New Germacrane Sesquiterpenes from Salvia chinensis

Wang, Yeling; Li, Zhan‐Lin; Zhang, Hailong; Yan, Sha; Pei, Yue‐Hu; Hua, Hui‐Ming

doi:10.1248/cpb.56.843

Cited by 15 publications

(6 citation statements)

References 16 publications

(21 reference statements)

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“…Salviadienol A ( 2 ) and salviadienol B ( 6 ) were the first germacrane sesquiterpenes obtained from S. chinensis . Compounds 2 and 6 were highly acetylated members with oxy-isovaleryl groups being the most unusual ones . From the whole plant of S. roborowskii , four new germacrane sesquiterpene esters, 3 , 4 , 5 , and 16 , were isolated in 2003 .…”

Section: Chemical Constituentsmentioning

confidence: 99%

“…Compounds 2 and 6 were highly acetylated members with oxy-isovaleryl groups being the most unusual ones. 42 From the whole plant of S. roborowskii, four new germacrane sesquiterpene esters, 3, 4, 5, and 16, were isolated in 2003. 43 In 2005, the same compound 16 was isolated from S. castanea Diels f. tomentosa Stib again and given another name: castanin B (16).…”

Section: Sesquiterpenoidsmentioning

confidence: 99%

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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: Chemical Constituentsmentioning

confidence: 99%

Section: Sesquiterpenoidsmentioning

confidence: 99%

Constituents from Salvia Species and Their Biological Activities

et al. 2012

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“…The coupling patterns of the H-6 (dd, J = 7.0, 3.6 Hz) and H-5α (dd, J = 11, 3.6 Hz); H-6‴ (dd, J = 7.0, 3.6 Hz) and H-5‴α (dd, J = 11, 3.6 Hz) led to confirmation of the cis -orientation of H-6/H-5α and H-6‴/H-5‴α [20,21], which are in line with those of 4-[2-(β- d -glucopyranosyloxy)ethyl]-4-hydroxy-5-methoxy-2-cyclohexen-1-one that was obtained from M. hortensis [19], and 1,6-dihydroxy-4-oxo-2-cyclohexene-1-cetic acid ethyl ester isolated from Senecio scandens [17], and thus the configuration of C-6 and C-6‴ were determined as S and S . Analysis of the 13 C NMR data of C-1 and C-1‴ in 4 indicated that they were greatly similar to that of C-1 (δ C 71.8) in 4-[2-(β- d -glucopyranosyloxy)ethyl]-4-hydroxy-5-methoxy-2-cyclohexen-1-one [19], and our compound 4 showed in MeOH of −26.4°, which is in accord with that observed in 1,6-dihydroxy-4-oxo-2-cyclohexene-1-acetic acid ethyl ester ( −12.5°) [17].…”

Section: Resultsmentioning

confidence: 99%

Four New Jacaranone Analogs from the Fruits of a Beibu Gulf Mangrove Avicennia marina

Chen

Xie

et al. 2014

Marine Drugs

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Four new jacaranone analogs, marinoids F–I (1–4), were isolated from the fruits of a Beibu Gulf mangrove Avicennia marina. The structures were elucidated based on analysis of spectroscopic data. Marinoids F and G are shown to be diastereoisomers of chlorocornoside, a new halogen containing marine secondary metabolite. The antioxidant activity of the isolates was evaluated using a cellular antioxidant assay, and 4 showed good antioxidant activity (EC50 = 26 μM).

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“…In the NOESY spectrum (Figure 3), the key NOE correlations of H-9/H-10 and H-6/H-11 showed that H-9 and H-10, H-6 and H-11 were on the same face, so the relative stereochemistry was determined. The coupling patterns of the H-9 (dt, J = 3.0 and 6.5 Hz) and H-10 (d, J = 3.0 Hz) led to confirmation of the cis -orientation of H-9/H-10 and possessed β -orientation [17], and thus the configuration of C-9 and C-10 were determined as R* and S* , respectively. The sign of [ α ] D for proline-containing DKPs is either negative or positive, depending only on the absolute configuration of Pro [12].…”

Section: Resultsmentioning

confidence: 99%

A New 1,4-Diazepine from South China Sea Marine Sponge Callyspongia Species

Huang

Dong

et al. 2010

Molecules

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A new 1,4-diazepine, callysponine (1), was isolated from a South China Sea Callyspongia sp. marine sponge, together with four known proline-based diketopiperazines: cyclo-(S-Pro-R-Leu) (2), cyclo-(S-Pro-R-Val) (3), cyclo-(S-Pro-R-Ala) (4), and cyclo-(S-Pro-R-Tyr) (5). The new structure was determined on the basis of NMR and MS analysis, and the absolute stereochemistry was defined by NOESY spectroscopy and optical rotation. The structures of the known compounds were identified by comparison of their spectroscopic data with those reported in the literature. Callysponine (1) did not inhibit the growth of HepG2 (hepatoma carcinoma cell), A549 (lung carcinoma cell), and HeLa (cervical cancer cell) cell lines.

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New Germacrane Sesquiterpenes from Salvia chinensis

Cited by 15 publications

References 16 publications

Constituents from Salvia Species and Their Biological Activities

Constituents from Salvia Species and Their Biological Activities

Four New Jacaranone Analogs from the Fruits of a Beibu Gulf Mangrove Avicennia marina

A New 1,4-Diazepine from South China Sea Marine Sponge Callyspongia Species

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