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NPC Natural Product
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EDITOR-IN-CHIEF DR. PAWAN K AGRAWAL
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EDITORS
PROFESSOR ALEJANDRO F. BARRERO Department of Organic Chemistry, University of Granada,
Campus de Fuente Nueva, s/n, 18071, Granada, Spain [email protected]
PROFESSOR ALESSANDRA BRACA
Dipartimento di Chimica Bioorganicae Biofarmacia, Universita di Pisa,
via Bonanno 33, 56126 Pisa, Italy [email protected]
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State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences,
Peking University, Beijing 100083, China [email protected]
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Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan [email protected]
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Texas Christian University, Forts Worth, TX 76129, USA [email protected]
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The University of Alabama in Huntsville Huntsville, AL 35809, USA
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Faculty of Pharmaceutical Sciences Hokuriku University
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Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy,
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Cladieunicellin J, a New Hydroperoxyeunicellin from
Cladiella sp.
Tsung-Hung Chena,b,†, Ching-Hsiao Chengc,†, Yung-Husan Chenb, Mei-Chin Lua,b, Lee-Shing Fangd,
Wu-Fu Chenc, Zhi-Hong Wene, Wei-Hsien Wangb,e, Yang-Chang Wuf,g,h,* and Ping-Jyun Sunga,b,g,i,*
aGraduate Institute of Marine Biotechnology, Department of Life Science and Institute of Biotechnology,
National Dong Hwa University, Pingtung 944, Taiwan
bNational Museum of Marine Biology and Aquarium, Pingtung 944, Taiwan
cDepartment of Neurosurgery, Kaohsiung Chang Gung Memorial Hospital-Kaohsiung Medical Center,
Kaohsiung 833, Taiwan
dDepartment of Sport, Health and Leisure, Cheng Shiu University, Kaohsiung 833, Taiwan eDepartment of Marine Biotechnology and Resources and Asia-Pacific Ocean Research Center,
fSchool of Pharmacy, College of Pharmacy, China Medical University, Taichung 404, Taiwan gChinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan
hCenter for Molecular Medicine, China Medical University Hospital, Taichung 404, Taiwan iGraduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan
†These authors contributed equally to this work. [email protected]; [email protected]
Received: January 28th, 2014; Accepted: February 19th, 2014
A new 6-hydroperoxyeunicellin diterpenoid, designated as cladieunicellin J (1), was isolated from an octocoral Cladiella sp., and its structure elucidated by
spectroscopic methods. Compound 1 was found to exhibit cytotoxicity toward CCRF-CEM human T-cell acute lymphoblastic leukemia.
Keywords: Eunicellin, Cladiella, Cladieunicellin, Cytotoxicity.
In our continuing research on novel natural substances from marine invertebrates distributed along the coast of Taiwan and Indonesia, a series of eunicellin diterpenoids, including cladieunicellins A–I, K and L, have been isolated from octocorals belonging to the genus
Cladiella (family Alcyoniidae) [1a-f] and the compounds of this
type were proven to display various bioactivities [2a,b]. Recently, chemical examination of an octocoral identified as Cladiella sp., collected in the Taiwan Sea, has resulted in the isolation of a new eunicellin, cladieunicellin J (1) (Figure 1). In this paper, we report the isolation, structure determination and cytotoxicity of compound 1.
Cladieunicellin J (1) was isolated as colorless oil. The HRESIMS ion of 1 at m/z 417.22473 established a molecular formula C22H34O6
(calcd for C22H34O6 + Na, 417.22476) (6º of unsaturation). The
presence of hydroxy and ester groups in 1 was suggested by the IR absorptions at 3439 and 1728 cm−1. The presence of an acetate
group was indicated by the 1H NMR signal (Table 1) at δH 1.93
(3H, s) and the 13C NMR resonances at δC 22.5 (CH3) and 169.8
(C). The 1H NMR data of 1 showed the presence of two secondary
methyls (δH 0.99, 3H, d, J = 7.2 Hz and 0.77, 3H, d, J = 6.8 Hz) of
an isopropyl group. From the 13C NMR data, two exocyclic carboncarbon
double bonds were deduced from the signals at δC 146.7 (C),
146.4 (C), 117.7 (CH2) and 116.2 (CH2), and confirmed by four
1.2 Hz), 5.12 (1H, d, J = 1.2 Hz) and 4.86 (1H, d, J = 1.2 Hz). A suite of resonances of proton signals at δH 2.23 (1H, m), 3.04 (1H,
dd, J = 10.8, 8.0 Hz), 3.80 (1H, s) and 4.53 (1H, dd, J = 10.8, 4.8 Hz) and carbon signals at δC 43.7 (CH), 46.0 (CH), 90.1 (CH) and
81.7 (CH) indicated the presence of a tetrahydrofuran moiety. From the above data, three degrees of unsaturation were accounted for and, therefore, 1 must be tricyclic.
