Guaianolide from Saussurea lappa

Dhillon, R. S.; Kalsi, P. S.; Singh, Wazir; Gautam, Veena; Chhabra, B. R.

doi:10.1016/s0031-9422(00)82384-5

Cited by 42 publications

(25 citation statements)

References 3 publications

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“…2 120.3 (C-13), 112.6 (C-15), 109.6 (C-14), 85.4 (C-5), 52.0 (C-4), 47.6 (C-6), 45.1 (C-10), 36.3 (C-2), 32.6 (C-8), 31.0 (C-7), 30.3 (C-1). The MS, 1 H and 13 C NMR data matched with previous reports (Dhillon et al 1987;Li et al 2004 (1H,d,J03.6 Hz,5.55 (1H,d,J03.2 Hz,4.91 (1H,dd,J011.5,5.5 Hz,4.76 (1H,br.d,J09.9 Hz,4.59 (1H,t,J09.6 Hz, H-6), 1.72 (3H, s, 15-CH 3 ), 1.44 (3H, s, 14-CH 3 ). 13 C NMR (125 MHz, CDCl 3 ) δ (ppm): 171.0 (C-12), 141.5 (C-11), 140.1 (C-4), 137.0 (C-10), 127.3 (C-5), 127.1 (C-1), 119.7 (C-13), 81.9 (C-6), 50.4 (C-7), 41.0 (C-3), 39.5 (C-9), 28.1 (C-2), 26.2 (C-8), 17.4 (C-15), 16.1 (C-14).…”

Section: Isolated Constituentssupporting

confidence: 87%

“…It possesses the function of spasmolysis, antihypertension and antibacteria infection (Jiangsu New Medical College 1977). The chemical constituents of this medicinal herb have been widely studied and many sesquiterpenes, sesquiterpene lactone, triterpenoids, alkaloids, flavonoids, steroids, lignan and tannins have been reported (Dhillon et al 1987;Yang et al 1997a, b;Chhabra et al 1998;Sun et al 2003;Yin et al 2005;Rao et al 2007;Robinson et al 2008;Wang et al 2008;Duan et al 2010). Sesquiterpene lactones including costunolide and dehydrocostus lactone are major components of the root and have been suggested to possess various biological activities, including antitumor, anti-ulcer, anti-inflammatory, neurocytotoxic and cardiotonic activities (Pandey et al 2007).…”

Section: Introductionmentioning

confidence: 99%

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Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera: Culicidae)

Liu

Chu

et al. 2011

Parasitol Res

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In recent years, uses of environment friendly and biodegradable natural insecticides of plant origin have received renewed attention as agents for vector control. The aim of this research was to determine larvicidal activity of the essential oil derived from roots of Saussurea lappa (Compositae) and the isolated constituents against the larvae of the Culicidae mosquito Aedes albopictus. Essential oil of S. lappa roots was obtained by hydrodistillation and analyzed by gas chromatography (GC) and GC-mass spectrometry (MS). A total of 39 components of the essential oil of S. lappa roots were identified. The essential oil has higher content of (79.80%) of sesquiterpenoids than monoterpenoids (13.25%). The principal compounds in S. lappa essential oil were dehydrocostus lactone (46.75%), costunolide (9.26%), 8-cedren-13-ol (5.06%), and α-curcumene (4.33%). Based on bioactivity-directed fractionation, dehydrocostus lactone and costunolide were isolated from S. lappa essential oil. Dehydrocostus lactone and costunolide exhibited strong larvicidal activity against A. albopictus with LC(50) values of 2.34 and 3.26 μg/ml, respectively, while the essential oil had an LC(50) value of 12.41 μg/ml. The result indicated that the essential oil of S. lappa and the two isolated constituents have potential for use in control of A. albopictus larvae and could be useful in search of newer, safer and more effective natural compounds as larvicides.

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Section: Isolated Constituentssupporting

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera: Culicidae)

Liu

Chu

et al. 2011

Parasitol Res

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“…The 13 C-NMR spectrum (CD 3 OD) exhibited 15 carbon signals including two sets of terminal double bonds at d 153.8 (s), 108.9 (t); 151.8 (s), 111.8 (t), a g-lactone carbonyl resonance at d 179.9 (s) and an oxygenbearing methine carbon at d 88.0 (d), suggestive of a skeleton of sesquiterpene lactone containing three rings. The NMR spectra were similar to those of dehydrocostus lactone (3), 1,4) isolated as the major sesquiterpene of this medicinal plant. Nevertheless, there were several significant differences as follows: a) the resonances of terminal double bond within lactone ring in 3 were absent and replaced by a set of signals at "d C 45.2 (d); d H 2.82 (ddd, Jϭ11.4, 5.5, 5.1 Hz)" and "d C 51.1 (t); d H 3.11 (dd, Jϭ14.6, 5.5 Hz), 3.35 (dd, Jϭ14.6, 5.1 Hz)"; b) the g-lactone carbonyl resonance was also evidently shifted downfield to the saturated zone at d 179.9 (s), which indicated that the terminal double bond was hydrogenated then substituted by a sulfonic acid group.…”

supporting

confidence: 55%

Sulfonated Guaianolides from Saussurea lappa

Wang

Xie²,

Gao³

et al. 2008

Chem. Pharm. Bull.

