Structure of inflexinol, a new cytotoxic diterpene from Rabdosia inflexa

Fujita, Tetsuro; Takeda, Yoshio; Yuasa, Eiji; Okamura, Akio; Shingu, Tetsuro

doi:10.1016/0031-9422(82)80090-3

Cited by 19 publications

(5 citation statements)

References 6 publications

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“…Compound 8 was determined to have molecular formula C 24 H 32 O 7 by HREIMS and was identical to a comparison sample of inflexin. Several NMR assignments were different from those reported in the previous papers, , and the NMR signals of inflexin were reassigned here according to 1D and 2D NMR experiments.…”

Section: Resultsmentioning

confidence: 99%

ent-Kaurane Diterpenoids from Isodon lungshengensis

Jiang

Hou

et al. 1999

J. Nat. Prod.

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Six new ent-kaurane diterpenoids, lungshengenins B-G (1-6), together with three known diterpenoids, lungshengenin A (7), inflexin (8), and lushanrubescinsin C (9), were isolated from the leaves and tender branches of Isodon lungshengensis. Their structures were elucidated by means of spectroscopy, mainly 1D and 2D NMR techniques. Lungshengenins A (7), C (2), and G (6) were cytotoxic toward K562 cells, having IC(50) values equal to or less than 10 microg/mL.

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Section: Resultsmentioning

confidence: 99%

ent-Kaurane Diterpenoids from Isodon lungshengensis

Jiang

Hou

et al. 1999

J. Nat. Prod.

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“…It has been reported that an exo-methylene conjugated with a ketone on a fivemember ring in ent-kaurene diterpenoids had anti-bacterial and anti-tumor activities [35], and that an exo-methylene group conjugated with cyclopentanone in entkaurene diterpenoids was the active center for their inhibitory effects [36,37]. In this investigation, every C-20 non-oxygenated-ent-kaurene had an exo-methylene conjugated with a ketone on a five-member ring and all of them had the same molecular skeleton.…”

Section: Discussionmentioning

confidence: 99%

Structure–activity relationships of eight ent-kaurene diterpenoids from three Isodon plants

et al. 2010

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Eight ent-kaurene diterpenoids were isolated from three Isodon plants, Isodon excisoides (Sun ex C. H. Hu) C. Y. Wu et H. W. Li, Isodon weisiensis C. Y. Wu, and Isodon racemosa (Hemsl.) Hara. Their cytotoxicities were tested by SRB assay against four human tumor cell lines, HepG2, Tb, HO-8910 and SGC-7901. The DNA damage degrees on their Hep G2 cells were evaluated by Comet assay. The results showed that ent-kaurene diterpenoids were selectively toxic against these four tumor cell lines. Weisiensic C had the lowest cytotoxicity against four cell lines and degree of DNA damage on the Hep G2 cell line. Leukamenin E and Glaucocalyxin A had similar IC 50 values and also induced a similar degree of DNA damage. The cytotoxicity and degree of DNA damage of eight entkaurene diterpenoids on Hep G2 was in the order Leukamenin E [ Glaucocalyxin A [ Wangzaozin A [ Kamebanin [ Macrocalyxin D [ Weisiensin B [ Excisanin K [ Weisiensic C. The structure-activity relationships indicated that there was some correlation between the substituents and their structures of ent-kaurene diterpenoids and their activities on Hep G2 cells.

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“…Fraction IEC-3 was subjected to flash column chromatography on RP-18 (2 × 30 cm, 40–63 μ m) eluting with : (30 : 70) and semiprepatative HPLC (column: YMC-ODC, 20 × 150 mm) eluting with : (23 : 77) at the flow speed of 6.5 mL/min. The structure of this compound was determined as ent -1 β ,3 α ,6 β ,11 α -tetrahydroxykaur-16-ene-15-one-3,11-diacetate (inflexinol), by comparison of its physicochemical and spectral data with those of literature [19]. …”

Section: Methodsmentioning

confidence: 99%

Inhibitory Effect of Inflexinol on Nitric Oxide Generation and iNOS Expression via Inhibition of NF-κBActivation

Lee

Kim

et al. 2007

Mediators of Inflammation

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Inflexinol, an ent-kaurane diterpenoid, was isolated from the leaves of Isodon excisus. Many diterpenoids isolated from the genus Isodon (Labiatae) have antitumor and antiinflammatory activities. We investigated the antiinflammatory effect of inflexinol in RAW 264.7 cells and astrocytes. As a result, we found that inflexinol (1, 5, 10 μM) suppressed the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) as well as the production of nitric oxide (NO) in LPS-stimulated RAW 264.7 cells and astrocytes. Consistent with the inhibitory effect on iNOS and COX-2 expression, inflexinol also inhibited transcriptional and DNA binding activity of NF-κB via inhibition of IκB degradation as well as p50 and p65 translocation into nucleus. These results suggest that inflexinol inhibits iNOS and COX-2 expression through inhibition of NF-κB activation, thereby inhibits generation of inflammatory mediators in RAW 264.7 cells and astrocytes, and may be useful for treatment of inflammatory diseases.

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Structure of inflexinol, a new cytotoxic diterpene from Rabdosia inflexa

Cited by 19 publications

References 6 publications

ent-Kaurane Diterpenoids from Isodon lungshengensis

ent-Kaurane Diterpenoids from Isodon lungshengensis

Structure–activity relationships of eight ent-kaurene diterpenoids from three Isodon plants

Inhibitory Effect of Inflexinol on Nitric Oxide Generation and iNOS Expression via Inhibition of NF-κBActivation

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