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In the present study, a new ceramide, namely 2S, 3R-4E, 8E-2-(heptadecanoylamino)-heptadeca-4, 8-diene-1, 3-diol (1), along with four known steroids, including 24-methylcholesta-5, 24(28)-diene-3β-ol (2), 24-methylcholesta-5, 24(28)-diene-3β-acetate (3), 4-methyl-24-methylcholesta-22-ene-3-ol (4), and cholesterol, was isolated and characterized from CH2Cl2/MeOH extract of Cespitularia stolonifera. A new acetate derivative of compound 1, termed 2S, 3R-4E, 8E-2-(heptadecanoylamino)-heptadeca-4, 8-diene-1, 3-diacetate (1a), was also prepared in the present study. All the structures were established on the basis of modern spectroscopic techniques, including FT-IR, 1D, 2D-NMR, HRESI-MS, and GC-MS, in addition of chemical methods. (-)-Alloaromadendren, ledane, (1)-alloaromadendren oxide, isoaromadendrene epoxide and (-)-caryophellen oxide were identified from the n-hexane fraction using GC-MS. The extract and the two ceramides (1) and (1a) exhibited significant cytotoxic activity against lung cancer A549 cells, while the extract and the two steroids (2) and (3) exhibited significant cytotoxic activity against breast cancer MCF-7 cells. The CH2Cl2/MeOH extract exhibited significant antiulcer activity in both ethanol and acetic acid induced ulcer models in rats, as evidenced by histopathological, histochemical, and biochemical examinations.

Graphical abstract This review furnishes an overview of all naturally isolated compounds, especially diterpenoids as well as biological activities of these species such as anticancer, immunomodulatory, antiviral, antimicrobial, and anti-inflammatory activities., Soft corals belonging to the genus Cespitularia have been well recognized as a rich source of bioactive secondary metabolites especially diterpenoids. This review furnishes an overview of all naturally isolated compounds from Cespitularia genus as, diterpenoids, nitrogen-containing diterpenes, sesquiterpenoids and steroids as well as biological activities of these species. Cespitularia species have been studied for their anticancer, immunomodulatory, antiviral, antimicrobial, and anti-inflammatory activities. This work is the first review published on this topic.

In our current study, alcyonolide and its congeners isolated from the Okinawan soft coral, Cespitularia sp., have shown an antitumor activity in HCT116 colon cancer cells. This study investigated the biological activities of these compounds (1-12) for the apoptotic activity in the HCT116 cells and the anti-inflammatory effect in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. As a result, the apoptotic cells with a nuclear condensation were detected by treatment with these compounds. The apoptotic cells dependent on the caspase 3/7 activation was also induced in the low concentration range of 2.5-10 μM. While a similar concentration of the compounds inhibited the NO production in the LPS-stimulated inflammatory RAW264.7 cells, the pro-inflammatory gene expressions of the iNOS and COX-2 mRNA were also suppressed. The structurally unique alcyonolides (5, 12) having the dual biological activity of apoptotic activity and anti-inflammatory effect could be a potential development as pharmaceutical agents.

When compared, principal octocorals collected in the Chagos Archipelago before and after the 1998 ENSO shared many common taxa. While a few discontinuities in their biodiversity revealed subtle changes in more persistent genera (Lobophytum, Sarcophyton), some fast-growing "fugitive" genera (e.g. Cespitularia, Efflatounaria, Heteroxenia) disappeared after the ENSO-related coral bleaching. Such transient fugitives might thus be eliminated from soft coral communities on isolated reef systems, possibly in the long term, by events of this nature. The appearance of Carijoa riseii, a species often considered a fouling organism, even an invasive, may well be indicative of reef degradation during the ENSO event. The post-ENSO recovery manifested by this fauna nevertheless gives cause for hope for their survival in the face of climate change.

Four novel diterpenoids, designated cespitulins A–D ( 1 – 4 ) were isolated and characterized from the Taiwanese soft coral Cespitularia taeniata . Their structures were determined by extensive spectroscopic analyses ( 1 H- 1 H COSY, HMQC, HMBC, NOESY). Compounds 1 – 4 possess an unprecedented bond cleavage between C-9 and C-10 with a hemiacetalic lactone ring rather than a verticillane skeleton.

Chemical investigation of the soft coral Cespitularia hypotentaculata resulted in the isolation of eight new diterpenes, cespihypotins E–L ( 1 – 8 ). The new metabolites comprise of six verticillene-type diterpenes, one cespitularane derivative, and one derivative with 14-membered lactone ring. The structures were determined through detailed spectroscopic analyses, especially high resolution ESIMS and 2D NMR techniques. The relative stereochemistry was deduced from NOESY spectrum and application of Mosher's ester technique. Immunomodulatory and antiviral activities of 1 – 8 were tested and evaluated. The biogenetic pathways for 1 – 8 were also proposed.

Four new norditerpenoids, designated as cespihypotins A ( 1 ), B ( 2 ), C ( 3 ) and D ( 4 ), were isolated from Cespitularia hypotentaculata Roxas (Xeniidae) that was collected in Taiwan. Compounds 1 and 2 are unprecedented structures having 13- and 14-membered lactone ring, respectively. Their structures were elucidated on the basis of extensive spectroscopic analysis. A plausible biogenetic pathway for compounds 1 – 4 was also proposed.

An Okinawan soft coral Cespitularia sp. has proven to be a good source of cytotoxic metabolites having a carbon skeleton of the seco-type variety of xenicin. This soft coral yielded alcyonolide, the major constituent, and other related compounds, all of which have proven to be cytotoxic. Reinvestigation of the cytotoxic ethyl acetate extracts of the coral yielded two new alcyonolide congeners, trisnorditerpenoid 1 and diterpenoid 2 , possessing the same carbon skeleton. Their structures were elucidated by a detailed analysis of spectroscopic data (1D, 2D NMR, and MS). Metabolites 1 and 2 showed cytotoxicity against HCT116 cells (IC 50 6.04 and 47.0 μM, respectively) and a dose dependent, anti-inflammatory effect in LPS/IFN-γ-stimulated inflammatory RAW 264.7 macrophage cells.

In order to demonstrate the power utility of the interactive computer program CONGEN, 5 an example describing its use in the identification of the tricyclic sesquiterpene alcohol, [+]-palustrol, in extracts of a marine Xeniid ( Cespitularia sp., aff subviridis ) is provided. The rotation of [+]-palustrol further supports the remarkable antipodal relationiship between sesquiterpenes from marine Coelenterates and their corresponding terrestrial forms. 6