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Bio-Active Sesquiterpenoids and Norsesquiternoids from the Red Sea Octocoral Rhytisma Fulvum Fulvum

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Bio-Active Sesquiterpenoids and Norsesquiternoids from the Red Sea Octocoral Rhytisma Fulvum Fulvum Natural Product Research Formerly Natural Product Letters ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: https://www.tandfonline.com/loi/gnpl20 Bio-active sesquiterpenoids and norsesquiternoids from the Red Sea octocoral Rhytisma fulvum fulvum Seif-Eldin Nasr Ayyad, Mohamed Ali Deyab, Tamer Kosbar, Walied Mohamed Alarif & Ahmed Hassan Eissa To cite this article: Seif-Eldin Nasr Ayyad, Mohamed Ali Deyab, Tamer Kosbar, Walied Mohamed Alarif & Ahmed Hassan Eissa (2019): Bio-active sesquiterpenoids and norsesquiternoids from the Red Sea octocoral Rhytismafulvumfulvum, Natural Product Research, DOI: 10.1080/14786419.2019.1709187 To link to this article: https://doi.org/10.1080/14786419.2019.1709187 View supplementary material Published online: 30 Dec 2019. Submit your article to this journal Article views: 96 View related articles View Crossmark data Full Terms & Conditions of access and use can be found at https://www.tandfonline.com/action/journalInformation?journalCode=gnpl20 NATURAL PRODUCT RESEARCH https://doi.org/10.1080/14786419.2019.1709187 Bio-active sesquiterpenoids and norsesquiternoids from the Red Sea octocoral Rhytisma fulvum fulvum Seif-Eldin Nasr Ayyada, Mohamed Ali Deyabb, Tamer Kosbara, Walied Mohamed Alarifc and Ahmed Hassan Eissaa aDepartment of Chemistry, Faculty of Science, Damietta University, Damietta, Egypt; bBotany Department, Faculty of Science, Damietta University, Damietta, Egypt; cDepartment of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, Jeddah, Saudi Arabia ABSTRACT ARTICLE HISTORY Three previously undescribed nardosinane-type sesquiterpenes Received 16 September 2019 (1–3), together with six known compounds (4–9) were isolated Accepted 11 December 2019 from the alcyonacean soft coral Rhytisma fulvum fulvum. 2 and 3 are 13-nornardosinane, and 6,7-seco-13-nornardosinane deriva- KEYWORDS tives, respectively. 2 could be an artifact due to C-6 epimerization Red sea; soft coral; sesquiterpenes; cytotoxic; of the known one 4. Chemical structures were elucidated based antimicrobial on 1 D, 2 D NMR and MS spectral data. Compounds 1-8 showed cytotoxic activity against NCI-H1299, HepG2 and MCF-7 with IC50 values between 0.0352–0.0974, 0.0717–0.3745 and 0.0341–0.1325 mM, respectively. The antibacterial activity of all isolated compounds have examined against a number of Gram- positive (Bacillus cereus, Staphylococcus aureas) and Gram-negative (Escherichia coli, Klebsiella pneumoniae and Pseudomonas sp.) bac- teria. Compounds 6 and 7 showed a high degree of inhibition against B. cereus, S. aureus and Pseudomonas sp. Interestingly, neolemnane (6) showed strong inhibition against two fungi, Aspergillus niger and Fusarium oxysporum; while 8 showed positive inhibition against Fusarium oxysporum at 150 mg/mL. CONTACT Seif-Eldin Nasr Ayyad [email protected] Department of Chemistry, Faculty of Science, Damietta University, Damietta, Egypt. Supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2019.1709187. ß 2019 Informa UK Limited, trading as Taylor & Francis Group 2 S.-E. N. AYYAD ET AL. 1. Introduction The Genera Rhytisma, family Alcyoniidae, an Indopacific soft coral exists in two colour morphs: yellow-brown and grey, was initially identified from the Red Sea waters (Benayahu and Loya 1983;Alderslade2000). Interestingly, in spite of its taxonomic classification as an Alcyoniidae member, the secondary metabolites profile of Rhytisma revealed its close similarity to those of two Genera Lemnalia and Paralemnalia belonging to the family Nephtheidae. Nevertheless, The DNA of Rhytisma showed its closeness to the family Xeniidae rather than the Alcyoniidae (Haverkort-Yeh et al. 2013). To the best of our knowledge, 28 metabolites were reported from the genus Rhytisma including: sesquiterpenes, norsesquiterpenes and bis-sesquiterpenes as well as steroids (Kashman 1979; Bowden et al. 1980; Green et al. 1992; Jurek and Scheuer 1993; Wessels et al. 2001; Bishara et al. 2008; Trifman et al. 2016). In The present work the secondary metabolite content of the soft coral Rhytisma fulvum fulvum (family Alcyoniidae), collected from the Red Sea Coast at Jeddah, Saudi Arabia was investigated. Fractionation and purification of the organic extract of this animal were achieved by successive column and preparative Thin-Layer chromatography (TLC), led to isolation and identification of nine compounds (1–9)(Figure 1). Figure 1. Isolated compounds from Rhytisma fulvum fulvum. NATURAL PRODUCT RESEARCH 3 2. Results and discussion 2.1. Structure elucidation Compound 1 was isolated as optical active yellow oil. HRESIMS and 13C NMR assigned the 1 13 molecular formula as, C17H26O3,andfivedouble-bondequivalents.The H- and CNMR