Elsevier

Phytochemistry

Volume 32, Issue 2, 20 January 1993, Pages 484-486
Phytochemistry

Short report
Dehydro-6-hydroxyrotenoid and lupenone from Tephrosia villosa

https://doi.org/10.1016/S0031-9422(00)95025-8Get rights and content

Abstract

A new dehydro-6-hydroxyrotenoid, 12a-dehydro-6-hydroxysumatrol and lupenone were isolated from whole plants of Tephrosia villosa. Their structures were elucidated from chemical and spectroscopic evidence. The new rotenoid structure was confirmed by its partial synthesis from 6a, 12a-dehydrosumatrol.

References (12)

  • G.L.D. Krupadanam et al.

    Tetrahedron Letters

    (1977)
  • D.M. Piatak et al.

    Phytochemistry

    (1975)
  • D. Shiengthong et al.

    Tetrahedron Letters

    (1974)
  • S.P. Ambasta
  • H.D. Rogers et al.

    Ind. Eng. Chem. Analyt. Edn

    (1936)
  • P.N. Sarma et al.

    Indian. J. Chem.

    (1976)
There are more references available in the full text version of this article.

Cited by (27)

  • Secoiridoids and triterpenoids from the traditional Tibetan medicine Gentiana veitchiorum and their immunosuppressive activity

    2021, Phytochemistry
    Citation Excerpt :

    Therefore, the structure of compound 12 was determined, and 12 was named as 17-hydroperoxide-28-norurs-12-en-3-one. The known compounds were respectively identified as swerimuslactone A (3) (Cao et al., 2015), gentiolactone (4) (Kakuda et al., 2003), swerimilegenin C (5) (Geng et al., 2013), swerimusaldehyde A (6) (Dong et al., 2017a, b), angelone (7) (Mulholland et al., 2006), erythrocentaurin (8) (Hou et al., 2020), 5-ethenyl-3,4-dihydro-1H-2-benzopyran-1-one (9) (Kawasaki et al., 2002), 5-ethyl-3,4-dihydro-1H-2-benzopyran-1-one (10) (Kawasaki et al., 2002), lupeol (13) (Prashant et al., 1993), betulin (14) (Siddiqui et al., 1988), betulinal (15) (Barthel et al., 2008), betulinic acid (16) (Siddiqui et al., 1988), commiphorane G3 (17) (Dong et al., 2017a, b), ursolic aldehyde (18) (Bonaduce et al., 2016), and ursolic acid (19) (Siddiqui et al., 1988), by comparing their NMR spectroscopic data with those described in the literature. Compounds 1–12 were evaluated for their immunosuppressive activity through inhibiting anti-CD3/CD28 induced T cell proliferation and IFN-γ production after T cell activation.

  • Beneficial health effects of lupenone triterpene: A review

    2018, Biomedicine and Pharmacotherapy
    Citation Excerpt :

    1H NMR (100 MHz, CDCl3): δ 1.75–1.98 (2 H, m, H-l), 2.20–2.40 (3 H, m, H-2, H-19), 0.69 (1 H, d, H-5), 1.45 (2 H, m, H-6), 1.40 (1 H, m, H-7), 1.17(1 H, d, H-9), 1.35 (2 H, m, H-11), 1.07, 1.68 (1 H, each, H-12), 1.67 (1 H, t, H-13), 1.02, 1.75 (1 H, each, H-15), 1.38, 1.41 (1 H, each, H-16), 1.35 (1 H, t, H-8), 1.30, 1.93 (1 H, each m, H-21), 1.20, 1.42 (1 H each, m, H-22), 0.97 (3 H, s, Me-23), 0.75 (3 H, s, Me-24), 0.82 (3 H, s, Me-25), 1.02 (3 H, s, Me-26), 0.94 (3 H, s, Me-27), 0.78 (3 H, s, Me-28), 4.63, 4.50 (1 H, each, br s, Me-29) and 1.76 (3 H, s, Me-30). 13C NMR (25 MHz, CDCl3); δ 39.6 (C-l), 34.1 (C-2), 218.2 (C-3), 47.2 (C-4), 54.9 (C-5), 19.6 (C-6), 33.5 (C-7), 40.7 (C-8), 49.8 (C-9), 36.8 (C-10), 21.4 (C-11), 25.1 (C-12), 38.1 (C-13), 42.8 (C-14), 27.4 (C-15), 35.5 (C-16), 42.9 (C-17), 47.9 (C-18), 48.2 (C-19), 150.8 (C-20), 29.8 (C-21), 39.9 (C-22), 26.6 (C-23), 20.9 (C-24), 15.7 (C-25), 15.9 (C-26), 14.4 (C-27), 17.9 (C-28), 109.5 (C-29), and 19.2 (C-30) [17,58]. The chemical structure of lupenone is presented in Fig. 1B.

