Isolation, structural assignment and synthesis of (SE)-2-methyloctyl 3-(4-methoxyphenyl) propenoate from the marine soft coral Sarcophyton ehrenbergi

Rao, Chitturi Bhujanga; Chanti Babu, Dokuburra; Vinay Bharadwaj, Tatipamula; Srikanth, Dudem; Shasi Vardhan, Kalivendi; Venugopal Raju, Tuniki; Bunce, Richard A.; Venkateswarlu, Yenamandra

doi:10.6084/m9.figshare.1172164.v2

gnpl_a_958742_sm6723.doc (788 kB)

Isolation, structural assignment and synthesis of (SE)-2-methyloctyl 3-(4-methoxyphenyl) propenoate from the marine soft coral Sarcophyton ehrenbergi

Version 2 2014-10-30, 11:54

Version 1 2014-10-30, 11:54

journal contribution

posted on 2014-10-30, 11:54 authored by Chitturi Bhujanga Rao, Dokuburra Chanti Babu, Tatipamula Vinay Bharadwaj, Dudem Srikanth, Kalivendi Shasi Vardhan, Tuniki Venugopal Raju, Richard A. Bunce, Yenamandra Venkateswarlu

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.