Identification of triterpene biosynthetic genes from Momordica charantia using RNA-seq analysis

References

• Mahato SB, Sen S. Advances in triterpenoid research, 1990–1994. Phytochemistry. 1997;44:1185–1236.
   PubMed Web of Science ®Google Scholar
• Thimmappa R, Geisler K, Louveau T, et al. Triterpene biosynthesis in plants. Annu Rev Plant Biol. 2014;65:225–257.
   PubMed Web of Science ®Google Scholar
• Seki H, Tamura K, Muranaka T. P450s and UGTs: key players in the structural diversity of triterpenoid saponins. Plant Cell Physiol. 2015;56:1463–1471.
   PubMed Web of Science ®Google Scholar
• Chen JC, Chiu MH, Nie RL, et al. Cucurbitacins and cucurbitane glycosides: structures and biological activities. Nat Prod Rep. 2005;22:386–399.
   PubMed Web of Science ®Google Scholar
• Huang S, Li R, Zhang Z, et al. The genome of the cucumber, Cucumis sativus L. Nat Genet. 2009;41:1275–1281.
   PubMed Web of Science ®Google Scholar
• Shang Y, Ma Y, Zhou Y, et al. Biosynthesis, regulation, and domestication of bitterness in cucumber. Science. 2014;346:1084–1088.
   PubMed Web of Science ®Google Scholar
• Zhou Y, Ma Y, Zeng J, et al. Convergence and divergence of bitterness biosynthesis and regulation in Cucurbitaceae. Nat Plants. 2016;2:1–8.
   Web of Science ®Google Scholar
• Murakami T, Emoto A, Matsuda H, et al. Medicinal foodstuffs. XXI. Structures of new cucurbitane-type triterpene glycosides, goyaglycosides-a, -b, -c, -d, -e, -f, -g, and -h, and new oleanane-type triterpene saponins, goyasaponins I, II, and III, from the fresh fruit of Japanese Momordica charantia L. Chem Pharm Bull. 2001;49:54–63.
   PubMed Web of Science ®Google Scholar
• Tan MJ, Ye JM, Turner N, et al. Antidiabetic activities of triterpenoids isolated from bitter melon associated with activation of the AMPK pathway. Chem Biol. 2008;15:263–273.
   PubMed Web of Science ®Google Scholar
• Tabata M, Tanaka S, Cho HJ, et al. Production of an anti-allergic triterpene, bryonolic acid, by plant cell cultures. J Nat Prod. 1993;56:165–174.
   PubMed Web of Science ®Google Scholar
• Akihisa T, Kimura Y, Kasahara Y, et al. 7-oxodihydrokarounidiol-3-benzoate and other triterpenes from the seeds of cucurbitaceae. Phytochemistry. 1997;46:1261–1266.
   Web of Science ®Google Scholar
• Suzuki Y, Kawazu T, Koyama H. RNA isolation from siliques, dry seeds, and other tissues of Arabidopsis thaliana. BioTechniques. 2004;37:542–544.
   Web of Science ®Google Scholar
• Han R, Takahashi H, Nakamura M, et al. Transcriptome analysis of nine tissues to discover genes involved in the biosynthesis of active ingredients in Sophora flavescens. Biol Pharm Bull. 2015;38:876–883.
   PubMed Web of Science ®Google Scholar
• Kushiro T, Shibuya M, Ebizuka Y. β-Amyrin synthase cloning of oxidosqualene cyclase that catalyzes the formation of the most popular triterpene among higher plants. Eur J Biochem. 1998;256:238–244.
   PubMedGoogle Scholar
• Lodeiro S, Schulz-Gasch T, Matsuda SP. Enzyme redesign: two mutations cooperate to convert cycloartenol synthase into an accurate lanosterol synthase. J Am Chem Soc. 2005;127:14132–14133.
   PubMed Web of Science ®Google Scholar
• Shibuya M, Adachi S, Ebizuka Y. Cucurbitadienol synthase, the first committed enzyme for cucurbitacin biosynthesis, is a distinct enzyme from cycloartenol synthase for phytosterol biosynthesis. Tetrahedron. 2004;60:6995–7003.
   Web of Science ®Google Scholar
• Kushiro T, Shibuya M, Masuda K, et al. Mutational studies on triterpene synthases: engineering lupeol synthase into β-amyrin synthase. J Am Chem Soc. 2000;122:6816–6824.
   Web of Science ®Google Scholar
• Morita M, Shibuya M, Lee M-S, et al. Molecular cloning of pea cDNA encoding cycloartenol synthase and its functional expression in yeast. Biol Pharm Bull. 1997;20:770–775.
   PubMed Web of Science ®Google Scholar
• Takai M, Tori M, Tsuyuki T, et al. Boron trifluoride etherate-catalyzed backbone rearrangement of 5α,10α-epoxyalnusan-3β-yl acetate and partial synthesis of isomultiflorenol. Bull Chem Soc Jpn. 1985;58:185–193.
   Web of Science ®Google Scholar
• Faure R, Gaydou EM. Application of inverse-detected two-dimensional heteronuclear-correlated NMR spectroscopy to the complete carbon-13 assignment of isomultiflorenyl acetate. J Nat Prod. 1991;54:1564–1569.
   Web of Science ®Google Scholar
• Chang Y-S, Lin M-S, Jiang R-L, et al. 20-Epibryonolic acid, phytosterols and ellagic acid from Coriaria intermedia. Phytochemistry. 1996;42:559–560.
   Web of Science ®Google Scholar
• Chen J, Tian R, Qiu M, et al. Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia. Phytochemistry. 2008;69:1043–1048.
   PubMed Web of Science ®Google Scholar
• Liu JQ, Chen JC, Wang CF, et al. New cucurbitane triterpenoids and steroidal glycoside from Momordica charantia. Molecules. 2009;14:4804–4813.
   PubMed Web of Science ®Google Scholar
• Zeng K, He Y-N, Yang D, et al. New compounds from acid hydrolyzed products of the fruits of Momordica charantia L. and their inhibitory activity against protein tyrosine phosphatase 1B. Eur J Med Chem. 2014;81:176–180.
   PubMed Web of Science ®Google Scholar
• Akihisa T, Higo N, Tokuda H, et al. Cucurbitane-type triterpenoids from the fruits of Momordica charantia and their cancer chemopreventive effects. J Nat Prod. 2007;70:1233–1239.
   PubMed Web of Science ®Google Scholar
• Hayashi H, Huang P, Inoue K, et al. Molecular cloning and characterization of isomultiflorenol synthase, a new triterpene synthase from Luffa cylindrica, involved in biosynthesis of bryonolic acid. Eur J Biochem. 2001;268:6311–6317.
   PubMedGoogle Scholar
• Fatope MO, Takeda Y, Yamashita H, et al. New cucurbitane triterpenoids from Momordica charantia. J Nat Prod. 1990;53:1491–1497.
   Web of Science ®Google Scholar