Rearranged icetexane diterpenoids from the roots of<i>Salvia thymoides</i>(Labiatae)

Esquivel, Baldomero; Sánchez, Ana Adela

doi:10.1080/14786410512331328731

Cited by 9 publications

(3 citation statements)

References 4 publications

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“…436 and 434 were neoclerodane diterpenes that possess an γ-hydroxy-α,β-unsaturated γ-lactone moiety. 20 Kerlinic acid (424) was isolated from S. keerlii with a carboxy group at C-5. 102 Thymonin (425) and 7β-hydroxythymonin (428) were two diterpenes that were isolated from S. thymoides, and 426 was an acetyl derivative of 425; allylic oxidation of 425 gave the α,β-unsaturated aldehyde 427, and 429 and 430 were acetyl derivatives of 428.…”

Section: Diterpenoidsmentioning

confidence: 99%

Constituents from Salvia Species and Their Biological Activities

et al. 2012

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24 (1R,5R)-1,5-epoxysalvial-4( 14)ene S. sclarea 49 2 salviadienol A S. chinensis 42 25 (2R,5E)-2,12-epoxycaryophyll-5ene S. sclarea 49 3 3β,6β,8a-triacetoxy-4β,5α-epoxy-1-oxogermacr-10(14)-ene S. roborowskii 43 26 (2R,5E)-caryophyll-5-en-12-al S. sclarea 49 4 3β,6β,8a-triacetoxy-4β,5α-epoxygermacr-1(10)E-ene S. roborowskii 43 27 (2S,5E)-caryophyll-5-en-12-al S. sclarea 49 5 3β,6β,8a-triacetoxy-4β,5α:1α,10β-diepoxygermacrane S. roborowskii 43 28 caryophyllene oxide S. sclarea 51, 47 6 salviadienol B S. chinensis 42 S. palaefolia 50 7 trijugin A S. trijuga 45 29 4,10-epoxy-6α-hydroxyguaiane (= buchariol) S. bucharica 343 8 trijugin B S. trijuga 45 30 isospathulenol S. sclarea 49 9 trijugin C S. trijuga 45 31 (1β,3β,4α,5α,6α,8α)-guai-10(14)ene-3,4,6,8-tetrol 3,6,8-triacetate S. roborowskii 48 10 trijugin D S. trijuga 45 32 spathulenol S. eupatorium 361 11 trijugin E S. trijuga 45 S. sclarea 51 12 trijugin F S. trijuga 45 33 nubiol S. nubicola 23 13 trijugin G S. trijuga 45 34 nubenolide S. nubicola 52 14 trijugin H S. trijuga 45 35 nubenolideacetate S. nubicola 52 15 trijugin I S. trijuga 45 36 bisnubidiol S. nubicola 23 16 (1aS*,6R*,6aS*,7aR*,9aR*)-1a,2,6,6a,7a,8,9,9a-octahydro-1a,5,7atrimethylbisoxireno[4,5:8,9]cyclodeca[1,2-b]furan-6-yl acetate (= castanin B) S. castanea 44 37 bisnubenolide S. nubicola 52 6-acetoxyglechomafuran S. roborowskii 43 38 1α,9β-dibenzoyloxy-2β,3β,4βtrihydroxydihydro-β-agarofuran S. palaefolia 50 17 glechomafuran S. palaefolia 47 39 lα-acetoxy-11-hydroxy-2,8-dioxoeudesman-3-en-12-oic acid methyl ester S. palaefolia 53 18 castanin C S. castanea 46 40 11-hydroxy-3,8-dioxo-eudesman-1,4-dien-12-oic acid methyl ester S. palaefolia 53 19 castanin D S. castanea 46 41 β-eudesmol S. microphylla 55 20 castanin E S. castanea 46 42 8α-hydroxy-β-eudesmol S. microphylla 55 21 castanin F S. castanea 46 43 1α-acetoxy-2-oxoeudesman-3,7(11)-dien-8β,12-olide S. palaefolia 53 22 (4R*,5R*,5aS*,8S*,8aR*,8bR*)-8-formyl-4,5,5a,6,7,8,8a,8b-octahydro-5,8b-dihydroxy-3,5a,8-trimethyl-2-oxo-2H-indeno[4,5-b]furan-4-yl acetate (= castanin A) S. castanea 44 44 1α-hydroxy-2-oxoeudesman-3,7(11)-dien-8β,12-olide S. palaefolia 53 23 (3β,4α,6α,8β,9β,10α)-8-(acetyloxy)-3,4:9,10-diepoxygermacr-7(11)-eno-12,6-lactone S. roborowskii 48 45 1α,8α-dihydroxy-2-oxoeudesman-3,7(11)-dien-8β,12-olide S. palaefolia 53, 54 46 1α-acetoxy-8α-hydroxy-2oxoeudesman-3,7(11)-dien-8,12olide S. palaefolia 54

