196
N. N. Win and H. Morita
R
1
R
2
R
3
R
4
309 (kaempulchraol A) R
1 = R
3 = H, R
2 = β-OH, R
4 = α-OMe
310 (kaempulchraol B) R
1 = R
3 = H, R
2 = β-OH, R
4 = β-OMe
311 (kaempulchraol C) R
1 = R
3 = H, R
2 = β-OH, R
4 = α-OH
312 (kaempulchraol D) R
1 = R
3 = H, R
2 = β-OH, R
4 = β-OH
315 (kaempulchraol G) R
1 = R
3 = H, R
2 = β-OH, R
4 = =O
322 (kaempulchraol N) R
1 = R
4 = α-OH, R
2 = β-OH, R
3 = H
323 (kaempulchraol O) R
1 = α-OH, R
2 = β-OH, R
3 = H, R
4 = β-OMe
327 (kaempulchraol S) R
1 = R
2 = H, R
3 = =O, R
4 = α-OH
329 (kaempulchraol U) R
1 = R
2 = R
3 =H, R
4 = α-OH
R
1
R
2
R
3
R
4
R
5
313 (kaempulchraol E) R
1 = α-OH, R
2 = R
3 = R
5 = R
6 = H, R
4 = β-OH
314 (kaempulchraol F) R
1 = R
3 = α-OH, R
2 = R
4 = R
5 = R
6 = H
316 (kaempulchraol H) R
1 = R
3 = α-OH, R
2 = R
5 = R
6 = H, R
4 = β-OH
317 (kaempulchraol I) R
1 = α-OH, R
2 = R
3 = R
4 = R
5 = R
6 =H
318 (kaempulchraol J) R
1 = α-OH, R
2 = R
3 = R
4 = R
6 =H, R
5 = =O
319 (kaempulchraol K) R
1 = R
2 = R
3 = R
5 = H, R
4 = β-OAc, R
6 = OH
320 (kaempulchraol L) R
1 = R
2 = R
3 = R
5 = H, R
4 = β-OH, R
6 = OMe
321 (kaempulchraol M) R
1 = R
2 = R
6 = α-OH, R
3 = R
4 = R
5 = H
324 (kaempulchraol P) R
1 = R
2 = R
3 = R
5 = R
6 = H, R
4 = β-OH
325 (kaempulchraol Q) R
1 = α-OAc, R
2 = R
3 = R
5 = R
6 = H, R
4 = β-OH
326 (kaempulchraol R) R
1 = R
2 = R
3 = R
4 = H, R
5 = α-OAc, R
6 = OH
328 (kaempulchraol T) R
1 = R
2 = R
3 = R
6 = H, R
4 = β-OH, R
5
= α-OAc
330 (kaempulchraol V) R
1 = R
2 = R
3 = H, R
4 = β-OH, R
5
= β-OAc, R
6 = OH
331 (kaempulchraol W) R
1 = R
2 = R
3 = H, R
4 = R
5 = β-OH, R
6 = OH
R
6
Fig. 65 Structures of the new isopimara-8(9),15-dienes 309–312, 315, 322, 323, 327, 329 and
the isopimara-8(14),15-dienes 313, 314, 316, 317–321, 324–326, 328, 330, 331, isolated from a
chloroform-soluble fraction of K. pulchra rhizomes grown in Myanmar
(14 kDa) that is conserved in HIV-1, HIV-2, and simian immunodeficiency virus
(SIV) [368, 369], and has been suggested as a promising drug target for comprehensive HIV/AIDS therapy [370, 371]. Fumagillin, damnacanthal, vipirinin, and
quercetin had been reported as Vpr inhibitors earlier [372–375]. The CHCl 3 -soluble
fraction of K. pulchra inhibited Vpr in TREx-HeLa-Vpr cells at an effective dose
of 25 μg/cm
3 . Furthermore, the assay results also revealed that kaempuchraols B
(310), D (312), G (315), Q (325), T (328), U (329), and W (331) exhibited anti-Vpr
activities at concentrations ranging from 1.56 to 6.25 μM. The inhibitory potencies
of compounds 310, 312, 315, 325, 328, 329, and 331 were comparable to that of