spectra revealed the presence of one carbonyl (dC 212.9 C), an acetyl (dC 170.7 C, 20.7 CH3; dH 2.02 s) and a tri-substituted double-bond (dC 137.5 C, 123.8 CH; dH 5.56 d) (cf. exp., Figure S2). The aforementioned functionalities account for three unsaturation degrees, sug- gesting a bicyclic structure. In addition to the methyl of acetate group, 1HNMRspectra indicated the presence two secondary methyls (dH 0.94, d and 0.81, d) and a tertiary one 13 3 (dH 0.90, s). Further analysis of the C and DEPT NMR experiments displayed one sp qua- 3 ternary carbon (dC 42.7), three sp methines (dC 61.9, 32.8 and 31.3), one oxygenated- methylene (dC 66.1), as well as four upfield-methylenes (40.5, 30.6, 26.6 and 25.5). With the aid of HSQC experiments, all protons were accounted and the compound contains no hydroxyl function. From the 1H-1H COSY spectrum, three separate couplings in the form of cross-peaks were observed between; the first one being between H-12 and H-11, H-11 and H-13, the second H-2 coupled with H-3, H-3 coupled with H-4, and H-4 coupled with H-14, while the third one noted started from the olefinic proton H-7 resonating at dH 5.56 to H- 8, H-8 to H-9 and H-9 to H-10 (As depicted in Figure S1). HMBC correlations established the connections of CH3-14 to C-4 and CH3-15 to C-5, as well as H-11 to C-6, C-13 and C12 (Figure S1). The above-mentioned observations and reviewing literatures on metabolites isolated from the genus Rhytisma reflect the presence of a nardosinane-type sesquiterpene. The locations of the carbonyl and the acetate functions were established from the HMBC spectra as shown in Figure S1.Thestructureofcompound1, namely, 12-O-acetyl-nardo- sinan-6-en-1-one is shown in Figure 1. The relative stereochemistry of 1 was concluded by studying the NOESY cross-peaks. NOEs observed between all the methyl protons (Me-13, 14 and 15) suggest their co-facial orientation, the b-side; consequently, the a-side is occu- pied by H-4 and H-10. The absolute stereochemistry of 1 was concluded as depicted in Figure 1, on the basis biogenetic considerations and on comparison of the obtained 13C NMR data with those in the literature (Bishara et al. 2008;Dalozeetal.1977). Compound 2 was isolated as optical active yellow oil. HRESIMS and 13C NMR assigned the molecular formula as, C14H20O3, and five double-bond equivalents. Analysis of its 13C NMR spectrum and DEPT spectra showed the presence of two car- bonyl functions (dC 207.3 and 206.1 ppm), which accounted for two oxygen-atoms (cf. exp., Figure S3). The absence absorption due to hydroxyl functions in the IR spectrum; assigned the third oxygen atom to an etheric function. Based on the absence of reso- nances in the low-field region, compound 2 is a tricyclic skeleton. The presence of 1 13 oxirane ring was evidenced from the H- and C NMR absorptions (dC 65.1 C and 61.8; 1 1 dH 3.16 d). Extensive studies of HSQC, H- H COSY and HMBC spectral data (Figure S1) indicated a 13-nornardosinane structure (Izac et al. 1982; Jurek and Scheuer 1993, Bishara et al. 2008). On comparing the obtained spectral data of 2 with these of the known co-occurred 6a-acetyl-4b,5b-dimethyl-1(10)-a-epoxy-7-oxodecalin (4) (Izac et al. 1982; Jurek and Scheuer 1993), the orientation of the H-6 proton is being the only dif- ference. The NOESY correlation cross-peaks were observed between the methyl pro- tons of CH3-14 and CH3-15, as well as H-1. No NOEs observed between the latter 4 S.-E. N. AYYAD ET AL. protons (b-side) and H-6, which assigns a-configuration to H-6. Analysis of coupling con- stants revealed the absence of w-coupling between H-6 and Heq-8, confirmed the C-6 b-substituent. Compound 2 was assigned as 6b-acetyl-1(10)-a-13-nornardosin-7-one. The new compound 2 is an isomer to 4 (which previously isolated from Paralemnalia thyrsoide) (Izac et al. 1982). Compound 4, also isolated in this article from R. fulvum ful- vum and the 1Hand13C NMR spectral data of 4 was in good agreement with those reported in the literature (Izac et al. 1982). However, adsorption of 4 on Si gel for hours resulted in epimerization at C-6 and provided a mixture of both compounds 2 and 4. Therefore, generation of 2 from 4 during isolation cannot be excluded. Compound 3 was isolated as faint yellow oil. EIMS, HRESIMS and 13C NMR assigned the molecular formula of 3 as, C15H24O4, with four unsaturation equivalents. Two sites of unsaturation were accounted as two carbonyl groups; a ketone and an ester functions (dC 208.6 and 173.7; respectively), implies a bicyclic skeleton. DEPT experiments showed the presence of 4 methyl, 5 methylene, 2 methine and 4 quaternary carbons. 1H- and 13C NMR spectra, as well as HSQC experiments (Figure S4), evidenced the presence of a tri-substituted epoxide ring (dC 62.9 C, 55.6 CH; dH 2.89 t), an oxygenated methyl (dC 51.4 CH3; dH 3.64 s), one secondary methyl (dC 15.8 CH3; dH 0.84 d) and two tertiary methyls (dC/dH 18.0 CH3/1.00 s and 32.4 CH3/2.19 s).
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