Cembrane Diterpenes Chemistry and Biological Properties

Yang, Bin; Zhou, Xuefeng; Lin, Xiuping; Liu, Juan; Peng, Yan; Yang, Xiong‐Li; Liu, Yonghong

doi:10.2174/138527212800672583

Cited by 80 publications

(82 citation statements)

References 206 publications

(413 reference statements)

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“…L-25-ES25-008, isolated from a sponge, collected from the Indian Ocean near the coast of Mozambique [66] and showed cytotoxic activity against mouse leukemia P-388 and human lung nonsmall cell A-549, colon adenocarcinoma HT-29 and melanoma MEL-28 cell lines [67]. Cembrane-type diterpenoids are a large and structurally varied group of natural products isolated from both terrestrial and marine organisms [68]. In the marine environment, coelenterates of the orders Alcyonacea and Gorgonacea are recognized as the most prominent source of cembranoids, which usually exhibit cyclic ether, lactone, or furane moieties around the cembrane framework [69][70][71].…”

Section: Miscellaneousmentioning

confidence: 99%

Introduction to Anticancer Drugs from Marine Origin

Kim

Kalimuthu

2014

Handbook of Anticancer Drugs From Marine Origin

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The chemical and biological diversity of the marine environment is extraordinary resource for the discovery of new anticancer drugs. Recent technological and methodological advances in elucidation of structure, synthesis, and biological assay have resulted in the isolation and clinical evaluation of various novel anticancer agents from marine pipeline. To understanding the marine derived anticancer compounds are useful in pharmaceutical industry and clinical applications. The marine sponges, algae, microbes, tunicates and other species from the marine pipeline are the important sources for biological active compounds. The past decade has seen a dramatic increase in the number of preclinical anticancer lead compounds from diverse marine life enter human clinical trials.Keywords Anticancer · Algae · Sponges · Marine · Bioactive compounds IntroductionCancer is a dreadful human disease, increasing with changing life style, nutrition, and global warming. A report released by the World Health Organization (WHO) showed that an estimated 12.7 million people were diagnosed with cancer globally and about 7.6 million people died of it in 2008. As estimated in this report, more than 21 million new cancer cases and 13 million deaths are expected by 2030. Although cancer accounts for around 13 % of all deaths in the world, more than 30 % of cancer deaths can be prevented by modifying or avoiding key risk factors [1]. However, almost all of the chemotherapy drugs currently in the market cause serious side effects. Natural products and their derivatives represent more than 50 % of all the drugs in clinical use of the world. Higher plants contribute not less than 25 % of the total. Almost 60 % of drugs approved for cancer treatment are of natural origin.S.-K. Kim and S. Kalimuthu 2 Although marine compounds are underrepresented in current pharmacopoeia, it is anticipated that the marine environment will become an invaluable source of novel compounds in the future [2].Marine nutraceuticals can be derived from a vast array of sources, including marine plants, microorganisms, and sponges. Marine nutraceutical products currently promoted to various countries include fish oil, chitin, chitosan, marine enzymes and chondroitin from shark cartilage, sea cucumbers and mussels. Polysaccharides derived from alga, including alginate, carrageenan and agar are widely used as thickeners and stabilizers in a variety of food ingredients. In addition, Omega PUFA (Polyunsaturated fatty acid) is an important ingredient to the nutraceutical industry [3]. It has been proven that Omega-PUFA, especially eicosapentaenoic acid (EPA) and docosahexenoic acid (DHA) play a significant role in number of aspects of human health [4].More than 70 % of our planet's surface is covered by oceans. An exciting "marine pipeline" of new anticancer clinical and preclinical agents has emerged from intense efforts over the past decade to more effectively explore the rich chemical diversity offered by marine life. The chemical adaptations generally take the form of ...

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Section: Miscellaneousmentioning

confidence: 99%

Introduction to Anticancer Drugs from Marine Origin

Kim

Kalimuthu

2014

Handbook of Anticancer Drugs From Marine Origin

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“…We report herein the development of a two‐step hydroxylation of the 14‐membered macrocyclic diterpenoid β‐cembrenediol ( 1 ). Cembranoids constitute a versatile class of natural metabolites, the members of which are found mainly in plants and marine invertebrates . Their structures differ in the number and kind of additional oxy functionalities .…”

Section: Introductionmentioning

confidence: 99%

One‐Pot, Two‐Step Hydroxylation of the Macrocyclic Diterpenoid β‐Cembrenediol Catalyzed by P450 BM3 Mutants

et al. 2016

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Cytochrome P450 monooxygenases (P450s) are involved in the biosynthesis of a wide range of bioactive secondary metabolites. They often introduce several oxy functionalities at different positions of a substrate through multiple steps and produce a range of oxidized derivatives. Herein, we describe a one‐pot two‐step hydroxylation of the diterpenoid β‐cembrenediol isolated from the plant Nicotiana tabacum. This 14‐membered macrocycle shows neuroprotective effects and is, along with its oxidized derivatives, of pharmaceutical interest. Sequential hydroxylations catalyzed by the regioselective P450 BM3 mutants F87A/I263L and V78A/F87G yielded the epimeric (9S,10R/S)‐β‐cembrenetetraols with a diastereomeric ratio of 48:52. The replacement of the mutant V78A/F87G with L75A/V78A/F87G in the second step improves the diastereomeric ratio up to 10:90. Absolute configurations of the newly introduced hydroxy groups were determined by quantum‐mechanical calculations of NMR spectra.

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“…Octocorals belonging to the genus Sinularia , which are distributed widely in the tropical and subtropical Indo-Pacific Ocean, have been proven to be rich sources of bioactive terpenoid analogues [1,2,3,4]. In ongoing studies on the chemical constituents from marine invertebrates collected off the waters of Taiwan, the intersection of the Kuroshio current and the South China Sea surface current, the octocorals Sinularia gaweli and Sinularia flexibilis (phylum Cnidaria, class Anthozoa, subclass Octocorallia, order Alcyonacea, family Alcyoniidae) were studied, as their organic extract was found to show meaning signals in NMR studies.…”

Section: Introductionmentioning

confidence: 99%

Cembrane Derivatives from the Soft Corals, Sinularia gaweli and Sinularia flexibilis

Yen

et al. 2013

Marine Drugs

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A new norcembranoidal diterpene, 1-epi-sinulanorcembranolide A (1), and a new cembranoidal diterpene, flexibilin D (2), were isolated from the soft corals, Sinularia gaweli and Sinularia flexibilis, respectively. The structures of new metabolites 1 and 2 were elucidated by spectroscopic methods, and compound 2 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS and COX-2 proteins of the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. In addition, S. flexibilis yielded a known cembrane, 5-dehydrosinulariolide (3); the structure, including its absolute stereochemistry, was further confirmed by single-crystal X-ray diffraction analysis.

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Cembrane Diterpenes Chemistry and Biological Properties

Cited by 80 publications

References 206 publications

Introduction to Anticancer Drugs from Marine Origin

Introduction to Anticancer Drugs from Marine Origin

One‐Pot, Two‐Step Hydroxylation of the Macrocyclic Diterpenoid β‐Cembrenediol Catalyzed by P450 BM3 Mutants

Cembrane Derivatives from the Soft Corals, Sinularia gaweli and Sinularia flexibilis

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