N. N. Win and H. Morita
R
1
R
2
R
3
R
4
309 (kaempulchraol A) R
1 = R
3 = H, R
2 = β-OH, R
4 = α-OMe
310 (kaempulchraol B) R
1 = R
3 = H, R
2 = β-OH, R
4 = β-OMe
311 (kaempulchraol C) R
1 = R
3 = H, R
2 = β-OH, R
4 = α-OH
312 (kaempulchraol D) R
1 = R
3 = H, R
2 = β-OH, R
4 = β-OH
315 (kaempulchraol G) R
1 = R
3 = H, R
2 = β-OH, R
4 = =O
322 (kaempulchraol N) R
1 = R
4 = α-OH, R
2 = β-OH, R
3 = H
323 (kaempulchraol O) R
1 = α-OH, R
2 = β-OH, R
3 = H, R
4 = β-OMe
327 (kaempulchraol S) R
1 = R
2 = H, R
3 = =O, R
4 = α-OH
329 (kaempulchraol U) R
1 = R
2 = R
3 =H, R
4 = α-OH
R
1
R
2
R
3
R
4
R
5
313 (kaempulchraol E) R
1 = α-OH, R
2 = R
3 = R
5 = R
6 = H, R
4 = β-OH
314 (kaempulchraol F) R
1 = R
3 = α-OH, R
2 = R
4 = R
5 = R
6 = H
316 (kaempulchraol H) R
1 = R
3 = α-OH, R
2 = R
5 = R
6 = H, R
4 = β-OH
317 (kaempulchraol I) R
1 = α-OH, R
2 = R
3 = R
4 = R
5 = R
6 =H
318 (kaempulchraol J) R
1 = α-OH, R
2 = R
3 = R
4 = R
6 =H, R
5 = =O
319 (kaempulchraol K) R
1 = R
2 = R
3 = R
5 = H, R
4 = β-OAc, R
6 = OH
320 (kaempulchraol L) R
1 = R
2 = R
3 = R
5 = H, R
4 = β-OH, R
6 = OMe
321 (kaempulchraol M) R
1 = R
2 = R
6 = α-OH, R
3 = R
4 = R
5 = H
324 (kaempulchraol P) R
1 = R
2 = R
3 = R
5 = R
6 = H, R
4 = β-OH
325 (kaempulchraol Q) R
1 = α-OAc, R
2 = R
3 = R
5 = R
6 = H, R
4 = β-OH
326 (kaempulchraol R) R
1 = R
2 = R
3 = R
4 = H, R
5 = α-OAc, R
6 = OH
328 (kaempulchraol T) R
1 = R
2 = R
3 = R
6 = H, R
4 = β-OH, R
5
= α-OAc
330 (kaempulchraol V) R
1 = R
2 = R
3 = H, R
4 = β-OH, R
5
= β-OAc, R
6 = OH
331 (kaempulchraol W) R
1 = R
2 = R
3 = H, R
4 = R
5 = β-OH, R
6 = OH
R
6
Fig. 65 Structures of the new isopimara-8(9),15-dienes 309–312, 315, 322, 323, 327, 329 and
the isopimara-8(14),15-dienes 313, 314, 316, 317–321, 324–326, 328, 330, 331, isolated from a
chloroform-soluble fraction of K. pulchra rhizomes grown in Myanmar
(14 kDa) that is conserved in HIV-1, HIV-2, and simian immunodeficiency virus
(SIV) [368, 369], and has been suggested as a promising drug target for comprehensive HIV/AIDS therapy [370, 371]. Fumagillin, damnacanthal, vipirinin, and
quercetin had been reported as Vpr inhibitors earlier [372–375]. The CHCl 3 -soluble
fraction of K. pulchra inhibited Vpr in TREx-HeLa-Vpr cells at an effective dose
of 25 μg/cm
3 . Furthermore, the assay results also revealed that kaempuchraols B
(310), D (312), G (315), Q (325), T (328), U (329), and W (331) exhibited anti-Vpr
activities at concentrations ranging from 1.56 to 6.25 μM. The inhibitory potencies
of compounds 310, 312, 315, 325, 328, 329, and 331 were comparable to that of