Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 35, 2021 - Issue 24
210
Views
3
CrossRef citations to date
0
Altmetric
Research Articles

Uvarmicranones A and B, two new benzoquinones and cytotoxic constituents from the stems of Uvaria micrantha (A. DC.) Hook. f. & Thomson

, , , , &
Pages 5643-5652 | Received 07 May 2020, Accepted 28 Aug 2020, Published online: 22 Sep 2020

References

  • Achenbach H, Hemrich H. 1991. Alkaloids, flavonoids and phenylpropanoids of the West African plant Oxymitra velutina. Phytochemistry. 30(4):1265–1267.
  • Akihisa T, Yamamoto K, Tamura T, Kimura Y, Iida T, Nambara T, Chang FC. 1992. Triterpenoid ketones from Lingnania chungii McClure: Arborinone, friedelin and glutinone. Chem Pharm Bull. 40(3):789–791.
  • Alias Y, Awang K, Hadi AH, Thoison O, Sévenet T, Païs M. 1995. An antimitotic and cytotoxic chalcone from Fissistigma lanuginosum. J Nat Prod. 58(8):1160–1166.
  • Auranwiwat C, Wongsomboon P, Thaima T, Rattanajak R, Kamchonwongpaisan S, Willis AC, Lie W, Pyne SG, Limtharakul T. 2017. 2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae). Fitoterapia. 120:103–107.
  • Awale S, Tawila AM, Dibwe DF, Ueda JY, Sun S, Athikomkulchai S, Balachandran CB, Saiki I, Matsumoto K, Esumi H. 2017. Highly oxygenated antiausterity agents from the leaves of Uvaria dac. Bioorg Med Chem Lett. 27(9):1967–1971.
  • Biswas P, Bhattacharyya A, Bose PC, Mukherjee N, Adityachaudhury N. 1981. Further studies on the sensitivity of plant pathogenic microorganisms towards some naturally occurring chalcones and flavanones. Experientia. 37(4):397–398.
  • Bohlmann F, Zdero C, Ziesche J. 1979. Neue flavone und phloroglucin-derivate aus Helichrysum herbaceum und Helichrysum chrysargyrum. Phytochemistry. 18(8):1375–1378.
  • Boonsombat J, Chawengrum P, Mahidol C, Kittakoop P, Ruchirawat S, Thongnest S. 2020. A new 22,26-seco physalin steroid from Physalis angulata. Nat Prod Res. 34(8):1097–1104.
  • Chalermglin P. 2001. Annonaceaous plants. Bangkok: Amarin Printing and Publishing Public Co. Ltd.; p. 17.
  • Chantrapromma K, Rat-A-Pa Y, Karalai C, Lojanapiwatana V, Seechamnanturakit V. 2000. A chalcone and a dihydrochalcone from Uvaria dulcis. Phytochemistry. 53(4):511–513.
  • Costa EV, Marques FA, Pinheiro MLB, Vaz NP, Duarte MCT, Delarmelina C, Braga RM, Sales Maia BHLN. 2009. 7,7-Dimethylaporphine alkaloids from the stem of Guatteriopsis friesiana. J Nat Prod. 72(8):1516–1519.
  • Gény C, Abou Samra A, Retailleau P, Iorga BI, Nedev H, Awang K, Roussi F, Litaudon M, Dumontet V. 2017. (+)- and (-)-Ecarlottones, uncommon chalconoids from fissistigma latifolium with pro-apoptotic activity. J Nat Prod. 80(12):3179–3185.
  • Ichino K, Tanaka H, Ito K, Tanaka T, Mizuno M. 1988. Two new dihydrochalcones from Lindera erythrocarpa. J Nat Prod. 51(5):915–917.
  • Kamperdick C, Van NH, Sung TV. 2002. Constituents from Miliusa balansae (Annonaceae). Phytochemistry. 61(8):991–994.
  • Kaweetripob W, Mahidol C, Prawat H, Ruchirawat S. 2015. Cyclohexene long-chain fatty acid esters from Uvaria dulcis (Dunal). Phytochemistry Lett. 12:248–251.
  • Kaweetripob W, Mahidol C, Thongnest S, Prawat S, Ruchirawat S. 2016. Polyoxygenated ursane and oleanane triterpenes from Siphonodon celastrineus. Phytochemistry. 129:58–67.
  • King RR, Calhoun LA. 2005. Characterization of cross-linked hydroxycinnamic acid amides isolated from potato common scab lesions. Phytochemistry. 66(20):2468–2473.
  • Koudokpon H, Armstrong N, Dougnon TV, Fah L, Hounsa E, Bankolé HS, Loko F, Chabrière E, Rolain JM. 2018. Antibacterial activity of chalcone and dihydrochalcone compounds from Uvaria chamae roots against multidrug-resistant bacteria. Bio Med Res Int. 2018:1–10.
  • Kruakaew S, Seeka C, Lhinhatrakool T, Thongnest S, Yahuafai J, Piyaviriyakul S, Siripong P, Sutthivaiyakit S. 2017. Cytotoxic cardiac glycoside constituents of Vallaris glabra leaves. J Nat Prod. 80(11):2987–2996.
  • Löbermann F, Mayer P, Trauner D. 2010. Biomimetic synthesis of (-)-pycnanthuquinone C through the Diels-Alder reaction of a vinyl quinone. Angew Chem Int Ed Engl. 49(35):6199–6202.