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Saussurea lappa (Costus root; Chinese name: Yun Mu Xiang; Asteraceae) is a famous traditional Chinese medicine and also an important spice since ancient times, and is now in common use in China and Japan. Its roots can be used for the treatment of abdominal distension, indigestion, nausea, abdominal pain, etc. The main chemical and bioactive constituents of this plant are several types of sesquiterpenoids 1-6) including two sulfonated eudesmanes. 7) Further to search for biologically active compounds, we have reinvestigated the chemical constituents of this plant. This paper reports the isolation and structure elucidation of two new guaiane sesquiterpene lactones with a sulfonic acid group named sulfocostunolide A (1) and sulfocostunolide B (2) ). The 13 C-NMR spectrum (CD 3 OD) exhibited 15 carbon signals including two sets of terminal double bonds at d 153.8 (s), 108.9 (t); 151.8 (s), 111.8 (t), a g-lactone carbonyl resonance at d 179.9 (s) and an oxygenbearing methine carbon at d 88.0 (d), suggestive of a skeleton of sesquiterpene lactone containing three rings. The NMR spectra were similar to those of dehydrocostus lactone (3), 1,4) isolated as the major sesquiterpene of this medicinal plant. Nevertheless, there were several significant differences as follows: a) the resonances of terminal double bond within lactone ring in 3 were absent and replaced by a set of signals at "d C 45.2 (d); d H 2.82 (ddd, Jϭ11.4, 5.5, 5.1 Hz)" and "d C 51.1 (t); d H 3.11 (dd, Jϭ14.6, 5.5 Hz), 3.35 (dd, Jϭ14.6, 5.1 Hz)"; b) the g-lactone carbonyl resonance was also evidently shifted downfield to the saturated zone at d 179.9 (s), which indicated that the terminal double bond was hydrogenated then substituted by a sulfonic acid group.Further validation was made by careful analysis of the HMBC spectrum (Fig. 2), in which the following significant correlations were observed: from H-11 to C-8, C-12; from H-13 to C-7, C-12. The correlation peaks in the ROESY spectrum (Fig. 3) between H-11 and H-8b, H-11 and H-6b, and H-6b and H-8b were clearly detectable, indicative of a orientation of the sulfomethyl group at C-11. Therefore the structure of 1 was elucidated as 13-sulfo-4(15),10(14)-guaiadien-12,6-olide, as shown in Fig. 1, named sulfocostunolide A.Compound 2 was also obtained as viscid solid, possessing the same molecule formula C 15 H 20 O 5 S as sulfocostunolide A (1) based on the negative-ion HR-ESI-MS. The IR and NMR (Table 1) spectra were considerably in accordance with those of 1, and their TLC behaviors (see Experimental) were very close but discriminable, suggesting a structurally wondrous similarity for both substances. Unexpectedly, analysis of the HMBC spectrum led to the same planar structure as sulfocostunolide A. Therefore the structure difference consequentially arose from the stereochemistry. The significant correlations in the ROESY experiment (Fig. 3): H-13 and H-8b, H-13 and H-6b, and H-6b and H-8b were observed, indicative of b orientation of the sulfomethyl group. Consequently, the structure of 2 was determin...

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“…Root powder ingested with cow's milk and cow's ghee Scalp scabies Essential oil of root is applied al., 1998a), 12-methoxydihydrodehydrocostuslactone (Dhillon et al, 1987), 4␤-methoxydehydrocostus lactone (Singh et al, 1992), saussurealdehyde, isodehydrocostus-lactone-15-aldehyde , sesquiterpene lactones (Kalsi et al, 1995;Ha et al, 1997), 11,13-epoxydehydrocostuslactone, 11,13-epoxy-isozazulanin C, 11,13-epoxydehydroisozaluzamine (Chhabra et al, 1997), 11,13-epoxy-3-keto dehydrocostus-lactone (Chhabra et al, 1998b), cynaropicrin, reynosin, santamarine (Cho et al, 1998), 6,10-dimethyl-9-methyleneunused-S-E-en-2-one (Stepanov and Veselovsky, 1999), (+)-germacrene A, germacra-1(10),4,11(13)-trien-12-al, germacra-1(10), 4,11(13)-trien-12-al, and germacra-1(10), 4,11(13)-trine-12-oic acid (Kraker et al, 2001) were also isolated. 22-Dihydrostigmasterol (Jain and Banks, 1968) and sesquiterpenoides (Maurer and Grieder, 1977) were reported from costus root oil.…”

Section: Conditions Methods Of Applications Referencementioning

confidence: 99%