A new acylated flavone glycoside, skullcapflavone I 2′-O-β-D-(6″-E-cinnamoyl) glucopyranoside (1), together with two known flavones, 5,2′-dihydroxy-7-methoxyflavone (2) and 5,2′,6′-trihydroxy-7-methoxyflavone-2′-O-β-D-glucopyranoside (3), and two known labdane diterpenoids, 14-deoxy-11,12-didehydroandrographolide (4) and andrographolide (5) were isolated from the whole plant of Andrographis nallamalayana. Structural elucidation of the new compound, as well as of the known compounds was achieved by various NMR techniques including 1H-1H COSY, HSQC, HMBC and ROESY experiments, ESITOF mass spectrometry, acid hydrolysis and saponification studies.
GovindachariTR, ParthasarathyPC, PaiBR, SubramaniamPS. (1965) Chemical examination of Andrographis echioides-II, structure and synthesis of echioidin. Tetrahedron, 21, 3715–3720.
2.
GovindachariTR, ParthasarathyPC, PaiBR, KalyanaramanPS. (1968) Chemical investigation of Andrographis serpyllifolia, isolation and structure of serpyllin, a new flavone. Tetrahedron, 24, 7027–7031.
3.
GovindachariTR, PaiBR, SrinivasanM, KalyanaramanPS. (1969) Chemical investigation of Andrographis paniculata.Indian Journal of Chemistry, 7, 306–307.
4.
JalalMAF, OvertonKH, RycroftDS. (1979) Formation of three new flavones by differentiating callus cultures of Andrographis paniculata.Phytochemistry, 18, 149–151.
5.
GuptaKK, TanejaSC, DharKL. (1996) Flavonoid glycoside of Andrographis paniculata.Indian Journal of Chemistry, 35B, 512–513.
6.
(a) DamuAG, JayaprakasamB, GunasekarD. (1998) A new flavone 2′-glucoside from Andrographis alata.Journal of Asian Natural Products Research, 1, 133–138
7.
(b) DamuAG, JayaprakasamB, RaoKV, GunasekarD. (1998) A flavone glucoside from Andrographis alata.Phytochemistry, 49, 1811–1813
8.
(c) DamuAG, JayaprakasamB, GunasekarD, BlondA, BodoB. (1999) Two acylated flavone glycosides from Andrographis serpyllifolia.Phytochemistry, 52, 147–151
9.
(d) JayaprakasamB, DamuAG, GunasekarD, BlondA, BodoB. (1999) Dihydroechioidinin, a flavone from Andrographis echioides.Phytochemistry, 52, 935–937
10.
(e) JayapraksamB, GunasekarD, RaoKV, BlondA, BodoB. (2001) Androechin, a new chalcone glucoside from Andrographis echioides.Journal of Asian Natural Products Research, 3, 43–48
11.
(f) JayakrishnaG, Hari KishoreP, RaoCV, GunasekarD, BlondA, BodoB. (2001) Two new 2′-oxygenated flavones from Andrographis elongata.Chemical and Pharmaceutical Bulletin, 49, 1555–1557
12.
(g) ReddyMVB, Hari KishoreP, RaoCV, GunasekarD, CauxC, BodoB. (2003) New 2′-oxygenated flavonoids from Andrographis affinis.Journal of Natural Products, 66, 295–297
13.
(h) ReddyMK, ReddyMVB, JayakrishnaG, GunasekarD, CauxC, BodoB. (2003) Two new flavonoids from Andrographis rothii.Chemical and Pharmaceutical Bulletin, 51, 191–193
14.
(i) ReddyMK, ReddyMVB, GunasekarD, MurthyMM, CauxC, BodoB. (2003) A flavone and an unusual 23-carbon terpenoid from Andrographis paniculata.Phytochemistry, 62, 1271–1275
(k) ReddyMK, ReddyMVB, ReddyBAK, GunasekarD, CauxC, BodoB. (2003) A new chalcone and a flavone from Andrographis neesiana.Chemical and Pharmaceutical Bulletin, 51, 854–856
17.
(l) ReddyBAK, ReddyMVB, GunasekarD, MurthyMM, CauxC, BodoB. (2005) Two new flavonoids from Andrographis macrobotrys.Indian Journal of Chemistry, 44B, 1966–1969.
KleipoolRJC. (1952) Constituents of Andrographis paniculata Nees. Nature, 169, 33–34.
20.
BalmainA, ConnollyJD. (1973) Minor diterpenoid constituents of Andrographis paniculata Nees. Journal of Chemical Society Perkin TransactionsI, 1247–1251.
21.
PuriA, SaxenaR, SaxenaRP, SaxenaKC, SrivastavaV, TandonJS. (1993) Immunostimulant agents from Andrographis paniculata.Journal of Natural Products, 56, 995–999.
22.
MatsudaT, KuroyanagiM, SugiyamaS, UmeharaK, UenoA, NishiK. (1994) Cell differentiation-inducing diterpenes from Andrographis paniculata Nees. Chemical and Pharmaceutical Bulletin, 42, 1216–1225.
23.
ShenY-H, LiR-T, XiaoW-L, GangXu, LinZ-W, ZhaoQ-S, SunH-D. (2006) ent-Labdane diterpenoids from Andrographis paniculata.Journal of Natural Products, 69, 319–322.
24.
KirtikarKR, BasuBD. (1975) Indian Medicinal Plants, Vol. 3, Periodical Experts, New Delhi, 1884–1886.
25.
ChopraRN, NayerSL, ChopraIC. (1980) Glossary of Indian Medicinal Plants. CSIR, New Delhi, 18.
KuroyanagiM, SatoM, UenoA, NishiK. (1987) Flavonoids from Andrographis paniculata.Chemical and Pharmaceutical Bulletin, 35, 4429–4435.
29.
KarlC, MullerG, PedersenPA. (1976) Flavonoide aus Salix alba. Die struktur des terniflorins und weiteren acyl flavonoides. Phytochemistry, 15, 1084–1085.
30.
AritomiM. (1963) Terniflorin, a new flavonoid compound in flowers of Clematis terniflora var. robusta. Chemical and Pharmaceutical Bulletin, 11, 1225–1228.
31.
TanakaT, IinumaM, MizunoM. (1986) Spectral properties of 2′-oxygenated flavones. Chemical and Pharmaceutical Bulletin, 34, 1667–1671.
32.
IinumaM, MatsuuraS, KusudaK. (1980) 13C Nuclear magnetic resonance (NMR) spectral studies on polysubstituted flavonoids. I. 13C NMR spectra of flavones. Chemical and Pharmaceutical Bulletin, 28, 708–716.
33.
MarkhamKR, Mohan ChariV, MabryTJ. (1982) In The Flavonoids: Advances in Research. HarborneJB, MabryTJ (Eds). Chapman and Hall, London, 44.
