Briaviolide Q,a New Briarane from the Cultured Briareum violaceum

Abstract

A new briarane-type diterpenoid, briaviolide Q (1), along with a known analogue, excavatolide Z (2), were obtained from a cultured octocoral Briareum violaceum. Details of the isolation and structure determination of briarane 1 from spectroscopic data are presented in this paper. In RAW264.7 cells, a macrophage-like murine cell line, briarane 1 was found to inhibit the protein expression of pro-inflammatory inducible nitric oxide synthase (iNOS) in cells stimulated by lipopolysaccharide (LPS).

Keywords

Briareum violaceum Briaviolide Briarane iNOS

References

Samimi-Namin

, van Ofwegen

L.P.

(2016) Overview of the genus Briareum (Cnidaria, Octocorallia, Briareidae) in the Indo-Pacific, with the description of a new species. ZooKeys, 557, 1–44.

(a) Sheu

J.H.

, Sung

P.J.

, Huang

L.H.

, Lee

S.F.

, Wu

, Chang

B.Y.

, Duh

C.Y.

, Fang

L.S.

, Soong

, Lee

T.J.

(1996) New cytotoxic briaran diterpenes from the Formosan gorgonian Briareum sp. Journal of Natural Products, 59, 935–938. (b) Xu L, Patrick BO, Roberge M, Allen T, van Ofwegen LP, Andersen RJ. (2000) New diterpenoids from the octocoral Pachyclavularia violacea collected in Papua New Guinea. Tetrahedron, 56, 9031–9037. (c) Iwasaki J, Ito H, Aoyagi M, Sato Y, Iguchi K. (2006) Briarane-type diterpenoids from the Okinawan soft coral Pachyclavularia violacea. Journal of Natural Products, 69, 2-6. (d) Ito, H, Iwasaki J, Sato Y, Aoyagi M, Iguchi K, Yamori T. (2007) Marine diterpenoids with a briarane skeleton from the Okinawan soft coral Pachyclavularia violacea. Chemical & Pharmaceutical Bulletin, 55, 1671-1676. (e) Liaw CC, Cheng YB, Lin YS, Kuo YH, Hwang TL, Shen YC. (2014) New briarane diterpenoids from Taiwanese soft coral Briareum violacea. Marine Drugs, 12, 4677-4692. (f) Xu JH, Lai KH, Su YD, Chang YC, Peng BR, Backlund A, Wen ZH, Sung PJ. (2018) Briaviolides K–N, new briarane-type diterpenoids from cultured octocoral Briareum violaceum. Marine Drugs, 16, 75.

Sheu

J.H.

, Sung

P.J.

, Su

J.H.

, Wang

G.H.

, Duh

C.Y.

, Shen

Y.C.

, Chiang

M.Y.

, Chen

I.T.

(1999) Excavatolides U–Z, new briarane diterpenes from the gorgonian Briareum excavatum. Journal of Natural Products, 62, 1415–1420.

Y.D.

, Su

J.H.

, Hwang

T.L.

, Wen

Z.H.

, Sheu

J.H.

, Wu

Y.C.

, Sung

P.J.

(2017) Briarane diterpenoids isolated from octocorals between 2014 and 2016. Marine Drugs, 15, 44, and previous reports in this series.

Groweiss

, Look

S.A.

, Fenical

(1988) Solenolides, new anti-inflammatory and antiviral diterpenoids from a marine octocoral of the genus Solenopodium. The Journal of Organic Chemistry, 53, 2401–2406.

Iwagawa

, Takayama

, Okamura

, Nakatani

, Doe

(1999) New briarane diterpenes from a gorgonacean Briareum sp. Heterocycles, 51, 1653–1659.

Iwagawa

, Takayama

, Okamura

, Nakatani

, Doe

, Takemura

, Shiro

(1999) Cytotoxic briarane diterpenes from a gorgonacean Briareum sp. Heterocycles, 51, 2619–2625.

Kwak

J.H.

, Schmitz

F.J.

, Williams

G.C.

(2001) Milolides, new briarane diterpenoids from the Western Pacific octocoral Briareum stechei. Journal of Natural Products, 64, 754–760.

Iwagawa

, Nishitani

, Kurosaki

, Okamura

, Nakatani

, Doe

, Takemura

(2003) Briarlides, briarane diterpenes from a gorgonian Briareum sp. Journal of Natural Products, 66, 1412–1415.

10.

Iwagawa

, Babazono

, Nakatani

, Doe

, Morimoto

, Takemura

(2005) Briarane diterpenes from a gorgonian Briareum sp. Heterocycles, 65, 607–617.

11.

Joyner

P.M.

, Waters

A.L.

, Williams

R.B.

, Powell

D.R.

, Janakiram

N.B.

, Rao

C.V.

, Cichewicz

R.H.

(2011) Briarane diterpenes diminish COX-2 expression in human colon adenocarcinoma cells. Journal of Natural Products, 74, 857–861.

12.

Gupta

, Sharma

, Schulz

T.C.

, Sherrer

E.S.

, McLean

A.B.

, Robins

A.J.

, West

L.M.

(2011) Bioactive diterpenoid containing a reversible “spring-loaded” (E,Z)-dieneone Michael acceptor. Organic Letters, 13, 3920–3923.

13.

Meginley

R.J.

, Gupta

, Sculz

T.C.

, McLean

A.B.

, Robins

A.J.

, West

L.M.

(2012) Briareolate esters from the gorgonian Briareum asbestinum. Marine Drugs, 10, 1662–1670.

Supplementary Material

Please find the following supplemental material available below.

For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.

For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.

0.00 MB

0.63 MB