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Mar. Drugs 2016, 14(2), 41; doi:10.3390/md14020041

Bisdioxycalamenene: A Bis-Sesquiterpene from the Soft Coral Rhytisma fulvum fulvum
Yuval J. Trifman 1, Maurice Aknin 2, Anne Gauvin-Bialecki 2, Yehuda Benayahu 3, Shmuel Carmeli 1 and Yoel Kashman 1,*
School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel
Laboratory of Chemistry of Natural Substances and Food Sciences, Faculty of Science and Technology, University of Reunion Island, 15 Avenue René Cassin, CS 92003, 97744 Saint-Denis Cedex 9, La Reunion, France
Department of Zoology, George S. Wise Faculty of Life Sciences, Tel Aviv University, Tel Aviv 69978, Israel
Correspondence: Tel.: +972-3-6408-419; Fax: +972-3-6409-293
Academic Editor: Orazio Taglialatela-Scafati
Received: 14 January 2016 / Accepted: 14 February 2016 / Published: 19 February 2016


: A dichloromethane extract of the soft coral Rhytisma fulvum fulvum collected in Madagascar afforded a novel compound possessing an unprecedented pentacyclic skeleton, bisdioxycalamenene (1), as well as seven known sesquiterpenes. The structures of the compounds were elucidated using 1D and 2D NMR techniques, as well as high-resolution mass spectrometry. The absolute configuration of 1 was determined using X-ray diffraction analysis and anomalous dispersion effects. The structure elucidation and a possible biogenesis of the compound are discussed.
Rhytisma fulvum fulvum; soft coral; bisdioxycalamenene; bis-sesquiterpene

1. Introduction

The soft coral Rhytisma fulvum fulvum (Forskål) (R. fulvum fulvum) (previously Parerythropodium), family Alcyoniidae, was originally described from the Red Sea [1,2]. Its present zoogeographical distribution extends south to the reefs of Madagascar and eastward to Indonesia [3,4]. The Genera Rhytisma is a rich source of sesquiterpenoids and norsesquiterpenoids containing a variety of skeletons as well as sterols [5,6,7,8,9]. Dozens of compounds have thus far been reported with different ring systems [5,6,7,8,9]. In previous research, our group compared the yellow and gray morphs that inhabit the reefs of the gulf of Eilat and found differences in the compounds they produce [6]. Inter alia, we isolated a volatile yellow pigment, fulfulvene, from the yellow morph. This pigment is responsible for the soft coral’s yellow color [6]. The pigment and other volatile compounds, mainly sesquiterpenes, are lost during freeze drying and/or evaporation [6].
The present study describes the isolation and structure elucidation of a novel bis-sesquiterpene designated bisdioxycalamenene (1) and of seven known sesquiterpenes, 5-hydroxy-8-methoxycalamenene (2) [10], 8-methoxycalamenene (3) [10], 5-hydroxy-8-methoxycalamenene-15-al (4) [10], (1S,4S,10S,12S,Z)-1,3,12-trimethyl-5-oxo-1,4,5,6,7,10,11,12-octahydrobenzo[8]-annulene-4,10-diyldi-acetate (5) [11], 2-oxolemnacarnol (6) [5], lemnacarnol (7) [5], and 6α-acetyl-4β,5β-dimethyl-1(10)-α-epoxy-2α-hydroxy-7-oxodecalin (8) [12], from a yellow morph specimen of Rhytisma fulvum fulvum collected on December 2012 at Banc du Castor, Mitsios Archipelago, Madagascar (Figure 1). Bisdioxycalamenene (1) is a bis-sesquiterpene possessing an unprecedented pentacyclic skeleton that is probably derived from dimerization of 5-hydroxy-8-methoxycalamenene (2) [10].

