Chemistry:Kuguacin
A kuguacin is one of several chemical compounds isolated from the bitter melon vine (Momordica charantia, kǔguā in Chinese) by J.-C. Chen and others.[1] Kuguacins are cucurbitacins, formally derived from the triterpene hydrocarbon cucurbitane. They include:
- Kuguacin A[2]
- Kuguacin B[2]
- Kuguacin C[2]
- Kuguacin D[2]
- Kuguacin E[2]
- Kuguacin F: C30H42O5; 47 mg/kg, needles, melts at 275–276 °C [1]:1
- Kuguacin G: C30H44O6; 23 mg/kg, needles, melts at 250–252 °C [1]:2
- Kuguacin H: C30H44O5; 27 mg/kg, needles, melts at 226–228 °C [1]:3
- Kuguacin I: C31H46O4; 20 mg/kg, needles, melts at 235–237 °C [1]:4
- Kuguacin J: C30H46O3; 243 mg/kg, powder, melts at 166–169 °C [1]:5
- Kuguacin K: C25H34O6; 130 mg/kg, powder, melts at 275–277 °C [1]:6
- Kuguacin L: C25H36O4; 30 mg/kg, needles, melts at 320–321 °C [1]:7
- Kuguacin M: C22H28O4; 7 mg/kg, needles, melts at 332–333 °C [1]:8
- Kuguacin N: C30H46O4; 247 mg/kg, powder, melts at 140–143 °C [1]:9
- Kuguacin O: C30H42O4; 20 mg/kg, needles, melts at 267–269 °C [1]:10
- Kuguacin P: C27H40O4; 293 mg/kg, prisms, melts at 229–231 °C [1]:11
- Kuguacin Q: C29H44O5; 11 mg/kg, needles, melts at 219–221 °C [1]:12
- Kuguacin R: C30H48O4; 1357 mg/kg [1]:13
- Kuguacin S: C30H44O4; 17 mg/kg, powder, melts at 174–177 °C [1]:14
Kuguacins F-S can be extracted with ethanol from the stems and leaves of M. charantia. Kuguacins I, J, and Q are artifacts of the extraction process. Kuguacin R is obtained as mixture of two epimers. In this process one also obtains momordicine I,[3] kuguacin E, 5β,19-epoxycucurbita-6,23-diene-3β,19,25-triol,[4] karavilagenin D,[5] 3β,7β,25-trihydroxycucurbita-5,(23E)-dien-19-al,[6] and 3β,7β-dihydroxy-25-methoxycucurbita-5,(23E)-dien-19-al[6] In vitro tests showed weak anti-HIV activity for kuguacins F-S, especially kuguacin Q and kuguacin S.[1]
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 1.15 Jian-Chao Chen, Wu-Qing Liu, Lu Lu, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang, Xian-Min Zhang, Lin Zhou and Zhong-Rong Li (2009), "Kuguacins F–S, cucurbitane triterpenoids from Momordica charantia". Phytochemistry, volume 70, issue 1, pages 133-140 doi:10.1016/j.phytochem.2008.10.011
- ↑ 2.0 2.1 2.2 2.3 2.4 J. C. Chen, R. R. Tian, M. H. Qiu, L. Lu, Y. T. Zheng, Z. Q. Zhang (2008), "Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia." Phytochemistry, volume 69, pages 1043–1048
- ↑ M. Yasuda, M. Iwamoto, H. Okabe, T. Yamauchi (1984), "Structures of momordicines I, II and III, the bitter principles in the leaves and vines of Momordica charantia L. Chem. Pharm. Bull., volume 32, pages 2044–2047.
- ↑ Dulcie A. Mulholland, Vikash Sewram, Roy Osborne, Karl H. Pegel and Joseph D. Connolly (1997), "Cucurbitane triterpenoids from the leaves of Momordica foetida." Phytochemistry, volume 45, issue 2, pages 391-395. doi:10.1016/S0031-9422(96)00814-X
- ↑ H. Matsuda, S. Nakamura, T. Murakami, M. Yoshikawa (2007). "Structures of new cucurbitane-type triterpenes and glycosides, karavilagenins D and E, and karavilosides VI, VII, VIII, IX, X, and XI, from the fruit of Momordica charantia." Heterocycles,volume 71, pages 331–341.
- ↑ 6.0 6.1 Majekodunmi Fatope, Yoshio Takeda, Hiroyasu Yamashita, Hikaru Okabe, and Tatsuo Yamauchi (1990), "New cucurbitane triterpenoids from Momordica charantia." Journal of Natural Products, volume 53, issue 6, pages 1491-1497.
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