their Src kinase inhibitory activity. Bioorg & Med Chem. 20(23):6821–6830.
Talapatra SK, Karmacharya B, De SC, Talapatra B. 1988. (-)-regiolone, an α-tetralone from Juglans regia:
structure, stereochemistry and conformation. Phytochemistry. 27(12):3929–3932.
Vinale F, Nicoletti R, Lacatena F, Marra R, Sacco A, Lombardi N, d’Errico G, Digilio MC, Lorito M, Woo SL.
2017. Secondary metabolites from the endophytic fungus Talaromyces pinophilus. Nat Prod Res.
31(15):1778–1785.
Yu ML, Guan FF, Cao F, Jia YL, Wang CY. 2017. A new antiviral pregnane from a gorgonian-derived
Cladosporium sp. fungus. Nat Prod Res. Latest articles. 1–7.
Zheng CJ, Huang GL, XuY, Song XM, Yao J, Liu H, Wang RP, Sun XP. 2016. A new benzopyrans derivatives
from a mangrove-derived fungus Penicillium citrinum from the south china sea. Nat Prod Res.
30(7):821–825.
Zhou XM, Zheng CJ, Chen GY, Song XP, Han CR, Li GN, Fu YH, Chen WH, Niu ZG. 2014. Bioactive
anthraquinone derivatives from the mangrove-derived fungus Stemphylium sp. 33231. J Nat Prod.
77(9):2021–2028.
Zhu ML, Gao HQ, Wu CM, Zhu TJ, Che Q, Gu QQ, Guo P, Li DH. 2015. Lipid-lowering polyketides from a
soft coral-derived fungus Cladosporium sp. TZP29. Bioorg Med Chem. 25(17):3606–3609.