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Casbane Diterpenes from Red Sea Coral Sinularia Polydactyla

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Casbane Diterpenes from Red Sea Coral Sinularia Polydactyla molecules Article Casbane Diterpenes from Red Sea Coral Sinularia polydactyla Mohamed-Elamir F. Hegazy 1, Tarik A. Mohamed 1, Abdelsamed I. Elshamy 2, Montaser A. Al-Hammady 3, Shinji Ohta 4 and Paul W. Paré 5,* 1 Department of Phytochemistry, National Research Centre, El-Tahrir Street, Dokki, Giza 12622, Egypt; [email protected] (M.-E.F.H.); [email protected] (T.A.M.) 2 Department of Natural Compound Chemistry, National Research Centre, El-Tahrir Street, Dokki, Giza 12622, Egypt; [email protected] 3 National Institute of Oceanography and Fisheries, Red Sea Branch, Hurghada 84511, Egypt; [email protected] 4 Graduate School of Biosphere Science, Hiroshima University, 1-7-1 Kagamiyama, Higashi-Hiroshima 739-8521, Japan; [email protected] 5 Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA * Correspondence: [email protected]; Tel.: +1-806-834-0461; Fax: +1-806-742-1289 Academic Editor: Derek J. McPhee Received: 11 February 2016 ; Accepted: 29 February 2016 ; Published: 3 March 2016 Abstract: The soft coral genus Sinularia is a rich source of bioactive metabolites containing a diverse array of chemical structures. A solvent extract of Sinularia polydactyla resulted in the isolation of three new casbane diterpenes: sinularcasbane M (1), sinularcasbane N (2) and sinularcasbane O (3); in addition, known metabolites (4–5) were isolated. Compounds were elucidated on the basis of spectroscopic analyses; the absolute configuration was confirmed by X-ray analysis. Keywords: soft coral; alcyoniidae; Sinularia polydactyla; diterpenes 1. Introduction In Alcyonacean soft coral, the genus Sinularia is a rich source of diverse natural products with over 500 metabolites including sesquiterpenes, diterpenes, polyhydroxylated steroids, alkaloids and polyamines already having been chemically characterized [1–5]. Sinularia consists of almost 90 species of which approximately 50 have been profiled for biological activity; such studies have established that the genus is a rich source of secondary metabolites with biological properties including cytotoxic, anti-inflammatory and antimicrobial activities [5–10]. While Sinularia species occur in marine waters around the world, S. polydactylais (Figure1) is endemic to the Red Sea. Although the marine environment contains extensive reef formations, this ecosystem is not as well characterized in terms of chemical studies of marine organisms compared to other large coral reef systems [11]. As a part of a comprehensive chemical inventory of marine natural products from Red Sea soft coral [12–14], herein, we reported the chemical characterization of solvent-extracted casbane diterpenes from S. polydactyla (Figure2). Casbane-type diterpene structures are related to the 14-membered cembrane ring system except for the dimethyl-cyclopropyl moiety instead of an isopropyl residue fused to the ring. These extremely-rare natural products are predominantly isolated from select coral species [15]. Several soft coral casbanes have been isolated from Sinularia depressa with biologically active 10-hydroxydepressin exhibiting cytotoxicity against several tumor cell lines with IC50 values near 50 µM[16]. Molecules 2016, 21, 308; doi:10.3390/molecules21030308 www.mdpi.com/journal/molecules Molecules 2016, 21, 308 2 of 8 Molecules 2016, 21, 308 2 of 8 Molecules 2016, 21, 308 2 of 8 Figure 1. Soft coral Sinularia polydactyla. FigureFigure 1. 1.Soft Soft coralcoral Sinularia polydactyla polydactyla. 18 18 18 18 16 O OH OH H 16 O H 4 OH4 OH H H 4 4 16 3 16 6 3 3 6 3 7 7 6 6 4 6 6 3 H H 7 4 7 7 3 HOHO 5 5 2 2 H 7 5 2 5 5 2 H 5 2 15 2 15 15 1717 O 15 1 1 O 1 1 8 8 19 19 11 88 1818 OO 14 14 15 15 8 8 13 1616 HH 11 11 13 17 17 9 9 99 1111 1313 10 10 13 13 1010 12 1414 9 9 14 14 11 11 12 12 1010 12 12 HH 17 17 OH HH O O 19 19 20 O 20 20 O 1 2 3 1 2 O 3 O 18 O O 6 6 18 O HH O HH 5 7 8 4 5 7 8 H 3 4 H 2 3 O 17 2 H O O 17 13 H 11 O 9 O 14 13 12 11 O 9 1 14 12 15 1 H 15 H H 10 HHH 10 16 HH19 H O 16 19 O H O O O O O O 4 5 4 5 FigureFigure 2. 2.Structures Structures of metabolites metabolites 1–15–. 5. Figure 2. Structures of metabolites 1–5. 2. Results2. Results and and Discussion Discussion 2. Results and Discussion 25 Compound 1 was obtained as a colorless oil with a negative optical rotation ([α]D −25 9.6 in MeOH). 