  • Meesakul P, Pyne SG, Laphookhieo S. 2020. Potent α-glucosidase inhibitory activity of compounds isolated from the leaf extracts of Uvaria hamiltonii. Nat Prod Res. 34:2495–2499.
  • Parmar VS, Tyagi OD, Malhotra A, Singh SK, Bisht KS, Jain R. 1994. Novel constituents of Uvaria species. Nat Prod Rep. 11(2):219–224.
  • Patra A, Mitra AK, Bhattacharyya A, Adityachaudhury N. 1982. Carbon-13 spectral studies of some chalcones and flavanones. Org Magn Reson. 18(4):241–242.
  • Pooma R, Suddee S. 2014. Thai plant names Tem Smitinant Revised Edition 2014k Office of the Forest Herbarium. Bangkok: Department of National Park, Wildlife and Plant Conservation; p. 574–575.
  • Prawat H, Mahidol C, Kaweetripob W, Intachote P, Pisutjaroenpong S, Ruchirawat S. 2016. Cytotoxic steroidal glycosides from the whole plant of Calamus acanthophyllus. Planta Med. 82(11–12):1117–1121.
  • Rathore JS, Garg SK, Nagar A, Sharma ND, Gupta SR. 1981. New phenolic components of Didymocarpus pedicellata. Planta Med. 43(1):86–88.
  • Ruangrangsi N. 2004. Thai herbs No. 1. Bangkok: B Healthy Publishing; p. 150.
  • Sakurai N, Yaguchi Y, Inoue T. 1987. Triterpenoids from Myrica rubra. Phytochemistry. 26(1):217–219.
  • Salae AW, Chairerk O, Sukkoet P, Chairat T, Prawat U, Tuntiwachwuttikul P, Chalermglin P, Ruchirawat S. 2017. Antiplasmodial dimeric chalcone derivatives from the roots of Uvaria siamensis. Phytochemistry. 135:135–143.
  • Seangphakdee P, Pompimon W, Meepowpan P, Panthong A, Chiranthanut N, Banjerdpongchai R, Wudtiwai B, Nuntasaen N, Pitchuanchom S. 2013. Anti-inflammatory and anticancer activities of (-)-zeylenol from stems of Uvaria grandiflora. Sci Asia. 39(6):610–614.
  • Sutthanut K, Sripanidkulchai B, Yenjai C, Jay M. 2007. Simultaneous identification and quantitation of 11 flavonoid constituents in Kaempferia parviflora by gas chromatography. J Chromatogr A. 1143(1–2):227–233.
  • Susidarti RA, Rahmani M, Ismail HBM, Sukari MA, Hin TYY, Lian GEEC, Ali AM, Kulip J, Waterman PG. 2006. A new coumarin and triterpenes from Malaysian Micromelum minutum. Nat Prod Res. 20(2):145–151.
  • Suthiphasilp V, Maneerat W, Andersen RJ, Patrick BO, Phukhatmuen P, Pyne SG, Laphookhieo S. 2019. Uvarialuridols A-C, three new polyoxygenated cyclohexenes from the twig and leaf extracts of Uvaria lurida. Fitoterapia. 138:104340
  • Thongnest S, Boonsombat J, Prawat H, Mahidol C, Ruchirawat S. 2017. Ailanthusins A-G and nor-lupane triterpenoids from Ailanthus triphysa. Phytochemistry. 134:98–105.
  • Thongnest S, Chawengrum P, Keeratichamroen S, Lirdprapamongkol K, Eurtivong C, Boonsombat J, Kittakoop P, Svasti J, Ruchirawat S. 2019. Vernodalidimer L, a sesquiterpene lactone dimer from Vernonia extensa and anti-tumor effects of vernodalin, vernolepin, and vernolide on HepG2 liver cancer cells. Bioorg Chem. 92:103197
  • Tip-Pyang S, Payakarintarungkul K, Sichaem J, Phuwapraisirisan P. 2011. Chemical constituents from the roots of Uvaria rufa. Chem Nat Compd. 47(3):474–476.
  • Varghese AE, Govindan B, Madhavankutty J, Valiyaveetil AT, Karadka M, Baby S. 2018. A new antifungal benzoic acid ester from Uvaria narum. Nat Prod Res. 32:2567–2662.
  • Vieira PC, De Alvarenga MA, Gottlieb OR, Gottlieb HE. 1980. 4-Hexadecenylphenol and flavonoids from Piper hispidum. Planta Med. 39(06):153–156.
  • Wijeratne EMK, Hatanaka Y, Kikuchi T, Tezuka Y, Gunatilaka AAL. 1996. A dioxoaporphine, and other alkaloids of two annonaceous plants of Sri Lanka. Phytochemistry. 42(6):1703–1706.
  • Wirasathien L, Pengsuparp T, Moriyasu M, Kawanishi K, Suttisri R. 2006. Cytotoxic C-benzylated chalcone and other constituents of Ellipeiopsis cherrevensis. Arch Pharm Res. 29(6):497–502.
  • Wittayalai S, Mahidol C, Prachyawarakorn V, Prawat H, Ruchirawat S. 2014. Terpenoids from the roots of Drypetes hoaensis and their cytotoxic activities. Phytochemistry. 99:121–126.
  • Zhang YN, Zhong XG, Zheng ZP, Hu XD, Zuo JP, Hu LH. 2007. Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr. Bioorg Med Chem. 15(2):988–996.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.