Pachycladins A−E, Prostate Cancer Invasion and Migration Inhibitory Eunicellin-Based Diterpenoids from the Red Sea Soft Coral Cladiella pachyclados

Abstract

Alcyonaria species are among the important marine invertebrate classes that produce a wealth of chemically diverse bioactive diterpenes. Examples of these are the potent microtubule disruptor sarcodictyins and eleutherobin. The genus Cladiella has proven to be a rich source of cytotoxic eunicellin-based diterpenoids. Five new eunicellin diterpenes, pachycladins A-E (1-5), were isolated from the Red Sea soft coral Cladiella pachyclados. The known sclerophytin A Cladiellisin, 3-acetylcladiellisin, 3,6-diacetylcladiellisin, (+)-polyanthelin A, klysimplexin G, klysimplexin E, sclerophytin F methyl ether, (6Z)-cladiellin (cladiella-6Z,11(17)-dien-3-ol), sclerophytin B, and patagonicol were also identified. The structures of the isolated compounds were elucidated by extensive interpretation of their spectroscopic data. These compounds were evaluated for their ability to inhibit growth, proliferation, invasion, and migration of the prostate cancer cells PC-3. Some of the new metabolites exhibited significant anti-invasive activity.

New 6-Hydroxyeunicellins from a Soft Coral Cladiella sp.

“…[2][3][4][5][6][7][8][9][10][11][12][13][14][15] The relative configuration of 1 was elucidated mainly by a nuclear Overhauser effect spectroscopy (NOESY) spectrum as compatible with those of 1 offered by computer modeling (Table 2), in which the close contacts of atoms calculated in space were consistent with the NOESY correlations. In the NOESY experiment for 1, H-1 correlated with H-10 and H 3 -20, suggesting that H-1, H-10, and the isopropyl group are situated on the same face as β protons.…”

“…[2][3][4][5][6][7][8][9][10][11][12][13][14][15] In our continuing research on new substances from octocorals distributed in the tropical West Pacific Ocean, the chemical constituents of an Indonesian soft coral identified as Cladiella sp. were examined and 11 new eunicellins, cladieunicellins A-F, 10,15) (−)-solenopodin C, and cladielloides A-D, were isolated.…”

Cladieunicellins A-E, New Eunicellins from an Indonesian Soft Coral Cladiella sp.

“…Octocorals belonging to the genus Cladiella (Alcyoniidae) were shown to be a rich source of marine natural products, 1) particularly with eunicellin-type metabolites, [2][3][4][5][6][7] and most compounds of this class were found to possess complex structures and interesting biological activities. In a continuation of our search for bioactive substances from the marine invertebrates distributed in the tropical West Pacific Ocean, a specimen of octocoral identified as Cladiella sp., collected off the Indonesian coast, was studied.…”

Sinulariolide Suppresses Cell Migration and Invasion by Inhibiting Matrix Metalloproteinase-2/-9 and Urokinase through the PI3K/AKT/mTOR Signaling Pathway in Human Bladder Cancer Cells

“…In the current therapeutic approach, inhibition of the mechanism associated with tumor cell migration/invasion is the key to controlling cancer metastasis [17]. Many of the active ingredients isolated from corals have been shown to possess properties that prevent cancer cell proliferation and metastasis [12,[18][19][20][21][22][23]. …”