25 Compound 1 was obtained as a colorless oil with a negative optical rotation+ (rasD ´ 9.6 in MeOH). HR-ESI-FTMSCompound analysis1 was obtained exhibited as aa molecularcolorless oil ion with peak a negativeat m/z 327.2293 optical [M rotation + Na] ([ correspondingα]D − 9.6 in MeOH). to a + HR-ESI-FTMS analysis exhibited a molecular ion peak at m/z 327.2293 [M + Na]+ corresponding to a HR-ESI-FTMSmolecular formula analysis of Cexhibited20H32O2 (calcd. a molecular for C20H 32ionO2 Na,peak 327.2300) at m/z 327.2293with five [Mdegrees + Na] of unsaturation.corresponding The to a molecularmolecularIR spectrum formula formula exhibited of of C C2020 bandsHH32OO2 for2 (calcd.(calcd. hydroxyl for for C and20 CH20 32olefinicHO322Na,O2 Na,substituents327.2300) 327.2300) with at 3409, withfive degreesand five 1650 degrees of cm unsaturation.−l, respectively. of unsaturation. The ´1 TheIR IRThespectrum spectrum 1 H-NMR exhibited exhibitedspectrum bands showed bands for hydroxyl four for hydroxylmethyl and olefinic signals, and substituents including olefinic substituents two at 3409,olefinic and methyls at 1650 3409, cm at− andlδ, Hrespectively. (1.56 1650 brs cm , 1 respectively.Theand 1 H-NMR 1.74 Thebrs, spectrumeachH-NMR 3H) and showed spectrum two tertiary four showed methyl methyls four signals, at methyl δH (1.00 including signals, s and 1.06 two including s, olefinic each 3H). two methyls Olefinic olefinic at protons δ methylsH (1.56 at brs at δ H (1.56andδ brsH 1.74 5.02 and brs, (brd, 1.74 each J = brs, 8.3 3H) Hz) each and and 3H)two 5.19 andtertiary (brd, two J methyls= tertiary 8.3 Hz) at were methyls δH (1.00attributed ats andδH to (1.001.06 two s, strisubstituted each and 1.063H). s,Olefinic eachdouble 3H). protons bonds; Olefinic at exomethylene singlets were observed at δH 4.89 and 5.04. In addition, two secondary oxygenated protonsδH 5.02 at (brd,δH 5.02J = 8.3 (brd, Hz) Jand= 8.3 5.19 Hz) (brd, and J =5.19 8.3 Hz) (brd, wereJ = attributed 8.3 Hz) were to two attributed trisubstituted to two double trisubstituted bonds; proton signals appeared at δH 3.93 (brd, J = 11.1 Hz) and 4.39 (dd, J = 10.0, 4.3 Hz). The 13C-NMR doubleexomethylene bonds; exomethylene singlets were singletsobserved were at δ observedH 4.89 and at 5.04.δH 4.89In addition, and 5.04. two In addition,secondary two oxygenated secondary spectrum displayed 20 carbon resonances which were classified by DEPT spectra as four methyls,13 six oxygenatedproton signals proton appeared signals at appeared δH 3.93 (brd, at δH J 3.93= 11.1 (brd, Hz)J and= 11.1 4.39 Hz) (dd, and J = 4.39 10.0, (dd, 4.3 JHz).= 10.0, The 4.3 C-NMR Hz). The methylenes, six methines and four quaternary carbons. In addition, two oxygenated carbons at δC 13C-NMRspectrum spectrum displayed displayed 20 carbon 20resonances carbon resonances which werewhich classified were by classifiedDEPT spectra byDEPT as four spectra methyls, as six four 71.2 and 77.0 and six olefinic carbons at δC 125.4, 137.9, 124.4, 136.9, 154.0, and 109.8 were observed. methylenes, six methines and four quaternary carbons. In addition, two oxygenated carbons at δC methyls,A casbane-type six methylenes, diterpene six skeleton methines was and predicted four quaternary based on NMR carbons. data Incomparisons addition, of two analogous oxygenated 71.2 and 77.0δ and six olefinic carbons at δC 125.4, 137.9, δ124.4, 136.9, 154.0, and 109.8 were observed. carbonsstructures at C 71.2previously and 77.0 isolated and from six olefinicthe same carbonsgenus [4,15,16]. at C 125.4, Characteristic 137.9, 124.4,signals 136.9,at δC 25.0, 154.0, 31.5, and and109.8 A casbane-type diterpene skeleton was predicted based on NMR data comparisons of analogous were20.1 observed. were proposed A casbane-type to constitute diterpene a cyclopropane skeleton moiety was assigned predicted to C-1, based C-14 onand NMR C-15, respectively data comparisons by structures previously isolated from the same genus [4,15,16]. Characteristic signals at δC 25.0, 31.5, and of analogousDQF-COSY structures and HMBC previously analyses. The isolated DQF-COSY from showed the same correlations genus [4 ,between15,16]. Characteristic signals at δH 0.69 signals (td, at 20.1 were proposed to constitute a cyclopropane moiety assigned to C-1, C-14 and C-15, respectively by δC 25.0,J = 10.9, 31.5, 2.6 and Hz) 20.1 and were 0.67 (td, proposed J = 10.9, to 4.0 constitute Hz) with methylene a cyclopropane mutiplet moiety signals assigned δH 1.26 and to C-1,1.80/2.19, C-14 and DQF-COSY and HMBC analyses.
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