Four new sesquiterpenoids from the soft coral Nephthea chabrollii

Rao, M. Rama; Sridevi, K. V.; Venkatesham, U.; Rao, T. Prabhaker; Lee, S.S.; Venkateswarlu, Y.

doi:10.3184/030823400103167165

Cited by 18 publications

(13 citation statements)

References 16 publications

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“…Compound 2, a white amorphous powder, exhibited a molecular ion peak M þ at m/z 292.1310 (calc. 292.1311) in the HR-EI-MS, which is consistent with the molecular formula C 16 (Table). The C-atom signals at d(C) 168.9 (C(12)), 137.9 (C(11)), 11.0 (C(13)), 144.8 (C (7)), and 139.1 (C(8)), were undoubtedly assigned to an a,b-unsaturated a-methyl-g-lactone ring.…”

Section: Sesquiterpenoids From the Resinous Exudates Of Commiphora Opsupporting

confidence: 67%

“…Compound 1 was isolated as colorless crystals, which showed a pseudomolecular ion at m/z 301.6 [M þ Na] þ in the positive-ion ESI-MS. Its molecular formula was determined to be C 16 (Table). The presence of an a,b-unsaturated a-methyl-g-lactone moiety was confirmed by the C-atom signals at d(C) 172.8 (C (12)), 129.6 (C(11)), 10.3 (C(13)), 158.7 (C(7)), and 80.9 (C (8) (9) (Fig.…”

Section: Sesquiterpenoids From the Resinous Exudates Of Commiphora Opmentioning

confidence: 99%

“…The known compounds 4 -9 were identified as (1E)-3-methoxy-8,12-epoxygermacra-1,7,10,11-tetraen-6-one (4) [13], rel-(1S,2S)-epoxy-(4R)-furanogermacr-10(15)-en-6-one (5) [14], 6a,7a-epoxy-1b-guai-10(14)-en-4a-ol (6) [15], (1R,4S,5R)-guaia-6,10(14)-diene (7) [16], cerotic acid (8) [17], and b-sitosterol (9) [17] C-NMR data with those reported in the cited references. The antifungal activities of compounds 1 -8 were tested against Candida albicans.…”

Section: Sesquiterpenoids From the Resinous Exudates Of Commiphora Opmentioning

confidence: 99%

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Sesquiterpenoids from the Resinous Exudates of Commiphora opobalsamum (Burseraceae)

Shen

Wan

Wang

et al. 2008

Helvetica Chimica Acta

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Phytochemical investigation of the exudates of Commiphora opobalsamum led to the isolation of three new sesquiterpenoids, 2α‐methoxy‐6‐oxogermacra‐1(10),7(11)‐dien‐8,12‐olide (1), 5β‐10α‐hydroxy‐2α‐methoxy‐6‐oxoguaia‐7(11),8‐dien‐8,12‐olide (2), and furanocadina‐1(10),6,8‐triene‐4‐ol (3), together with six known compounds. Their structures were elucidated on the basis of spectroscopic methods.

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Section: Sesquiterpenoids From the Resinous Exudates Of Commiphora Opsupporting

confidence: 67%

Section: Sesquiterpenoids From the Resinous Exudates Of Commiphora Opmentioning

confidence: 99%

Section: Sesquiterpenoids From the Resinous Exudates Of Commiphora Opmentioning

confidence: 99%

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Sesquiterpenoids from the Resinous Exudates of Commiphora opobalsamum (Burseraceae)

Shen

Wan

Wang

et al. 2008

Helvetica Chimica Acta

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“…The relative configuration of 1 was deduced from the 1 H, 1 H coupling constants and the ROESY data. Since HÀC(5) was supposed to be b-oriented [6], HÀC(1) should be a-oriented from the coupling constant between HÀC(1) and HÀC(5) (J ¼ 15.3 Hz). The ROESY cross-peaks HÀC(1)/HÀC(9) and H trans ÀC(14) (trans to C(9))/Me (15) indicated that HÀC(9) was a-oriented, while Me(15) was boriented (Fig.…”

mentioning

confidence: 99%

A Guaianolide Sesquiterpene, a Chromenone, and a Flavanone from Ligularia macrophylla

Wang

Chen

2007

Helvetica Chimica Acta

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Three new compounds, (5b,9b)-guaia-6,10(14)-dien-9-ol (¼ rel-(1R,3aS,5R,8aR)-1,2,3,3a,4,5,6,8a-octahydro-1-methyl-4-methylene-7-(1-methylethyl)azulen-5-ol; 1), 6-acetyl-8-methoxy-2,3-dimethylchromen-4-one (¼ 6-acetyl-8-methoxy-2,3-dimethyl-4H-1-benzopyran-4-one; 2), and (2S)-3'-hydroxy-5',7-dimethoxyflavanone (¼ (2S)-2,3-dihydro-2-(3-hydroxy-5-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one; 3) were isolated from the roots and rhizomes of Ligularia macrophylla, together with seven known compounds. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques.Introduction. -Much attention has been focused on the Ligularia (Asteraceae) plants for the long history of use as folk remedies and the abundant sesquiterpenes distributed in this genus. The roots and rhizomes of Ligularia macrophylla (Ledeb.) DC. are used as a Chinese folk medicine for the treatment of tracheitis, phthisis, hemoptysis, cough, and asthma [1]. In the previous reports, fatty acids, polyenes, pyrrolizidine alkaloids, and eremophilane sesquiterpenes have been isolated [2 -4]. Our preliminary study showed that the AcOEt-soluble fraction from an EtOH extract of the roots and rhizomes of L. macrophylla, a plant growing in the Tianshan mountains of China, exhibited cytotoxic activity against human breast adenocarcinoma cells (MCF-7) in vitro. This prompted us to investigate its chemical constituents. The phytochemical study led to the isolation and characterization of three new compounds 1 -3, together with seven known ones; however, no isolate showed cytotoxicity (EC 50 > 20 mg/ml). This paper deals with the isolation and structural elucidation of the three new compounds 1 -3.

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“…Chemical investigation of soft corals of the genus Nephthea (i.e. N. chabrolii [3][4][5][6][7]14 , N. brassica, 8,15,16 N. tixera, 11 N. albida 11,12 , N. erecta 13 and other Nephthea spp. 9,10,[17][18][19][20][21][22] ) collected from various locations led to the isolation of varied extractives viz., sesquiterpenoids (guaianes 3,4,6,7,8,22 and eudesmanes 17,21 ), tetraprenylbenzenoids 9,21 , diphenylpropane-1,3-diol 10 , sterols (24-methylenecholesterols [11][12][13][14][15][16] ) and diterpenoids (bicyclic 6,22 , brassicolides, 8 xeniaphyllanes 17 , and cembranes [18][19][20]23,24 ).…”

Section: Introductionmentioning

confidence: 99%