2. Results and Discussion

Bisdioxycalamenene (1) was isolated from the crude extract using solvent partition, followed by separations on Sephadex LH-20 and Silica gel-H. The positive atmospheric pressure photoionization high-resolution mass spectrometry (APPI HRMS) of 1 exhibited a molecular ion [M]+ at m/z 478.3080 consistent with the molecular formula C31H42O4 and eleven double bond equivalents. The structure elucidation of 1 was based on its mass-spectrometric and NMR data (Table 1, CDCl3). The 1H NMR exhibited two singlet signals in the lower and mid-field of the spectrum (δH 6.36 and 4.39), a methoxyl (δH 3.74), six protons resonating between 3.40 and 2.50 ppm, ten sp3 protons resonating between 2.00 and 1.40 ppm, a singlet methyl (δH 1.33) and six doublet methyl signals resonating between 1.10 and 0.75 ppm. The 13C NMR presented two ketone carbonyls (δC 199.4 s and 195.3 s), eight sp2 carbon atoms (δC 151.7, 150.3, 147.3, 144.0, 130.6, 129.1 and 115.4, all quaternary carbons, and 107.5, CH), a oxymethine carbon (δC 83.9, CH), and a methoxyl (δC 55.2, CH3). In the high field, one quaternary sp3 carbon (δC 48.0), six methine carbons (δC 37.0, 36.9, 32.3, 31.1, 27.2 and 26.5), four methylene carbons (δC 25.6, 25.5, 19.5 and 18.5) and seven methyl carbons (δC 21.7, 21.4, 21.3, 20.2, 21.9, 20.0 and 21.8) were observed. The above proton and carbon signals counted to 31 carbons and 42 protons, agreeing with the molecular formula of 1.
The C-H correlations from a heteronuclear single quantum coherence (HSQC) experiment established the one bond connectivity between the carbons and protons (Table 1). The H-H correlations from a correlation spectroscopy (COSY) experiment furnished two similar segments; a and b, shown in Figure 2, leaving an additional isolated strong coupled methylene group (δH 3.35 and 2.53 ppm) and four isolated proton signals (δH 6.36, s, 1H; 4.39, s, 1H; 3.74, s, 3H; 1.33, s, 3H) uncorrelated. Segments a and b are similar each other and both to the aliphatic portion of the calamenene sesquiterpenes (24) [10].
Using long-range C-H correlations from a heteronuclear multiple bond correlation (HMBC) experiment enabled the connection of all the proton and carbon signals to the final gross planar structure of 1 (Figure 3). H-1 and -4 exhibited correlations with C-8 and -5, respectively, and both with C-9 and -10, extending fragment a to a 1-isopropyl-4-methyl-2-cyclohexene moiety substituted at positions 2 and 3 by two ketone groups. Oxymethine-7 presented HMBC correlations with C-5, -6, -8 and -9, while methyl-15-protons exhibited correlations with C-5, -6, and -7, closing a second six-membered ring. H-1′ and -4′ demonstrated a similar pattern of correlations (Figure 3), extending fragment b to a 1,4-disubstituted cyclohexene ring. H-7′ exhibited HMBC correlations with C-1′, -5′, -6′, -8′, -9′ and -15′, while methylene-15′-protons presented correlations with C-5′, -6′, -7′ and -8′, and the methoxy-protons exhibited correlations with C-8′, supporting a substituted 15-methylene-8-methoxy-5-oxy-calamenene substructure. The HMBC correlations of H-7 with C-5′ and -15′, of methyl-15-protons with C-15′ and of both protons of methylene-15′ with C-5, -6 and -7 suggested the connection of C-6 with C-15′ and C-7 through the oxygen to C-5′, establishing the planar structure of 1.
The relative trans relationships of the 1,4- and 1′,4′-substituents of the two cyclohexene rings were suggested when comparing the chemical shifts of the corresponding protons and carbons with those of the known calamenenes (24). The cis 6–7 junction was established based on the NOE between H-7 and methyl-15. The complete structure including absolute configuration was confirmed by the X-ray diffraction analysis.
Crystallization of bisdioxycalamenene (1) from CHCl3/MeOH solution furnished suitable crystals for an X-ray diffraction analysis. Bisdioxycalamenene (1) comprises of a pentacyclic structure derived from coupling of two sesquiterpenes. The asymmetric unit contains assemblages of two molecules of 1, thus in one monoclinic cell there are four molecules of 1. Anomalous dispersion effects and relation of the two enantiomeric forms of the structural model to the diffracted intensities established the absolute configuration. The preferred fit is indicated by the Flack and Parsons parameter (Flack parameter, x = 0.01 (9)) [13]. The X-ray diffraction analysis established the complete structure of 1 including the absolute configuration of the six chiral centers (1S,1′S,4R,4′R,6S,7R) shown in Figure 4.
To the best of our knowledge, there are no earlier reports of such a skeleton. A possible biogenetic route to 1 is a hetero Diels Alder condensation of the para-quinone c with the ortho-quinonemethide, d [14,15] (Figure 5).
Compound 1 was evaluated for lethal toxicity in a brine shrimp toxicity assay (Artemia salina) [16] and displayed mild toxicity (LD50 15 μg/mL). Compound 1 was assayed for antibacterial activity against Pseudomonas aeruginosa and Escherichia coli and found to be inactive at 10 μg/mL.

