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Marner, Franz‐Josef; Hanisch, Bernadette

doi:10.1002/1522-2675(20010418)84:4<933::aid-hlca933>3.3.co;2-p

Cited by 5 publications

(7 citation statements)

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“…Although a number of cycloiridals were reported before 1998, only two of these triterpenes have been described in the last ten years, namely, hoogianal (127) from Iris hoogiana 91 and iridotectoral B (128) from Iris tectorum. 91 Onoceranes. 91 Onoceranes.…”

Section: Triterpenes Deriving From Two Independent Cyclization Procesmentioning

confidence: 99%

“…90 Cycloiridals. Although a number of cycloiridals were reported before 1998, only two of these triterpenes have been described in the last ten years, namely, hoogianal (127) from Iris hoogiana 91 and iridotectoral B (128) from Iris tectorum. 80 The oxidative degradation of hoogianal yielded b-irone, a compound of interest in perfumery due to its violet aroma.…”

Section: Triterpenes Deriving From Two Independent Cyclization Proces...mentioning

confidence: 99%

“…80 The oxidative degradation of hoogianal yielded b-irone, a compound of interest in perfumery due to its violet aroma. 91 Onoceranes. Two onoceranes (129-130), tetracyclic triterpenes with a symmetrically substituted bisdecalin skeleton, and one seco-onocerane (131) were isolated in 2002 from the fruit peel of Lansium domesticum.…”

Section: Triterpenes Deriving From Two Independent Cyclization Proces...mentioning

confidence: 99%

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Unusually cyclized triterpenes: occurrence, biosynthesis and chemical synthesis

et al. 2009

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The biosynthetic origin of most of triterpenes lies in cascade cyclizations and rearrangements of the acyclic precursors squalene (S) and 2,3-oxidosqualene (OS), processes leading to tetra- and pentacyclic triterpene skeleta. Apart from these, a number of triterpenoid structures derived from cyclization processes, that are different from those leading to tetra- and pentacyclic triterpenes, are also found in Nature. We have defined these processes as unusual cyclizations, and grouped them in three blocks, namely, incomplete cyclizations of the corresponding S-derived precursors, cyclizations of S or OS towards polycyclic triterpenes and subsequent cleavage of the preformed ring systems, and two independent cyclizations of the S- or OS-derived precursor. Apart from the molecules obtained from intact organisms, we will also consider the compounds obtained from in vitro cyclizations promoted by enzyme systems. After establishing which compounds could unambiguously be grouped under the term 'unusually cyclized triterpenes', this review moves on to the advances achieved in this kind of structure during the last ten years. These advances are presented in three parts. The first one presents the structure and biological properties of the unusual triterpenes reported in the last decade. The second part considers the main biosynthetic pathways which justify the formation of these triterpenes from their corresponding acyclic precursors. Finally, we look at the achievements made in different synthetic strategies directed at some of these molecules. One hundred and twenty-three references are cited.

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Section: Triterpenes Deriving From Two Independent Cyclization Procesmentioning

confidence: 99%

Section: Triterpenes Deriving From Two Independent Cyclization Proces...mentioning

confidence: 99%

Section: Triterpenes Deriving From Two Independent Cyclization Proces...mentioning

confidence: 99%

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Unusually cyclized triterpenes: occurrence, biosynthesis and chemical synthesis

et al. 2009

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“…The possible biosynthesis pathways to polycycloiridals E−J were similar to those of polycycloiridals A−D. 14 Their biosynthesis precursors were likely the (13R)-spirobicyclic hemiacetal (I) and its geometrical isomer (II), 4,22 which underwent a series of transformations including epoxidation, nucleophilic addition, and intramolecular dehydration to form 1−6 (Scheme 1).…”

Section: ■ Results and Discussionmentioning

confidence: 98%

Polycycloiridals with a Cyclopentane Ring from Iris tectorum

et al. 2016

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Six new iridal-type triterpenoids containing an unprecedented cyclopentane ring, polycycloiridals E-J (1-6), were isolated from a large-scale re-extraction of Iris tectorum. A possible biosynthesis pathway is postulated. The known spirioiridotectal D (7) was also obtained in the current investigation, and its structure was unequivocally defined using X-ray diffraction data. Compound 7 suppressed LPS-activated NO production in the BV2 cell line with an IC value of 0.54 μM.

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“…Hoogianal 313 is a new constituent of Iris hoogiana. 235 A range of sipholane derivatives has been identified in Siphonochalina siphonella including sipholenols F 314, G 315 and H 316, sipholenone D 317, sipholenosides A 318 and B 319, neviotine B 320, siphonellinol B 321 and dahabinone A 322. 236 New isomalabaricane derivatives include 323-325 from a Jaspis sponge, 237 stelliferin riboside 326 from Geodia globostellifera 238 and the 27nor-derivatives geoditins A 327 and B 328 from Geodia japonica.…”

Section: Miscellaneous Compoundsmentioning

confidence: 99%

Triterpenoids

Connolly¹,

Hill²

2003

Nat. Prod. Rep.

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This review covers the isolation and structure determination of triterpenoids including squalene derivatives, lanostanes, cycloartanes, dammaranes, euphanes, tirucallanes, tetranortriterpenoids, quassinoids, lupanes, oleananes, friedelanes, ursanes, hopanes, fernanes, sipholanes, isomalabaricanes, serratanes and saponins The literature from January to December 2001 is reviewed and 242 references are cited.

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Cited by 5 publications

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Unusually cyclized triterpenes: occurrence, biosynthesis and chemical synthesis

Unusually cyclized triterpenes: occurrence, biosynthesis and chemical synthesis

Polycycloiridals with a Cyclopentane Ring from Iris tectorum

Triterpenoids

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