O H H H H OAc HO R 1 10 11 12 13 14 17 18 19 20 2 3 4 5 6 8 7 9 16 15 1 : R = OOH 2 : R = OH 9R* 7 6S* 1R* 10R* 14R*
17 12S* 19 15 16 2R* 3R* 20 H H H OH H H O OAc H OOH H : NOESY
Figure 1: The structures of eunicellins 1 and 2 and the selective NOESY correlations for 1.
From the 1H–1H COSY spectrum of 1, the separate spin systems of
H2-4/H2-5/H-6; H2-8/H-9/H-10/H-1/H-14/H2-13/H-12; and H-14/
H-18/H3-19 (H3-20) were differentiated. These data, together with
the key HMBC correlations between protons and quaternary carbons such as H-1, H-2, H2-4, H2-5/C-3; H2-8, H-9/C-7; and H-9,
H-10/C-11, established the main carbon skeleton. The exocyclic carbon-carbon double bonds at C-7 and C-11 were confirmed by the HMBC correlations between H2-16/C-6, 7, 8 and H2-17/C-10, 11,
12, respectively. The ether bridge between C-2 and C-9 was supported by an HMBC correlation between H-2/C-9. The upfield chemical shift for H3-15 (δH 1.64, 3H, s) determined the position of
an acetoxy group at C-3. It was found that the spectra of 1 were similar to those of a known eunicellin, klymollin S (2) (Figure 1), which was isolated from the soft coral Klyxum molle [3a], except for the signal of CH-6, which was downfield shifted (δH 4.75, dd, J = 11.2, 4.0 Hz; δC 85.9) relative to that of 2 (δH 4.40, br s;
δC 72.2), revealing the presence of a hydroperoxy group at C-6.
This was further confirmed by the signal of a hydroperoxy proton at δH 7.80 (s) [3a-c]. Thus, the remaining proton of the hydroxybearing
NPC Natural Product
Communications
2014
Vol. 9
No. 5
613 - 614
614 Natural Product Communications Vol. 9 (5) 2014 Chen et al.
In the NOESY experiment (Figure 1), H-1 correlated with H-10 and H3-20, indicating that H-1, H-10 and the isopropyl group were
β-oriented. The coupling constants between H-12 and C-13
methylene protons (J = 2.8, 2.8 Hz) indicated that H-12 possessed a β-orientation in the cyclohexane ring. No coupling constant was detected between H-1 and H-2, indicating that the dihedral angle between H-1 and H-2 is approximately 90° and H-2 should be α-oriented. H3-15 showed correlations with H-2 and H-6,
demonstrating the β-orientation of the acetoxy and hydroperoxy groups at C-3 and C-6, respectively. A large coupling constant (J = 10.8 Hz) was detected between H-9/H-10, which reflected the α-orientation of H-9. Based on the above findings, the structure of 1 was elucidated unambiguously.
The cytotoxicity of compound 1 toward K-562, MOLT-4, CCRFCEM and DLD-1cells was studied (IC50 = 10.9, 6.6, 4.3, 13.4
μg/mL, respectively); moderate cytotoxicity against CCRF-CEM cells was found.
Experimental
General: Optical rotations, Jasco P-1010 digital polarimeter; IR,
Varian Diglab FTS 1000 FT-IR spectrometer; NMR, Varian Mercury Plus 400 NMR; ESIMS and HRESIMS, Bruker APEX II FT-mass spectrometer; CC, silica gel (230–400 mesh); TLC, Kieselgel 60 F254 (0.25 mm); compounds were visualized by
spraying with 10% H2SO4 solution followed by heating. Normal
phase HPLC (NP-HPLC) was performed using a system comprised of a Hitachi L-7110 pump and a Rheodyne 7725 injection port. A normal phase column (Supelco Ascentis® Si Cat #:581515-U, 25 cm
× 21.2 mm, 5 μm) was used for NP-HPLC. Reverse phase HPLC (RP-HPLC) was performed using a system comprised of a Hitachi L-7100 pump, a Hitachi L-2455 photodiode array detector, a
Rheodyne 7725 injection port and a Varian Polaris C-18-A column (250 mm × 10 mm, 5 μm).