3. Experimental Section

3.1. General Experimental Procedures

Optical rotations were determined on a JASCO P-1010 polarimeter. UV spectra were recorded on an Agilent 8453 spectrophotometer. NMR spectra were recorded on a Bruker DMX-500 spectrometer at 500.13 MHz for 1H and 125.76 MHz for 13C and a Bruker Avance 400 spectrometer at 400.13 MHz for 1H and 100.62 MHz for 13C. DEPT, COSY-45, gTOCSY (mixing time 60 ms), gROESY (spinlock pulse 0.2 s), gHSQC, and gHMBC spectra were recorded using standard Bruker pulse sequences. Mass spectra were recorded on a Synapt High Definition Mass Spectrometry (Waters Inc., Milford, MA, USA) instrument. For the GC MS analysis, separation of the crude samples was performed on an Agilent-7890-GC equipped with Agilent-5977A-MSD with an HP-5MS UI column (30 meter × 0.25 mm × 0.25 μm). The X-ray diffraction patterns were obtained with CuKα radiation from an Imus microsource, on an ApexDuo Bruker-AXS diffractometer.

3.2. Biological Material

A sample of the soft coral R fulvum fulvum (yellow morph, Phylum Cnideria, Class Anthozoa, Order Alcyonacea, Family Alcyoniidae) was collected in December 2012 at a depth of 15 m at Banc du Castor, Mitsios Archipelago, Madagascar. It was identified by Professor Yehuda Benayahu. A voucher specimen (MAD12-IM052) was deposited at the Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments (LCSNSA) at the University of Reunion Island, France. The soft coral sample was frozen immediately after collection and kept at −20 °C until processed.

3.3. Isolation Procedure

The wet sample (0.3 kg wet weight) of the soft coral was extracted with CH2Cl2–MeOH (1:1, 300 mL) at room temperature overnight. The aqueous phase was separated from the organic layer, which was dried and evaporated to afford an oily crude extract (9 g, 3% of dry weight). The crude organic extract was separated in 2 g portions using Kupchan solvent partition [17]. The petroleum ether fraction (970 mg) was chromatographed on a Sephadex LH-20 column (petroleum ether/CH2Cl2/MeOH, 2:1:1) followed by several separations on Silica gel 60 H (Merck) columns (VLC and gravitational columns), eluting with EtOAc-petroleum ether mixtures to afford bisdioxycalamenene (1) (eluted with 2% EtOAc in petroleum ether, 15 mg, 0.023% yield from wet sample) and seven known compounds: 5-hydroxy-8-methoxycalamenene (2) [10] (46.5 mg, 0.29% yield from wet sample), 8-methoxycalamenene (3) [10] (6 mg, 0.009% yield wet sample), 5-hydroxy-8-methoxycalamenene-15-al (4) [10] (0.0045% yield from wet sample), (1S,4S,10S,12S,Z)-1,3,12-trimethyl-5-oxo-1,4,5,6,7,10,11,12-octahydrobenzo[8]annulene-4,10-diyl diacetate (5) [11] (6 mg, 0.0045% yield from wet sample), 2-oxolemnacarnol (6) [5] (2 mg, 0.0024% yield from wet sample), lemnacarnol (7) [5] (4 mg, 0.003% yield from wet sample), and 6α-acetyl-4β,5β-dimethyl-1(10)-α-epoxy-2α-hydroxy-7-oxodecalin (8) [12] (3 mg, 0.0024% yield from wet sample).
Bisdioxycalamenene (1): yellowish crystals from CHCl3/MeOH; [ α ] D 23 −175 (c 0.20, hexane); UV (Hexane) λmax (log ε) 204 (4.07), 258 (3.44), 656 (1.70) nm; IR (ATR Diamond) νmax 1684, 1613 cm−1; 1H and 13C NMR data, see Table 1; HRMS APPI+ exhibited a molecular ion [M]+ at m/z 478.3080 (calculated for C31H42O4, 478.3083).