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Section: Diterpenoidsmentioning

confidence: 99%

Constituents from Salvia Species and Their Biological Activities

et al. 2012

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“…From the roots of S. thymoides Benth. (section Flocculosae), a shrub endemic to the semiarid regions of southern Mexico, tilifolidione (67) and several related salvifolane diterpenoids (68-70) were isolated [54]. The structure of the quinone (68) is closely related to tilifolidione (67).…”

Section: Smentioning

confidence: 99%

Rearranged Clerodane and Abietane Derived Diterpenoids from American Salvia Species

Esquivel

2008

Natural Product Communications

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The genus Salvia L. (Tribe Mentheae) is the largest of the Lamiaceae with 1000 species widespread throughout the world. Phytochemical studies of several Salvia species have established an interesting chemical profile for the genus including sterols, flavonoids and triterpenoids. However, the most characteristic secondary metabolites of the genus are diterpenoids. One of the most distinguishing features of Salvia genus is the number of rearranged diterpene skeletons isolated from these plants. Until now, over 30 rearranged diterpene skeletons have been described for both Old and New World representatives of the genus. In this review, a survey of recent literature data regarding rearranged clerodane and abietane diterpenoids from American Salvia species is presented.

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“…The excessive production of these inflammatory mediators may cause necrosis, cavitation formation, and lung tissue damage [ 16 , 17 ]. On the other hand, Mexico has the largest number of the genus salvia plant species, whose main compounds of this genus are terpenes [ 18 , 19 ], these compounds have shown important biological activities such as: antimicrobial, anti-inflammatory and immunomodulatory [ 20 , 21 ]. Thus, the aim of this study was to evaluate the immunomodulatory activity of diterpenes (icetexone, anastomosine and 7,20-dihydroanastomosine) isolated from Salvia ballotiflora ( S. ballotaeflora ) over innate immunity and cytokine production in a human alveolar epithelial cell line (A549) infected with M.tb.…”

Section: Introductionmentioning

confidence: 99%

Immunomodulatory Activity of Diterpenes over Innate Immunity and Cytokine Production in a Human Alveolar Epithelial Cell Line Infected with Mycobacterium tuberculosis

Hernández-Herrera

Luna-Herrera

González-Martínez

et al. 2023

CMP

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Background: Mexico has the largest number of the genus salvia plant species, whose main chemical compounds of this genus are diterpenes, these chemical compounds have shown important biological activities such as: antimicrobial, anti-inflammatory and immunomodulatory. Objective: This study aimed to evaluate the immunomodulatory activity of three diterpenes: 1) icetexone, 2) anastomosine and 3) 7,20-dihydroanastomosine, isolated from Salvia ballotiflora, over innate immunity and cytokine production in a human alveolar epithelial cell line infected with Mycobacterium tuberculosis. Method: The immunomodulatory activity of diterpenes over innate immunity included reactive oxygen and nitrogen species (ROS and RNS) induction in response to infection; cytokine production included TNF-α and TGF-β induction in response to infection. Results: The diterpenes anastomosine and 7,20-dihydroanastomosine showed a statically significant (p<0.01) increase of RNS after 36 h of infection and treatment of 2.0 µg/mL. Then, the ROS induction in response to infection showed a consistent statically significant (p<0.01) increase after 12 h of diterpenes treatments. The cell cultures showed an anti-inflammatory effect, in the case of TGF-β induction, in response to infection when treated with the diterpenes. On the other hand, there was not any significant effect on TNF-α release. Conclusion: the diterpenes anastomosine and 7,20-dihydroanastomosine increased the production of RNS after 36 h of infection and treatment. Besides, the three diterpenes increased the production of ROS after 12 h. This RNS and ROS modulation can be considered as an in vitro correlation of innate immunity in response to Mycobacterium tuberculosis infection; and an indicator of the damage of epithelial lung tissue. This study also showed an anti-inflammatory immune response by means of TGF-β modulation when compared with control group.

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Rearranged icetexane diterpenoids from the roots ofSalvia thymoides(Labiatae)

Abstract: From the roots of Salvia thymoides Benth., three new rearranged icetexane diterpenoids (2-4) were isolated together with the previously described quinone tilifolidione (1). The proposed structures were established by extensive NMR analysis, including HMBC and HMQC pulse sequences.

Cited by 9 publications

References 4 publications

Constituents from Salvia Species and Their Biological Activities

Constituents from Salvia Species and Their Biological Activities

Rearranged Clerodane and Abietane Derived Diterpenoids from American Salvia Species

Immunomodulatory Activity of Diterpenes over Innate Immunity and Cytokine Production in a Human Alveolar Epithelial Cell Line Infected with Mycobacterium tuberculosis

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