Nemorosonol, a derivative of tricyclo-[4.3.1.03,7]-Decane-7-hydroxy-2,9-dione from Clusia nemorosa

Monachè, Franco Delle; Monache, Giuliano Delle; Pinheiro, Rogerio Moura; Radics, L.

doi:10.1016/0031-9422(88)80148-1

Cited by 44 publications

(14 citation statements)

References 7 publications

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“…Nemorosonol (78), a derivative of tricyclo[4.3.1.0]decane, was the rst PPBS isolated from the Clusia genus by Delle Monache et al 41 As there is no isopropyl group in the eightmembered ring, it is difficult to arrange into type-A, -B or -C, and we classify it as a type-D PPBS. Its structure was further conrmed by X-ray crystallography.…”

Section: Type-d Ppbsmentioning

confidence: 99%

Structural diversity and bioactivities of natural benzophenones

2014

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Natural benzophenones are a class of compounds consisting of more than 300 members, which exhibit great structural diversity and bioactive properties. Many benzophenones have been reported from higher plants or fungi, most with polyisoprenylated benzophenone skeletons, and are mainly found in the Clusiaceae (formerly Guttiferae) family, a number from edible or medicinal species. Owing to their variable substituents and complex ring systems, many new polyisoprenylated benzophenones (PPBS), including ones with unusual skeletons, were isolated and identified. These natural benzophenones exhibit a range of biological activities including antifungal, anti-HIV, antimicrobial, antioxidant, antiviral and cytotoxic. Because of the increased numbers and biological importance of these unique natural product polyphenols, we will review natural benzophenones and provide an in-depth discussion of their structural diversity and biological activity. By focusing on these key developments in benzophenones, we will contribute a focused review, selecting examples mostly from the last 15 years, but extending our scope to other historically important benzophenones discovered prior to that time.

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Section: Type-d Ppbsmentioning

confidence: 99%

Structural diversity and bioactivities of natural benzophenones

2014

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“…Such is the case for Clusia and Garcinia (Rheedia), all in the Clusiaceae, which contain complex polyprenylated benzophenones. 27 Secondary metabolites may have importance at the sectional level: species in Populus section Tacamahaca have high amounts of dihydrochalcones, while flavanonols and phenylpropenoic acids and their esters characterize section Aigeiros. 28 Plant genera and species may thus be chemically characterized, because chemical composition is genetically controlled 23,29 and often involves complex suites of enzymes.…”

Section: Maria Luiza Salatinomentioning

confidence: 99%

Propolis research and the chemistry of plant products

et al. 2011

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“…[33] Prior to the discovery of chloropupukeananin (1), [15] chloropupukeanolides A (5) and B (6), [19] and chloropupukeanone A (7), [19] the only example with a tricyclo-[4.3.1.0 3,7 ]-decane carbon skeleton from terrestrial sources was nemorosonol, a polyisoprenylated pupukeanane from the fruits of the South-American plant Clusia nemorosa and the leaves of the Vietnamese plant Garcinia bracteata (both of the Clusiaceae family). [35,36] Chloropupukeanolides C-E (8-10) are new chlorinated pupukeanane metabolites featuring a unique spiroketal skeleton derived from the highly functionalized tricyclo-[4.3.1.0 3,7 ]-decane and 2,6-dihydroxy-4-methylbenzoic acid moieties. Structurally, compounds 8 and 9 are new analogues of 5 and 6, [15] all with a 5-hydroxy- ]-decane core via C10, but differ by the absence of the six-membered peroxide moiety, and the hybridization states of C8 and C9.…”

Section: Discussionmentioning

confidence: 99%

Chloropupukeanolides C–E: Cytotoxic Pupukeanane Chlorides with a Spiroketal Skeleton from Pestalotiopsis fici

Liu

Bruhn

Guo

et al. 2011

Chemistry A European J

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Chloropupukeanolides C-E (8-10), three highly functionalized secondary metabolites featuring a novel spiroketal skeleton derived from the chlorinated tricyclo-[4.3.1.0(3, 7)]-decane (pupukeanane) and the 2,6-dihydroxy-4-methylbenzoic acid moieties, were isolated from the scale-up fermentation extract of the plant endophytic fungus Pestalotiopsis fici. The constitutions of compounds 8-10 were elucidated primarily by NMR experiments. Their relative configurations were deduced by analogy to metabolites 4-6, which were previously isolated from the same fungus. The absolute configuration of 8 was assigned by X-ray crystallography and those of 9 and 10 by quantum-chemical CD calculations. Biogenetically, chloropupukeanolides C-E (8-10) are presumably derived from the same oxidation-induced Diels-Alder reaction pathway as compounds 1 and 4-7, via the putative biosynthetic precursors 2 and 3. The opposite configurations of the complete "Southern parts" of 8 and 9 suggests that this Diels-Alder reaction is stereochemically not very selective. Compounds 8-10 showed significant cytotoxicity against a small panel of human tumor cell lines and weak activities against the pathogens of tropical diseases.

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Nemorosonol, a derivative of tricyclo-[4.3.1.03,7]-Decane-7-hydroxy-2,9-dione from Clusia nemorosa

Cited by 44 publications

References 7 publications

Structural diversity and bioactivities of natural benzophenones

Structural diversity and bioactivities of natural benzophenones

Propolis research and the chemistry of plant products

Chloropupukeanolides C–E: Cytotoxic Pupukeanane Chlorides with a Spiroketal Skeleton from Pestalotiopsis fici

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