3.4. X-Ray Crystallography

The structure of 1 was confirmed by single crystal X-ray diffraction analysis of a crystal obtained from a CHCl3/MeOH solution. The measurements were carried out on an ApexDuo (Bruker-AXS) diffractometer with CuKα radiation at low temperature in order to optimize the precision of the crystallographic determinations.
Crystal data: C31H42O4, M = 478.65, monoclinic space group P21, T = 110(2) K, DC = 1.217 g·cm−3, F(000) = 1040.0. Crystal structure approximate dimensions 0.106 × 0.265 × 0.493 mm3.
A total of 4174 frames were collected. The frames were integrated with the Bruker SAINT Software package using a narrow-frame algorithm. The integration of the data using a monoclinic unit cell yielded a total of 16,453 reflections to a maximum θ angle of 66.84° (0.84 Ǻ resolution), of which 7667 were independent (average redundancy 2.146, completeness = 97.0%, Rint = 3.22%, Rsig = 4.10%) and 7399 (96.50%) were greater than 2σ (F2). The final cell constants of: a = 9.5661(4) Ǻ, b = 10.5930(5) Ǻ, c = 25.8443(13) Ǻ, β = 93.725(3)°, volume = 2613.4(2) Ǻ3, are based upon the refinement of the XYZ-centroids of 132 reflections above 20 σ(I) with 19.19° < 2θ < 75.06°. Data were corrected for absorption effects using the multi-scan method (SADABS). CCDC number: 1414246.

3.5. Brine Shrimp Toxicity Assay

Bisdioxycalamenene (1) was evaluated for lethal toxicity in a brine shrimp (Artemia salina) toxicity assay [16], which displayed mild toxicity (LD50 > 10 μg/mL). The evaluation of brine shrimp toxicity (Artemia salina) was performed as previously reported [16].

4. Conclusions

The soft coral R. fulvum fulvum is widely distributed throughout the Indopacific [1,2,3,4] and present several color morphs. The genus Rhytisma is very rich in sesquiterpenes, norsesquiterpenes and other metabolites such as fulfulven that gives the yellow morph of R. fulvum fulvum its color [1,2,3,4,5,6,7,8,9]. In the present study, we have isolated, from a specimen collected in Madagascar, a sesquiterpene dimer of new pentacyclic skeleton, bisdioxycalamenene (1), along with seven previously described metabolites of R. fulvum fulvum. Although 1 did not present significant biological activity in the set of bioassays, we believe that there should be a good reason for its biosynthesis and for the investment of considerable amount of energy in it. Such purpose might be, for example, involvement in the reproduction process of soft coral as demonstrated for alkyl acetylenes produced by the hard coral Montipora digitata and the cembrane type diterpenoids in the soft coral Lobophytum compactum [18].

Supplementary Materials

1D (1H, 13C) and 2D NMR (HSQC, HMBC, COSY) spectra and HR MS data of compound 1, and photograph of the soft coral, are available.


The authors thank Yardena Abudi for technical assistance; Sophia Lipstman, the X-ray Diffractometer Facility of the School of Chemistry, Tel Aviv University, for the measurements and analysis of the X-ray diffraction; Noam Tal, the Mass Spectrometry Facility of the School of Chemistry, Tel Aviv University, for the measurements of the mass spectra; and Sigal Shefer from the Department of Zoology, for guidance with the brine shrimp toxicity assay.

