title: Isolation, structural assignment and synthesis of (SE)-2-methyloctyl 3-(4-methoxyphenyl) propenoate from the marine soft coral Sarcophyton ehrenbergi.
abstract: A new metabolite 1 has been isolated from the marine soft coral Sarcophyton ehrenbergi along with two known diterpenoids 2 and 3 and cholesterol 4. The structure of 1 was determined by means of detailed spectroscopic analysis and unambiguously confirmed to have the S configuration by the synthesis of both enantiomers using 4-benzyl-2-oxazolidinone auxiliaries. (S)- and (R)-1, 3 and some of the synthetic intermediates were evaluated for cytotoxic activity against human lung cancer (A549), prostate cancer (DU145), cervical cancer (HeLa) and breast cancer (MCF-7) cell lines in an in vitro bioassay.
authors.affiliation: a Natural Products Chemistry Division , Indian Institute of Chemical Technology , Hyderabad 500 007 , India.
authors.forename: Chitturi
authors.initials: C
authors.lastname: Bhujanga Rao
authors.forename: Dokuburra Chanti
authors.initials: DC
authors.lastname: Babu
authors.forename: Tatipamula Vinay
authors.initials: TV
authors.lastname: Bharadwaj
authors.forename: Dudem
authors.initials: D
authors.lastname: Srikanth
authors.forename: Kalivendi Shasi
authors.initials: KS
authors.lastname: Vardhan
authors.forename: Tuniki Venugopal
authors.initials: TV
authors.lastname: Raju
authors.forename: Richard A
authors.initials: RA
authors.lastname: Bunce
authors.forename: Yenamandra
authors.initials: Y
authors.lastname: Venkateswarlu
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001943:Breast Neoplasms; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006367:HeLa Cells; D006801:Humans; D008297:Male; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000596035:(S,E)-2-methyloctyl 3-(4-methoxyphenyl)propenoate; D000970:Antineoplastic Agents; D004224:Diterpenes; D023303:Oxazolidinones; D011422:Propionates
keywords: (S,E)-2-methyloctyl 4-(3-methoxyphenyl)propenoate; Sarcophyton ehrenbergi; cytotoxic assay; marine natural products; synthesis