  • Chemical constituents from bark of Millettia mannii Baker (Papilionoideae-Leguminosae)

    2012, Biochemical Systematics and Ecology
    Citation Excerpt :

    Fr. C (3% MeOH) was purified using silica gel CC eluted with n-hexane to afford lupeol (7, 258 mg) (Filho et al., 1975; Lin and Kuo, 1995; Tagatsing et al., 2011) and lupenone (8, 135 mg) (Prashant and Krupadanam, 1993; Lin and Kuo, 1995; Jang et al., 2003; Martelanc et al., 2009). Fr.

  • Flavonoids from Tephrosia deflexa and T. albifoliolis

    2005, Biochemical Systematics and Ecology
    Citation Excerpt :

    Numerous polyphenols have been already isolated from the genus Tephrosia: isoflavones in Tephrosia viridiflora (Gómez-Garibay et al., 1985b), flavans in Tephrosia hildebrandtii (Delle Monache et al., 1986), flavonones in Tephrosia leiocarpa (Gómez-Garibay et al., 1991), biflavanols in Tephrosia crassifolia (Gómez-Garibay et al., 1999) and chalcones in Tephrosia aequilata (Tarus et al., 2002). Rotenone and other rotenoids like tephrosine (oxydegueline) are well known for their insecticidal, piscidal and repellent properties (Delobel and Malonga, 1987) and described notably in Tephrosia villosa (Krupadanam et al., 1977; Prashant and Krupadanam, 1993), Tephrosia vogelii (Marston et al., 1984), Tephrosia interrupta and Tephrosia linearis (Were, 1988), Tephrosia candida (Andrei et al., 1997), Tephrosia tunicata (Andrei et al., 2000) and more recently in Tephrosia vogelli (Boeke et al., 2004). Although the presence of C-prenylflavonoids appears widespread in this genus (Gómez-Garibay et al., 1983; Gómez-Garibay et al., 1985a; Gómez-Garibay et al., 1988; Gómez-Garibay et al., 1997), our results show only the presence of rotenone in T. deflexa, along with other common flavonoids.

  • Pentacyclic triterpenes and other constituents in propolis extract from Melipona beecheii collected in Yucatan, México

    2019, Revista Brasileira de Farmacognosia
    Citation Excerpt :

    The metabolites 4 and 5 presented a base ion peak at m/z 218 and the fragment ions at m/z 203 and m/z 189 which allowed identified as β-amyrenone (4) and α-amyrenone (5) (Mathe et al., 2004; Cely-Veloza et al., 2014; Ferreira et al., 2017a,b). The metabolite 6 presented a base ion peak at m/z 205 and an ion peak at 189 characteristic of a lupane triterpen skeleton, which allowed to identify it as lupenone (6) (Prashant and Krupadanam, 1993). The metabolites 7 (tR 29.02 min) and 8 (tR 30.29 min) presented parent ion peak at m/z 438 (C31H50O) and m/z 468 (C32H52O2) respectively and according to their fragmentation patterns were identified as 24-methylencycloartan-3-one (7) (Alsaadi and Al-Maliki, 2015) and moretenol acetate (8) (Abdel El-Fattah et al., 1992).

View all citing articles on Scopus
View full text