Animal material: Specimens of the octocoral Cladiella sp. [4] were
collected by hand using SCUBA equipment off the coast of Penghu Archipelago, Taiwan on September, 2011, and stored at -20°C until extraction. A voucher specimen (NMMBA-TWSC-11011) was deposited in the National Museum of Marine Biology and Aquarium, Taiwan.
Extraction and isolation: Specimens of the soft coral Cladiella sp.
(wet weight 1.25 kg, dry weight 457 g) were minced and extracted with ethyl acetate (EtOAc). The EtOAc extract (12.4 g) was
separated by silica gel and eluted using n-hexane/EtOAc in a stepwise fashion from 100:1–pure EtOAc to yield 17 fractions A–Q. Fraction N (786 mg) was chromatographed on silica gel, using a mixture of n-hexane and acetone in a stepwise fashion from 6:1–pure acetone to obtain 15 sub-fractions N1–N15. Fraction N9 (48.7 mg) was repurified by NP-HPLC using a mixture of n-hexane and acetone (3:1, flow rate: 2.0 mL/min) to yield 5 sub-fractions N9A–N9E. Fraction N9C (7.5 mg) was further separated by RP-HPLC, using a mixture of methanol and water (7:3) to yield 1 (1.4 mg, tR = 30 min). Cladieunicellin J (1) [α]21 D: -2 (c 0.5, CHCl3). IR (neat): υmax 3439, 1728 cm-1. 1H NMR (400 MHz, CDCl3): δH 7.80 (1H, s, hydroperoxy proton), 5.45 (1H, d, J = 1.2 Hz, H-16a), 5.21 (1H, d, J = 1.2 Hz, H-16b), 5.12 (1H, d, J = 1.2 Hz, H-17a), 4.86 (1H, d, J = 1.2 Hz, H-17b),
4.75 (1H, dd, J = 11.2, 4.0 Hz, H-6),
4.53 (1H, dd, J = 10.8, 4.8 Hz, H-9), 4.45 (1H, dd, J = 2.8, 2.8 Hz, H-12), 3.80 (1H, s, H-2), 3.04 (1H, dd, J = 10.8, 8.0 Hz, H-10), 2.76 (1H, dd, J = 14.0, 4.8 Hz, H-8), 2.37 (1H, d, J = 14.0 Hz, H-8′), 2.28 (1H, m, H-4), 2.23 (1H, m, H-1), 2.19 (1H, m, H-5), 1.97 (1H, m, H-18), 1.93 (3H, s, acetate methyl), 1.89 (1H, m, H-13), 1.85 (1H, m, H-14), 1.80 (1H, m, H-4′), 1.64 (3H, s, H3-15), 1.56 (1H, m, 5′), 1.30 (1H, m, H-13′), 0.99 (3H, d, J = 7.2 Hz, H3-19), 0.77 (3H, d, J = 6.8 Hz, H3 -20). 13C NMR (100 MHz, CDCl3): δC 169.8 (acetate carbonyl), 146.7(C-7), 146.4 (C-11), 117.7 (CH2-16), 116.2 (CH2-17), 90.1 (CH-2),
85.9 (CH-6), 84.8 (C-3), 81.7 (CH-9), 71.6 (CH-12), 46.0 (CH-10), 43.7 (CH-1), 39.2 (CH2-8), 35.7 (CH-14), 31.0 (CH2-13), 29.9
(CH2-5), 28.1 (CH2-4), 26.9 (CH-18), 22.5 (acetate methyl), 22.0
(CH3-15), 21.7 (CH3-19), 15.3 (CH3-20).
ESIMS: m/z (%) = 417 [M + Na]+; HRESIMS: m/z [M + Na]+ calcd
for C22H34O6 + Na: 417.22476; found 417.22473.
Cytotoxicity testing: Cytotoxicity of compound 1 was assayed with
a modification of the MTT colorimetric method according to previously described procedures [5].
Acknowledgments - This research was supported by grants from
the NMMBA; the NDHU; the Kaohsiung Chang Gung Memorial Hospital (Grant No. CMRPG8C1281); the Asia-Pacific Ocean Research Center, NSYSU; and the National Science Council, Taiwan, awarded to Y.-C.W. and P.-J.S.
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Natural Product Communications Vol. 9 (5) 2014
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Natural Product Communications
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Volume 9, Number 5
Contents
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