Trocheliophorin: A novel rearranged sesquiterpenoid from the Indian Ocean soft coralSarcophyton trocheliophorum

Abstract

A novel rearranged sesquiterpenoid, trocheliophorin (1) has been isolated from the soft coral Sarcophyton trocheliophorum besides the known compounds, sarcophytin, methyl arachidonate, and two polyhydroxy steroids (24S)-24-methylcholestane-3beta,5alpha,6beta,25-tetrol-25-monoacetate and (24S)-24-methylcholestane-3beta,5alpha,6beta,25-tetrol. The structure of the new sesquiterpenoid was elucidated by a study of its spectral data.

Oxygenated Cembrene Diterpenes from Sarcophyton convolutum: Cytotoxic Sarcoconvolutum A–E

“…The corresponding FTIR broad bands to hydroxyls and carbonyl groups at 3456 cm −1 and 1763 cm −1 were assigned. The 1 H NMR (Table 1) revealed two oxygenated protons at δ H 2.65 dd (J = 6.8, 3.6 Hz), and 5.45 d (J = 9.4 Hz), three olefineic protons at δ H 5.00 d (J = 9.4 Hz), 5.42 m, and 5.47 m, in addition to four methyls at δ H 1.31 s, 1.41 s, 1.86 s, and 1.87 s. From 13 C NMR, twenty carbon resonances were characterized and categorized to six quartenary (consisting of carbonyl at δ C 174.8; three olefinics at δ C 123.6, 144.4, and 161.7; and two oxygenated carbons at δ C 60.0 and 84.6, five methenes (comprising two oxygenated carbons at δ C 57.0, and 78.8; and two olefinic carbon (at δ C 125.8 and 135.5), five methylenes, four methyls based on DEPT-135 and HSQC analysis. The compound is very similar to 1 except for an up-field shift of δ H 2.65 dd (J = 6.8, 3.6 Hz) by 0.67 ppm and an up-field shift of δ C 57.0 by 14.6 ppm both associated with C-7 and an up-field shift of δ C 60 by 14.5 ppm associated with C-8.…”

“…From 1 H NMR spectrum (Table 1), two oxygenated protons at δH 3.26 br d (J = 10.8 Hz) and 5.53 d (J = 10.4 Hz), three olefinic protons at δH 4.84 br d (J = 10.4 Hz), 5.48 br d (J = 16.3 Hz), and 5.50 m, in addition to four methyls were at δH 1.28 s, 1.37 s, 1.83 s, and 1.87 s were characterized. Twenty carbon resonances were predicted from 13 C NMR (Table 1) and categorized into 6 quaternary (including carbonyl at δC 175.3; three olefinics at δC 123.1, 143.9 and 162.3; alongside of two oxygenated carbons at δC 74.5 and 84.1), five methines (comprising two oxygenated carbons at δC 71.6 and 79.4; as well as three olefinic at δC 121.1, 127.8, and 134.8), five methylenes, four methyls (δC 8.8, 16.5, 20.3, and 24.2) depending upon DEPT and HSQC experiments. The above analyses of 1D NMR of 1 revealed the cembrene-based diterpenoid [6,7,24].…”

“…Such biologically active metabolites are characterized by scaffold diversity and structural complexity. For example, within Sarcophyton soft coral, isolated metabolites include cembrenoids [ 2 , 6 , 7 , 8 , 9 ], diterpene dimers [ 10 , 11 ], sesquiterpenes [ 12 , 13 ], ceramides [ 14 ], steroids [ 15 , 16 ], and prostaglandins [ 17 , 18 ]. Cembrenoids in particular exhibit a significant number of sp 3 carbon centers and oxygen atoms with no nitrogen or halogen atoms.…”

Chemical Diversity in Species Belonging to Soft Coral Genus Sacrophyton and Its Impact on Biological Activity: A Review

“…Continuing the abovementioned isolation from S. glaucum sesquiterpenoid, 6-oxo-germacra-4(15),8,11-triene 373 was also reported [78]. dehydration of ring B of sarcophytin which co-exist in the extract, and removal of ring C and the ring junction methyl and breakage of ring A [112]. In addition, aromadendrene sesquiterpenoid, palustrol 370 from S. trocheliophorum was reported [77].…”

“…Trocheliophorin 369 was isolated from S. trocheliophorum ethyl acetate extract. Through spectral data, its structure was elucidated, revealing that it could be the result of aromatization with dehydration of ring B of sarcophytin which co-exist in the extract, and removal of ring C and the ring junction methyl and breakage of ring A [112]. In addition, aromadendrene sesquiterpenoid, palustrol 370 from S. trocheliophorum was reported [77].…”