Author Contributions

Y.J.T. contributed to the isolation and structure elucidation and writing of the manuscript with the supervision of S.C. and Y.K. M.A. and A.G.-B. contributed to the collection and extraction of the sample of the soft coral; Y.B. contributed to the identification the soft coral. S.C. and Y.K. contributed to the structure elucidation, writing and editing of the manuscript.

Conflicts of Interest

The authors declare no conflict of interest.


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Figure 1. Rhytisma fulvum fulvum metabolites isolated in the current study.
Figure 1. Rhytisma fulvum fulvum metabolites isolated in the current study.
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Figure 2. COSY (bold line) correlations of 1.
Figure 2. COSY (bold line) correlations of 1.
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Figure 3. COSY (bold line) and key HMBC correlations (arrows) of 1.
Figure 3. COSY (bold line) and key HMBC correlations (arrows) of 1.
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Figure 4. Oak Ridge Thermal-Ellipsoid Plot Program (ORTEP) presentation of 1.
Figure 4. Oak Ridge Thermal-Ellipsoid Plot Program (ORTEP) presentation of 1.
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Figure 5. A possible biogenetic route for 1.
Figure 5. A possible biogenetic route for 1.
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Table 1. NMR Data of Bisdioxycalamenene (1) in CDCl3 a.
Table 1. NMR Data of Bisdioxycalamenene (1) in CDCl3 a.
PositionδC, Type bδH, Mult (J in Hz)HMBC Correlations cCOSY Correlations
127.2, CH2.99, ddq (1.3, 6.8, 7.0)2, 3, 5, 8, 9, 10, 112a, 11
225.5, CH21.84, m 101
1.46, m3a, 3b, 12
318.5, CH21.74, m 10 2b, 3b, 4, 12
1.61, m4, 102b, 3a, 4
436.9, CH2.66, dt (2.3, 6.0)2, 3, 5, 9, 10, 12, 143a, 3b, 12
5199.4, qC
648.0, qC
783.9, CH4.39, s5, 6, 8, 9, 15, 5′, 15′
8195.3, qC
9150.3, qC
10147.3, qC
1120.1, CH31.10, d (7.0)1, 2, 9, 101
1231.1, CH1.82, m3, 42b, 3a, 4, 13, 14
1321.3, CH30.87, d (7.0)4, 12, 1412
1420.2, CH30.85, d (7.0)4, 1212
1521.8, CH31.33, s5, 6, 7, 6′, 15′
1′26.5, CH3.09, dq (6.5,7.0)2′, 3′, 8′, 9′, 10′, 11′2′a, 11′
2′25.6, CH21.93, m 10′ 1′, 2′b, 3′
1.41, m4′, 9′3′
3′19.5, CH21.70, m1′, 4′, 10′, 12′2′a, 2′b, 4′
4′37.0, CH2.72, dt (2.3, 5.9)2′, 5′, 9′, 10′, 12′, 14′1′, 3′, 12′
5′144.0, qC
6′115.4, qC
7′107.5, CH6.36, s5′, 8′, 9′, 15′
8′151.7, qC
9′130.6, qC
10′129.1, qC
11′21.9, CH31.07, d (7.0)1′, 2′, 9′1′
12′32.3, CH1.86, m3′, 10′, 14′4′, 13′, 14′
13′21.7, CH30.86, d (7.0)4′, 12′12′
14′21.4, CH30.77, d (7.0)4′, 12′12′
15′33.1, CH23.35, d (16.5) 5, 6, 7, 8, 15, 5′, 6′, 7′, 8′, 9′
2.53, d (16.5)5, 6, 7, 15, 5′, 6′, 7′, 8′, 9′, 10′
16′55.2, CH33.74, s7′, 8′
a 500 MHz for 1H, 125 MHz for 13C; b Multiplicity and assignment from HSQC experiment; c HMBC correlations, optimized for 8 Hz, are from the proton(s) stated to the indicated carbon.
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