Sesquiterpenes from the Vietnamese Marine Sponge Dysidea Fragilis

Abstract

Two new sesquiterpenes, named dysinidins A-B (3, 4) along with two known sesquiterpenes, furodysinin lactone (1) and O-methyl furodysinin lactone (2), were isolated from the Vietnamese marine sponge Dysidea fragilis. Their structures were determined by 1D-and 2D-NMR spectroscopies and HR ESI MS, as well as by comparison with reported literature data. None of compounds showed inhibitory growth of human lung cancer cell lines, A-549 and H-1975 (IC 50 > 30μM).

The chemical constituents and biological activity of some sponges in Northern Vietnam: A review

“…Meanwhile, steroid 16 has only toxic effects on two tested cancer cell lines P388 and PC-3 (IC50 31.37 and 81.93 µg/mL), and steroid 18 with double bond at C-4/C-5 and a hydroxy group at C-6 did not show cytotoxic activity on experimental cancer cell lines. Besides the above steroids, from Amorphinopsis excavans, Stylissa flabelliformis and Haliclona oculata, we isolated more other steroids as 24-methylenecholest-4-en-3β,6β-diol (19), 3βhydroxy-5-cholenic acid methyl ester (20), ergosta-6,22-dien-3β,5α,8α-triol (21), (24S)-ergostane-3β,5α,6β,25-tetraol (22), 29-hydroxystigmasta-5,24(28)-dien-3β-ol (23), and cholest-7-en-3β,5α,6βtriol (24). [14,15] Among the steroids 19-24, compound 24 exhibited the best cytotoxic effect, with IC50 values between 10.32-13.99 µg/mL.…”

“…From Dysidea, D. fragilis, we found 11 sesquiterpenes with similar carbon frames to those of furodysin and spirodysin sesquiterpene, including 8 new compounds named as dysinidine I (46), dysinidine II (47), dysinidine III (48), dysinidin A (52), dysinidin B (53), dysinidin C (49), dysinidin D (50), and dysinidin E (51). [19,[23][24][25] Compounds 46 and 47 were identified as two homologous epimer sesquiterpene at C-3 and form the spirodysin carbon frame. The difference in stereochemistry at C-3 of these two compounds is demonstrated by a clear difference in the chemical shift of C-3 and the spatial interactions of protons H-3 and H2-9.…”

“…In addition, three sesquiterpene compounds previously published such as furodysinin lactone (54), O-methyl furodysinin lactone (55), and O-methyl-9-oxofurodysinin lactone (56) were also isolated from Dysidea fragilis. [26] The content of compound 55 (0.85 %, w/w) in methanol extract of D. fragilis species was quantified by HPLC-DAD method. In addition, three previously conquiterpene compounds such as furodysinin lactone (54), O-methyl furodysinin lactone (55), and O-methyl-9-oxofurodysinin lactone (56) were also isolated from species Dysidea fragilis.…”

“…In addition, three previously conquiterpene compounds such as furodysinin lactone (54), O-methyl furodysinin lactone (55), and O-methyl-9-oxofurodysinin lactone (56) were also isolated from species Dysidea fragilis. [26] The content of compound 55 (0.85 %, w/w) in methanol extract of D. fragilis species was quantitatively analyzed by HPLC-DAD method. [27] Results of the assessment of the cytotoxic effects of sesquiterpene 46-53 showed that most compounds did not show cytotoxic effects (IC50 > 100 µg/mL), particularly, compound 48 has been found to cause death of cancer cells LU-1, LNCaP, SK-Mel2, HepG2, MCF-7, and PC-3 with IC50 values of 43.51, 40.77, 38.84, 45.43, 42.96, and 48.53 µg/mL, respectively.…”

Điểm lại các nghiên cứu hóa học và hoạt tính sinh học một số loài sinh vật biển Việt Nam trong giai đoạn 2013‐2017

“…Tiếp đó, một seteroit 5α,6α-epoxy-24ethylcholesta-8-en-3β,7α-diol (60) là đồng phân về vị trí liên kết đôi (tại C-8/C-9) của 59, cùng với bốn hợp chất steroit khác là 5α,8α-epidioxy-24Rethylcholest-6-en-3β-ol (61), 24-norcholesta-5,22dien-3β-ol (62), 24-methylenecholest-5-en-3β-ol (63) và hợp chất 46 đã được tìm thấy khi nghiên cứu về thành phần hóa học loài hải miên Tethya aurantium. [23] Các steroit có cấu trúc vòng epoxy tại C-5/C-6 còn được phát hiện thấy có trong loài hải miên Ircinia echinata bao gồm melithasterol A (64), 5α,6α-epoxycholest-8(14)-ene-3β,7α-diol (65) và topsentisterol B 5 (66). [24,25] Các hợp chất này đều thể hiện tác dụng gây độc tế bào đáng kể với giá trị IC 50 từ 4,53 tới 23,99 µg/mL trên các dòng tế bào ung thư HepG2, HL-60, KB, LNCaP, LU-1 và MCF-7.…”