New Biologically Active Marine Sesquiterpenoid and Steroid from the Okinawan Sponge of the Genus Axinyssa.

Nat. Prod. Bioprospect.

2013

mentioning

confidence: 99%

Peroxy natural products

Nat. Prod. Bioprospect.

2013

“…1) Previous chemical investigations on sponges of the genus Axinyssa (order Halichondrida, family Halichondriidae) have led to the isolation and identification of various sesquiterpenes containing unusual nitrogenous functional groups as an isocyano, isothiocyanate, thiocyanate, bisabolene and formamide group. [2][3][4][5][6][7][8][9][10][11][12][13][14][15] Some of these N-containing compounds have been found to possess several kinds of biological activities, such as antithelmintic, 2) antimicrobial, 4) antimalarial, 6) antifouling, 11) cytotoxic activities 12) and lethality for brine shrimp. 10) Our investigation of the chemical constituents of a sponge Axinyssa sp.…”

mentioning

confidence: 99%

New Nitrogenous Bisabolene-Type Sesquiterpenes from a Formosan Sponge <i>Axinyssa</i> sp.

CHEMICAL & PHARMACEUTICAL BULLETIN

Liang

Chiang

et al. 2014

Key words sponge; Axinyssa sp.; bisabolene-type; cytotoxicity Studies in the chemistry of marine natural products, the marine sponges have emerged as one of the most prolific sources for discovery of novel secondary metabolites.1) Previous chemical investigations on sponges of the genus Axinyssa (order Halichondrida, family Halichondriidae) have led to the isolation and identification of various sesquiterpenes containing unusual nitrogenous functional groups as an isocyano, isothiocyanate, thiocyanate, bisabolene and formamide group.2-15) Some of these N-containing compounds have been found to possess several kinds of biological activities, such as antithelmintic, 2) antimicrobial, 4) antimalarial, 6) antifouling, 11) cytotoxic activities 12) and lethality for brine shrimp. 10) Our investigation of the chemical constituents of a sponge Axinyssa sp. yielded two new nitrogenous bisabolene-type sesquiterpenes, axinysalines A (1) and B (2), along with three known sesquiterpenes. The structures of 1 and 2 were established by detailed spectroscopic analysis and comparison of their NMR data with those of known analogues. The known sesquiterpenes were readily identified as 3-isocyanotheonellin (3), 16) 3-isocyano-7,8-epoxy-α-bisabolane (4) 7) and 3-formamidotheonellin (5), 17) by comparison of their spectral data with those reported in the literature. The cytotoxicity of metabolites 1-5 against the six cancer cell lines, human erythromyeloblastoid leukemia (K562), human T lymphoblast, acute lymphoblastic leukemia (Molt 4), human colon adenocarcinoma (HCT-116 and DLD-1), and human breast carcinoma (MDA-MB-231 and T47D) was studied.Compound 1, named axinysaline A, was isolated as an optically active, colorless oil. The molecular formula was determined to be C 21 H 35 NO 3 by high resolution-electrospray ionization (HR-ESI)-MS (m/z 372.2515, C 21 H 35 NO 3 Na) and NMR data, which corresponded to five degrees of unsaturation. The IR spectrum of 1 showed absorption bands at 3375, 1679 and 1746 cm −1 , suggesting the presence of an amide CO group and an ester CO group, which were supported by 13 C-NMR chemical shifts at δ 171.9 and 169.2 ppm, respectively. The 13 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectral data of 1 showed the presence of 21 carbons (Table 1): seven methyls, four sp 3 methylenes, two sp 3 methines, three sp 2 methines, and two sp 3 quaternary carbons. The remaining three signals appearing in the lower field region of the spectrum are due to the quaternary carbons of one olefinic carbon (δ 140.2), one amide carbonyl and one ester carbonyl. From the 1 H-NMR spectrum of 1, the resonances of three olefinic protons (δ H 6.22, dd, J=14.5, 11.0 Hz; 5.81, d, J=11.0 Hz; 5.59 dd, J=15.5,7.0 Hz) were observed. Moreover, analysis of the 1

“…-Sponges of the genus Axinyssa have previously been reported to yield a variety of sesquiterpenes containing unusual nitrogenous functional groups, such as isothiocyanate, formamide, isonitrile, and thiocyanate [1 -5]. Most of these Ncontaining compounds have exhibited various biological activities such as antithelmintic [1], antimicrobial [3], antimalarial [5] activities, and lethality for brine shrimp [6], which attracted considerable attention from natural-product chemists and pharmacologists.…”

mentioning

confidence: 99%

“…Many bisabolene-type sesquiterpenes exhibited broad bioactivities such as antithelmintic [1], antimicrobial [3], antimalarial [5] activities, and lethality for brine shrimp [6]. Compounds 1 -5 have been evaluated for cytotoxity against several tumor cell lines, but they were all inactive at a concentration of 10 mg/ml.…”

mentioning

confidence: 99%

New Epoxy‐Substituted Nitrogenous Bisabolene‐Type Sesquiterpenes from a Hainan Sponge Axinyssa sp.

Sun

Chen

et al. 2010

Helvetica Chimica Acta

Two new uncommon epoxy-substituted nitrogenous bisabolene-type sesquiterpenes, 3-formamido-7,8-epoxy-a-bisabolane (4), 3-isocyano-7,8-epoxy-a-bisabolane (5), together with three known related sesquiterpenes, 1 -3, were isolated from the Hainan sponge Axinyssa sp. Their structures were determined on the basis of extensive spectroscopic analyses and by comparison of their NMR data with those of structurally related compounds.